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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.

543 E Lake Sue Ave, Winter Park FL, 32789

25 Photo
  • Beds: 4
  • Baths: 4 full & 1 half
  • Days on Homes.com: 3
  • Sqft: 3,657
  • Lot Size: 0.36 acres
  • Year Built: 1986
$999,000
Price per Sqft: $273

3074 Coral Vine Ln, Winter Park FL, 32792

Video
18 Photo
  • Beds: 4
  • Baths: 4 full
  • Days on Homes.com: 46
  • Sqft: 2,431
  • Lot Size: 0.42 acres
  • Year Built: 1994
Offered By:
Winter Park
$324,900
Price per Sqft: $134

2161 Sharon Rd, Winter Park FL, 32789

Video
25 Photo
  • Beds: 6
  • Baths: 6 full & 2 half
  • Days on Homes.com: 117
  • Sqft: 6,007
  • Lot Size: 0.58 acres
  • Year Built: 1992
Offered By:
Winter Park
$1,325,000
Reduced $45,000 (12/24/15)
Price per Sqft: $221

2889 Old Castle Dr, Winter Park FL, 32792

Video
25 Photo
  • Beds: 4
  • Baths: 3 full & 1 half
  • Days on Homes.com: 131
  • Sqft: 3,406
  • Lot Size: 0.47 acres
  • Year Built: 1993
Offered By:
Oviedo
$584,900
Reduced $5,000 (11/07/15)
Price per Sqft: $172
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1442 Palm Ave, Winter Park FL, 32789

25 Photo
  • Beds: 4
  • Baths: 4 full
  • Days on Homes.com: 11
  • Sqft: 3,670
  • Lot Size: 0.26 acres
  • Year Built: 1993
$899,000
Price per Sqft: $245

304 Santiago Drive, Winter Park FL, 32789

25 Photo
  • Beds: 5
  • Baths: 4 full & 1 half
  • Days on Homes.com: 12
  • Sqft: 4,213
  • Lot Size: 0.51 acres
  • Year Built: 1999
$1,095,000
Price per Sqft: $260

911 Greentree Drive, Winter Park FL, 32789

24 Photo
  • Beds: 5
  • Baths: 4 full
  • Days on Homes.com: 11
  • Sqft: 3,672
  • Lot Size: 0.3 acres
  • Year Built: 1999
$1,125,000
Price per Sqft: $306

1000 Anchorage Court, Winter Park FL, 32789

25 Photo
  • Beds: 6
  • Baths: 5 full & 2 half
  • Days on Homes.com: 19
  • Sqft: 6,378
  • Lot Size: 0.59 acres
  • Year Built: 1982
$3,188,000
Price per Sqft: $500

1781 Via Tuscany, Winter Park FL, 32789

25 Photo
  • Beds: 5
  • Baths: 4 full & 1 half
  • Days on Homes.com: 38
  • Sqft: 3,465
  • Lot Size: 0.29 acres
  • Year Built: 1991
$1,179,000
Reduced $70,900 (02/06/16)
Price per Sqft: $340

1521 Sugarwood Cir, Winter Park FL, 32792

25 Photo
  • Beds: 4
  • Baths: 4 full
  • Days on Homes.com: 22
  • Sqft: 2,791
  • Lot Size: 0.31 acres
  • Year Built: 1984
$300,000
Price per Sqft: $107

715 Via Bella, Winter Park FL, 32789

25 Photo
  • Beds: 4
  • Baths: 4 full
  • Days on Homes.com: 16
  • Sqft: 4,328
  • Lot Size: 0.27 acres
  • Year Built: 1976
$1,375,000
Price per Sqft: $318

1712 Barcelona Way, Winter Park FL, 32789

25 Photo
  • Beds: 5
  • Baths: 4 full & 2 half
  • Days on Homes.com: 32
  • Sqft: 4,233
  • Lot Size: 0.46 acres
  • Year Built: 1979
$1,100,000
Price per Sqft: $260

2888 Old Castle Dr, Winter Park FL, 32792

25 Photo
  • Beds: 4
  • Baths: 4 full
  • Days on Homes.com: 68
  • Sqft: 3,595
  • Lot Size: 0.34 acres
  • Year Built: 1993
$575,000
Reduced $14,000 (01/02/16)
Price per Sqft: $160

1250 Woodmere Drive, Winter Park FL, 32789

25 Photo
  • Beds: 4
  • Baths: 3 full & 1 half
  • Days on Homes.com: 68
  • Sqft: 3,606
  • Lot Size: 0.32 acres
  • Year Built: 1992
$897,500
Price per Sqft: $249

8041 Lake Waunatta Drive, Winter Park FL, 32792

20 Photo
  • Beds: 4
  • Baths: 4 full & 1 half
  • Days on Homes.com: 47
  • Sqft: 5,329
  • Lot Size: 0.58 acres
  • Year Built: 1984
$899,000
Price per Sqft: $169
1 - 15 of 26 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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