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Winter Park, FL Real Estate Subdivision Directory

Are you considering moving to a certain Winter Park, FL subdivision? Select the subdivision from the list below and browse its real estate and homes for sale.

Click any of the Winter Park Subdivisions below to view real estate listings for sale in that respective Subdivision.

City Subdivision Listings Avg Asking Price Avg Days on Market
Winter Park Alabama Condo 1 $1,250,000 75
Winter Park Albert Lee Ridge 3 $616,633 73
Winter Park Albert Lee Ridge 1st 1 $439,000 133
Winter Park Alexander Place 1 $4,250,000 40
Winter Park Aloma 3 $564,500 138
Winter Park Aloma Park 1 $310,000 46
Winter Park Aloma Trails 2 $367,000 45
Winter Park Arrowhead Cove 1 $600,000 2
Winter Park Autumn Glen 1 $415,000 9
Winter Park Banks Colonial Estates 1 $1,200,000 103
Winter Park Brookshire Heights 1 $500,000 26
Winter Park Brookshire Heights 1st 1 $530,000 24
Winter Park Brookshire Heights 2nd 1 $630,000 36
Winter Park Canton Ave Cottages 1 1 $849,000 68
Winter Park Capens 2 $725,000 415
Winter Park Casa Aloma 2 $491,950 71
Winter Park Casa Jardin Condo 1 $799,000 4
Winter Park Cedar Ridge 1 $490,000 68
Winter Park Cedarwood Village 2 $266,950 30
Winter Park Cedarwood Village 1 8 $262,375 102
Winter Park Charmont 6 $2,167,833 93
Winter Park Chateaux Du Lac 5 $235,160 85
Winter Park Cloister Grove 1 $3,975,000 420
Winter Park Cloisters Condo 1 $1,795,000 123
Winter Park College Place Rep 1 $1,849,900 23
Winter Park Colonies 4 $136,975 243
Winter Park Comstock Park 2 $3,697,500 65
Winter Park Conwill Estates 2 $1,485,000 40
Winter Park Coronation 1 $268,950 218
Winter Park Country Lane 2 $442,500 66
Winter Park Dubsdread Heights 2 $337,000 82
Winter Park Eastbrook 17 $412,576 83
Winter Park Eastgate 3 $758,000 106
Winter Park Edgewood 2 $610,000 16
Winter Park Elizabeth Heights 2 $444,450 5
Winter Park Ellno Willo 1 $3,275,000 163
Winter Park Enclave At Hawks Crest 1 $419,900 11
Winter Park Fairbanks Park 2 $849,000 128
Winter Park Fairbanks Shores 5th 1 $435,000 150
Winter Park Fairshores Place 1 $569,000 43
Winter Park Fairview Heights Rep 1 $354,999 17
Winter Park Flamingo Shores 2 $669,950 53
Winter Park Fontainebleau 2 $1,745,000 10
Winter Park Forest Hills 2 $4,092,500 205
Winter Park Four Seasons Condo 2 $197,500 58
Winter Park Fremar 2 $1,299,000 129
Winter Park Garden Acres 1 $655,000 17
Winter Park Garden Grove 1 $420,000 10
Winter Park Garden Lake Estates 8 $442,212 47
Winter Park Georgetown Estates 1 $435,000 162
Winter Park Glencoe 9 $553,953 118
Winter Park Glenmoor 2 $512,250 46
Winter Park Golfside 2 $754,950 20
Winter Park Golfside Villas Condo 5 $127,800 43
Winter Park Golfview 1 $459,900 244
Winter Park Grand Pines 2 $450,450 27
Winter Park Grayson Square 4 $405,350 38
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,780,000 155
Winter Park Greenview At Winter Pines 1 $840,000 142
Winter Park H Vanwies 2 $899,000 117
Winter Park Hamilton Place 1 $1,295,000 127
Winter Park Henkel 1 $1,079,000 88
Winter Park Hidden Oaks Condo 8 $194,788 122
Winter Park Horton Aaron 1 $1,800,000 86
Winter Park Howell Branch Woods 2 $414,995 55
Winter Park Howell Estates 1st 1 $460,000 210
Winter Park Howell Estates Rep 1 $450,000 2
Winter Park Hyde Park 1 $449,000 36
Winter Park J Kronenberger 2 $4,587,500 101
Winter Park Justamere Camp Rep 1 $409,900 36
Winter Park Karolina On Killarney 3 $922,666 131
Winter Park Kawilla Crest 1 $639,000 44
Winter Park Kenilworth Shores 12 $1,820,791 48
Winter Park Killarney Bay Condo 1 $475,000 205
Winter Park Killarney Circle 3 $624,633 417
Winter Park Killarney Estates 6 $1,554,167 57
Winter Park Killarney Point 1 $689,000 84
Winter Park Kings Cove 1 $599,900 58
Winter Park Knowles Manor North Condo 1 $424,400 56
Winter Park Lake Ann Estates 2 $805,000 11
Winter Park Lake Bell Terrace 2 $629,500 101
Winter Park Lake Florence Preserve 2 $1,412,450 76
Winter Park Lake Forest Park 3 $2,186,000 78
Winter Park Lake Killarney Condo 3 $274,999 241
Winter Park Lake Killarney Condominium Assn Inc. 1 $199,900 65
Winter Park Lake Killarney Shores 1 $1,389,500 305
Winter Park Lake Knowles Terrace 7 $1,296,714 50
Winter Park Lake Knowles Terrace 2nd 1 $1,150,000 37
Winter Park Lake Maitland 1 $4,750,000 26
Winter Park Lake Monte 1 $998,000 92
Winter Park Lake Sylvan Shores 1 $2,200,000 43
Winter Park Lake Virginia 1 $999,000 197
Winter Park Lake Waunatta Wods 1 $599,000 18
Winter Park Lake Waunatta Woods 2 $559,000 37
Winter Park Lakeside Estates 2 $1,110,000 48
Winter Park Lakeside Manor 5 $191,740 198
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 562
Winter Park Lakeview Terrace 3 $1,026,333 18
Winter Park Lancelot/winter Park 2 $172,400 12
Winter Park Landings At Hawks Crest 3 $743,332 82
Winter Park Landmark Winter Park Condo 1 $2,350,000 66
Winter Park Laurel Spgs 1 $389,500 132
Winter Park Lawndale 5 $1,248,740 91
Winter Park Lazy Oaks Condo 3 $279,967 66
Winter Park Lords 1 $1,050,000 665
Winter Park Lost Creek 1 $685,000 154
Winter Park Lugano Terrace 1 $2,195,000 283
Winter Park Mack Peter Rev 1 $650,000 32
Winter Park Magnolia Gardens 2 $694,450 42
Winter Park Maitland Shores 1st 1 $3,500,000 78
Winter Park Maitland Shores First 2 $4,175,000 32
Winter Park Mc Intyre Place Condo 1 $635,000 3
Winter Park Mead Garden 1 $190,000 47
Winter Park Meadows At Hawks Crest 5 $770,000 66
Winter Park Metzingers 1 $574,900 170
Winter Park Mondrian/winter Park Twnhms 1 $1,339,000 40
Winter Park Morse & Pennsylvania Twnhms 1 $2,800,000 58
Winter Park Morseland 2 $910,500 67
Winter Park New England Bldg 1 $425,000 103
Winter Park None 5 $1,709,000 74
Winter Park Northwood Terrace 2 $1,747,000 35
Winter Park Not On The List 1 $490,000 68
Winter Park Oakcrest-516 3 $375,000 55
Winter Park Olympia Heights 1 $340,000 1
Winter Park Olympia Heights Annex 1 $499,000 8
Winter Park Orange Grove 1 $2,569,999 45
Winter Park Orange Terrace 1 $459,900 57
Winter Park Orangewood Park 2 $617,500 54
Winter Park Orwin Manor Westminster 3 $842,633 70
Winter Park Osceola Heights 1 $1,199,000 162
Winter Park Osceola Or Lakeview Deed 1 $1,775,000 15
Winter Park Osceola Shores 2 $2,150,000 73
Winter Park Park Grove 3 $4,466,333 13
Winter Park Park Hill 1 $3,500,000 81
Winter Park Park Manor First 1 $1,500,000 28
Winter Park Park North 1 $2,200,000 149
Winter Park Park Pointe Rep 1 $1,000,050 19
Winter Park Park West Condo 2 $724,500 50
Winter Park Parklando 1 $1,049,000 134
Winter Park Parklando #3 1 $1,649,000 171
Winter Park Parklando 03 1 $1,894,000 26
Winter Park Parkview Village 4 $153,375 118
Winter Park Parkview Village Condo 1 $150,000 349
Winter Park Pennsylvania Place Rep 1 $1,895,000 93
Winter Park Pervis Survey For R E 1 $1,799,999 194
Winter Park Phillips Circle Rep 3 $534,667 147
Winter Park Pines 1 $439,900 44
Winter Park Preserve At Hawks Crest 1 $770,000 8
Winter Park Quarters At Winter Park Condo 2 $550,000 45
Winter Park Ridge High 1 $284,000 1
Winter Park Ridge High 1st 1 $299,000 7
Winter Park Robert Dhu Macdonald Park 1 $7,250,000 194
Winter Park Seville Park 2 $537,000 36
Winter Park Shores Lake Killarney 1 $624,900 33
Winter Park Sicilian Shores 1 $2,689,000 135
Winter Park Slovak Village 1 $235,000 60
Winter Park South Interlachen Place 2 $3,522,500 23
Winter Park South Lakemont Shores 3 $1,399,333 119
Winter Park Stansbury Estates 2 $388,500 50
Winter Park Stratford A Winter Park Condo 4 $182,075 105
Winter Park Stratford Winter Park 1 $144,000 187
Winter Park Suburban Homes 1 $535,000 114
Winter Park Suburban Homes First 1 $370,000 44
Winter Park Swoope Park 2 $697,000 127
Winter Park Sylvan Heights 3 $1,760,000 165
Winter Park Sylvan Lake Shores 3 $2,495,000 80
Winter Park Sylvan Park 2 $3,625,000 56
Winter Park Talman Mews 1 $1,450,000 24
Winter Park Tanglewood 1 $562,000 1087
Winter Park Tantum 3 $1,097,667 52
Winter Park Temple Estates 1 $2,385,000 159
Winter Park Temple Terrace 1 $950,000 159
Winter Park Temple Terrace Annex 1 $299,900 9
Winter Park Temple Trail Village 1 $575,000 11
Winter Park Terrazo Del Sol 1 $499,000 158
Winter Park The Enclave Winter Park 10 $1,966,300 111
Winter Park Timberlane Shores 2 $2,520,000 61
Winter Park Town Of Winter Park 1 $2,695,000 77
Winter Park Townhomes/harper Place 1 $540,000 124
Winter Park Trinity Bay 2 $437,450 74
Winter Park Trotters Rep 2 $685,000 74
Winter Park Tuscany Terrace 2 $1,595,000 135
Winter Park Twin Acres 1 $1,675,000 157
Winter Park Unrecorded Plat 1 $540,000 23
Winter Park Urban Green 12 1 $550,000 80
Winter Park Via Lago/hanging Moss Condo 1 $335,000 37
Winter Park Vilasa Twnhms 1 $1,399,000 65
Winter Park Villa View Park 2 $2,120,000 89
Winter Park Village Green 2 $494,000 66
Winter Park Village Winterset Inc 1 $989,500 93
Winter Park Villas Of Aragon Condo 1 $510,000 23
Winter Park Villas Of Casselberry 3 $369,967 83
Winter Park Virginia Heights 1 $995,000 78
Winter Park Virginia Heights Rep 2 $1,325,000 86
Winter Park Virginia Hgts Rep 1 $810,000 72
Winter Park Vistas At Lake Howell 2 $325,000 75
Winter Park Waterbridge 1 $660,000 5
Winter Park Waterfall Cove 4 $121,725 111
Winter Park Waterfall Cove At Winter Park 1 $205,000 536
Winter Park Waterfall Cove At Winter Park Condominium D107 1 $180,000 17
Winter Park Waterfall Cove Of Winter Park 1 $88,999 46
Winter Park Waterfall Cove/winter Park 1 $108,000 136
Winter Park Whispering Waters/phillips Circle Rep 1 $1,825,000 106
Winter Park Whisperwood Condo 4 $209,450 99
Winter Park Windsong Elizabeths Walk 43/81 1 $1,450,000 71
Winter Park Windsong-preserve Point 1 $8,950,000 320
Winter Park Windward Square 5 $286,300 69
Winter Park Winflor Court Pt Rep 1 $4,285,000 129
Winter Park Winter Park 6 $3,413,815 118
Winter Park Winter Park Estates 5 $493,000 64
Winter Park Winter Park Gardens Condo 1 $350,000 92
Winter Park Winter Park Oasis 1 $1,599,000 75
Winter Park Winter Park Pines 8 $651,600 146
Winter Park Winter Park Pines Merrie Oaks 3 $504,967 106
Winter Park Winter Park Pines Patio Homes 2 $309,493 77
Winter Park Winter Park Pines Rep 3 $592,800 92
Winter Park Winter Park Residential 1 $1,849,900 66
Winter Park Winter Park Rev 1 $1,770,000 144
Winter Park Winter Park Village 8 $1,322,063 74
Winter Park Winter Park Villas Condo 1 $199,900 2
Winter Park Winter Park Woods Condo 5 $90,880 93
Winter Park Winter Woods 2 $437,000 148
Winter Park Woodcrest 3 $393,300 43
Winter Park Woodmere Terrace Rep 1 $4,900,000 46
Winter Park Wrenwood 1 $362,000 31
Winter Park Wrenwood Condo 3 $178,300 108
Winter Park Wrenwood Heights 2 $417,500 66
751 Duval Station Road
Jacksonville, FL 32218
(904) 445-7064
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 08/22/2026. The listing information on this page last changed on 08/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 08/22/2026 12:34:14 AM EST) or GAMLS (last updated Fri 08/21/2026 11:15:16 PM EST) or Stellar MLS (last updated Sat 08/22/2026 12:28:50 AM EST) or SPC MLS (last updated Fri 08/21/2026 11:21:14 PM EST) or Martin MLS (last updated Fri 08/21/2026 11:38:12 PM EST) or Indian River MLS (last updated Fri 08/21/2026 11:30:08 PM EST) or Daytona MLS (last updated Fri 08/21/2026 11:36:47 PM EST) or Northeast Florida MLS (last updated Sat 08/22/2026 12:18:54 AM EST) or Beaches MLS (last updated Sat 08/22/2026 12:27:21 AM EST) or BORMLS (last updated Fri 08/21/2026 11:17:41 PM EST) or Scout MLS (Golden Isles) (last updated Fri 08/21/2026 7:06:22 AM EST) or Amelia/Nassau MLS (last updated Fri 08/21/2026 11:25:20 PM EST) or Dixie Gilchrist Levy MLS (last updated Fri 08/21/2026 11:42:19 PM EST) or NFLMLS (last updated Fri 08/21/2026 9:06:38 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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