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Homes for Sale with a Pool in Winter Park, FL
168 homes
New
2634 Cayman Way, Winter Park, FL 32792
Welcome to this enchanting one-story townhome, a rare gem in today's market. Nestled in the coveted Winter Park community of Windward Square, this spacious, open-concept home is perfect for both rela...
New
7794 Country Pl Unit 7794, Winter Park, FL 32792
Very CLEAN Move In Ready. Upgraded unit with newer high end cabinets in kitchen and both baths, Granite counters in kitchen and baths. Custom tiled backsplash, NEW carpet in both bedrooms. Features a...
New
5422 S Bracken Ct, Winter Park, FL 32792
Discover the charm of 5422 S Bracken Ct, a serene 3-bedroom, 2-bathroom home nestled on a peaceful cul-de-sac in the sought-after Winter Park area. This delightful residence boasts a bright and invit...
New
1312 Golfside Dr, Winter Park, FL 32792
Discover your dream oasis in this exquisite 3-bedroom, 2-bathroom POOL home nestled on a coveted street in Winter Park on the 3rd hole on the GOLF COURSE. With designer-inspired upgrades and custom f...
New
1830 Pineview Cir, Winter Park, FL 32792
Welcome to this newly completed 4-bedroom, 3.5-bathroom home, located in the Lakemont Heights neighborhood of Winter Park. Spanning 2,843 square feet and built by the renowned Barefoot Brothers Const...
New
465 Genius Dr, Winter Park, FL 32789
WINDSONG - WINTER PARK – A Maroon Fine Homes masterpiece and COMPLETELY renovated in 2022. This property combines luxury, functionality, and location, making it a perfect choice for those looking to ...
New
104 S Interlachen Ave Unit 215D, Winter Park, FL 32789
Lovely updated Cloister's unit with LAKE VIEW. This 2 bed 2 bath large unit offers 1267 square feet of living space. Enjoy your expansive views of the picturesque lawn, pool, and LAKE OCSEOLA. Your ...
New
1521 Magnolia Ave, Winter Park, FL 32789
Nestled in the heart of Winter Park's prestigious "Tree Streets" neighborhood, this exquisite residence stands as a testament to refined living and architectural splendor. This four-bedroom, four-bat...
New
1421 Place Picardy, Winter Park, FL 32789
Welcome to this renovated traditional home, ideally situated on a corner lot in one of the most desirable neighborhoods in all of Central Florida. This charming, white-washed brick exterior Winter Pa...
New
266 N Ranger Blvd, Winter Park, FL 32792
FULLY REHABBED property with Mother-in-law suite, no HOA, community pool/park/trail, and golf course. Located adjacent to Cady Way Trail, the property features an open floor plan with Luxury Vinyl P...
New
301 Lewfield Cir, Winter Park, FL 32792
Great 1 bedroom condo located on the first floor! This cute condo offers newer kitchen cabinets and granite counter tops and a new dishwasher, new luxury vinyl flooring in the living and dining rooms...
New
4013 Quenita Dr, Winter Park, FL 32792
Come see this "diamond in the rough" located in the sought-after city of Winter Park! This home boasts a dining area, a separate family/lounge room, a spacious living room, which includes a fireplace...
2252 Shadowland Loop, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to Your Dream Home at The Enclave at Hawk's Crest!
Discover this beautifully maintained 3-bedroom, 2.5-bathroom townhome in the sought-after...
1049 Tuscany Pl, Winter Park, FL 32789
This rare opportunity to own a ONE STORY LAKEFRONT home on A HALF ACRE lot located in the highly desirable Via’s of Winter Park. Tuscany Place is nestled on a quiet cul-de-sac and zoned for top A-rat...
1981 Blue Ridge Rd, Winter Park, FL 32789
One or more photo(s) has been virtually staged. LOVE IT OR LIST IT! Don’t miss this rare chance to design your dream home in the desirable Timberlane Shores community! Take it AS-IS for $949K, or cus...
417 Gilbert Rd, Winter Park, FL 32792
Welcome to this spacious and charming home located in the sought-after Winter Park Pines neighborhood! As you approach the property, a covered porch invites you to relax before stepping inside. The e...
1458 Aloma Ave, Winter Park, FL 32789
Lakefront living in Winter Park! Enjoy serene views from this single-story ranch charmer, featuring 5 beds, 4 baths and 3,446 sq ft nestled behind a front block wall on the shores of Lake Sylvan. Wi...
4768 Tangerine Ave Unit 4768, Winter Park, FL 32792
Back on Market. Buyer financing fell through. Seller Motivated! Clean and charming, this one-story concrete block and stucco building offers an inviting space. The open floor plan creates a sense of ...
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