Winter Park Real Estate

Winter Park Real Estate

Welcome to Winter Park, Florida—a charming city that beautifully blends small-town allure with vibrant urban life. Nestled just north of Orlando, Winter Park is renowned for its picturesque tree-lined streets, historic architecture, and an abundance of outdoor recreational opportunities. With its rich cultural scene and a strong sense of community, it’s no wonder that Winter Park is a sought-after destination for both residents and visitors alike.

One of the city’s crown jewels is the stunning Central Park, a lush oasis that invites you to unwind amid its serene landscapes, sparkling lakes, and vibrant gardens. The park is a hub of activity, hosting seasonal events, art shows, and concerts that bring the community together. Just a short stroll away, you can explore the charming boutiques, art galleries, and cafes that dot Park Avenue, making it a perfect spot for a leisurely afternoon.

Winter Park is also home to a number of prestigious educational institutions, including Rollins College, which adds to the city’s intellectual and cultural vibrancy. The city’s commitment to the arts is evident in its numerous museums and galleries, including the Charles Hosmer Morse Museum of American Art, which houses an impressive collection of Tiffany glass.

With its blend of natural beauty, cultural richness, and a welcoming atmosphere, Winter Park is more than just a place to live; it’s a lifestyle. Whether you’re looking to buy your first home, retire in peace, or enjoy an active lifestyle, Winter Park offers a unique and enchanting environment that feels like home. Come discover the magic of Winter Park—your dream home awaits!

Newest Listings in Winter Park

2067 Poinciana Road, Winter Park
$560,000
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code
No need to look further! This move-in-ready 4-bedroom, 2-bathroom home in Winter Woods is ready for you! Enjoy a fenced yard, no rear neighbors, lush greenery, and private country club views. Inside, you are greeted by a modern Scandinavian-inspired kitchen and split-bedroom floor plan. The primary suite offers a bonus room, walk-in closet, and private bath, while three additional bedrooms and a second full bath complete the home. All appliances are included, plus a generator that connects through the electrical panel—an ideal Florida feature during power outages. The owner is open to negotiating other select furnishings throughout the home. Conveniently located near Semoran Boulevard/SR 436, with easy access to Winter Park amenities. Schedule your showing of 2067 Poinciana Road today!

2067 Poinciana Road, Winter Park
510 Fitzwalter Drive, Winter Park
$530,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Looking for your next investment, a renovation project, or the perfect spot to build your dream home? This Brookshire Heights property is full of possibilities. Situated on a 70 x 110 lot in one of the area’s most desirable neighborhoods, this home is ready for its next chapter—and you get to decide what that looks like. Renovate the existing home and make it your own, add it to your investment portfolio, or start fresh and take advantage of the beautiful new construction popping up throughout the neighborhood. The existing home already has several important updates in place, including a new roof in 2019, updated electrical panels and wiring in 2020, HVAC system in 2020, new windows in 2020, and water heater in 2017. The location is just as appealing, with easy access to the Cady Way Trail for biking, walking, and enjoying the outdoors. With a great lot, an established and highly desirable neighborhood, and exciting new construction all around, the opportunity is here. Bring your contractor, your architect, or simply your imagination—this one is ready for its next chapter!

510 Fitzwalter Drive, Winter Park
330 W Morse Boulevard Unit 104, Winter Park
$1,379,000
Winter Park Comm SubDv. ⋅ 32789 Zip Code
An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The interior space is professionally decorated with high end finishes and highly aesthetic. The turnkey floorplan offers open reception/waiting, full kitchen, bathroom, operating and pre-op rooms plus up to five private office spaces. Adjacent Unit 105 (separately listed in MLS) can also be purchased. Reserved parking spaces plus a wealth of street and public parking available nearby.

330 W Morse Boulevard Unit 104, Winter Park
328 W Morse Boulevard Unit 105, Winter Park
$1,420,000
Winter Park Comm SubDv. ⋅ 32789 Zip Code
An excellent and rare opportunity to expand your existing group practice or establish a new high-profile practice in the Winter Park market. Class A medical office space located on the ground floor of the highly desirable Douglas Grand building. This high visibility location fronts a pedestrian sidewalk with tall glass windows just a block from Park Avenue business district. Approved visible signage allowed on front exterior windows and main interior entrance. The turnkey space is professionally decorated with high end finishes and highly aesthetic.Floorplan offers five multi-purpose office, three patient rooms, open reception/waiting, lounge/kitchen area and common restrooms (secure lobby). The adjoining/adjacent unit 104 can be combined with this unit (see separate listing for Unit 104 in MLS) for a total of 3652 hsf. Reserved parking spaces plus a wealth of street and public parking available nearby.

328 W Morse Boulevard Unit 105, Winter Park
3307 Amber Wood Way Unit 106, Winter Park
$169,000
2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 06 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Whether you are looking for a home for yourself, or a great investment, don’t miss this opportunity close to Full Sail, UCF, and Valencia all while being zoned for Winter Park High! The property features 2 bedrooms with en-suite upstairs and a guest half bath downstairs. The unit comes nicely finished with laminate flooring throughout (no carpet!), granite countertops in the kitchen and a private gated back patio with storage! The community features a pool and the HOA covers all exterior maintenance along with the roof!

3307 Amber Wood Way Unit 106, Winter Park
2020 Leanne Court, Winter Park
$479,900
4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 14 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome home to 2020 Leanne Ct, a spacious pool residence offering versatile living and classic Florida charm in Winter Park! According to updated Seminole County tax and public records, this property features 4 bedrooms, 3 full bathrooms, and 2,088 square feet of functional interior living space set on an expansive 0.31-acre lot (13,504 sq ft). Inside, bright common areas feature formal living and dining spaces alongside a open central kitchen with breakfast bar overlooking a cozy family room. The desirable split-bedroom floor plan includes four well-proportioned bedrooms and three full baths, ideal for family accommodations, a primary suite, or dedicated home workspace options. Outside, enjoy a private backyard setting complete with a sparkling swimming pool and garden space—perfect for outdoor entertaining. Conveniently located near top-rated local schools, parks, shopping, and major routes

2020 Leanne Court, Winter Park
304 Santiago Drive, Winter Park
$2,195,000
5 Beds ⋅ 5 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code
Located in the highly desirable Sevilla neighborhood of Winter Park, this exceptional 5-bedroom, 4.5-bath pool home offers over 4,200 square feet of thoughtfully designed living space on a half-acre corner lot. A circular front driveway, oversized 3-car side-entry garage, and abundant parking provide plenty of room for family and guests. Engineered hardwood floors flow throughout the main living areas. The well-designed floor plan features separate living and dining rooms, a spacious family room, dedicated office, downstairs primary suite, and downstairs guest suite. The completely redesigned chef’s kitchen is a true dream featuring a Thermador induction cooktop and vent hood, built-in Miele coffee maker, warming drawer, under-counter microwave, and large center island with pop-up outlet tower. Custom cabinetry includes soft-close drawers and doors, appliance garage, toe-kick drawers, pull-out pantry, under-cabinet lighting, and built-in wine refrigerator. Open to the family room, the kitchen overlooks a stunning stone fireplace wall with abundant natural light and remote-controlled window shades. The dining room features a stylish wet bar with Quartzite countertops, soft-close cabinetry, under-cabinet lighting, and drawer bottle dividers. The separate living room provides direct access to the outdoor living area. The spacious downstairs primary suite includes a sitting area w/outdoor access and a spa-inspired bath w/dual granite-topped vanities, jetted spa tub, glass-enclosed shower with dual shower heads, two walk-in closets, and an additional wall closet. A private downstairs guest suite with full bath featuring Quartzite countertops offers comfortable accommodations for guests or extended family. The dedicated front-facing office provides an ideal work-from-home space. Upstairs, two generously sized guest bedrooms share a Jack-and-Jill bath, while a large bonus room w/ full bath and abundant storage offers flexibility as a 5th bedroom, media room, playroom, or gym. All upstairs bathrooms have been updated with Quartzite countertops, painted cabinetry, and resurfaced tubs. The outdoor living spaces are designed for entertaining and everyday enjoyment. The covered patio features large ceiling fans and direct access to a convenient half bath. An outdoor kitchen includes Quartz countertops, beverage refrigerator and sink, plus wiring for TV and stereo. The propane-heated pool and spa were renovated in 2024 and feature LED lighting, brick pavers, and a black aluminum fence. A propane hookup is in place for a future grill or outdoor fireplace. Storage is abundant, including custom closets in all bedrooms, a full standing-height attic spanning the length above the 3-car garage, and additional second-floor attic access. Recent improvements include a 2017 roof w/gutter guards and transferable warranty, upstairs A/C replaced in 2023, and exterior paint completed in 2022. The half-acre corner lot provides plenty of room to roam with a tree-fort play deck, spacious side yard, and expansive driveway. Zoned for coveted Audubon K-8 and Winter Park High School, this home is also conveniently located within a short walk or bike ride of Park Avenue, Mead Gardens, Rollins College, SunRail, the Winter Park Farmers’ Market, shopping, and dining. With its exceptional floor plan, lovely outdoor living space, abundant storage, and fantastic Winter Park location, this home is designed for comfortable family living and effortless entertaining. Welcome home!

304 Santiago Drive, Winter Park
518 Gilbert Road, Winter Park
$649,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to 518 Gilbert Road, a beautifully updated 3-bedroom, 2-bath pool home offering 1,573 square feet of single-story living in the desirable Winter Park Pines neighborhood - with no HOA. Freshly installed front yard sod and mulch, mature palms, and distinctive stone accents create an inviting first impression. Inside, the home is light and bright with original terrazzo flooring and spacious living and dining areas. The living room features a wood-burning fireplace and architectural ceiling detail that adds character to the space. The beautifully updated kitchen offers white cabinetry, granite countertops, stainless steel appliances, a gas cooktop, convection oven, subway tile backsplash, modern lighting, and a large peninsula with bar seating. Both bathrooms have been renovated, including the primary bath with a walk-in shower and an updated guest/pool bath with convenient direct access to the backyard. Step outside to a private screened pool and an expansive pool deck, recently resurfaced in May 2026, providing plenty of room for outdoor dining, entertaining, and relaxing. Fully paid solar pool-heating panels extend the enjoyment of the pool, while the fully fenced PVC backyard adds privacy. A spacious two-car garage and outdoor storage provide additional room for everyday needs. Additional improvements include updated windows and sliding doors, replumbing, a newer HVAC system with gas/propane furnace, gas line, and partial updated ductwork. Enjoy an exceptional Winter Park location close to Cady Way Trail, Winter Park Pines Golf Club, Cady Way Park and its recreational amenities, Baldwin Park, and Downtown Winter Park. AdventHealth Winter Park, Rollins College, Full Sail University, UCF, shopping, dining, and everyday conveniences are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School, this move-in-ready pool home combines classic Winter Park character, thoughtful updates, and an outstanding location.

518 Gilbert Road, Winter Park
4910 Seminole Avenue, Winter Park
$329,900
3 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code
Welcome! This centrally located 3-bedroom, 2-bathroom home provides quick access to major roadways and highways, putting you minutes from shopping, dining, and essential services while maintaining easy connections to Orlando's key destinations. The home includes a brand-new water heater, a 2024 HVAC system, and a metal roof, ensuring peace of mind for years to come. Inside, features a split bedroom plan that separates the primary suite from the guest bedrooms, offering privacy and flexibility. Laminate flooring flows through the main living room, primary bedroom, and guest bedrooms, while tile covers the kitchen, laundry room, and bathrooms for durability and easy maintenance. A screened lanai extends the living space outdoors, providing a comfortable retreat year-round, while the fenced backyard and open patio create additional outdoor options for relaxation or entertaining in a private space. Beyond the home itself, the impeccable location connects you to everything that matters. Park Avenue Shopping and the local Farmers Market are nearby, while Costco, Target, Walmart, and Sam's Club provide convenient shopping access. Multiple restaurants and shopping plazas are around the corner for quick dining options and daily needs. Medical services and hospitals are close by, providing ample options when needed. Kraft Azalea Garden, Lake Baldwin Park, multiple museums, and the Winter Park Golf Club, along with the Winter Park Pines Golf Club, offer recreation and natural beauty right at your fingertips. Full Sail University and grade schools are also nearby. The property delivers a 15-minute drive to Orlando International Airport and Downtown Orlando, making commuting and travel straightforward. This combination of a practical interior design, cozy backyard, and strategic location provides everything you need right in the heart of Central Florida. Schedule your private showing today and experience the convenience and lifestyle this property has to offer firsthand.

4910 Seminole Avenue, Winter Park
2613 Lafayette Avenue, Winter Park
$1,699,900
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Under Construction. Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringing warm contemporary design and effortless living to Winter Park. Offering 2,661 square feet, four bedrooms, three-and-a-half baths and a two-car garage, the home pairs a refined architectural presence with light-filled interiors and a highly considered floor plan. At the heart of the home, an expansive open-concept living space brings together the kitchen, dining and family areas for an easy sense of connection. The designer kitchen makes a statement with an oversized island, extensive cabinetry, integrated appliances and sophisticated finishes, while large windows and glass doors invite natural light throughout the main living areas. A first-floor guest suite offers added flexibility for visitors, a private office or multigenerational living. Upstairs, the primary suite is joined by two additional bedrooms, creating a comfortable separation between everyday living and private spaces. The primary retreat features a generous walk-in closet and a spa-inspired bath designed with a soaking tub, dual vanities and an oversized shower. Outside, the covered lanai extends the living space into the backyard, overlooking a private pool and landscaped surroundings, an inviting setting for relaxed afternoons, entertaining and year-round Florida living. With its soft neutral palette, natural textures, modern detailing and thoughtfully connected spaces, 2613 Lafayette Avenue offers a fresh take on new construction in Winter Park, sophisticated without feeling overly formal and designed for the way people live today. Ideally situated near the area’s dining, shopping, parks and everyday conveniences, the residence pairs the ease of new construction with the lifestyle and sense of place that make Winter Park so desirable.

2613 Lafayette Avenue, Winter Park
112 Bell Place, Winter Park
$575,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
Welcome to 112 Bell Place, a spacious 3-bedroom, 2-bath home offering 2,253 square feet in an established Winter Park neighborhood. Tucked away on a quiet cul-de-sac with a large lot and minimal through traffic, this home offers a great opportunity for buyers looking to move right in and make updates over time, or for an investor looking for a property with great bones and plenty of potential. Inside, you’ll find generous living spaces including a living room with laminate wood flooring and vaulted ceiling, plus a large family room featuring a brick accent wall. The kitchen offers solid wood cabinetry, cooktop, oven and microwave with plenty of opportunity to update and make it your own. All three bedrooms feature built-in closets, while the primary suite includes wood-look laminate flooring and a private bath with shower. The guest bath offers a tub and tile flooring. Additional features include a one-car garage, exterior laundry area, and a hall closet already plumbed for a washer and dryer should the new owner prefer to bring the laundry indoors. With its spacious floor plan, large lot and solid foundation for future improvements, this home has so much potential. Conveniently located in Winter Park and currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School, this is a great opportunity to get into a sought-after area and add your own style over time. Move in now, renovate at your own pace, and make this Winter Park home your own! Buyer to independently verify school zoning.

112 Bell Place, Winter Park
2322 Woodcrest Drive, Winter Park
$675,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, Winter Park
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