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Homes for Sale in Winter Park, FL

Winter Park, Florida, is a paradise to vacationers and residents alike. Located adjacent and northeast to Orlando, this lush and lovely area boasts multiple parks, golf courses, and all the amenities that create a fine resort area. Home buyers looking for quaint styles on old-fashioned brick streets will be delighted by the offerings in the Olde Winter Park area, which are often punctuated by Spanish moss-draped trees. Canals and interconnected lakes provide water-loving residents recreational opportunities all year long.

7039 Hammock Way, Winter Park FL, 32792

Just Listed
14 Photo
  • Beds: 3
  • Baths: 2 full
  • Days on Homes.com: 1
  • Sqft: 1,976
  • Lot Size: --
  • Year Built: 1978
Offered By:
Weichert Realtors
$186,000
Price per Sqft: $94
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971 Harmon Ave, Winter Park FL, 32789

Just Listed
5 Photo
  • Beds: 3
  • Baths: 1 full
  • Days on Homes.com: 3
  • Sqft: 1,256
  • Lot Size: 0.33 acres
  • Year Built: 1957
Offered By:
Evelyn Pilchick
$184,900
Price per Sqft: $147
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410 Carvell Drive, Winter Park FL, 32792

25 Photo
  • Beds: 3
  • Baths: 2 full
  • Days on Homes.com: 1
  • Sqft: 1,570
  • Lot Size: 0.37 acres
  • Year Built: 1959
$298,300
Price per Sqft: $190

203 Ranch Road, Winter Park FL, 32792

25 Photo
  • Beds: 4
  • Baths: 3 full
  • Days on Homes.com: 3
  • Sqft: 2,640
  • Lot Size: 2.94 acres
  • Year Built: 1980
$499,000
Price per Sqft: $189

535 Park North Court, Winter Park FL, 32789

25 Photo
  • Beds: 5
  • Baths: 4 full
  • Days on Homes.com: 3
  • Sqft: 5,169
  • Lot Size: 0.34 acres
  • Year Built: 1991
$1,350,000
Price per Sqft: $261

320 Cortland Avenue, Winter Park FL, 32789

25 Photo
  • Beds: 4
  • Baths: 3 full & 1 half
  • Days on Homes.com: 3
  • Sqft: 4,321
  • Lot Size: 0.64 acres
  • Year Built: 1940
$1,425,000
Price per Sqft: $330

834 Cabot Court, Winter Park FL, 32792

21 Photo
  • Beds: 4
  • Baths: 2 full
  • Days on Homes.com: 3
  • Sqft: 1,582
  • Lot Size: 0.22 acres
  • Year Built: 1969
$245,000
Price per Sqft: $155

1581 Palm Avenue, Winter Park FL, 32789

20 Photo
  • Beds: 4
  • Baths: 3 full & 1 half
  • Days on Homes.com: 3
  • Sqft: 4,295
  • Lot Size: 0.32 acres
  • Year Built: 2008
$1,325,000
Price per Sqft: $308

3178 Battersea Way, Winter Park FL, 32792

12 Photo
  • Beds: 2
  • Baths: 2 full
  • Days on Homes.com: 3
  • Sqft: 1,367
  • Lot Size: 0.12 acres
  • Year Built: 1986
$194,500
Price per Sqft: $142

3120 Queens Way 10, Winter Park FL, 32792

8 Photo
  • Beds: 3
  • Baths: 2 full & 1 half
  • Days on Homes.com: 3
  • Sqft: 1,565
  • Lot Size: 0.02 acres
  • Year Built: 2008
$159,900
Price per Sqft: $102

3119 Fairwood Ct, Winter Park FL, 32792

2 Photo
  • Beds: 2
  • Baths: 2 full
  • Days on Homes.com: 2
  • Sqft: 1,068
  • Lot Size: 0.09 acres
  • Year Built: 1981
$76,000
Price per Sqft: $71

1840 Maywood Rd, Winter Park FL, 32792

1 Photo
  • Beds: 3
  • Baths: 2 full
  • Days on Homes.com: 2
  • Sqft: 1,570
  • Lot Size: 0.21 acres
  • Year Built: 1957
$169,900
Price per Sqft: $108

2138 Brookview Dr, Winter Park FL, 32792

17 Photo
  • Beds: 4
  • Baths: 4 full
  • Days on Homes.com: 3
  • Sqft: 2,913
  • Lot Size: 0.21 acres
  • Year Built: 1971
$325,000
Price per Sqft: $112

880 N Lakemont Ave, Winter Park FL, 32792

Just Listed
5 Photo
  • Beds: 3
  • Baths: 2 full
  • Days on Homes.com: 8
  • Sqft: 1,454
  • Lot Size: 0.27 acres
  • Year Built: 1958
Offered By:
Winter Park Land Company
$305,000
Price per Sqft: $210
Video Save Request Info

3513 Balsam Drive, Winter Park FL, 32792

13 Photo
  • Beds: 3
  • Baths: 2 full
  • Days on Homes.com: 6
  • Sqft: 1,323
  • Lot Size: 0.2 acres
  • Year Built: 1965
$169,000
Price per Sqft: $128
1 - 15 of 537 Results
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Those who like warm weather and outdoor activities will find no end to the possibilities in Winter Park. Festivals abound, including the Winter Park Sidewalk Art Festival, one of the oldest and top-rated outdoor festivals in the United States. Music lovers will discover that this is the home of the Bach Festival Society of Winter Park, central Florida's oldest performing arts organization. Combine love of the outdoors and the love of music to experience the Annual Winter Park Jazz Festival, which features multiple acts over a two-day period. Foodies will find a treasure trove of restaurant options representing popular regional flavors as well as international-themed cuisine. Parks such as Dinky Dock provide picnic facilities, swimming, and fishing.

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  • Imagination Realty
    Celebration, FL
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    Orlando, FL
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    Winter Park, FL

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