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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
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
Valuable architectural and interior design plans (being offered with the list price!) are available to provide a jump start on your stunning new custom home. Click the VI...
- O6397264 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 Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value...
- 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.
Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranqu...
- 3 Beds
- 2 Baths
- O6395355 MLS
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
Virtually Staged. Virtually Staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with al...
- 2 Beds
- 1 Baths
- S5146352 MLS
- Waterfall Cove / Bldg E Bldg.
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
One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Winter Park home at 405 Lake Fair Ln has been completely transformed from top to b...
- 3 Beds
- 2 Baths
- O6393594 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
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
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