Homes for Sale in Winter Park

Under contract-accepting backup offers. Nestled in upscale Winter Park, this studio apartment offers an updated kitchen, flooring, and beautiful floor to ceiling windows in the sun room overlooking the luscious garden and resort style community pool. This studio is located in the Winter Park Gardens Condominiums, a 55+ community and is just steps away from any number of spectacular places where to wine and dine or go shopping. From your front balcony you can hear the crack of tennis racquets as the ball is lobbied back and forth, or if you choose, take the stairs (or elevator) and join the game yourself. Come take a look, you'll never want to leave!

Under contract-accepting backup offers. Stunning Winter Park modern home on the tree streets.

Step into this captivating 3-bedroom, 2-bathroom second-floor end unit, nestled in a beatiful community. Spanning 1,117 square feet, this nicely upgraded home seamlessly blends style and comfort. Modern Upgrades: Enjoy a beautifully remodeled kitchen and bathrooms, featuring sleek finishes and high-quality materials. Open Concept Living: The spacious living and dining areas are perfect for entertaining, bathed in abundant natural light that creates a warm, inviting atmosphere. Privacy & Views: As an end unit, you’ll relish added privacy and tranquil creek views from your windows, offering a peaceful retreat. Community Amenities: Take advantage of the pool and delightful playground, ideal for families and relaxation. Convenient Location: Situated in a well-maintained two-story development, you’ll have easy access to shopping, dining, and top-grade schools, plus proximity to Full Sail University, the University of Central Florida, and Valencia Community College and much more Don’t miss this exceptional opportunity to own a stunning, move-in-ready condo in one of Winter Park’s most desirable communities. Schedule a showing today and make this enchanting space your new home!

Great place to call home; live, work and study close to everything imaginable in one of the best areas of Winter Park next to Full Sail University. Completely renovated unit with brand new appliances and as well as granite counter tops and porcelain floors throughout. Enjoy everything life has to offer close to Publix, Costco and myriad restaurants and shops near downtown Orlando. Only 20 minute drive to Orlando International Airport with no turns on the way there. Easy access to major highways. Hurry today for this won't be in the market for long.

Discover an exceptional opportunity with this one-of-a-kind townhome that includes a private boat slip! Nestled in the picturesque Winter Park, Florida, this brand-new home boasts breathtaking views of Lake Killarney and offers a perfect blend of luxury and comfort. With 3 bedrooms and 3.5 baths spread across over 2,300 sq ft, you'll be greeted by a grand 17-foot foyer that leads into an expansive great room featuring soaring 11-foot ceilings. The floor-to-ceiling windows flood the space with natural light while framing stunning lake and nature views, creating an inviting atmosphere perfect for both entertaining and everyday living. The gourmet kitchen is a chef's dream, equipped with top-of-the-line Wolf and Subzero appliances, elegant double-stacked soft-close cabinetry, and designer lighting. Enjoy the convenience of a spacious walk-in pantry and motorized window shades. Step outside to the unique rear lanai, where you can savor serene lake vistas or stroll along the community sidewalk that encircles the property. Retreat to the luxurious second-level primary suite, thoughtfully positioned for tranquility. It features expansive storefront-style windows, dual walk-in closets, and a spa-inspired bath adorned with designer-selected tiles, a dual sink vanity, a frameless glass shower, and a private water closet. The versatile bonus loft area is perfect for a home office or a cozy reading nook, while the adjacent outdoor balcony with a cocktail kitchen offers unparalleled views of the lake. Two additional bedrooms, one with an en suite bath, ensure comfort and privacy for family or guests, complemented by a conveniently located laundry room that separates the primary suite from the secondary bedrooms. This townhome exemplifies modern living, complete with a desirable two-car garage featuring an epoxy-painted floor, an EV charging plug, and ample storage. Experience the pinnacle of elegance and comfort in this prime Central Florida location—your dream home awaits!

Curious about what makes Winter Park so weirdly wonderful? Live like a local and find out for yourself at our renovated, stylish, modern 4 bedroom home in the heart of Winter Park! Comfortably blending modern designs with historic charm, it is perfectly situated in a short drive to preeminent downtown of Winter Park and Orlando. Like getting lost at Park Avenue and downtown dining, drinking districts with copious amounts wines and gourmet signature dishes! Conveniently located about 10 minutes' drive to FullSail, Rollins College, Starbucks and shopping, and 15 minutes drive to UCF. The home has been tastefully presented by wood-look porcelain tiles throughout, top-ranking Samsung Stainless appliances, modern light-fixtures, spacious yard with a modern patio. The home has been replumbed and rewired in 2020. Roof is in 2019. Did i mention the AC is brand-new installed in 2022? So here you have it all for living in a renowned school district and signature Park Ave, while enjoying city life day and night! Come to see it today before it is gone!!!

Under contract-accepting backup offers. Welcome to your beautifully updated Winter Park home! This inviting property features an expansive, open living area with modern laminate flooring throughout—no carpet here! The kitchen is complete with sleek stone countertops, updated cabinetry, and contemporary light fixtures. Both the primary and guest bathrooms have been tastefully updated within the past 5 years, featuring new tile work and stylish vanities. Step outside to a completely fenced-in backyard, perfect for privacy and outdoor enjoyment. Key upgrades include a new roof and HVAC system installed in 2018, ensuring peace of mind and energy efficiency. Centrally located, this home is a short drive from local shops and restaurants, downtown Winter Park, the 417 and is about 25 minutes from both the Orlando and Sanford airports.

Welcome to your Winter Park dream home! This stunning 4-bedroom, 3.5-bathroom residence offers a spacious open floor plan, a gourmet kitchen with updated counters (2022), a luxurious master suite, and a backyard oasis perfect for entertaining. The outdoor living space features a private heated saltwater pool with a new screen enclosure (2022) and brand new pool equipment (pump, filter, chlorinator, and heater, all 2023). The outdoor kitchen boasts a Jenn-Air cooktop, a retractable screen dining area, and a separate half bath and outdoor shower. Recent upgrades include a new roof (2021), plumbing (2022), solar panels (2022), new downstairs carpet (2022), a vinyl privacy fence (2023), outdoor shed, and plantation shutters throughout. Situated on almost a quarter-acre corner lot in a beautiful, well-cared-for neighborhood with Seminole County Schools, this well-maintained home offers easy access to 417, is less than 20 minutes from the famous Park Avenue with some of the best shops and restaurants in the city, and 25 minutes from the airport. Schedule your showing today!

Under contract-accepting backup offers. This 3 bedroom, 2 bathroom, block POOL home boasts a highly desirable Winter Park address, & has been lovingly cared for by its current owner for nearly 50 years. Fall in love from the moment you pull up, as the home boasts beautiful curb appeal on the outside & a charming interior. Recent upgrades include a renovated kitchen (2022), NEW ROOF (2020), NEW garage door (2020), NEW laminate flooring (2024) & 4 NEW Anderson Windows. Interior features include crown molding throughout, plantation shutters, chair railing molding, built-ins & a wood burning fireplace. For all the mid century lovers out there, you will find the original terrazzo flooring underneath the current floor (except in the fireplace room)! The layout is ideal, with a generously sized living room, formal dining room, which is conveniently located next to the remodeled kitchen and dining nook. All three bedrooms & 2 full bathrooms are conveniently stacked on one side of the home, privately tucked away from the living areas. The back porch has been enclosed for additional square footage and could be used as a tv room, playroom, office, or whatever you desire, truly the possibilities are endless! The backyard is an oasis, private & fully fenced, with an open air swimming pool, a porch swing, a natural gas grill (conveys with the home!) and a shed that has electricity. Zoned for Lakemont Elementary, Maitland Middle & Winter Park High School, and just 3 miles from Park Avenue, 1 mile from Full Sail University & 7 miles from the University of Central Florida, the location is truly ideal! This home is ready for new owners to come in & start building beautiful memories of their own. Don't delay! Schedule your showing today.

Charming Cottage in the Heart of Winter Park. Step into a world of timeless charm with this delightful 3-bedroom, 2-bath cottage that exudes warmth and character at every turn. Boasting nearly 1,700 square feet, this enchanting home features a thoughtfully designed split plan, providing both privacy and functionality. The moment you approach, you’ll be captivated by its amazing curb appeal, nestled on a picturesque .15-acre parcel adorned with low-maintenance landscaping. Inside, discover an adorable eat-in kitchen that beckons for casual gatherings, where memories are made over delicious meals. High vaulted ceilings create an airy ambiance, amplifying the sense of space and light throughout the home. Generous closets ensure great storage, while the convenient inside laundry room adds to the ease of everyday living. The 3 outdoor sitting areas allow for great relaxation spots and fabulous entertaining areas in the fresh air. Recent updates include a new roof (2022), AC system (2017), and a new electrical panel (2019). Plantation Shutters throughout. Whether you choose to move in, renovate, or envision a brand-new dream home, the possibilities are endless. Located just a 5-minute drive or a leisurely 25-minute stroll from Winter Park's fabulous Park Avenue, you’ll find yourself immersed in a vibrant community filled with delightful shops, art galleries, and exquisite dining options, all complemented by the natural beauty of Central Park. With top-rated Winter Park schools nearby and nestled on one of the most charming brick streets in the 32789 area, this cottage offers the perfect blend of lifestyle and location. Don’t miss this rare opportunity to make this adorable cottage your own or use the ample lot to build the home of your dreams.

This stunning & revived one-story Winter Park home is the perfect mix of classic charm & modern comforts. Featuring NEW oak hardwood floors, crown molding, two master suites & soaring ceilings, no expense was spared in the recent extensive remodel with top-of-the-line luxury finishes. The split floor plan is both wonderful & fascinating. As you go into the home you enter the living room & close by is the sun room, two bedrooms, NEW bathroom w/ tiled shower/tub & built in shelves. The bonus room off the living room can be a fifth bedroom, office, nursery, workout room, wine room, etc. The formal dining room nearby opens to a tranquil private courtyard & near that is the laundry room w/ utility sink. Next to the kitchen is an additional living room w/ natural gas fireplace & built in cabinets/shelves. Now step outside to your shaded backyard oasis w/ a NEW privacy fence w/ gate, oversized patio for dining/entertaining & a large storage shed/workshop. You'll love the abundance of natural light especially through the large outdoor courtyard in the middle of the home w/ views & access from the kitchen, primary master suite & living room. Featuring NEW impact rated 8 ft. tall sliding glass doors including a 12 ft wide grand entrance which opens from both directions in the middle near the living room. With views of towering trees this area offers endless possibilities & is the perfect transition for indoor & outdoor entertaining & relaxation. The open kitchen has been transformed into a spectacular masterpiece featuring vaulted ceilings, skylight, Calcutta quartz, center island, large peninsula w/ bar seating & decorative pendant lighting, new stainless appliances including Brama microwave, vented hood, custom backsplash & solid wood cabinets, including 42 in. upper cabinets & four large pantry cabinets. The primary master suite is spacious w/ vaulted ceilings, two walk-in closets & one w/ a closet organizer. The NEW master bathroom is exquisite boasting a large glass shower w/ two shower heads & dual vanities w/ quartz. The second master has a private entrance which is perfect for guests or mother-in-law suite, walk-in closet & NEW bathroom w/ spacious glass shower & a vanity w/ quartz. The air conditioned two car garage has a NEW garage door/opener, NEW epoxy floor & lots of extra storage areas. The long driveway is perfect for guests, multiple cars & parking. Other upgrades include a NEW roof/gutters, NEW plumbing/electrical/AC, NEW windows/doors, NEW int/ext paint, NEW pavers/landscaping/irrigation & Rinnai tankless gas water heater. Please ask for a list of the $290K in improvements & is attached to MLS. Centrally located on the famous tree lined Palmer Ave, you're a short stroll to Phelps Park & the YMCA, and minutes to shopping & dining on Park Ave, Interlachen Country Club & Winter Park Racquet Club. Don't miss your chance to make this truly breathtaking home yours!

Nestled in Winter Park on a brick paved street this beautiful and deceptively large 2 bedroom residence with over 1600sqft of living space. Includes 2 masters, 2.5 bathrooms, a large recreation/study bonus area, full kitchen with accessories, and laundry. Lovely secluded garden. Attached 1 car garage with driveway parking for 2. Walk to your favorite Park Ave restaurants, stores, and coffee shops. Minutes from farmers market. Winter Park High school district and close to Rollins College. Call today to schedule a viewing.