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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

3032 Antique Oaks Circle Unit 145, Winter Park image
3032 Antique Oaks Circle Unit 145, Winter Park — 3032 $129,000 ▼

*Photos virtually staged.* Investment opportunity in the heart of Winter Park! This tenant-occupied 1-bedroom, 1-bath condo in Parkview Village offers 749 square feet of ...

  • 1 Beds
  • 1 Baths
  • O6446981 MLS
  • 3032 Bldg.
310 Granada Drive, Winter Park image
310 Granada Drive, Winter Park $325,000 ▼

Welcome to 310 Granada Drive, an excellent opportunity to own a single-family home in the highly desirable Winter Park 32789 area. Situated in the established Fairview He...

  • 3 Beds
  • 2 Baths
  • O6447315 MLS
302 Lewfield Circle Unit 302, Winter Park image
302 Lewfield Circle Unit 302, Winter Park — 302 $140,000

ENJOY THE WINTER PARK LIFESTYLE from this charming one-bedroom, one-bath condo offering low maintenance living in a convenient Central Florida location. Step inside to a ...

  • 1 Beds
  • 1 Baths
  • O6447007 MLS
  • 302 Bldg.
918 Enclave Place, Winter Park image
918 Enclave Place, Winter Park $2,125,000

Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. The Hawthorn, an exceptional new custo...

  • 5 Beds
  • 5 Baths
  • O6439116 MLS
100 S Interlachen Avenue Unit 401, Winter Park image
100 S Interlachen Avenue Unit 401, Winter Park — Cloisters $825,000 ▼

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windo...

  • 3 Beds
  • 2 Baths
  • O6443942 MLS
  • Cloisters Bldg.
2500 Lee Road Unit 123, Winter Park image
2500 Lee Road Unit 123, Winter Park — Na $159,900 ▼

NEW PRICE! REDUCED $10,000 — NOW ONLY $159,900! LIVE THE WINTER PARK LAKEFRONT LIFESTYLE WITHOUT THE LAKEFRONT PRICE TAG! This UPDATED, GROUND-FLOOR 1-bedroom, 1-ba...

  • 1 Beds
  • 1 Baths
  • O6445068 MLS
  • Na Bldg.
188 Sandlewood Unit 1, Winter Park image
188 Sandlewood Unit 1, Winter Park — 1 $290,000

Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this h...

  • 2 Beds
  • 3 Baths
  • O6445407 MLS
  • 1 Bldg.
712 Baffie Avenue, Winter Park image
712 Baffie Avenue, Winter Park $419,900 ▼

Welcome to 712 Baffie Avenue, a charming and thoughtfully updated bungalow in one of Winter Park’s most sought-after areas. This home blends classic character with modern...

  • 3 Beds
  • 1 Baths
  • O6445837 MLS
200 Saint Andrews Boulevard Unit 704, Winter Park image
200 Saint Andrews Boulevard Unit 704, Winter Park — 200 $159,000

LOCATION, LIFESTYLE & OPPORTUNITY IN THE HEART OF WINTER PARK! Welcome to 200 Saint Andrews Boulevard #704, a charming top-floor, 1-bedroom, 1-bath condominium in the est...

  • 1 Beds
  • 1 Baths
  • O6445691 MLS
  • 200 Bldg.
5405 Justine Way, Winter Park image
5405 Justine Way, Winter Park $399,900

Welcome to 5405 Justine Way, a charming 3-bedroom, 2-bathroom single-family home in the desirable Winter Park area. This well-located residence offers approximately 1,247...

  • 3 Beds
  • 2 Baths
  • O6444915 MLS
2823 Parkland Circle, Winter Park image
2823 Parkland Circle, Winter Park $3,250,000

JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, thi...

  • 5 Beds
  • 6 Baths
  • O6444919 MLS
2007 Edwin Boulevard, Winter Park image
2007 Edwin Boulevard, Winter Park $1,995,000

Virtually Staged. Pre-Construction. To be built. POOL + SAUNA • DOUBLE PRIMARY SUITES • 3-CAR GARAGE • CUSTOM NEW CONSTRUCTION IN WINTER PARK Pool, sauna, double prima...

  • 4 Beds
  • 4 Baths
  • O6439783 MLS
513 Dunraven Drive, Winter Park image
513 Dunraven Drive, Winter Park $1,950,000

Under Construction. Anticipated for completion in January 2027, this new-construction luxury home in Winter Park's Kenilworth Shores neighborhood offers five bedrooms, 4....

  • 5 Beds
  • 5 Baths
  • O6444889 MLS
266 N Ranger Boulevard, Winter Park image
266 N Ranger Boulevard, Winter Park $724,900

FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where mode...

  • 4 Beds
  • 3 Baths
  • O6444727 MLS
1760 Oakhurst Avenue, Winter Park image
1760 Oakhurst Avenue, Winter Park $2,500,000

Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-...

  • 5 Beds
  • 5 Baths
  • O6441988 MLS

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