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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

708 Balmoral Road, Winter Park image
708 Balmoral Road, Winter Park $1,690,000

A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Su...

  • 4 Beds
  • 3 Baths
  • O6423883 MLS
1754 Taylor Avenue, Winter Park image
1754 Taylor Avenue, Winter Park $2,569,999

Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredibl...

  • 5 Beds
  • 5 Baths
  • O6421927 MLS
5781 Shale Court, Winter Park image
5781 Shale Court, Winter Park $315,000 ▼

**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
  • 2 Baths
  • O6422583 MLS
1695 Lee Road Unit B108, Winter Park image
1695 Lee Road Unit B108, Winter Park — Waterfall Cove Of Winter Park $88,999 ▼

This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and ever...

  • 1 Beds
  • 1 Baths
  • O6422568 MLS
  • Waterfall Cove Of Winter Park Bldg.
1180 Via Lugano, Winter Park image
1180 Via Lugano, Winter Park $4,900,000

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom b...

  • 5 Beds
  • 6 Baths
  • O6413198 MLS
1823 Sunset Drive, Winter Park image
1823 Sunset Drive, Winter Park $2,549,000

Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of time...

  • 5 Beds
  • 5 Baths
  • O6421690 MLS
1250 S Denning Drive Unit 109, Winter Park image
1250 S Denning Drive Unit 109, Winter Park — 109 $190,000 ▲

Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright...

  • 1 Beds
  • 1 Baths
  • R4911491 MLS
  • 109 Bldg.
5184 Lazy Oaks Drive, Winter Park image
5184 Lazy Oaks Drive, Winter Park — Na $280,000

Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you i...

  • 2 Beds
  • 2 Baths
  • O6422366 MLS
  • Na Bldg.
2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park image
2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park — 19 $279,900

Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigne...

  • 2 Beds
  • 2 Baths
  • O6421422 MLS
  • 19 Bldg.
252 Scottsdale Sq Unit 252, Winter Park image
252 Scottsdale Sq Unit 252, Winter Park — 252 $85,000

Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

  • 2 Beds
  • 2 Baths
  • O6421977 MLS
  • 252 Bldg.
722 S Ranger Boulevard, Winter Park image
722 S Ranger Boulevard, Winter Park $799,900 ▼

JUST REDUCED! Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated...

  • 4 Beds
  • 3 Baths
  • O6421873 MLS
2372 Sun Valley Circle Unit 2372, Winter Park image
2372 Sun Valley Circle Unit 2372, Winter Park — Bldg 16 $285,000

Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the livin...

  • 2 Beds
  • 2 Baths
  • O6421135 MLS
  • Bldg 16 Bldg.
1695 Lee Road Unit A116, Winter Park image
1695 Lee Road Unit A116, Winter Park — . $135,000

Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living ar...

  • 3 Beds
  • 2 Baths
  • O6420863 MLS
  • . Bldg.
341 E Reading Way, Winter Park image
341 E Reading Way, Winter Park $1,625,000 ▼

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exc...

  • 4 Beds
  • 4 Baths
  • O6420387 MLS
1000 S Semoran Boulevard Unit 408, Winter Park image
1000 S Semoran Boulevard Unit 408, Winter Park — 4 $138,000 ▼

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Gre...

  • 1 Beds
  • 1 Baths
  • R4911527 MLS
  • 4 Bldg.

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