Winter Park Homes for Sale

Winter Park Homes for Sale

Welcome to Winter Park, Florida – a charming city that beautifully blends the allure of old-world elegance with modern sophistication. Nestled just north of Orlando, Winter Park is renowned for its picturesque landscapes, vibrant arts scene, and rich history. With its tree-lined streets, stunning lakes, and historic architecture, this city offers a serene yet lively atmosphere that attracts residents and visitors alike.

Winter Park boasts an impressive array of cultural attractions, including the renowned Charles Hosmer Morse Museum of American Art, home to the world’s most comprehensive collection of Tiffany glass. Stroll through the enchanting Park Avenue, lined with boutique shops, gourmet eateries, and delightful cafes, or take a scenic boat tour through the city’s charming chain of lakes. With an abundance of parks and recreational facilities, there’s no shortage of outdoor activities to enjoy, from picnicking in Central Park to cycling along the scenic trails.

For those looking to call Winter Park home, you’ll find an exceptional selection of homes for sale. From elegant historic residences to contemporary masterpieces, the real estate market here caters to a diverse range of tastes and budgets. Whether you’re seeking a cozy bungalow or a sprawling estate, Winter Park offers properties that reflect the city’s unique charm and character.

Experience the best of Florida living in Winter Park, where you can enjoy a vibrant community, top-rated schools, and an array of cultural experiences. Your dream home awaits in this enchanting city!

Newest Winter Park Homes for Sale

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

Charming 4-bedroom, 2-bath single-story home in the established Eastbrook neighborhood of Winter Park. Built in 1959 and situated on a 0.19-acre lot, this home features an open living and kitchen area with vaulted ceilings and wood-look laminate flooring. The kitchen offers stainless steel range and microwave, tile countertops, and tile backsplash. All bedrooms feature carpet and ceiling fans, with the primary suite offering an en-suite bath with a walk-in tiled shower. Enjoy the covered back patio and fully fenced backyard. Roof is approximately 5 years old. Interior laundry closet. Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High.

3484 Seagrape Drive, Winter Park

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

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Tanglewood Rep SubDv. ⋅ 32792 Zip Code

FABULOUS WINTER PARK LOCATION!!! This 3 BEDROOM, 2 BATH, 1873sf CONCRETE BLOCK HOME represents QUALITY FROM THE PAST, and is CENTRALLY LOCATED in the heart of Winter Park. You can walk to the Winter Park YMCA or Interlachen Golf and Country Club, while the exclusive shoppes and restaurants on Winter Park’s famed “Park Avenue” are just 5 minutes away as well as Central Park, Rollins College, and Advent Health’s Winter Park Hospital. Nestled among several “million-dollar homes” and just two houses away from the gated “Reserve at Interlachen” community, this property has high potential! From the moment you enter, you will notice pride of ownership in the classic décor and cleanliness. The Kitchen features two breakfast bars, one of which is a pass-thru to the living room, along with copious (25) light birch cabinetry with roll out shelving and undermount lighting. The 19’ by 12’ Kitchen opens to a 10’x12’ Dinette area which opens to the living room. There is also a separate and formal 11’x12’ Dining Room. The expansive 31’x18’ Living Room features a dramatic wood-burning fireplace with a mantle and hearth encased in a beautiful brick accent wall which also houses built-in shelving and cabinetry. Sky lights serve to bring in an abundance of natural light. The Primary Bedroom is En Suite. The Guest Bathroom has been renovated with granite counters, decorative inset tile in the tub area, and updated fixtures. Additional features of this home include an attic fan, recently replaced hurricane rated garage door and opener, newer exterior electrical box (interior electrical box will be replaced prior to closing), a 10’x20’ screened porch, a .22-acre lot with a fully fenced back yard and single gate access on each side of the home. The entire house has been re-piped, and the roof is less than 8 years old. Don’t miss this opportunity to live in the heart of Winter Park! Call us today for your private showing!

1818 Dover Road, Winter Park

4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, Winter Park

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

FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. Major updates include a NEW ROOF (2021), FULL HOUSE REPIPE (2025), and NEW FLOORING (2025), giving buyers peace of mind on several important big-ticket items. Situated on an OVERSIZED 0.24-ACRE LOT with NO HOA, the property offers a spacious yard with plenty of room to enjoy the outdoors. Inside, the home features a comfortable and functional layout with an eat-in kitchen, indoor laundry, and inviting living spaces. Even better, the home is being sold FULLY FURNISHED, making it an easy option for a primary residence, second home, or investment property. The location is hard to beat, with convenient access to Full Sail University, Rollins College, UCF, Park Avenue, Baldwin Park, shopping, dining, and major roadways connecting you throughout Central Florida. With NO HOA and short-term rental potential, this property provides flexibility that can be difficult to find in Winter Park. Whether you're looking for a place to call home or an investment opportunity, 5080 Seminole Ave is ready for its next chapter!

5080 Seminole Avenue, Winter Park

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring, and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021, and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020, and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024.Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing, and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional—conveniently situated in a wonderful community with Cady Way pool and Cady Way trail which spans 7.2 miles and connects to the Seminole trail for bike riding, running and walking. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas, and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Timeless elegance meets effortless modern living in this exceptional 5 bedroom, 5.5 bath residence In Park Grove, one of Winter Parks most coveted neighborhoods. Designed for gracious living and sophisticated entertaining, the home features formal living and dining spaces alongside an expansive open-concept family room and gourmet kitchen. The first floor offers a serene primary suite, private guest suite, and a dedicated office, while the second level provides three generously sized guest suites, a versatile bonus room and a second laundry room. Retractable accordion doors extend the living space outdoors, creating a seamless connection between the sophisticated interiors and outdoor living areas. Outside you will find retractable screens along the porch area along with a putting green conveniently located beside the pool. Rich hardwood floors, custom trim and molding, and exceptional interior finishes add warmth and refinement throughout. The gourmet kitchen is beautifully appointed with solid wood cabinetry, quartz countertops, and premium appliances. Ideally situated in Park Grove, this distinguished residence offers the rare combination of privacy, luxury, and walkability, just moments from Park Avenue, the Winter Park Village, and the Winter Park Golf course.

662 Granville Drive, Winter Park

3 Beds ⋅ 1 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer’s dream—opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.

1421 Chestnut Avenue, Winter Park

5 Beds ⋅ 7 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. PRE-CONSTRUCTION: Introducing an exceptional new construction residence by Nautilus Homes, ideally positioned in the heart of Winter Park near Lake Osceola, with convenient side access from Via Bella. This remarkable five-bedroom, full bath and two half bath residence brings together Organic Modern architecture with Contemporary West influences, combining clean architectural lines with natural stone, warm wood elements, expansive glass, and organic textures throughout. Step through the entrance into a dramatic grand foyer, where expansive glass and architectural floating stairs immediately introduce the home's modern design. Natural materials and thoughtfully selected organic elements transition seamlessly from the exterior into the interior, creating warmth and continuity throughout the residence. Beyond the foyer, the home opens into an impressive great room, where expansive glass fills the space with natural light and creates a strong connection to the outdoor living areas. A sleek linear electric fireplace serves as an architectural focal point, complementing the clean lines and warm organic materials found throughout the home. At the heart of the residence is a thoughtfully designed chef's kitchen featuring top-of-the-line appliances sub Zero and Wolf and a dramatic double-island configuration, providing exceptional space for preparation, casual dining, and entertaining. Just beyond the kitchen, a thoughtfully designed combination mudroom and pantry provides additional storage and everyday functionality while maintaining the home's clean, luxurious aesthetic. An impressive wine storage wall adds another distinctive element to the main entertaining spaces. The primary suite is designed as a private retreat, complete with the added convenience of a dedicated laundry room positioned just off the primary suite. An extensive architectural lighting package and integrated smart-home technology further enhance the home's combination of luxury, functionality, and modern living. A dedicated entertainment room provides an additional space for gathering and relaxing, while the second floor offers additional bedroom accommodations and a versatile bonus room, ideal for a media lounge, game room, home office, or secondary entertainment space. The home's indoor living spaces transition naturally to one of its signature features—an impressive 42-foot-long lanai designed for year-round Florida living. Anchored by a gas fireplace, this expansive covered outdoor space creates an exceptional setting for entertaining, dining with automatic drop screens for relaxing while extending the home's Organic Modern design into the outdoors. Completing the residence with a perfect size pool/spa with ample yard space. A three-car garage configuration, including a separate detached one car garage. Depending on final dimensions and equipment specifications, the detached one-car garage may potentially accommodate a vehicle lift for additional automobile storage, creating an attractive feature for the automotive enthusiast or collector. Winter Park is renowned for its upscale retail, high-end dining, and vibrant culinary community, offering an exceptional blend of luxury and lifestyle. Just minutes away, enjoy the boutiques, restaurants, cafés, and charm of Park Avenue, along with convenient access to two nearby golf courses, making this an ideal location for experiencing the best of Winter Park living.

1166 Palmer Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code

Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.

2215 Woodcrest Drive, Winter Park

4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code

LOCATION! LOCATION! Winter Park property located in Seminole County. Proximity to Rollins, Full Sail, UCF, and Valencia colleges. Great income producer, with "Flex Space" as a two income rental or live on one side and rent the other. Main area has 3 bedrooms and 2 full baths, flex space has a private entrance, 1 bedroom and full bath, kitchenette, and it's own laundry area. Two driveways and parking pad for your use. Great side and separate rear yard, with lard storage shed, Home was recnently updated, with fresh paint, granite countertops, shaker cabinets, updated bathrooms, new windows, new mini-splits in flex space and tankless water heater. Fully fenced in backyard and mature trees. Plumbing has already been updated to PEX, cast iron wasteline has been updated to PVC. New flooring in main house, new baseboards installed, and freshly painted. MOVE IN READY!

1386 Clematis Lane, Winter Park

3 Beds ⋅ 3 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code

Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating inviting spaces for entertaining, casual gatherings, or simply relaxing with family. The kitchen serves as a natural gathering point, featuring white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a convenient coffee/wine bar, and a breakfast bar with seating for four. Whether hosting friends for dinner or enjoying a quiet morning together, the layout offers space for every occasion. The primary suite, thoughtfully added in 2017, is a private retreat designed for both comfort and relaxation. A dedicated sitting room or office provides additional flexibility, while the spacious walk-in closet offers abundant storage. The expansive ensuite bathroom delivers a true spa-like experience, featuring a large tiled shower with multiple shower heads and a frameless glass enclosure, creating a luxurious place to unwind at the end of the day. A dual vanity with elegant marble countertops and a separate water closet complete this serene retreat. A secondary bedroom with its own ensuite bathroom provides additional comfort and privacy for guests or family members. All bathrooms have been updated, and the bedrooms feature brand-new carpet, while recessed lighting and ceiling fans throughout add to the home's comfort. Step outside to enjoy the privacy of the fully fenced backyard, with fencing replaced in 2025, a brand-new deck, and beautiful new landscaping. The outdoor space offers another inviting setting for relaxing, entertaining, or enjoying Florida's year-round lifestyle. Beyond the home, the location places you just steps from Brookshire Elementary and close to the Cady Way pool, playground, beach volleyball, tennis and pickleball courts, Cady Way Trail, and Winter Park Pines Golf Course. You'll also enjoy convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. With its welcoming entry, versatile living spaces, spa-inspired primary retreat, private setting, and exceptional Winter Park location, this home offers an ideal backdrop for gathering, relaxing, and making memories with family and friends. ROOF(S) - Main - 2022, Family Room - 2019, Primary Suite - 2017 HVAC - 2021 MINI-SPLIT - 2026

2345 Brookshire Avenue, Winter Park

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