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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
Rare hospitality-yield opportunity in Winter Park's Class A core, directly in the Hillstone trade area on South Orlando Avenue. The offering consists of 12 short-term ren...
- O6450599 MLS
Virtually Staged. Welcome to your dream estate inside the highly sought-after, gated enclave of Lakeside Estates in Winter Park! This magnificent 2-story residence, built...
- 6 Beds
- 6 Baths
- O6449663 MLS
Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition wit...
- 5 Beds
- 4 Baths
- O6449669 MLS
Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabin...
- 5 Beds
- 7 Baths
- O6449269 MLS
- Wooten Built Bldg.
Virtually Staged. Situated along one of Winter Park's charming, tree-lined brick streets, this beautifully maintained traditional residence offers over 4,100 square feet ...
- 5 Beds
- 6 Baths
- O6450044 MLS
Rare Find - 3 BR/2 BA - 2nd Floor CONDO at The Stratford a Winter Park Condominium! Spacious Living Room accesses 2nd Floor Balcony with a gorgeous view of one (1) of th...
- 3 Beds
- 2 Baths
- O6450087 MLS
- 9 Bldg.
Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rar...
- 5 Beds
- 7 Baths
- O6442410 MLS
This 3-bedroom, 2.5-bath home offers approximately 1,776 square feet of living space on a spacious 0.24-acre lot. The two-story floor plan provides flexible living arrang...
- 3 Beds
- 3 Baths
- TB8557964 MLS
Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering near...
- 4 Beds
- 4 Baths
- O6449003 MLS
Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless characte...
- 2 Beds
- 2 Baths
- O6449441 MLS
Welcome to The Enclave at Hawks Crest! This 2019-built townhome offers 3 bedrooms, 2.5 baths, and 2,308 sqft of modern, open-concept living. The main level flows from the...
- 3 Beds
- 3 Baths
- O6448996 MLS
- 1407 Bldg.
WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an im...
- 4 Beds
- 4 Baths
- S5158760 MLS
Completely Renovated Winter Park Pool Home on a Spacious Corner Lot! Discover this beautifully renovated Winter Park home featuring a spacious corner lot, private swim...
- 4 Beds
- 3 Baths
- O6448911 MLS
**A rare jewel in Winter Park's coveted Vias!** This oversized 0.36-acre lot (112' x 140') has been cleared and is ready for your custom estate home. Set on a charming br...
- O6448788 MLS
Charming 2BD/1.5BA Wrenwood Condo in Winter Park! Adorable & affordable townhome-style condo with immaculate flooring, well maintained kitchen and appliances, brand-new ...
- 2 Beds
- 2 Baths
- O6448605 MLS
- 4882 Bldg.
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