Winter Park Homes for Sale

Winter Park Homes for Sale

Welcome to Winter Park, Florida – a picturesque city that seamlessly blends charm, culture, and a vibrant community spirit. Nestled just north of Orlando, Winter Park is renowned for its stunning tree-lined streets, historic architecture, and a rich tapestry of art and outdoor activities. With its serene lakes, beautiful parks, and a thriving downtown area, Winter Park offers residents a lifestyle that is both relaxed and invigorating.

As you explore Winter Park, you’ll discover a delightful mix of boutique shops, gourmet restaurants, and cultural landmarks, including the renowned Charles Hosmer Morse Museum of American Art, home to an impressive collection of Tiffany glass. The city's commitment to preserving its lush landscapes and historical sites adds to its allure, making it an ideal place to call home.

For those considering a move to this enchanting city, there are numerous homes for sale that cater to a variety of tastes and budgets. From charming bungalows with vintage character to modern estates with all the latest amenities, Winter Park's real estate market is as diverse as its community. Whether you’re seeking a cozy family home or a luxurious retreat, you’ll find properties that feature spacious layouts, beautiful gardens, and easy access to the city’s best attractions.

Living in Winter Park means enjoying a vibrant community filled with events, festivals, and a strong sense of belonging. With its prime location, stunning homes, and a lifestyle that celebrates both relaxation and activity, Winter Park is not just a place to live – it’s a place to thrive. Come discover your dream home in this enchanting Florida gem!

Newest Winter Park Homes for Sale

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

PHENOMENAL DEAL, newer updates INCLUDE: beautifully renovated 4-bedroom, 2-bathroom, two car garage home that perfectly blends modern design with everyday comfort. From the moment you step inside, you’ll appreciate the open-concept floor plan, thoughtfully designed to create a bright, spacious atmosphere that’s perfect for both entertaining and daily living. This move-in-ready home features custom finishes throughout, including stylish fixtures, updated flooring, and a beautifully remodeled kitchen and living space. The expansive primary suite offers a private retreat with a generous bedroom and a stunning ensuite bathroom designed with comfort and luxury in mind. Additional updates include newer roof, AC, water heater, Updated kitchen and bathrooms, The Kitchen is Large with all major appliances: Fridge, Stove, and Dishwasher. You don't want to miss this opportunity to make this house your home!

7786 Fox Knoll Place, Winter Park

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

5 Beds ⋅ 4 Baths ⋅ Sharon Place SubDv. ⋅ 32789 Zip Code

Tucked away near the end of a peaceful cul-de-sac, 1225 Sharon Place offers space, privacy, and a location that's hard to beat, just two blocks from the Winter Park Racquet Club. This single-story home sits on nearly 16,000 square feet of land and has 5 bedrooms, 3 full bathrooms, and a half bath. The split floor plan puts the primary suite on its own side of the house, away from the other bedrooms, so everyone gets more privacy. Two-zone air conditioning keeps each area comfortable and helps with efficiency. The large covered patio overlooks the screened pool enclosure. It's a natural place to dine outdoors, host friends, or relax in the shade year-round. A two-car garage adds storage and convenience. The same owners have loved this home for 30 years, and it's the first time it's been on the market in decades. Homes this close to the Racquet Club with this much land don't come up often. Schedule your showing today.

1225 Sharon Place, Winter Park

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park

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

Set on a quarter-acre lot on a tree-lined street in Winter Park Pines, this 5-bedroom, 3-bath pool home offers 2,194 sq ft of single-story living with room for everyone. The split floor plan places a spacious primary suite on its own side of the home, with a walk-in closet and French doors that open directly to the covered patio. The four guest bedrooms are generously sized, and one pair shares a Jack-and-Jill bath. The kitchen has a breakfast bar, a pantry, and views of the pool. It opens to a family room anchored by a wood-burning fireplace and a built-in desk. The formal living and dining rooms, crown molding, and three sets of French doors bring in natural light and a connection to the outdoors. Outside, the large covered, insulated patio overlooks a sparkling pool and a fenced backyard with real yard space. There is no mandatory HOA, and the oversized 2-car garage includes workshop space. You're minutes from Winter Park Pines Golf Club, Aloma Ave shopping, and Park Avenue. Zoned for Winter Park High.

739 Roughbeard Road, Winter Park

3 Beds ⋅ 2 Baths ⋅ Metzingers Add SubDv. ⋅ 32789 Zip Code

Welcome to 1211 Schultz Avenue—a charming 3-bedroom, 2-bath bungalow offering an opportunity to enjoy the Winter Park lifestyle in highly sought-after 32789 for under $500,000. Full of character and warmth, this inviting home features beautiful hardwood floors throughout and a stylish kitchen with butcher block countertops, subway tile backsplash, a combination of cabinetry and open shelving, and plenty of personality. The functional layout includes three bedrooms, two full bathrooms, and an updated laundry room with additional shelving and storagev via loft. A 2019 roof adds to the home's appeal, while the cozy bungalow style makes this one feel like home from the moment you arrive. Adding even more value, the home's solar panel system, installed in Nov 2022, will be paid in full by the seller at closing, allowing you to enjoy the benefits of solar without assuming a solar loan! The location is where 1211 Schultz really shines. Enjoy a truly walkable lifestyle with Foxtail Coffee, Buttermilk Bakery, Publix, dining, shopping, and everyday conveniences just minutes from your front door. Park Avenue and everything Downtown Winter Park has to offer are also just a short drive or bike ride away. If you've been waiting for an adorable 3/2 in 32789 that combines character, convenience, and one of Central Florida's most desirable locations—all at a price point under $500K—this is one you'll want to see.

1211 Schultz Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Winter Park Estates Sec 5 SubDv. ⋅ 32792 Zip Code

Welcome home to this charming Winter Park residence located in the desirable 32792 zip code. Nestled on a quiet street at 2818 Ambergate Road, this inviting property offers the perfect blend of comfort, style, and everyday convenience. Step inside to discover a bright, open floor plan featuring original Terrazzo, generous living spaces, natural light, and a warm atmosphere ideal for both relaxing and entertaining. Newer roof 2023. The private backyard provides a wonderful outdoor oasis for weekend gatherings or peaceful morning coffee. Situated just minutes from top-rated schools, local parks, bustling shopping centers, and vibrant downtown Winter Park, this move-in-ready home puts the best of Central Florida right at your doorstep. Don't miss this exceptional opportunity - Schedule your private showing today!

2818 Ambergate Road, Winter Park

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

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts, this Louisiana-inspired 4-bedroom, 4-bath home pairs classic double-gallery porches with 3,479 sq ft of open, light-filled living in Winter Park's established Charmont neighborhood. Inside, rich hardwood floors, tray ceilings, crown molding and walls of French doors set the tone. The formal living and dining rooms open to a spacious great room and a chef's kitchen with an oversized granite island seating six, statement pendant lighting, stainless steel appliances, double wall ovens, abundant cabinetry, a walk-in pantry and a separate coffee/beverage bar with wine fridge. The main-level primary suite is a true retreat with a tray ceiling, French doors to the covered lanai, a custom walk-in closet and a spa bath with a freestanding soaking tub, dual vanities and a frameless glass shower. Upstairs, a large loft offers flexible space for a media room, gym or home office, with French doors to the second-story porch, along with generously sized secondary bedrooms. Step outside to your private backyard oasis: a covered lanai with outdoor kitchen, bar seating and ceiling fans overlooks the paver pool deck, sparkling pool with raised spa and fire bowls, all framed by mature landscaping and privacy fencing. Additional highlights include a laundry room with sink and cabinetry, a two-car garage and a paver driveway. Just half a mile from Audubon Park K-8, with Lake Baldwin Park, Mead Botanical Garden, East End Market, Baldwin Park Village and downtown Winter Park's shops and restaurants all close by, and about 4 miles to downtown Orlando.

1951 Winter Park Road, Winter Park

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

Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-square-foot homesite in the fast growing Kenilworth Shores neighborhood. Striking curb appeal introduces the home, while a marble mosaic foyer provides an elegant first impression and leads into the expansive great room. At the center of the living space is a dramatic custom entertainment wall featuring illuminated built-in shelving and a sleek electric fireplace. The adjoining dining room is equally impressive, complete with an oversized dry bar, wine refrigerator, and glass-front cabinetry, creating the perfect setting for hosting family and friends. The designer kitchen makes a statement with Taj Mahal countertops, a marble mosaic backsplash, custom cabinetry, and a full suite of Thermador appliances, including a paneled built-in refrigerator. A massive butler’s pantry extends the kitchen’s functionality with abundant storage and preparation space, a second microwave and oven, and an additional dishwasher, making entertaining effortless. The downstairs primary suite offers a private retreat accented by warm wood beams and separate his-and-hers closets. Its jaw-dropping spa-inspired bathroom is wrapped in 12-by-24-inch marble tile and features dual vanities, a freestanding soaking tub, and an oversized walk-in shower with LED-illuminated niches. A dedicated home office is also located on the main level, providing a quiet and refined space for working from home. Upstairs, a massive bonus room creates a flexible second living area ideal for movie nights, a game room, or a children’s retreat. Four additional spacious bedrooms offer comfort and privacy for family and guests, while an upper-level balcony provides another inviting place to unwind. The outdoor living spaces are designed to take full advantage of the oversized lot. A large covered lanai with a complete summer kitchen overlooks the resort-style pool and spa, all framed by an elegant marble deck. Beyond the pool, the expansive backyard offers valuable green space for recreation, entertaining, or relaxation. Additional highlights include a complete impact-rated window and door package for added efficiency and peace of mind. Perfectly positioned near Cady Way Park, AdventHealth Winter Park, and just a golf-cart ride from Park Avenue, this extraordinary new residence presents a rare opportunity to experience uncompromising luxury, exceptional space, and the very best of the Winter Park lifestyle.

532 Langholm Drive, Winter Park

4 Beds ⋅ 4 Baths ⋅ Parklando 03 SubDv. ⋅ 32789 Zip Code

PRICED BELOW APPRAISED VALUE | FULLY REMODELED WINTER PARK POOL HOME Pre-approval or proof of funds required in advance of showing. A rare opportunity to own more than 3,300 square feet of fully remodeled living space in Winter Park’s 32789 zip code, zoned for the highly sought-after Audubon Park School K–8 and Winter Park High School; all at a price below appraised value. Welcome to 2614 Parkland Drive, a completely reimagined luxury residence where sophisticated interiors meet resort-style Florida living. Extensively remodeled in late 2022 and topped with a brand-new architectural barrel tile roof, this home combines timeless character with modern finishes and major system upgrades. Inside, solid light-oak flooring, custom railings, and an open-concept layout create a warm, elevated feel throughout. The chef’s kitchen anchors the main living space with quartz countertops, full-height designer tile, abundant cabinetry, and a layout designed equally well for entertaining and everyday living. Step outside and the home transforms into a private resort. The custom heated pool and spa are finished in striking Caribbean-blue tile and surrounded by dramatic waterfalls, dual natural-gas fire features, porcelain privacy walls, and a built-in grill—creating an exceptional setting for entertaining or unwinding at home. The first-floor primary suite opens directly to the outdoor oasis. Upstairs, three oversized bedrooms are joined by a spacious loft and private patio; offering flexible space for family, guests, an office, or additional entertaining. Additional features include a brand-new barrel tile roof, dual tankless water heaters, central vacuum, natural-gas appliances, and extensive updates throughout. With more than 3,300 SF, a luxury pool and spa, extensive renovations, highly desirable school zoning, and a 32789 address, this home represents an exceptional opportunity in the Winter Park market. Luxury. Location. Lifestyle. And priced below appraised value.

2614 Parkland Drive, Winter Park

3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code

Welcome! This three-bedroom, two-bathroom home in Winter Park presents a genuine opportunity for buyers ready to reimagine this one-story residence. The open floor plan creates a flexible living space, and the thoughtful layout gives you a solid foundation to work with. Inside, the cathedral ceiling in the main living area draws the eye upward and enhances the sense of openness throughout the home. The covered rear lanai extends your entertaining and living space outdoors, perfect for relaxation or gatherings. The location delivers great convenience, with proximity to Publix-anchored shopping and Walmart for everyday needs, Red Bug Lake for outdoor recreation activities, grade schools, and the Winter Park Village for shopping and dining. Schools are nearby, making this neighborhood accessible for residents. The central location means you're less than 30 minutes from Orlando International Airport, Universal, Downtown Orlando, and UCF, offering both lifestyle flexibility and strong rental demand drivers for those considering income-producing use. Convenient access to major roadways makes commuting and daily needs straightforward. Schedule your private showing today and bring your vision for what this home can become.

7348 Grand Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Sanctuary At Aloma SubDv. ⋅ 32792 Zip Code

POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, a dedicated den/flex/home office, and a separate formal dining room, all on one level with no stairs. The open-concept great room flows into a light-filled kitchen featuring a large center island, stone countertops, a sleek backsplash, and abundant cabinetry, perfect for entertaining. The private primary suite is a true retreat with a separate soaking tub and shower plus plenty of storage. Secondary bedrooms are well sized with great closet space. Step outside to your screen-enclosed in-ground pool, added in 2020, with a covered sitting area and a fully fenced, beautifully landscaped backyard, privacy rarely found at this price point. Additional features include tile and laminate flooring, an owned security system, an attached 2-car garage, public water and sewer, and excellent curb appeal with stucco exterior and carriage-style garage door. Low quarterly HOA and NO CDD. Minutes from SR-417 at Aloma Ave, placing UCF, Research Park, Oviedo, and downtown Orlando within an easy commute. Close to Winter Park Village, historic Park Avenue, Full Sail, Rollins College, and Orlando International Airport. All information deemed reliable but not guaranteed; buyer and buyer's agent to verify all measurements and features. Schedule your private showing today!

5303 Pine Lily Circle, Winter Park

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