Winter Park FL Real Estate, Homes with Pool for Sale - Pinecrest Real Estate Management

1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code

Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 306, Winter Park

$410,000

4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the property could use some TLC, it features solid major updates and endless potential to add value. Situated on an oversized lot with NO HOA, this home features a spacious enclosed lanai, perfect for enjoying Florida living year-round. The thoughtfully designed split floor plan offers added privacy, with the primary suite separated from the secondary bedrooms. The recently updated kitchen serves as the heart of the home, while major improvements including a 2023 HVAC system, 2019 water heater, and newer roof, to provide peace of mind for years to come. Whether you're an investor or a buyer looking to personalize a home in one of Central Florida's most desirable locations, this property offers exceptional potential and a rare opportunity in Winter Park.

1610 Gladiolas Drive, Winter Park

$5,600,000

5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park

$179,900

2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 09 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.

3381 Cedar Springs Place Unit 151, Winter Park

$614,990

4 Beds ⋅ 2 Baths ⋅ Kings Cove SubDv. ⋅ 32792 Zip Code

MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the moment you arrive, you'll appreciate the spacious layout and impressive updates throughout. The heart of the home features a beautifully appointed kitchen with quartz countertops, ample cabinetry, and a seamless flow into the family room, making it perfect for everyday living and entertaining. Vaulted ceilings and a cozy wood-burning fireplace create a warm and inviting atmosphere. Step outside to your own private outdoor oasis. The screened-in pool area is designed for year-round enjoyment and features a spacious patio, covered lanai, and a fully equipped outdoor kitchen complete with refrigerator, sink, and cabinetry—ideal for hosting family and friends. The primary suite offers a relaxing retreat with dual sinks and plenty of space to unwind. Additional highlights include a fenced backyard, new windows (2021), new roof (2019), and a new AC system (2024), providing peace of mind for years to come. Conveniently located with easy access to SR 417, shopping, dining, and everyday conveniences, this exceptional home combines comfort, style, and location. Don't miss this opportunity—schedule your private showing today!

4353 Steed Terrace, Winter Park

$154,900

1 Beds ⋅ 1 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Cute as a button and move-in ready! This charming top floor 1-bedroom, 1-bath condo offers a bright, airy feel with an open-concept layout designed for comfortable living. Literally just steps away, you will enjoy peaceful views overlooking the hot tub and community pool from your private retreat above it all! The updated kitchen features beautiful white cabinetry with SOFT-CLOSE DRAWERS, providing both style and functionality. The spacious living area is enhanced by a vaulted ceiling that creates an expansive feel and allows natural light to pour in throughout the day. The primary bedroom continues the open, inviting atmosphere with vaulted ceilings and a generous walk-in closet. The bathroom offers a raised-height vanity with ample countertop space, making your daily routine both convenient and comfortable. This unit also comes with an INTERIOR LAUNDRY so you don’t have to worry about going off-site! Whether you’re relaxing at home on your SCREENED PATIO, enjoying the pool or hot tub, or taking in the view from your top floor location, this condo is the perfect blend of charm, comfort, and convenience. Come see it today!

3037 Antique Oaks Circle Unit 156, Winter Park

$549,000

3 Beds ⋅ 2 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code

POOL HOME WITH A WOOD-BURNING FIREPLACE, HOME OFFICE, AND PRIME WINTER PARK LOCATION! This single-family home is packed with the features today's buyers are looking for, including a private pool, spacious backyard, dedicated office/den, and a cozy wood-burning fireplace. Inside, you'll find a versatile floor plan designed for both everyday living and entertaining. The family room is warm and inviting, featuring a beautiful wood-burning fireplace that adds character and charm. A separate office/den provides the flexibility needed for remote work, a playroom, home gym, or additional living space. Step outside to your private backyard oasis, complete with a sparkling swimming pool and plenty of room for outdoor entertaining, family gatherings, pets, and play. The expansive yard offers endless opportunities to create the outdoor lifestyle you've been dreaming of. Situated on a cul-de-sac in a desirable Winter Park neighborhood and zoned for sought-after schools, you'll enjoy easy access to Park Avenue's renowned restaurants, boutique shopping, community events, parks, and entertainment. Conveniently located near Downtown Orlando, major highways, hospitals, and top employers, this home offers the perfect combination of location, comfort, and lifestyle. If you're searching for a Winter Park pool home with a home office, fireplace, large backyard, and exceptional location, this home deserves a spot at the top of your list.

4053 Cool Water Court, Winter Park

$475,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed for both everyday living and entertaining. The well-appointed kitchen features stainless steel appliances, granite countertops, and ample cabinetry, creating a functional and stylish space for preparing meals and gathering with family and friends. The home's well-maintained interior reflects pride of ownership throughout, offering a warm and welcoming atmosphere from the moment you arrive. The spacious living areas and comfortable bedrooms provide plenty of room to relax and unwind, while the thoughtful layout maximizes both comfort and convenience. Whether you're hosting guests, working from home, or simply enjoying a quiet evening in, this home is designed to fit a variety of lifestyles. Located in the heart of Winter Park, you'll enjoy easy access to the area's renowned dining, shopping, parks, and cultural attractions. Spend weekends exploring the boutiques and cafés along Park Avenue, enjoying a scenic boat tour through Winter Park's picturesque lakes, or visiting nearby gardens, museums, and recreational trails. With convenient access to Downtown Orlando, major employers, top-rated schools, and world-famous attractions, this location offers the perfect balance of suburban charm and urban convenience. Don't miss this opportunity to own a well-cared-for home in one of Central Florida's premier neighborhoods. Schedule your private showing today and discover everything this wonderful Winter Park property has to offer!

3641 Hawthorne Lane, Winter Park

$2,499,000

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

426 Worthington Drive, Winter Park

$220,000

2 Beds ⋅ 3 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code

Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered parking plus additional guest parking, Community pool. The HOA covers exterior maintenance, roof, trash, landscaping and community pool, allowing owners to enjoy a low maintenance lifestyle. Why You'll Love It !! This well maintained townhome offers the perfect combination of comfort, convenience, and value. The bright, open floor plan is ideal for everyday living, while the two upstairs ensuite bedrooms provide privacy for homeowners, guests, or roommates. Enjoy your morning coffee or unwind in the evening on the private fenced patio—your own outdoor retreat. Prime Winter Park Location: Conveniently located just minutes from: Full Sail University, University of Central Florida (UCF), Downtown Winter Park, Major highways (417 & 408), Shopping, dining, parks, and entertainment Great Opportunity, Whether you're a first-time homebuyer, downsizing, or looking for an investment property, this home offers exceptional value in one of Central Florida's most convenient locations. Schedule your private showing today and discover everything this Winter Park townhome has to offer.

7488 Whisperwood Drive Unit 28, Winter Park

$229,500

2 Beds ⋅ 2 Baths ⋅ Goldenrod Villas Condo SubDv. ⋅ 32792 Zip Code

Step into a remodeled condominium in Goldenrod Villas, a peaceful, well-established community. This renovated, 2-bedroom, 2-bath villa features a light and airy layout and puts you in one of Central Florida's most coveted zip codes. With more than 1000 square feet of updated, move-in-ready living space, it's the perfect low-maintenance home base for a busy homeowners who wants style, comfort, and location all in one. The refurbished kitchen features quartz countertops, a tiled backsplash, new stainless-steel appliances (including a built-in microwave), freshly painted cabinets, and a laundry closet. No more laundromats!!The living room opens to a private, shaded, custom designed, screened patio, along with a fenced backyard that offers a quiet escape after a long day or space for a pet or other outdoor activities. Both bedrooms are generously sized with more than ample walk-in closets. Both bathrooms have new tile floors, new cabinets, sinks, toilets, and bright lighting. Practical upgrades have already been done for you: brand-new HVAC, duct work, water heater, plumbing, lighting, knock-down ceilings, flooring, and updated fixtures throughout. Custom windows will soon be installed, too. The roof was recently replaced, too. Home-buying worries be gone! What are we near—that is enticing? Drive outside the community and you're minutes from Aloma Avenue shopping, and major corridors including SR 436, 417, and 408.

7733 Country Place Unit G2, Winter Park

$299,999

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.

2339 Inagua Way, Winter Park

$1,799,000

4 Beds ⋅ 5 Baths ⋅ Winter Park Place 45/148 SubDv. ⋅ 32789 Zip Code

Nestled on one of Winter Park’s most exclusive streets, this exceptional residence is located within Park Place—the only gated neighborhood in the coveted 32789 ZIP code—and is zoned for highly sought-after Audubon Park K–8 School. From the moment you arrive, you'll appreciate the rare combination of privacy, charm, and convenience that defines this remarkable home. Designed with both everyday living and effortless entertaining in mind, the versatile floor plan features elegant formal living and dining rooms, creating a welcoming setting for gatherings both large and small. The spacious primary suite is conveniently located on the first floor, along with a secondary bedroom ideal for guests or multigenerational living. Upstairs, you'll find two additional bedrooms, a full bath, and a generous bonus room perfect for a home office, media room, playroom, or fitness space. At the heart of the home is a beautifully appointed kitchen featuring granite countertops, crisp white cabinetry, a center island, and a sunlit breakfast nook surrounded by windows. The kitchen flows seamlessly into the inviting family room, where custom built-ins, a cozy fireplace, and French doors create the perfect blend of comfort and sophistication. Step outside to your own private Florida oasis. The covered paver lanai, summer kitchen, and sparkling saltwater pool provide an ideal backdrop for year-round entertaining, weekend gatherings, or peaceful evenings at home. Rich hardwood floors extend throughout the entire residence—there’s not a stitch of carpet anywhere. Architectural details such as crown molding, plantation shutters, 10-foot ceilings, and 8-foot doors enhance the home’s timeless elegance and spacious feel. Additional conveniences include a first-floor laundry room with pantry storage and a guest powder bath. A standout feature is the oversized detached two-car garage, complete with a private upstairs studio and full bath—perfect for a home office, guest suite or creative space. Surrounded by lush professional landscaping and shaded by magnificent mature oak trees, the fully fenced backyard offers beauty, privacy, and natural cooling throughout Florida’s warmer months. Tucked away on a quiet cul-de-sac, the property also benefits from added privacy provided by the neighborhood’s surrounding brick wall and direct access to a nearby open field. Park Place is more than a neighborhood—it’s a rare opportunity to enjoy a secure, friendly lifestyle.

2625 Park Place Drive, Winter Park

$535,000

3 Beds ⋅ 3 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained pool home in the highly desirable Lost Creek community, where comfort, functionality, and location come together perfectly. This spacious residence features three generously sized bedrooms and a thoughtfully designed floor plan offering both formal and casual living spaces, including a living room, formal dining room, and a large family room that flows seamlessly into the kitchen beneath soaring vaulted ceilings. The private primary suite serves as a true retreat, dual vanities, a relaxing garden tub, and a separate glass-enclosed shower. The secondary bedrooms are well-proportioned and share a convenient Jack-and-Jill bathroom. Step outside and enjoy Florida living year-round from the covered patio overlooking the screened pool enclosure, creating the perfect space for entertaining or unwinding in privacy. Ideally located in Winter Park's Lost Creek community, residents enjoy easy access to top-rated Seminole County schools, abundant shopping and dining options, major commuter routes, and popular recreational destinations including Red Bug Lake Park with its sports fields, playgrounds, walking trails, tennis courts, and family-friendly activities. This is an exceptional opportunity to enjoy the lifestyle and convenience that make Lost Creek one of the area's most sought-after communities.

1232 Valley Creek Run, Winter Park

$1,300,000

4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

beautiful home

1434 Via Sangro Pl, Winter Park

$1,725,000

6 Beds ⋅ 6 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code

Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.

2914 Reef Knot Place, Winter Park

$1,262,500

4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code

Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.

2015 Summerfield Road, Winter Park

$244,900

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park

$1,795,000

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one. Step through the custom pivot front door into a home that immediately announces its intentions. Soaring 10-ft ceilings throughout rise to a dramatic 22-ft volume in the great room, framed by sliding glass walls that dissolve the line between interior living and the private outdoor retreat beyond. Level 5 smooth drywall finish — the standard reserved for the finest custom builds — runs throughout, while wide-plank hardwood flooring flows across every living area. Italian porcelain tile anchors all bathrooms and the laundry room with precision and permanence. Every window and exterior door is imported from Germany — Unilux® precision-engineered for thermal performance, acoustic excellence, and longevity that no domestic product can match. Grohe® plumbing fixtures, also made in Germany, carry that same philosophy through every bathroom. Countertops are Cambria or Silestone® quartz with a thickened 3cm mitered edge throughout. Custom solid wood cabinetry is built to plan in the kitchen, laundry, and all bathrooms, finished with Emtek® hardware and 8-ft solid core architectural doors with 7" baseboard throughout. The Winter Park Chain of Lakes — 12 interconnected lakes spanning 2,781 acres of pristine Florida waterways — is moments away, offering boating, paddleboarding, and the beloved Winter Park Scenic Boat Tour. Over 70 parks, Kraft Azalea Gardens, Mead Botanical Garden, and more than a dozen walkable green spaces define the outdoor lifestyle. The Winter Park Farmers' Market, held every Saturday at the historic train station, is a community institution. Rollins College, one of the South's most respected liberal arts institutions, sits lakeside just minutes away, bringing cultural programming, the Bach Festival, and vibrant intellectual energy to the neighborhood year-round. Families are served by highly rated Orange County public schools, with Winter Park High School renowned for its academic rigor and championship programs, as well as exceptional private options, including Trinity Preparatory School and St. Margaret Mary. New construction in 32789 is genuinely rare — historic preservation standards and limited land availability make it so. For international buyers, Orlando International Airport is 30 minutes south. Disney, Universal, and the theme park corridor are under 30 minutes via I-4. Atlantic beaches are under an hour away. This is not a production home dressed up with upgrades. It is a ground-up, custom-built, German-engineered, the most coveted zip code in Central Florida. Schedule your private showing today.

2501 Lafayette Avenue, Winter Park

$1,395,000

3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the property offers a setting that few locations can rival. The existing residence features approximately three bedrooms, two-and-a-half bathrooms, and generously proportioned living spaces filled with warmth and character. Lovingly maintained over the years, the home provides a comfortable foundation for renovation, restoration, or reimagination. Outdoors, a screened pool creates a private retreat for year-round enjoyment, while a detached two-car garage and separate studio shed offer exceptional flexibility for hobbies, creative pursuits, a home office, fitness space, or guest accommodations. What truly distinguishes this offering is the double lot itself. Opportunities of this scale within the heart of Winter Park are increasingly rare, providing the space and flexibility to construct a custom estate tailored to your vision while preserving ample room for outdoor living, gardens, and recreation. Life here extends far beyond the property lines. Enjoy morning walks beneath majestic oak canopies, afternoons on the Chain of Lakes, outdoor concerts, art festivals, sidewalk cafés, and some of Florida's most picturesque streetscapes. Whether renovating the existing residence or creating the home of your dreams, this exceptional property represents a rare chance to secure a legacy homesite in one of the most desirable addresses in Central Florida.

321 Sylvan Boulevard, Winter Park

$5,500,000

4 Beds ⋅ 5 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

313 Sylvan Drive, Winter Park

$725,000

4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an exceptional blend of luxury, comfort, and modern convenience. Upon entry, you're greeted by a dramatic two-story foyer with soaring 20-foot ceilings and abundant natural light. The open-concept living spaces feature luxury vinyl plank flooring throughout, plantation shutters, and corner sliding glass doors that seamlessly connect indoor and outdoor living. Enjoy breathtaking west-facing water views, a picturesque fountain and bridge backdrop, and spectacular sunset views from your private backyard. One of the home's standout features is its generously sized, aluminum-fenced backyard, offering ample space for outdoor entertaining, play, pets, gardening, or even a future pool while still enjoying tranquil waterfront views. Thoughtful smart-home upgrades include electric curtains on the sliding doors, Eufy security cameras, smart door locks, and a MyQ-enabled garage door. The oversized two-car garage also features convenient touchpad access. Residents of Hawks Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic walking trails. Outdoor enthusiasts will appreciate direct access to Lake Howell for kayaking and canoeing. HOA dues include professional landscaping maintenance, allowing homeowners to enjoy a beautifully maintained property with less upkeep. This move-in-ready home offers the perfect combination of elegant design, premium upgrades, abundant outdoor space, low-maintenance living, and an unbeatable waterfront lifestyle.

1316 Blue Stem Lane, Winter Park

$3,500,000

5 Beds ⋅ 7 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.

1836 Whitehall Drive, Winter Park

$440,000

4 Beds ⋅ 3 Baths ⋅ Trinity Bay SubDv. ⋅ 32792 Zip Code

Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

8433 Commander Cove, Winter Park

$3,795,000

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

$1,450,000

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

1421 Chapman Circle, Winter Park

$445,000

3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code

Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

1535 Lawndale Circle, Winter Park

$2,250,000

5 Beds ⋅ 5 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

240 N Phelps Avenue, Winter Park

$759,000

4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Completely reimagined and professionally renovated, this stunning Winter Park POOL home offers approximately 1,950 square feet of thoughtfully designed living space with a rare 4-bedroom, 3-full bathroom floor plan, a 2-car garage, and an exceptional blend of style, function, and quality craftsmanship. At the heart of the home is a show-stopping open-concept kitchen featuring custom shaker cabinetry, quartz countertops, a dramatic oversized center island, designer lighting, a custom range hood, and a striking tile feature wall that creates a true focal point for the home. Warm wood accents, curated finishes, and seamless flow into the living and dining spaces make this home ideal for both everyday living and entertaining. The split-bedroom floor plan provides privacy and flexibility, with the primary suite situated on one side of the home and the secondary bedrooms located on the opposite side. All three bathrooms have been completely gutted and beautifully remodeled with high-end finishes and timeless design selections. Luxury vinyl plank flooring extends throughout the home, creating a cohesive and modern aesthetic. Major improvements include a NEW roof (2026), NEW AC system, NEW windows, NEW electrical, NEW water heater, RESURFACED POOL, updated lighting throughout, inside laundry room, and extensive interior renovations that allow buyers to enjoy the benefits of a truly move-in-ready home. Situated in the highly desirable Winter Park Pines area, residents enjoy convenient access to Park Avenue, Downtown Winter Park, Cady Way Trail, Rollins College, Full Sail University, UCF, shopping, dining, major roadways, and Orlando International Airport. Combining designer finishes, an open modern layout, a private pool, and an unbeatable location, this is a rare opportunity to own a fully renovated home in one of Central Florida's most sought-after communities. Schedule your private showing today.

275 N Ranger Boulevard, Winter Park

$4,950,000

4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park

$254,900

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a light granite sink, and carefully selected high-end finishes, including antique brass hardware and faucet. Vinyl flooring creates a clean, cohesive look across the residence. Additional recent improvements include: Renovated primary shower featuring Italian porcelain tile and added storage shelving (2026) , Dining room chandelier and bedroom ceiling fans (2026), Fresh paint throughout (2026) Tankless water heater (2025) , New A/C system (2024), professionally serviced in June 2026, Renovated hallway bathroom and added storage shelving (2024). The floor plan offers a bright, open living space with two points of entry and an easy flow between the kitchen, dining, and living areas. Beyond the unit itself, residents enjoy an exceptional list of community amenities. The HOA includes water, trash, Spectrum high-speed internet, cable television with 150+ channels, and access to popular streaming services including Disney+, HBO Max, Peacock, and more. Set along scenic Lake Killarney, the community features a private dock, water access for boating and kayaking, a peaceful courtyard, abundant guest parking, and newly completed landscaping enhancements. The association has also recently completed significant infrastructure improvements to the community's incoming water system, with paving improvements and painting coming soon. A great opportunity to purchase a truly turnkey residence.

2500 Lee Road Unit 104, Winter Park

$199,900

1 Beds ⋅ 1 Baths ⋅ Lake Killarney Condominium Assn Inc. SubDv. ⋅ 32789 Zip Code

**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time buyers, downsizers, or savvy investors looking to capture the ultimate Winter Park lifestyle. Step inside to an open, inviting living space featuring brand-new, modern Luxury Vinyl Plank (LVP) flooring running seamlessly throughout for a sophisticated look and maximum durability. The kitchen is freshly upgraded with brand-new, gleaming appliances and plenty of counter space. As a coveted first-floor unit, you will enjoy the ultimate convenience of easy, stair-free access, dual private entry points, and a private, screened-in patio perfect for sipping your morning coffee or winding down. One of the standout features of this property is its accessibility. **Great news for buyers shopping with FHA financing: the community is under the limit for single-unit approvals, making this an incredible opportunity to purchase with an FHA loan.** Additionally, the fairly low monthly HOA fee covers water, sewer, trash, pest control, and exterior/grounds maintenance. As a resident of Lake Killarney Condominiums, you will enjoy premium lakeside community amenities: **Sparkling Lakeside Pool** with stunning views over the water. **Private Community Boat Dock & Boat Ramp Access**, ideal for paddleboarding or sunset strolls. **On-site Fitness Room & Laundry Facilities** located steps from your door. **Clubhouse, Shuffleboard Courts, and Picnic Areas** with grills for effortless entertaining. Location is everything, and this address boasts an incredible walkability factor. You are quite literally around the corner from some of Central Florida’s finest dining, shopping, and entertainment: **Walk to Grocery & Dining:** Step next door or take a quick stroll to Trader Joe’s, the iconic Hillstone Restaurant overlooking the lake, and the completely revitalized Winter Park Village, which features a luxury movie theater, boutique shopping, and endless cafes. **Park Avenue District:** Just minutes away is Park Avenue, Winter Park’s historic cobblestone main street, renowned for its upscale boutiques, award-winning sidewalk dining, local art galleries, and the Saturday Farmers Market. **Commuter’s Dream:** The property offers lightning-fast access to Interstate 4 (I-4), putting downtown Orlando, Maitland Center, and major employment hubs just minutes away. The Winter Park SunRail Station is also less than a mile down the road for a stress-free commute. Don't miss out on this rare opportunity to own a fully updated, low-maintenance slice of paradise in one of Winter Park's most vibrant, lakeside neighborhoods. Schedule your private showing today!

151 North Orlando Avenue Unit 142, Winter Park

$199,900

2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2500 Lee Road Unit 220, Winter Park

$1,429,000

5 Beds ⋅ 4 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features 10-foot ceilings, 8-foot doors, luxury vinyl plank flooring throughout, and an expansive great room with an electric fireplace. The gourmet kitchen is designed to impress with quartz countertops, custom cabinetry, stainless steel appliances, a large center island, and abundant storage. A unique under-stair wine cellar adds character and sophistication, while a first-floor guest suite provides privacy and flexibility. Upstairs, the spacious primary suite overlooks the backyard and pool area and includes a spa-inspired bathroom with dual vanities, a soaking tub, walk-in shower, and generous walk-in closet. Three additional bedrooms comfortable accommodations, including a Jack-and-Jill layout and a private In-suite bedroom. A conveniently located upstairs laundry room completes the second level. Step outside to your private outdoor retreat featuring a beautifully landscaped backyard, sparkling in-ground pool, covered lanai, and summer kitchen with built-in grill—perfect for entertaining year-round. Ideally located just minutes from Winter Park’s renowned shopping, dining, parks, and cultural attractions, this exceptional home offers the rare opportunity to enjoy the benefits of brand-new construction in one of Central Florida’s most sought-after communities. Schedule your private showing today.

1473 Berkshire Avenue, Winter Park

$1,888,888

5 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code

A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. The home is within the acclaimed Winter Park school district, less than four miles from Trinity Preparatory School, and minutes from Rollins College and the University of Central Florida, placing premier educational opportunities nearby. Thoughtfully designed with a Zen-inspired aesthetic, the home blends clean architectural lines with warm natural elements to create a refined, restorative living experience. From the moment you arrive, a sense of calm surrounds you, offering a peaceful escape while remaining minutes from everything Winter Park offers. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A semi-floating steel staircase with solid white oak treads serves as a dramatic focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining. A Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private executive office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, dual-entry marble shower with a semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-style outdoor living space evokes the serenity of a Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, it is a sanctuary where timeless design, resort-inspired living, and one of Central Florida's finest educational settings create an unparalleled lifestyle.

2032 Kimbrace Place, Winter Park

$2,099,990

4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code

Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Featuring 4 spacious bedrooms and 4 beautifully appointed bathrooms, this masterpiece showcases custom cabinetry and closets throughout, ensuring every space is both functional and refined. The chef’s kitchen is a true showpiece, complete with a coffee bar, walk-in pantry with customized shelving and designer lighting, and seamless flow into the open-concept living and dining areas. A wine room adds sophistication and convenience for the entertainer at heart. Upstairs, enjoy a spacious loft area with a wet bar, perfect for hosting guests or creating an additional entertainment lounge. Step outside to your private outdoor oasis, featuring a heated pool, fireplace, outdoor kitchen, and surround sound system—designed for year-round entertaining and relaxation. This home is pre-wired for security cameras and enhanced by custom landscaping and lighting, offering beauty and privacy from day to night. Located in highly sought-after Winter Park, Florida, near world-class dining, shopping, and top-rated schools. Contact us today for a private showing!

525 S Lakemont Avenue, Winter Park

$459,000

3 Beds ⋅ 2 Baths ⋅ Trinity Bay Ph 2 SubDv. ⋅ 32792 Zip Code

Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation just moments from home. This meticulously maintained residence stands out with fresh exterior paint, updated landscaping, and inviting curb appeal. Inside, soaring vaulted ceilings and abundant natural light create an open, airy atmosphere, enhanced by fresh interior paint throughout. The thoughtfully designed split-bedroom floor plan makes excellent use of every square foot, offering comfortable living with no wasted space. An indoor laundry room, spacious 2-car garage, and desirable semi cul-de-sac location add to the home's appeal. Beyond the lake, residents enjoy a community pool, playground, boat launch, and dock along with being located directly across the street from the Cross-Seminole Bike Trail, creating a true lifestyle community. Conveniently located with easy access to SR 417, shopping, dining, and everyday essentials, this home offers the perfect blend of recreation, convenience, and value. Experience the rare opportunity to enjoy private lake-access living in one of the area's most desirable neighborhoods.

5340 N Lake Burkett Lane, Winter Park

$3,500,000

4 Beds ⋅ 4 Baths ⋅ Maitland Shores 1st Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*

2240 Venetian Way, Winter Park

$175,000

2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code

Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or entertaining. Enjoy an open living and dining area that flows seamlessly to a private screened porch with additional storage space, perfect for relaxing and enjoying the peaceful surroundings. The home offers generous room sizes, ample storage throughout, and a comfortable living environment within a quiet and established community. Residents enjoy access to community amenities including a sparkling swimming pool, fitness center, clubhouse/conference room, beautifully maintained grounds, and ample parking. HOA benefits may include exterior maintenance, landscaping, water, trash service, and roof maintenance, providing added convenience and value. Ideally situated in East Winter Park, this property offers exceptional access to everything Central Florida has to offer. Conveniently located just minutes from Full Sail University, the University of Central Florida (UCF), Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Enjoy nearby shopping, dining, entertainment, golf courses, parks, grocery stores, and everyday conveniences all within close proximity. Commuters will appreciate the easy access to major highways including SR-417 and SR-408, while Orlando International Airport is only a short drive away. Whether you are a first-time homebuyer, downsizing, investing, or searching for a centrally located primary residence, this home presents an outstanding opportunity to enjoy the Winter Park lifestyle in a peaceful and well-connected community.

4798 Tangerine Avenue Unit 4798, Winter Park

$430,000

3 Beds ⋅ 3 Baths ⋅ Trinity Bay SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. "Price Improvement" This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. The water heater was replaced in 2025, the AC was replaced in late 2021, and the roof in 2017. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.

5530 S Lake Burkett Lane, Winter Park

$275,000

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

311 E Morse Boulevard Unit 6-12, Winter Park

$1,250,000

2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Nestled along one of Winter Park's most cherished brick-lined streets, this elegantly appointed two-bedroom, two-bath residence at the prestigious Alabama offers a rare opportunity to experience the very best of lakeside luxury living. With 1,574 square feet of thoughtfully designed interior space, this exceptional unit captures the timeless charm and sophistication that have made the Alabama one of the most coveted addresses in the heart of Winter Park. From the moment you step through the gracious foyer entry, complete with a coat closet, you are welcomed by an atmosphere of warmth and refined taste. Reclaimed wood floors flow seamlessly throughout the entire residence, lending an organic richness that perfectly complements the grass cloth covered walls and classic crown molding found in every room. Recessed lighting adds a soft, curated ambiance, while the expansive living and dining area serves as the heart of the home, offering sweeping views of the beautifully maintained gardens and the shimmering waters of Lake Maitland just beyond. The well-appointed kitchen is a chef's delight, featuring stainless steel appliances, an induction range, a Subzero refrigerator, stone countertops, a charming penny tile backsplash, and a central island ideal for both casual dining and entertaining. A dedicated interior laundry room adds a layer of everyday convenience that is rarely found in residences of this era and character. The primary bedroom is a true retreat, featuring double built-in closets and a beautifully finished en suite bath with a walk-in shower. The second bedroom is comfortably proportioned and well-suited for guests, a home office, or whatever lifestyle demands require. The hall bath offers a classic tub and shower combination to serve residents and visitors alike. One reserved covered parking space is included, and monthly HOA dues of $1,600 cover the care and maintenance that keep this distinguished property in impeccable condition. The location is simply unmatched. Kraft Azalea Park, one of Central Florida's most scenic and beloved green spaces along the shores of Lake Maitland, is just moments away, offering a tranquil setting for morning walks and golden-hour evenings. The legendary shops, restaurants, and galleries of Park Avenue are easily accessible, placing world-class dining and boutique retail practically at your doorstep. Tennis enthusiasts will appreciate the proximity to the Winter Park Racquet Club, while golf aficionados will find the storied Interlachen Country Club well within reach, rounding out a lifestyle that is as active as it is refined. This is Winter Park living at its most authentic, offering history, elegance, and an unbeatable sense of place in one of the most desirable communities in all of Central Florida.

1600 Alabama Drive Unit 402, Winter Park

$500,000

4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.

2054 Eastbrook Boulevard, Winter Park

$485,000

4 Beds ⋅ 3 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to the heart of Winter Park. This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming floor plan designed with both everyday living and entertaining in mind. The updated kitchen features stainless steel appliances, a spacious island, abundant cabinet storage, and seamless flow into the main living areas. A formal living area adds flexibility, offering the perfect space for a cozy sitting room, playroom, home office, or additional entertaining area. Natural light throughout the home creates a bright and airy atmosphere. Upstairs, you’ll find all four bedrooms and two full bathrooms, providing privacy and functionality for growing families. The screened-in porch overlooks a stunning backyard retreat complete with a sparkling pool, beautiful landscaping, and no rear neighbors for added privacy. Peaceful, quiet, and surrounded by nature and wildlife, this outdoor space makes it perfect for summer pool days, evening dinners outside, and making lifelong memories.

1850 Aster Drive, Winter Park

$695,000

4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, louvered window shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!

715 S Ranger Boulevard, Winter Park

$1,669,000

3 Beds ⋅ 5 Baths ⋅ Winter Park Oasis SubDv. ⋅ 32789 Zip Code

Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary aesthetic, with clean lines and seamless flow designed for everyday living and effortless entertaining. Step outside to your own private oasis- complete with a pool and tranquil outdoor spaces- perfect for enjoying Florida living year-round. The home's prime location allows for an exceptional lifestyle- just a short stroll to Park Avenue's renowned shops and dining and an even shorter stroll to the golf course. Offering a unique combination of modern design and in-town convenience, this is Winter Park living at its most elevated.

641 Northwood Circle, Winter Park

$865,000

3 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code

Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Now offering $10,000 Seller Credit! Call to schedule your showing today!

338 Blue Heron Drive, Winter Park

$1,995,000

4 Beds ⋅ 3 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Welcome to this extraordinary, better-than-new residence in the heart of Winter Park, a thoughtfully designed and impeccably upgraded custom, one-owner home built in 2020 that effortlessly blends timeless elegance with today’s most sought-after luxury features. Situated on a wonderfully deep, private lot with no HOA, this remarkable two-story home was crafted for elevated everyday living, unforgettable entertaining and seamless indoor-outdoor enjoyment. Offering 3,696 square feet, the flexible floor plan features four bedrooms, three full baths, a loft and a bonus room with a coffee/cocktail bar adjacent to accommodate a variety of lifestyles. The expansive first-floor primary suite is a true retreat, featuring a spa-inspired bath with heated floors, a soothing tub, an oversized walk-in shower and two large walk-in closets. The downstairs office with an en suite bath can easily function as a private guest suite or fourth bedroom. Quality craftsmanship shines throughout with detailed ceilings, engineered oak hardwood flooring, crown molding and baseboards, designer doors and hardware and plantation shutters throughout, creating a sophisticated yet inviting atmosphere. A rare combination of warmth and sophistication, this home beautifully balances luxury and functionality for modern living. The exceptional chef’s kitchen features a 60-inch Wolf gas range with a large griddle and double ovens, an expansive center island, a Sub-Zero refrigerator, a dining area and an adjacent butler’s pantry with an additional dishwasher and sink and a laundry room. Spacious gathering areas flow effortlessly into the spectacular outdoor retreat, complete with a covered lanai with remote screens, summer kitchen, outdoor fireplace, sparkling saltwater pool, separate heated spa and incredible privacy. Additional highlights include a Sonos sound system, high-definition security cameras, natural gas, a full-house generator, a separate air-conditioned workshop and a two-car garage. This exceptional Winter Park home offers the rare opportunity to enjoy newer construction elevated far beyond builder standards. Check out the 3D walk through home tour! The separate hobby garage and the 2 car garage are not included in the video tour. Call today to schedule your private showing!

2261 Mulbry Drive, Winter Park

$340,000

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.

2676 Barbados Drive, Winter Park

$6,000,000

5 Beds ⋅ 8 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.

1571 Woodland Avenue, Winter Park

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