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Discover the refined charm of Winter Park, FL, a picturesque city just north of Orlando where oak-lined streets, scenic lakes, and elegant architecture create an atmosphere of timeless beauty. Stroll across Park Avenue — Winter Park’s cultural and culinary heart — filled with boutique shops, sidewalk cafés, and lush Central Park hosting seasonal festivals. Immerse yourself in the arts at gems like the Charles Hosmer Morse Museum of American Art or the Rollins Museum of Art, tour historic Casa Feliz, or unwind in the green tranquility of Mead Botanical Garden or Kraft Azalea Park. Whether you love lakeside walks, weekend farmers’ markets, or exploring unique museums, there’s always something delightful here — and plenty of opportunity when you explore homes for sale Winter Park FL to call this sophisticated oasis home.
Homes for Sale in Winter Park
Virtually Staged. One or more photos have been virtually staged. Why compromise on cramped rooms when you can have over 2,250 square feet of versatile space with a huge b...
- 4 Beds
- 2 Baths
- O6414369 MLS
Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle th...
- 3 Beds
- 3 Baths
- O6414283 MLS
Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an ex...
- 4 Beds
- 3 Baths
- O6416828 MLS
Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perc...
- 5 Beds
- 7 Baths
- O6416158 MLS
NEW ROOF TO BE INSTALLED OCTOBER 2026 + NEW WATER HEATER! Welcome to 8433 Commander Cove, a spacious 4-bedroom, 2.5-bath home located on a quiet cul-de-sac in the desi...
- 4 Beds
- 3 Baths
- O6416635 MLS
Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment yo...
- 4 Beds
- 4 Baths
- O6415941 MLS
Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. T...
- O6416144 MLS
Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and di...
- 3 Beds
- 2 Baths
- C7527235 MLS
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollin...
- 3 Beds
- 4 Baths
- O6415981 MLS
- Na Bldg.
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desira...
- 5 Beds
- 5 Baths
- O6415360 MLS
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury...
- 4 Beds
- 7 Baths
- O6414890 MLS
Back on market due to buyer circumstances unrelated to property condition. Inspection completed successfully. Price improvement! Move-in ready in Winter Park 32789. Th...
- 2 Beds
- 2 Baths
- TB8517242 MLS
**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condomini...
- 1 Beds
- 1 Baths
- O6412768 MLS
- 142 Bldg.
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly paymen...
- 2 Beds
- 1 Baths
- O6411927 MLS
- 220 Bldg.
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 ...
- 5 Beds
- 4 Baths
- O6415098 MLS
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