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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
Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 be...
- 5 Beds
- 3 Baths
- O6397997 MLS
INVESTMENT OPPORTUNITY near Lake Killarney! This Winter Park gem offers a flexible layout perfect for multigenerational living, house-hacking, or rental income that can e...
- 6 Beds
- 3 Baths
- O6397890 MLS
Lakefront home on over 1 acre in Winter Park with approximately 95 feet of frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rar...
- O6396791 MLS
Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to b...
- 3 Beds
- 2 Baths
- O6396357 MLS
Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Id...
- 2 Beds
- 1 Baths
- O6396190 MLS
- D Bldg.
Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficienc...
- 4 Beds
- 4 Baths
- O6396971 MLS
Short Sale. SHORT SALE – SUBJECT TO THIRD-PARTY LENDER APPROVAL. Investor and builder opportunity in Winter Park. This property is situated on a generously sized lot with...
- 3 Beds
- 2 Baths
- S5147029 MLS
Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one o...
- 4 Beds
- 4 Baths
- O6391469 MLS
- Deep Roots Construction Bldg.
Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come toget...
- 3 Beds
- 4 Baths
- O6394464 MLS
One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that red...
- 4 Beds
- 4 Baths
- O6394208 MLS
Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view l...
- 4 Beds
- 4 Baths
- O6392218 MLS
Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functiona...
- 4 Beds
- 4 Baths
- O6383529 MLS
Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orl...
- 4 Beds
- 4 Baths
- O6389829 MLS
Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom...
- 4 Beds
- 4 Baths
- O6391179 MLS
Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, ...
- 4 Beds
- 4 Baths
- O6383602 MLS
- 901 Bldg.
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