Winter Park FL 4 Bedroom Real Estate, Homes, Condos for Sale

4 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

2323 Devon Court, Winter Park

$1,419,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1546 Miller Avenue, Winter Park

$2,275,000

4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.

1271 Palmer Avenue, Winter Park

$684,000

4 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's most established neighborhoods, celebrated for its tree-lined streets, oversized homesites, exceptional schools, and proximity to world-class dining, shopping, golf, and cultural attractions. With no HOA, this thoughtfully renovated home offers the perfect balance of refined living and everyday comfort in one of Central Florida's most desirable locations. This 1,605 sqft, 4-bedroom, 2-bath residence, has been transformed with modern finishes, upgraded systems, and thoughtful design throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a bright and inviting space ideal for both everyday living and entertaining. The interior features new luxury vinyl flooring in all main areas and fully remodeled bathrooms with floor and wall tile, elongated modern toilets, updated vanities, and premium finishes. The main bathroom includes a new bathtub, medicine cabinet, and mirror cabinet, while the master bathroom offers a glass-walled shower with a niche and a double floating vanity with mirrored cabinets. The kitchen is a true centerpiece, showcasing a large island, quartz countertops, high-end custom cabinetry with soft-close drawers, and a pantry with built-in shelving. Luxury FORNO white-and-gold appliances elevate the space, including an induction cooktop and range, hood fan, double-door refrigerator with ice maker, and a microwave built into an island drawer. The kitchen is completed with a high-end white sink bowl and garbage disposal, adding both style and functionality. Major improvements were completed with permits, including new HVAC (2026), new water heater (2026), new 200 Amps electrical panel (2026), and a full plumbing repipe (2026). Additional upgrades include new wired smoke alarms and new doors throughout. The living room features modern potlights, and all bedrooms include contemporary ceiling fans. The lanai has been renovated, offering a comfortable outdoor retreat. Exterior enhancements include an updated roof (2020), fresh interior and exterior paint, a refinished garage floor, and an upgraded garage door opener (2026). The property also features a brand-new irrigation system (2026) to keep the grounds lush and easy to maintain. Smart-home additions include a smart Blink doorbell and a smart front-door lock, providing added convenience and security. The spacious, fully-fenced backyard offers privacy and endless possibilities for outdoor enjoyment, gardening, or future enhancements. Perfectly positioned just minutes from Winter Park Pines Golf Club, Cady Way Trail, Park Avenue, Rollins College, AdventHealth Winter Park, and the boutiques, fine dining, and cafés that have made Winter Park one of Central Florida's most coveted destinations, you'll also enjoy convenient access to Downtown Orlando, Baldwin Park, major highways, Orlando International Airport, and countless entertainment venues. With meticulous renovations, modern systems, smart-home upgrades, and an unbeatable Winter Park Pines location, this home is truly move-in ready and prepared to welcome its next owner.

2833 Prince John Road, Winter Park

$6,700,000

4 Beds ⋅ 3 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Stunning Custom Estate on the Shores of Lake Osceola

405 Lakewood Drive, Winter Park

$624,900

4 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Completely updated and move-in ready, this stunning Winter Park home offers the perfect blend of timeless charm and modern comfort! Located in the desirable Shores of Lake Killarney, this 4-bedroom, 2-bath home features 1,933 square feet of thoughtfully updated living space, deeded access to Lake Killarney, and NO HOA! As you step inside, an open layout creates a seamless flow between the kitchen, dining, and living area. The updated kitchen features quartz countertops, stainless steel appliances, generous cabinetry, an island with breakfast bar, and dining area. Sliding doors off the living area open to a private, fully fenced backyard! Whether you're enjoying a quiet morning coffee or hosting outdoor gatherings, this large, inviting space provides the perfect extension of the home's living space! Enjoy peace of mind knowing the major updates have already been completed, including a new roof (2023), new A/C and hot water heater (2025), new windows (2024), complete re-pipe (2021), new electrical panel (2021), and many additional improvements throughout the home. Conveniently located near Winter Park Village, Park Avenue, Rollins College, top-rated dining, shopping, entertainment, and major roadways, this location puts the best of Winter Park and Greater Orlando within easy reach. This is the perfect opportunity to own a move-in-ready Winter Park home that offers the character of an established neighborhood with the peace of mind and convenience of modern updates. Call to set up a private showing today!

216 Blossom Lane, Winter Park

$1,250,000

4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Virtually Staged. Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park

$920,000

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

Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

1492 Via Sangro Pl, Winter Park

$1,150,000

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circular driveway, charming front porch with brick flooring, and mature landscaping. Inside, a spacious foyer with soaring ceilings welcomes you, while engineered hardwood flooring runs throughout the main living areas. The recently renovated kitchen is the heart of the home, featuring quartz countertops, custom oak cabinetry with gold hardware, a center island with seating, stylish backsplash, and stainless steel appliances, including a gas range. The kitchen opens to the spacious dining room and inviting family room with built-ins, high ceilings, and French doors that fill the space with natural light. One of the home's most unique features is its thoughtfully designed layout. The original 1951 portion of the home offers two bedrooms, including the original primary suite with a large walk-in closet and private bath, plus a beautifully renovated hall bathroom. An addition completed in the early 2000s created an impressive owner's retreat on the opposite side of the home, complete with vaulted ceilings, French doors to the backyard, an oversized walk-in closet with custom organization, and a spacious bathroom with double vanities, soaking tub, separate shower, and private water closet. A fourth bedroom, tucked away in its own wing off the dining room, features built-ins, a large walk-in closet, and is conveniently located near the indoor laundry room. Situated on a generous .24-acre lot, the backyard offers plenty of room to add a pool while still leaving space to enjoy the yard. A long driveway leads to the rear one-car carport and an oversized storage room. Major updates include a 2020 roof and 2021 AC. All of this is just minutes from Park Avenue's renowned shopping, dining, and events, with easy access to top-rated Winter Park schools, parks, and everything that makes this neighborhood one of Central Florida's most sought-after places to call home.

1351 Oneco Avenue, Winter Park

$820,000

4 Beds ⋅ 3 Baths ⋅ Golfside Sec 2 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. **Due to the interest in the property, offers need to be in by Monday evening (7/20). ** Perfectly positioned on the 6th tee and 8th hole of the Winter Park Pines Golf Course, this home sits on an oversized quarter-acre lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views. **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, and the flexible layout also offers the potential for a fifth bedroom.** While the interior offers an exciting opportunity to update, the sellers have already completed nearly $190,000 in major infrastructure and system improvements. One of the home's most valuable features is the fully paid-off solar panel system, which generates excess electricity that is returned to the utility company, resulting in an average monthly electric bill over 12 months is approximately $90. Additional capital improvements include a newer roof (2021), a new high-efficiency, variable-speed Lennox HVAC system (2025), a new energy-efficient, heat-pump water heater (2025), complete home repipe (2020), restoration of the cast-iron sewer system (2022) and plumbing stacks, upgraded attic insulation for enhanced energy efficiency (2023), a newer pool heater and pump (2024), added French drains (2025), new gutters with leaf guards, a deep irrigation well, an expanded circular paver driveway for ample parking space, and much more. Inside, the flexible floor plan offers endless possibilities. Beyond the spacious, front-facing living/dining room, the kitchen opens to a comfortable family room with a wood-burning fireplace. The kitchen window and pocket sliding glass doors frame beautiful views of the expansive covered lanai, screened pool, and rolling fairways beyond. The current 3-bedroom/2-bath layout on the left side can easily be reconfigured to restore the original 4th bedroom, which now serves as an oversized walk-in closet for the primary suite. The corner bedroom functions as both a guest room and home office, featuring a custom Murphy bed concealed behind a built-in bookcase, providing exceptional flexibility. On the opposite side of the home, an enormous bonus room with a full bath, offers direct pool access, and sweeping golf course views. Whether envisioned as a private guest suite or 5th bedroom, recreation room, home office, fitness studio, media room, or multigenerational living space, the bonus room has endless possibilities. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. Move in today, enjoy the exceptional location, and renovate at your own pace! Be sure to request a complete list of improvements, along with the floor plan, to fully appreciate the incredible potential this home presents.

938 Golfside Drive, Winter Park

$775,000

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes - not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park

$429,900

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

Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.

1401 Aster Court, Winter Park

$925,000

4 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Welcome home to this stunningly renovated 4-bedroom, 2.5-bath with TWO additional rooms that can be used as an office space, playroom etc single-family residence located in the heart of Winter Park! This home offers an abundance of space, comfort, and modern convenience in one of Central Florida’s most desirable areas. Step inside to find a bright and open kitchen overlooking a spacious living area—perfect for entertaining family and friends. The additional office space provides a quiet spot for work or study, while the split floor plan ensures privacy and comfort for everyone. Each bedroom features ample closet space, and the home’s thoughtful layout makes daily living a breeze. Enjoy outdoor relaxation on the large backyard and covered porch, ideal for gatherings or peaceful evenings at home. The property also includes an exterior laundry room with washer and dryer for added convenience.

1310 Fairview Avenue, Winter Park

$1,600,000

4 Beds ⋅ 4 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, stainless steel appliances, ample amount of cabinetry and counter space, and a breakfast bar, great for entertaining family and friends. Open floor plan. Home features a separate dining area off the kitchen. Spacious living space and bedrooms. Spend your evenings and weekends relaxing on the beautiful lakefront of Lake Killarney, enjoying the incredible sunsets under the shade of huge cypress trees OR poolside in the private fenced in backyard.

250 Killarney, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

$750,000

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

Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

$4,250,000

4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park

$385,000

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.

885 Carnation Drive, Winter Park

$719,900

4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!

436 W Swoope Avenue, Winter Park

$2,195,000

4 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.

1750 Walnut Avenue, Winter Park

$375,000

4 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. **MULTIPLE OFFERS - SUBMIT YOUR HIGHEST AND BEST BY 5PM ON MONDAY 7/13** Bank-owned opportunity in Winter Park near Interlachen Country Club, Park Avenue, Full Sail, Rollins, and UCF. Set in Winter Woods, one of the area’s established neighborhoods, this 4/2.5 two-story home sits on a fenced lot w/pool and offers 1,776 sqft, block and brick construction, a 2-car garage, and a primary bedroom with a walk-in closet and private balcony overlooking the pool. The home needs a full renovation, including a new roof. Flooring, kitchen, and HVAC, and the property is priced accordingly. Optional HOA and flood zone X help keep carrying costs simple. Sold As-Is by the REO seller. Cash or renovation financing only.

2189 Sussex Road, Winter Park

$379,900

4 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code

Updated Winter Park home with major improvements already completed and no HOA! Located at 4965 Orange Ave., this move-in ready property offers a desirable Central Florida location with convenient access to shopping, dining, parks, major roadways, and everything the Winter Park area has to offer. Recent updates include a NEW Roof, Dual-pane, Energy-efficient Windows, 2 NEW A/C systems, fresh interior and exterior paint, upgraded baseboards, Beautifully Remodeled Bathrooms, and terrazzo & ceramic tile flooring throughout (no carpet!!). The galley-style kitchen features stainless steel appliances, a decorative backsplash, and an efficient layout designed for everyday functionality. Both bathrooms have been beautifully refreshed, while the durable flooring and fresh finishes create a clean, cohesive feel throughout the home. Outside, the large fenced yard provides excellent outdoor space for entertaining, gardening, pets, or future possibilities. The attached carport includes a convenient storage and laundry room for added practicality. With no HOA, updated major systems, energy-efficient windows, and a centrally located Winter Park address, this home is an excellent opportunity for buyers searching for an updated home in Winter Park, FL with modern improvements, low-maintenance features, and easy access to the Greater Orlando area.

4965 Orange Avenue, Winter Park

$1,690,000

4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.

708 Balmoral Road, Winter Park

$639,000

4 Beds ⋅ 3 Baths ⋅ Kawilla Crest SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to this gorgeous 4-bedroom, 3-bathroom WINTER PARK home that perfectly blends elegance, comfort, and functionality. From the moment you step inside, you'll be impressed by the soaring 12–14-foot ceilings, beautiful CROWN MOLDINGS, and classic PLANTATION SHUTTERS that add timeless charm throughout. Designed with an exceptional flow, this home features formal living and dining rooms, along with a spacious family room centered around a charming fireplace, creating a warm and inviting space for relaxing or gathering with family and friends. The family room seamlessly connects to the heart of the home—a stunning CUSTOM chef's kitchen equipped with high-end appliances, thoughtfully designed cabinet organizers, and abundant workspace, making it a dream for cooking and entertaining. The desirable split floor plan offers both privacy and flexibility, with two bedrooms located in the right wing and two in the left, including a spacious primary suite. Every detail has been carefully considered to create a warm, inviting atmosphere that's ideal for everyday living and hosting guests. Step outside to your private backyard oasis, where a large swimming pool and spacious outdoor living area create the perfect setting for entertaining, weekend gatherings, or simply relaxing. The fully fenced yard provides both privacy and plenty of room to enjoy Florida living year-round. Additional highlights include a **NEW ROOF**installed in 2021**,** NEW LUXURY VYNIL PLANKS FLOORING** in 4 rooms, brand NEW interior painting offering added value and peace of mind for the next owner. This exceptional Winter Park home is a true showstopper that offers luxury, comfort, and timeless appeal. Don't miss the opportunity to make it yours!

1908 Cyril Court, Winter Park

$625,000

4 Beds ⋅ 2 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Nestled within the gated community of Hawks Crest, this thoughtfully designed single-story residence offers an exceptional blend of comfort, style and convenience in the heart of Winter Park. Spanning 1,920 square feet, this home features an open-concept floor plan that seamlessly connects the living, dining and kitchen areas, creating an inviting setting for both everyday living and entertaining. The kitchen serves as the centerpiece of the home, appointed with granite countertops, stainless steel appliances and a spacious center island with seating. The private owner's suite offers a walk-in closet and a well-appointed bath, while three additional bedrooms provide flexibility for guests, a home office or evolving lifestyle needs. A covered lanai overlooks the tranquil pond, creating the perfect backdrop for outdoor relaxation and year-round Florida living. Residents of Hawks Crest enjoy access to an impressive collection of amenities, including a clubhouse, fitness center, resort-style pool, splash pad, dog park, playgrounds, virtual guard gate and private access to Lake Howell for kayaking and paddleboarding. Ideally located just minutes from highways, Park Avenue, downtown Maitland, top-rated schools, Foxtail Coffee and Kelly's Ice Cream, this residence offers the opportunity to enjoy one of Winter Park's most sought-after gated communities.

2087 Laurelwood Way, Winter Park

$799,000

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

Under contract-accepting backup offers. Completely reimagined with an extensive top-to-bottom renovation, this stunning four-bedroom, three-bathroom pool home offers over 2,300 square feet of beautifully curated living space in one of Winter Park's most desirable locations. Every detail was thoughtfully selected to blend timeless design with modern functionality, creating a truly move-in-ready home. Inside, large wood-look plank tile flooring installed throughout in 2024 creates a seamless flow, complemented by recessed lighting, plantation shutters, all-new designer lighting and ceiling fans, and energy-efficient windows replaced in 2024. A cozy wood-burning fireplace provides character to the beautiful living space while French doors installed in 2024 provide effortless access to the outdoor living space. Additional upgrades completed in 2024 include blown-in insulation and a gas tankless water heater. The showstopping kitchen was completely remodeled in 2024 and is designed to impress. Custom hardwood cabinetry accented with elegant gold hardware is paired with luxurious quartz countertops and a dramatic full-height quartz backsplash. A large center island with seating for four, a black farmhouse sink, pot filler, and abundant prep space make this kitchen equally suited for everyday living and entertaining. Split from the secondary bedrooms for added privacy, the spacious primary suite is a peaceful retreat featuring French doors leading directly to the pool, a dedicated makeup vanity, walk-in closet, and a beautifully renovated ensuite bathroom with a double vanity and an oversized tiled shower enclosed by frameless glass. All three bathrooms were tastefully remodeled in 2024 with timeless, high-end finishes. The oversized laundry room is as functional as it is attractive, offering built-in cabinetry for exceptional storage along with an included washer and dryer. Step outside to your own private backyard oasis situated on a beautifully landscaped .26-acre lot. The screened in-ground pool was resurfaced with mini pebble finishes in 2025, while a custom flagstone outdoor shower with a decorative rock bed creates a true resort-inspired atmosphere. Additional exterior improvements completed in 2024 include new exterior doors, gutters, French drains, and an updated two-car garage featuring epoxy flooring along with new torsion springs and rollers. Ideally located just minutes from UCF, Rollins College, Full Sail University, AdventHealth Winter Park, the Crosby Wellness Center, Winter Park Pines Golf Club, and the Cady Way Trail, residents also enjoy access to Cady Way Park with its community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Zoned for highly rated Aloma Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines a remarkable renovation with an unbeatable Winter Park lifestyle. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2024 PLUMBING - 2024 TANKLESS WATER HEATER - 2024

729 Monmouth Way, Winter Park

$445,000

4 Beds ⋅ 2 Baths ⋅ Springview SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to your own private backyard oasis in the heart of Winter Park! This beautifully maintained two-story home offers 4 bedrooms, 2 bathrooms, and the perfect blend of comfort, style, and outdoor living. With no HOA, a fully fenced backyard, and a sparkling pool, this home delivers the Florida lifestyle buyers have been searching for. From the moment you arrive, you'll appreciate the pride of ownership throughout. The home features a 2022 metal roof, 2021 gutters, 2020 insulation, a 2019 A/C, and a new garage door and opener installed in 2023, giving buyers peace of mind for years to come. Inside, the home has been refreshed with fresh interior paint, updated door hardware throughout, updated kitchen hardware, and tasteful finishes that create a bright and welcoming atmosphere. Just beyond the living spaces, the screened patio provides the perfect transition to your backyard oasis. The backyard is truly the highlight of the home, featuring a pool resurfaced in 2024, a replaced pool pump motor, an expansive patio, a pergola, and a built-in sound system that conveys with the home, creating the perfect setting for relaxing or entertaining family and friends. The generous, fully fenced backyard offers plenty of space for pets, play, gardening, and enjoying the outdoors. Move-in ready and loaded with valuable updates, this exceptional Winter Park pool home offers comfort, functionality, and an unbeatable outdoor lifestyle. Conveniently located near shopping, dining, parks, and major roadways, this is one you won't want to miss!

1189 Lazy Hollow Place, Winter Park

$825,000

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

Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.

722 S Ranger Boulevard, Winter Park

$1,695,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park

$495,000

4 Beds ⋅ 3 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Experience the Florida lifestyle in this beautifully updated 4-bedroom, 3-bath Winter Park pool home! From the renovated bathrooms and spacious family room to the all-new flooring and fresh paint, this move-in-ready home offers comfort, style, and room to entertain. Step through the new French doors into your private backyard oasis featuring a sparkling pool with new pavers, a new pool pump (2026), and a child safety fence for added peace of mind. The homes roof was replaced in 2016 and other updates include HVAC system with ductwork, water heater, all-new windows, an updated utility room, a new garage door with remote, plus an extended driveway for spacious parking. Conveniently located near shopping, dining, and downtown Orlando. This home is zoned for highly rated Lake Monte Elementary, Maitland Middle, and Winter Park High School. Don't miss this exceptional opportunity to own a beautifully updated home in one of Central Florida's most desirable communities.

4887 N Magnolia Avenue, 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

$1,189,000

4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Reimagined from the ground up for modern living while honoring its original mid-century modern heritage, this 1953 Winter Park residence pairs authentic MCM character with the ease of all-new finishes and systems. Four bedrooms and three full bathrooms are arranged around an open living, dining, and kitchen core that opens to a light-filled sitting area. White oak floors run throughout, while designer lighting and ceiling fans, clean horizontal lines, and warm natural finishes carry the home's MCM soul. The kitchen anchors the home with Taj Mahal quartzite counters and brand new KitchenAid stainless steel appliances. Step out to an expanded rear patio overlooking a private fenced backyard, ideal for entertaining or quiet evenings at home. Move in with confidence: new roof, all-new windows, new 200-amp electrical service, all-new plumbing with new water heater, new HVAC ductwork, and a new Nest thermostat. The attached garage and dedicated interior laundry complete the layout. The location is the rare kind you can live on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and the sought-after Audubon Park K-8 School. Winter Park High and the shops and dining of Park Avenue are just minutes away. A thoughtfully rebuilt classic in one of the area's most established and connected neighborhoods.

3006 Northwood Boulevard, Winter Park

$449,900

4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

Welcome home to this beautifully remodeled **4-bedroom, 2-bath** residence in sought after Winter Park! BRAND NEW ROOF IN 2024! Thoughtfully renovated from top to bottom, this move-in-ready home offers the perfect combination of modern style, quality craftsmanship, and peace of mind with virtually every major system already updated. Step inside to discover beautiful new luxury vinyl flooring throughout, a stunning kitchen featuring brand-new cabinetry, elegant quartz countertops, and updated finishes designed for both everyday living and entertaining. Both bathrooms have been completely remodeled with stylish tile, new vanities, fixtures, and toilets, creating a fresh, contemporary feel throughout the home. The spacious primary suite has been completely reimagined and now features a beautifully remodeled bathroom along with a custom built-in closet organization system. New double patio doors provide abundant natural light while creating a seamless transition to the screened patio—perfect for enjoying Florida's beautiful weather. Beyond the cosmetic updates, this home offers the kind of improvements buyers truly appreciate, including a **new HVAC system with all-new ductwork, complete house replumb, new water heater, new electrical panel, new switches and outlets throughout, fresh interior and exterior paint, and a newly rescreened patio with a new screen door.** These significant upgrades provide years of worry-free ownership. Located within the highly sought-after Seminole County Public School District, this home is zoned for Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. You'll also enjoy an incredibly convenient location just minutes from shopping, restaurants, parks, entertainment, major roadways, and everything Winter Park and the surrounding area have to offer. With its extensive renovations, desirable **4-bedroom** floor plan, exceptional location, and true move-in-ready condition, this is a rare opportunity you won't want to miss. Schedule your private showing today!

3009 Nicholson Drive, 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

$429,900

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Welcome to one of Orlando's most beloved neighborhoods, where tree-lined streets, golf course views, and a true sense of community create the lifestyle buyers are searching for. Perfectly positioned across from the 5th tee of historic Dubsdread Golf Course, this beautifully renovated home places you in the heart of the Dubsdread bubble—just minutes from the dining, shopping, and charm of both College Park and Winter Park. Set on an oversized .22-acre lot, this move-in-ready residence offers over 1,500 square feet of thoughtfully updated living space, blending classic character with today's most desired upgrades. Inside, you'll find refinished original hardwood floors, a fully renovated kitchen featuring stunning quartz countertops, new cabinetry, and new stainless steel appliances, plus two completely renovated bathrooms with fresh, timeless finishes. A 2023 rear addition adds valuable living space, while the inviting Florida room and screened porch provide the perfect spots to enjoy morning coffee, entertain friends, or unwind after a round of golf. Beyond the cosmetic improvements, the heavy lifting has already been done. Enjoy peace of mind with updated plumbing (2026) including removal of cast iron piping, updated electrical (2026), roof (2020), tankless water heater (2023), and energy-efficient windows (2023). Homes in the Dubsdread District rarely offer this combination of location, charm, lot size, and major renovations. Whether you're drawn to the golf course views, the walkable neighborhood feel, or the proximity to Orlando's best restaurants, parks, and entertainment, this home delivers the lifestyle that makes this area one of Orlando's most desirable places to call home. Move-in ready, extensively updated, and perfectly located—schedule your private showing today!

2249 Minnesota Avenue, Winter Park

$779,000

4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Beautiful corner 4 bedroom home in the heart of Kenilworth Shores in Winter Park.

1826 Banchory Road, Winter Park

$450,000

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

Discover the potential of this spacious 4-bedroom, 2.5-bath home located at 1564 Lawndale Cir in desirable Winter Park. Featuring a comfortable floor plan with generous living space, this home offers flexibility for everyday living, entertaining, working from home, or hosting guests. The bedroom layout provides privacy and functionality, while the location offers convenient access to shopping, dining, parks, schools, major roadways, and nearby Orlando destinations. With its size, layout, and prime Winter Park location, this property is a great opportunity for buyers looking to personalize a home and create lasting value. Don’t miss your chance to schedule a private showing.

1564 Lawndale Circle, 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

$469,900

4 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. 4 BEDROOM | 2 BATH | 1,863 SQ FT + TINY HOUSE GUEST SUITE | CUSTOM BUILD | NO HOA | WINTER PARK | Located just minutes from the charm and energy of Downtown Winter Park, this exceptional custom-built residence offers a rare opportunity to enjoy thoughtfully crafted living in one of Central Florida's most convenient and desirable corridors. Built in 2011 in a quiet community with no HOA restrictions, the home combines quality construction, modern aesthetics, and an outstanding lifestyle location that is difficult to replicate at this price point. From its welcoming front porch to its expansive backyard retreat, the property is designed for both comfortable everyday living and effortless entertaining. Situated on a generous 70-foot wide lot, the double-wide driveway, attached garage, and extra-wide side yard with a double-wide 11'6" gate provide exceptional utility for those with a boat, RV, or trailer — a rare and coveted feature with no association limitations. Throughout the interior, custom solid wood built-ins and cabinetry lend a warmth and permanence seldom found in production construction. The kitchen serves as the true centerpiece of the home, featuring custom solid wood cabinetry with pull-out pantry shelves, an extra-large entertaining island with abundant storage, solid stone countertops, and a striking tray ceiling with LED lighting that creates an elevated, modern ambiance. The open layout connects seamlessly to the living spaces and flows naturally toward the screened rear porch and the large, private backyard beyond. The private primary suite offers a genuine retreat experience, complete with a tray ceiling, generous walk-in closet, and a beautifully appointed en-suite bath featuring both a separate shower and soaking tub. Custom built-ins throughout the additional bedrooms add function and character at every turn. At 1,863 square feet, the main residence is complemented by a fully finished 156-square-foot backyard suite constructed in 2022, complete with a kitchenette and full bathroom — bringing the total living footprint to just over 2,000 square feet. Whether utilized for guests, extended family, a home office, or income-generating potential, this additional structure adds a remarkable dimension of flexibility and value rarely found in this market. The durable metal roof and quality of construction throughout speak to a home built with longevity in mind. Freshly painted and brand new, high-end Waterproof Laminate flooring throughout. Energy efficiency is woven into the fabric of the home as well, with open-cell spray foam insulation in the attic and a smart water heater working together to meaningfully reduce utility costs — a genuine and ongoing financial benefit that discerning buyers will appreciate. All of this, positioned less than ten minutes from Publix, Starbucks, and Costco, and within fifteen minutes of the boutique dining, shopping, and cultural offerings of Downtown Winter Park.

5350 Orange Avenue, Winter Park

$1,300,000

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

beautiful home

1434 Via Sangro Pl, 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

$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

$400,000

4 Beds ⋅ 2 Baths ⋅ Laurel Spgs SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to this beautifully maintained four-bedroom, two-bathroom home offering 1,677 square feet of thoughtfully designed living space nestled in a quaint neighborhood of the highly desirable Winter Park. Featuring a split-bedroom floor plan, extensive interior updates, and exceptional indoor-outdoor living spaces, this move-in-ready residence combines comfort, functionality, and convenience with access to top-rated Winter Park schools. Step inside to discover a bright and inviting interior, freshly repainted in 2026, complemented by refinished ceilings, elegant crown molding, ceiling fans throughout, and charming French doors that add character and architectural appeal. The versatile floor plan offers multiple living and gathering spaces, including a spacious den or family room ideal for entertaining, working from home, or everyday relaxation. Abundant storage throughout the home ensures there is a place for everything. At the heart of the home, the kitchen features warm honey-toned wood cabinetry, stainless steel appliances, a brand-new microwave, and a convenient dining area perfect for casual meals and family gatherings. The functional layout allows for seamless flow between the kitchen and living spaces, making entertaining effortless. Privately situated away from the secondary bedrooms, the spacious primary suite serves as a peaceful retreat. The suite includes a walk-in closet with custom organizational features, a ceiling fan, and a beautifully updated ensuite bathroom designed with spa-inspired finishes. The luxurious bath showcases floor-to-ceiling marble-look tile, a pedestal sink, a spacious tiled shower with glass enclosure, dual shower heads, a built-in bench seat, and custom linen and towel cabinetry for added convenience and storage. Three additional bedrooms and an updated hall bathroom renovated in 2022 provide comfortable accommodations for family members, guests, or flexible workspace options. One of the home's standout features is the expansive Florida room, offering an incredible extension of the living space. Filled with natural light, this inviting retreat features a vaulted ceiling, tile flooring, and large sliding windows that create the perfect setting for morning coffee, reading, entertaining, or enjoying Florida's beautiful weather year-round. Step outside to a fully fenced backyard designed for relaxation and outdoor enjoyment. Gather around the fire pit on cool evenings, enjoy weekend barbecues in the dedicated grilling area, or unwind beneath the shade of the quaint wooden swing. The private outdoor space offers endless possibilities for entertaining, gardening, pets, and play. Ideally located in Winter Park, this home offers exceptional convenience to everything Central Florida has to offer. Residents enjoy zoning for top-rated Winter Park schools, easy access to State Road 417 within five minutes, Full Sail University within five minutes, and the University of Central Florida within approximately fifteen minutes. Orlando International Airport is just twenty minutes away, while Target, Costco, grocery stores, shopping, dining, and everyday conveniences are all nearby. Combining spacious living areas, thoughtful updates, desirable schools, and an unbeatable location, this exceptional Winter Park home offers the perfect opportunity to enjoy comfortable Florida living in one of the area's most sought-after communities. ROOF - 2019 HVAC - 2022 PLUMBING - 2026 WATER HEATER - 2018

7514 Laurel Springs Drive, 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

$490,000

4 Beds ⋅ 2 Baths ⋅ Cedar Ridge SubDv. ⋅ 32792 Zip Code

Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.

2008 Houndslake 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

$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

$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

$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

$399,900

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

Under contract-accepting backup offers. Located on a quiet cul-de-sac in Winter Park, this home has the kind of layout and lot that are hard to find at this price point. Vaulted ceilings open up the main living area, and built-in display niches along the wall give the space character you won't find in newer construction. The kitchen has a breakfast bar peninsula and connects to a sunny dining space with a pendant light overhead. The primary suite is generously sized with two windows, a ceiling fan, walk-in closet, and a private bath with a double vanity and soaking tub. A second full bath features detailed tile work and a vanity with granite-look countertops. Additional bedrooms have ceiling fans and solid closet space. Out back is a large covered patio that opens to a fenced yard shaded by mature oak trees, the kind of backyard that actually works for people who want to spend time outside in Florida. There's room to run, entertain, or just let the week decompress. All of this in Winter Park, minutes from Park Avenue dining and shopping, Rollins College, Winter Park Village, and with quick access to I-4 and downtown Orlando.

3949 Cool Water Court, Winter Park

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