Between $700,000 - $800,000 Winter Park FL Real Estate, Homes, Condos for Sale

5 Beds ⋅ 4 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code

Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition with; new interior paint, new carpet, 2 heating and cooling systems replaced in 2024! The open concept center island kitchen has upgraded counters, 42" cabinets and a double convection oven! Downstairs there is a formal living and dining room, an open concept kitchen, nice warm low maintenance ceramic tile, a convenient downstairs bedroom that would also be a great office/craft/game/guest room!! Upstairs are the other private bedrooms and a huge bonus theater/media/entertainment space.. The oversized primary bedroom is upstairs for complete privacy and has a well appointed bathroom as well as two walk in closets!! Come home and relax in your fenced back yard that has a peaceful forest behind it, set up a hammock and.... This fine gated community is located so close to so much, The University of Central Florida, Winter Park, Downtown Orlando, Trinity Preparatory Academy, The Masters Academy, The Geneva School, the Space Coast, Cocoa Beach and more!!

8061 Pleasant Pine Circle, Winter Park

$745,000

2 Beds ⋅ 2 Baths ⋅ Park Aire Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. Welcome to 640 N Park Avenue, the iconic "pink building" in the heart of downtown Winter Park! This first-floor corner unit captures views of the WP 9 golf course, Casa Feliz and the Park Avenue streetfront from every window. Taken down to the studs and completely reimagined in 2023, this residence is filled with high-end upgrades throughout. Step inside and notice the hand-scraped walnut hardwood flooring as you enter the kitchen, which features custom cabinetry, Danby marble countertops, a European tile backsplash, and top-tier appliances, including a La Cornue range, Fisher & Paykel refrigerator, and GE Monogram dishwasher. Two appliance garages and a hidden butcher block that pulls out when needed make the most of every inch.The living room showcases beautiful views of the WP 9, along with a bar-height eating space with under-cabinet storage and additional built-ins. In the hallway, you'll find a half bath added during the renovation and a full wall of custom cabinetry. The primary bedroom sits in the corner of the building, with large windows framing the views, a spacious walk-in closet, and another full wall of built-ins. Down the hall, a second bedroom with a laundry closet sits beside the full bathroom, finished with a custom vanity and porcelain tile floors. Additional finishes include solid wood doors with Emtek hardware, Visual Comfort lighting throughout, Perrin & Rowe plumbing fixtures, and new windows (2025). Mechanical updates include rewiring, a new electric panel, plumbing updates, and new AC & ductwork (all 2023), plus a new hot water heater (2026). Step out your front door and you're steps from the community pool and everything Park Avenue has to offer. The unit includes one underground parking space and a private storage unit. Truly one of a kind, this like-new condo delivers the best of downtown Winter Park living, with every thoughtful, high-end finish you could want.

640 N Park Avenue Unit 3, Winter Park

$724,900

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

FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park

$759,900

3 Beds ⋅ 3 Baths ⋅ Golfside Sec 02 SubDv. ⋅ 32792 Zip Code

Welcome to 1003 Golfside, a fully reimagined single-story pool home in the Winter Park area, set beneath a mature oak canopy on a beautifully landscaped lot. Major updates include a NEW ROOF (2025) and a RENOVATED POOL (2025). Inside, the open-concept layout features high-gloss marble-look porcelain tile, recessed lighting, designer ceiling fans and built-in ceiling speakers. The chef's kitchen offers high-gloss cabinetry, quartz countertops with a full-height quartz backsplash, built-in wall oven and microwave, induction cooktop and a large quartz island with bar seating. The living area showcases a custom accent wall, a brick fireplace and French doors to the pool. Bathrooms are updated with quartz vanities, vessel sinks, frameless glass showers and marble-look tile. The spacious primary bedroom offers plantation shutters and room for a sitting or office area. Outside, enjoy a private fenced backyard with the renovated pool, composite decking and an L-shaped outdoor kitchen with sink and grill. Just minutes from Baldwin Park, where you can enjoy the 2.5-mile Lake Baldwin Trail, Lake Baldwin Park with its dog beach, playground and boat ramp, the Cady Way Trail, and the Village Center's restaurants, shops and community events. Schedule your private showing today!

1003 Golfside Drive, Winter Park

$799,999

Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautiful lot located in one of Winter Park’s most desirable neighborhoods. This exceptional location presents the perfect opportunity to build your dream home in one of the most sought after school zones Winter Park has to offer. Set along picturesque brick streets shaded by mature trees, the location is hard to beat. It is within walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. Enjoy the chance to create a home tailored to your lifestyle with a perfect blend of classic Winter Park character, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

$769,000

4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code

Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

$739,777

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

Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friendships feel more like family. This charming enclave of homes is a sanctuary of warmth, connection, and tranquility in a well-established Winter Park neighborhood. At the heart of this exceptional community is a beautifully renovated one-story residence, thoughtfully designed and built by its owners with a modern flair. From the moment you arrive, you are greeted by an elegant neutral palette, charming architectural windows and a beautifully pavered driveway leading to the stately four-pane glass front door. Step inside to soaring ceilings, art niches, elegant and an abundance of natural light that creates a warm and inviting atmosphere. To the right of the entry, the formal living room offers versatility and could easily serve as a home office, library, or additional gathering space. The heart of the home is the extraordinary chef's kitchen, beautifully appointed with custom Dovetail Gray cabinetry, oak cabinetry accented with ebony pulls, stacked white subway tile backsplash, farmhouse sink, wine cooler, state-of-the-art appliance package and a spectacular 10-foot island topped with luxurious white quartzite accented by subtle veining. This stunning kitchen flows effortlessly into the family room, creating an ideal space for everyday living and entertaining. Luxury plank flooring, neutral earth tones, and a dramatic wood-burning fireplace surrounded by natural floor-to-ceiling stone add warmth and character, while the abundance of natural light brings the beauty of the outdoors inside. The primary suite is a private retreat styled in a calming ivory palette, with wood floors, beautifully dressed windows and double doors opening directly to the poolside. The primary bath offers a distinctive custom vanity with a charming wooden treasure-chest design and a luxurious walk-in shower finished with stacked white subway tile, sitting bench and multiple shower heads for the ultimate in comfort and relaxation. Each bedroom is thoughtfully equipped with a California Closet system. Two additional generously sized bedrooms and a beautifully updated shared bath complete the one-story floor plan, offering flexibility for every lifestyle. This home has been lovingly maintained and thoughtfully refreshed, with major systems and improvements recently completed, including Andersen windows in 2024, roof in 2024, renovated baths in 2023, blown attic insulation in 2023, water heater in 2025, pool resurfacing in 2021, new salt system in 2026, and a Trane variable-speed air-conditioning system with UV light purification. The fully fenced PVC backyard provides a private setting surrounded by peaceful wooded views and beautifully landscaped grounds featuring Blue Bamboo, Foxtail trees, flower beds, and decorative river rock. Step outside to your own private backyard retreat, complete with a sparkling saltwater swimming pool and generous space for outdoor entertaining, relaxing, and enjoying the Florida lifestyle. A separate detached office/den adds exceptional versatility, featuring electricity, soundproofing and internet connectivity, making it ideal for a private home office, gym, playroom, studio, or creative space. The European-style pergola is equipped with power for lighting and a unique roof and gutter removal system and was thoughtfully designed for outdoor living space.

4039 Cool Water Court, Winter Park

$700,000

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

This exceptional homesite on Arbor Ridge sits in one of Winter Park's most prestigious and tightly held residential pockets—where elegant estates, mature canopy trees, and enduring property values define the neighborhood. Perfectly positioned, and ready for your vision, the lot places you just two blocks from the Winter Park YMCA and half a mile from highly regarded Lakemont Elementary. The combination of privacy, convenience, and top-tier location ensures a strong demand for a custom residence of distinction. Surrounded by new construction and the graceful shade of established trees, the property offers the ideal canvas for a high-end home that honors the neighborhood’s timeless character while delivering the refined finishes and modern living today’s discerning buyers expect. This is more than a lot—it’s a prime development opportunity in a location that rarely becomes available. Create the legacy residence that belongs here.

1592 Arbor Park Drive, Winter Park

1278 S Pennsylvania Avenue Unit 13, Winter Park

$799,000

3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms, two-and-a-half baths and a thoughtfully designed floor plan that lives like a private home. Bathed in natural light, the interiors are framed by expansive window walls and floor-to-ceiling glass doors that create a bright, airy ambiance throughout. Architectural details including graceful arched passageways, column-lined hallways, and a custom wrought-iron spiral staircase add timeless character and sophistication. Beautifully updated and meticulously maintained, every room reflects a sense of warmth and refinement. The spacious primary retreat is a sanctuary, featuring soaring cathedral ceilings, dual walk-in closets and a spa-inspired bath designed for relaxation. Two additional bedrooms offer versatility for guests, family or a home office. The open-concept living and dining areas are enhanced by travertine and luxury vinyl plank flooring, coffered ceilings, designer lighting, and a beautifully appointed chef’s kitchen complete with solid wood cabinetry, granite countertops, a center island and generous walk-in pantry. French doors open to a freshly painted screened courtyard, creating a private outdoor escape ideal for entertaining or quiet evenings at home. Above, the freshly painted rooftop terrace provides a spectacular setting for alfresco dining, sunset gatherings or simply enjoying Florida’s year-round sunshine. Additional features include a powder bath, plantation shutters, ceiling fans throughout, an oversized two-car garage, and a third-floor walk-in attic offering abundant storage and exciting future expansion possibilities. Residents of Casa Jardin enjoy a beautifully refreshed community, recently enhanced with a new roof, exterior paint and professional landscaping. Ownership also includes exclusive access to Lake Virginia and renowned Winter Park Chain of Lakes through College Point, featuring a private lakefront gathering area along with kayak and paddleboard storage. Ideally near Azalea Lane Recreation Center, the Winter Park Tennis Center, Orange Avenue’s popular restaurants and shops, and top-rated schools, this remarkable residence offers a rare opportunity to enjoy one of Central Florida’s desirable lifestyles.

1278 S Pennsylvania Avenue Unit 13, Winter Park

$745,000

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

Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park

250 Carolina Avenue Unit 205, Winter Park

$739,000

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This beautifully remodeled second-floor corner residence offers the privacy, comfort, and convenience you've been looking for. The thoughtfully updated kitchen features wood cabinetry and granite countertops, while both bathrooms have been tastefully remodeled. Spacious bedrooms, generous storage, and a comfortable flow throughout the home provide plenty of room for everyday living or welcoming guests. Enjoy the simplicity of a well-maintained community with beautifully landscaped grounds, a sparkling swimming pool, and tennis courts. As a corner unit, this residence also offers enhanced privacy and convenient access into and out of the building—perfect for those seeking a low-maintenance lifestyle or an easy lock-and-leave retreat. With Rollins College and Full Sail University nearby and Park Avenue just moments away, this condo puts the best of Winter Park right at your doorstep. Whether you're looking for a full-time residence, a seasonal escape, or simply a home that allows you to spend less time on maintenance and more time enjoying life, Park West offers an exceptional combination of location, comfort, and convenience.

250 Carolina Avenue Unit 205, Winter Park

$770,000

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

Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on a premium corner lot just steps from the clubhouse and resort-style amenities, and is one of the few corner homes in the community permitted to have a private fenced backyard. With more than 2,100 square feet of thoughtfully designed, energy-efficient living space, the home showcases an impressive collection of upgrades and finishes selected to highlight the best Hawk’s Crest has to offer. From the moment you enter, high ceilings and an inviting entryway set the tone. As a former model, the home features upgraded interior doors, cabinetry, baseboards, bathroom vanities, and custom details throughout. The expansive kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, granite countertops, double ovens, a walk-in pantry, stainless steel appliances, and a large center island with pendant lighting overlooking the living and dining spaces. The spacious owner’s suite offers a true retreat with an oversized walk-in closet and en-suite bath featuring dual vanities and a walk-in shower. Three additional bedrooms, two full bathrooms, and a generous laundry room with a utility sink and custom built-in drop zone provide plenty of space, storage, and everyday functionality. Outside, the covered lanai opens to a private fenced backyard surrounded by lush landscaping and complete with a fire pit, an ideal setting for entertaining, pets, or simply enjoying the outdoors. Hawk’s Crest residents enjoy an impressive collection of amenities including a resort-style pool, clubhouse, fitness center, splash pad, playgrounds, dog park, virtual guard gate, and access to Lake Howell. Former model home. Rare fenced corner lot. Extensive upgrades. And one of the shortest walks to the clubhouse in the entire community. This is an opportunity that truly stands apart in Hawk’s Crest.

2286 Marsh Sedge Lane, Winter Park

$799,999

2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows that frame the living spaces. The spacious living room flows seamlessly into a bright, functional kitchen featuring newer appliances and a large window overlooking the front yard. Just off the kitchen, an indoor laundry room adds everyday convenience. A beautiful sunroom overlooks the private, landscaped backyard and offers a versatile space that could easily serve as a home office, reading room, or additional sitting area. Down the hallway, the spacious primary suite features an en-suite bathroom, ample closet space, and abundant natural light with peaceful views of the backyard. The second bedroom is generously sized and includes a walk-in closet. Step outside to discover a true gardener’s paradise. The lush, private backyard features a beautiful paved patio, winding paved pathway, mature landscaping, and plenty of space to relax, entertain, or enjoy the outdoors. The location is hard to beat, walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. The home also offers access to top-rated Orange County schools. Important updates include a complete remodel and added square footage (2009), a newer roof (2022), regularly maintained HVAC system (2020), hot water heater (2024), updated bathrooms (2025), kitchen appliance updates (2026), and a regularly maintained irrigation system. This special home offers the perfect blend of classic Winter Park character, modern updates, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, 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

$759,675

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

Pictures simply do not convey the beauty and feel of true ‘Sanctuary’ in this beautifully and breath-taking renovation! One of the biggest houses in Winter Park Pines and the only house in the community with a full kitchen butler's pantry. Spatially designed and updated for modern family living with separate bedroom wings for privacy, it also features quiet areas for contemplation and large areas for gatherings. It’s a hard choice of which is more impressive, the classic white kitchen with an open 9’x5’ island and 11’ butler's pantry featuring a 2nd sink and additional refrigerator, or the magazine-worthy design of the spacious Primary Bath. You get to choose! The Primary bedroom space (13x22) qualifies as a true retreat. All of this in the beauty of an established neighborhood on a quiet street where you can walk to the Winter Park Pines golf course, or take in many recreational opportunities the area has to offer (Cady Way Trail, Cady Way Pool, sports courts and ball fields galore) as well as a top-ranked hospital and healthcare facilities (Crosby Wellness Center or WP YMCA). Relax, the 2026 renovation has you covered for many years: New Roof, New wiring, New plumbing and water heater. The HVAC was new in 2019. Beautiful floors and fresh paint complete the package that is a rare find in such a fabulous location. Hurry! This one should be at the top of your list.

724 Monmouth Way, Winter Park

$775,000

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

” TURN-KEY,” “PRIVATE POOL,” “NO HOA,” “RENOVATED,” and “POSSIBLE ADU Welcome to this beautifully renovated 4-bedroom, 3-bathroom home where modern updates, exceptional outdoor living, and true pride of ownership come together. Move-in ready and designed for effortless Florida living, this home offers an incredible combination of style, comfort, and flexibility. Engineered wood floorings & tile throughout, no carpets to clean! Everything for a 4.0 Inspection has an updated permit with warranty! A NEW ELECTRIC PANEL(2026), WATER HEATER,(2024) HVAC (2024) all NEW PEX PIPING (Oct 26)& ROOF with transferrable warranty. CUSTOM painted kitchen cabinets with granite countertops & backsplash and numerous additional improvements that make this home truly turn-key. The open, inviting layout flows seamlessly toward the spectacular backyard, where a kitchen pass-through window opens directly to the expansive covered SCREENED (2026) patio, creating the perfect setup for entertaining family and friends. Step outside to your own private resort-style backyard oasis! The freshly RESURFACED swimming pool, CUSTOM beautiful NEW PAVERS with OUTDOOR SHOWER sets the stage for relaxing afternoons and memorable gatherings. A large PERGOLA, generous covered outdoor living space, & LARGE YARD make this backyard the ultimate retreat for enjoying the Florida lifestyle year-round. Great potential for an ADU/guest suite, (subject to zoning and county approval). PRIVATE WELL for irrigation (front yard) & EPOXY garage floor. Location is another standout! Zoned for highly rated schools with Winter Park High just one mile away. Conveniently located near Cady Way Park & trails, Winter Park Pines Golf Course, Rollins College, UCF, and Full Sail University. Enjoy easy access to the dining, shopping, and entertainment of Park Avenue, just approximately 4 miles away.

722 S Ranger Boulevard, 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

$774,900

3 Beds ⋅ 4 Baths ⋅ Virginia Hgts Rep SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

1265 Arlington Pl, Winter Park

$745,000

2 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.

408 Holt Avenue, Winter Park

$799,000

5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

A rare single family home with a HUGE guest house, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park

$725,000

32792 Zip Code

Property currently used as "Doggie Day Care" - zone C-3 Wholesale Commercial. Small building (600 sq ft) at back of property currently not used - could be for storage. Used to be resident. Corner Lot - Forsyth Rd 152 ft and Mills Rd 187 ft.

3377 N Forsyth Road, Winter Park

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