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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

2038 Ponderosa Avenue, Winter Park image
2038 Ponderosa Avenue, Winter Park $415,000

Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the highly desirable Eastbrook neighborhood of Winter Park! Light, bright, and ...

  • 3 Beds
  • 2 Baths
  • O6453339 MLS
257 Lincolnshire Road, Winter Park image
257 Lincolnshire Road, Winter Park $550,000

Welcome to 257 Lincolnshire Road, a 3-bedroom, 2-bath home offering 1,610 square feet of living space in the established Winter Park Pines neighborhood. Situated at the e...

  • 3 Beds
  • 2 Baths
  • O6453656 MLS
1825 Chilean Lane, Winter Park image
1825 Chilean Lane, Winter Park $450,000

Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home ...

  • 5 Beds
  • 3 Baths
  • O6452415 MLS
3027 Aaron Bur Avenue Unit L1, Winter Park image
3027 Aaron Bur Avenue Unit L1, Winter Park — Na $169,999

STUNNING FULLY REMODELED TWO-STORY CORNER-UNIT CONDO IN THE HEART OF WINTER PARK! GREAT OPPORTUNITY FOR HOMEOWNERS AND INVESTORS! Welcome to this beautifully renovated...

  • 2 Beds
  • 3 Baths
  • TB8562681 MLS
  • Na Bldg.
2168 Ridge Drive, Winter Park image
2168 Ridge Drive, Winter Park $359,900 ▼

STOP THE SCROLL! ?? Your Dream Home Is Calling! ? Welcome to this beautifully updated 3-bedroom, 2-bath gem where style, comfort, and location come together! Enjoy taste...

  • 3 Beds
  • 2 Baths
  • O6453370 MLS
345 Beloit Avenue, Winter Park image
345 Beloit Avenue, Winter Park $1,625,000

Historic Winter Park charm with modern updates, close to N Park Avenue. Set on a picturesque, tree-lined street, this thoughtfully renovated home puts you minutes from...

  • 3 Beds
  • 3 Baths
  • O6448919 MLS
2352 Sun Valley Circle, Winter Park image
2352 Sun Valley Circle, Winter Park — Na $280,000

Welcome to the established and well-maintained community of Cedarwood Village in highly desirable Winter Park! TREE-LINED STREETS lead to this END UNIT, COMPLETELY REMODE...

  • 2 Beds
  • 2 Baths
  • O6441394 MLS
  • Na Bldg.
1830 Gladiolas Drive, Winter Park image
1830 Gladiolas Drive, Winter Park $375,000

Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022...

  • 3 Beds
  • 2 Baths
  • O6452778 MLS
1386 Clematis Lane, Winter Park image
1386 Clematis Lane, Winter Park $417,000

LOCATION! LOCATION! Winter Park property located in Seminole County. Proximity to Rollins, Full Sail, UCF, and Valencia colleges. Great income producer, with "Flex Space"...

  • 4 Beds
  • 3 Baths
  • S5160217 MLS
1021 Princess Gate Boulevard, Winter Park image
1021 Princess Gate Boulevard, Winter Park $410,000

Virtually Staged. Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this si...

  • 3 Beds
  • 2 Baths
  • O6451435 MLS
7463 Canford Court Unit 15, Winter Park image
7463 Canford Court Unit 15, Winter Park — Whisperwood Condo $270,000

Welcome to this beautifully updated corner home in the Whisperwood community of Winter Park! Featuring 3 bedrooms and 2.5 bathrooms, this property offers an open-concept ...

  • 3 Beds
  • 3 Baths
  • O6452947 MLS
  • Whisperwood Condo Bldg.
1940 Magnolia Avenue, Winter Park image
1940 Magnolia Avenue, Winter Park $1,190,000

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This s...

  • 4 Beds
  • 4 Baths
  • O6421587 MLS
1200 Via Salerno, Winter Park image
1200 Via Salerno, Winter Park $5,995,000

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live...

  • 5 Beds
  • 6 Baths
  • O6447322 MLS
603 Carnation Drive, Winter Park image
603 Carnation Drive, Winter Park $399,900 ▼

Private in-ground pool on a 9,000+ sq ft lot in Winter Park, with no HOA. This 4 bed, 2 bath home has 1,427 sq ft of updated living space and an open floor plan with hard...

  • 4 Beds
  • 2 Baths
  • TB8561386 MLS
2330 Westminster Ct., Winter Park image
2330 Westminster Ct., Winter Park $985,000

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigne...

  • 5 Beds
  • 3 Baths
  • O6452380 MLS

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