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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 147 Interlachen Place 1 $2,195,000 108
Winter Park Albert Lee Ridge 1st 1 $470,000 38
Winter Park Albert Lee Ridge First 1 $490,000 75
Winter Park Aloma 3 $564,500 173
Winter Park Aloma Park 1 $295,000 15
Winter Park Aloma Trails 1 $390,000 39
Winter Park Aragon Condo 1 $209,999 152
Winter Park Autumn Glen 1 $535,000 23
Winter Park Banks Colonial Estates 1 $1,200,000 8
Winter Park Bear Gully Forest 1 $524,900 133
Winter Park Bldg 6 1 $155,000 95
Winter Park Brookshire Heights 2 $1,237,500 53
Winter Park Brookshire Heights 1st 3 $1,231,333 45
Winter Park Brookshire Heights 2nd 1 $595,000 10
Winter Park Brookshire Heights 4th 2 $899,500 23
Winter Park Campo Bello 1 $649,800 33
Winter Park Capens 3 $649,667 250
Winter Park Carolyn Estates 1 $439,995 25
Winter Park Carver Town 2 $462,500 43
Winter Park Casa Aloma 4 $467,475 162
Winter Park Cedarwood Village 1 5 $273,580 85
Winter Park Charmont 8 $2,455,863 74
Winter Park Chateaux Du Lac 4 $237,850 105
Winter Park Cinnamon Shores 1 $2,200,000 74
Winter Park Cloister Grove 3 $3,996,667 161
Winter Park Cloisters Condo 4 $1,372,000 118
Winter Park College Place Rep 1 $2,200,000 53
Winter Park Colonies 10 $124,580 164
Winter Park Comstock Park 4 $2,832,250 145
Winter Park Conwill Estates 3 $2,049,000 38
Winter Park Coronado Twnhms 1 $339,900 34
Winter Park Coronation 2 $284,500 111
Winter Park Cortland Park 1 $950,000 46
Winter Park Country Lane 2 $482,500 16
Winter Park Dixie Terrace 2 $2,889,450 64
Winter Park Dubsdread Heights 2 $562,000 66
Winter Park Eastbrook 14 $400,228 79
Winter Park Eastgate 4 $659,700 46
Winter Park Ellno Willo 2 $2,572,500 52
Winter Park Enclave At Aloma 1 $599,000 21
Winter Park Enclave At Hawks Crest 2 $425,000 83
Winter Park Fairbanks Park 1 $899,000 151
Winter Park Fairbanks Shores 5th 1 $459,000 55
Winter Park Fernbrook Trails 2 $247,000 78
Winter Park Fontainebleau 2 $1,891,500 128
Winter Park Forest Hills 5 $2,461,000 95
Winter Park Four Seasons 1 $169,000 95
Winter Park Four Seasons Condo 4 $186,000 69
Winter Park Fremar 2 $1,299,000 34
Winter Park Garden Acres Rep 02 Blk E 1 $485,000 32
Winter Park Garden Lake Estates 4 $495,750 84
Winter Park Georgetown Estates 2 $484,995 88
Winter Park Glencoe 7 $577,000 77
Winter Park Goldenrod Villas Condo 4 $233,450 239
Winter Park Golfside 3 $647,967 50
Winter Park Golfside Villas Condo 2 $148,845 74
Winter Park Golfview 2 $431,750 89
Winter Park Golfview Heights 2 $810,000 134
Winter Park Grand Pines 1 $280,000 20
Winter Park Grayson Square 4 $433,475 201
Winter Park Green Oaks Rep 2 $3,422,500 61
Winter Park Green Oaks Rep 02 2 $2,785,000 191
Winter Park Green Oaks Rep 03 1 $1,425,000 132
Winter Park Green Terrace 1 $1,005,000 22
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,890,000 60
Winter Park Greenview At Winter Pines 1 $899,000 47
Winter Park H Vanwies 2 $899,000 42
Winter Park Hamilton Place 1 $1,349,000 32
Winter Park Hawks Crest 1 $845,000 55
Winter Park Hidden Oaks Condo 9 $186,822 95
Winter Park Hidden Oaks Condominium Association, Inc 1 $169,500 19
Winter Park Howell Branch Woods 2 $427,500 27
Winter Park Howell Estates 1st 1 $470,000 115
Winter Park Howell Estates Rep 3 $473,000 23
Winter Park Howell Heights 2 $408,440 36
Winter Park Hyde Park 1 $470,000 6
Winter Park J Kronenberger 3 $3,616,000 67
Winter Park Karolina On Killarney 5 $970,778 53
Winter Park Kawilla Crest 1 $890,000 18
Winter Park Kenilworth Estates 1st 2 $604,500 12
Winter Park Kenilworth Shores 7 $1,308,686 62
Winter Park Killarney Bay Condo 3 $410,000 140
Winter Park Killarney Circle 4 $622,000 275
Winter Park Killarney Estates 2 $2,795,000 159
Winter Park Kings Cove 1 $824,000 11
Winter Park La Casas De Indiana 1 $524,000 15
Winter Park Lake Bell Terrace 3 $786,333 171
Winter Park Lake Florence Preserve 2 $894,000 263
Winter Park Lake Forest Park 5 $1,796,760 34
Winter Park Lake Killarney Condo 1 $298,000 168
Winter Park Lake Killarney Shores 1 $1,499,900 210
Winter Park Lake Knowles Terrace 4 $2,325,000 41
Winter Park Lake Monte 1 $1,689,000 112
Winter Park Lake Virginia 1 $999,000 102
Winter Park Lake Virginia Pt Rep 1 $1,875,000 40
Winter Park Lake Waunatta Village 1 $457,000 118
Winter Park Lakeside Estates 2 $1,172,500 78
Winter Park Lakeside Manor 7 $183,771 167
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 467
Winter Park Lakeview Terrace 3 $1,165,667 80
Winter Park Lancelot/winter Park 2 $169,500 45
Winter Park Landings At Hawks Crest 2 $774,950 91
Winter Park Las Casas De Indiana 1 $545,000 97
Winter Park Laurel Spgs 2 $410,000 24
Winter Park Laurel Springs 1 $400,000 1
Winter Park Lawndale 8 $1,110,325 82
Winter Park Lazy Oaks Condo 3 $268,333 53
Winter Park Lords 1 $1,050,000 570
Winter Park Lost Creek 2 $574,950 39
Winter Park Lugano Terrace 1 $2,265,000 188
Winter Park Lyman Ave Villas 1 1 $1,375,000 10
Winter Park Maitland Shores 2 $3,725,000 263
Winter Park Maitland Shores First 2 $2,786,500 101
Winter Park Mead Garden 1 $240,000 26
Winter Park Meadows At Hawks Crest 4 $786,250 46
Winter Park Metzingers 1 $589,900 75
Winter Park Mondrian/winder Park Twnhms 2 $1,247,000 71
Winter Park Morseland 1 $1,185,999 20
Winter Park New England Bldg 1 $425,000 8
Winter Park None 4 $1,350,500 152
Winter Park Northwood Terrace 1 $659,000 207
Winter Park Oakcrest-516 1 $200,000 43
Winter Park Orange Terrace 1 $484,000 285
Winter Park Orwin Manor Stratford 1 $725,000 19
Winter Park Orwin Manor Westminster 5 $1,081,800 112
Winter Park Osceola Place 1 $6,495,000 209
Winter Park Osceola Shores 2 $2,049,500 58
Winter Park Park Aire Condo 1 $450,000 152
Winter Park Park Grove 1 $2,895,000 13
Winter Park Park Grove W/125 Lot 10 Blk D 1 $2,200,000 54
Winter Park Park Hill 1 $4,295,000 5
Winter Park Park Manor 2 $1,037,000 101
Winter Park Park North 1 $2,495,000 54
Winter Park Parklando 3 $1,366,250 87
Winter Park Parklando #3 1 $1,649,000 76
Winter Park Parklando 03 1 $1,949,500 394
Winter Park Parkview Village 4 $183,850 541
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 69
Winter Park Pervis Survey For R E 1 $1,850,000 99
Winter Park Phillips Circle Rep 3 $319,600 234
Winter Park Preserve At Hawks Crest 2 $694,450 266
Winter Park Quail Hollow 1 $1,295,000 26
Winter Park Quail Run 1 $649,900 32
Winter Park Quarters At Winter Park Condo 1 $595,000 176
Winter Park Replat Of Lts 1 2 & 3 Brookside 1 $510,000 26
Winter Park Robert Dhu Macdonald Park 3 $3,316,667 78
Winter Park Sanctuary At Aloma 1 $665,000 109
Winter Park Sandlewood Creek Condo 1 $314,000 101
Winter Park Sevilla 2 $2,175,000 153
Winter Park Seville Park 2 $554,950 50
Winter Park Shores Lake Killarney 1 $750,000 14
Winter Park Sicilian Shores 2 $3,042,500 63
Winter Park Sicilian Shores Rep 02 1 $4,650,000 53
Winter Park Slovak Village 1 $317,500 209
Winter Park South Lakemont Shores 2 $1,350,000 40
Winter Park Stratford A Winter Park Condo 6 $175,148 127
Winter Park Stratford Winter Park 1 $144,000 92
Winter Park Suburban Homes 3 $461,667 22
Winter Park Swoope Park 1 $695,000 118
Winter Park Sylvan Heights 4 $1,519,750 77
Winter Park Sylvan Hgts 1 $739,000 19
Winter Park Sylvan Lake Shores 3 $2,263,333 44
Winter Park Sylvan Park 2 $1,022,000 50
Winter Park Tanglewood 2 $518,500 521
Winter Park Temple Estates 1 $2,385,000 64
Winter Park Temple Terrace 2 $1,149,500 49
Winter Park Terazzo Del Sol Condo Assn Inc 1 $549,000 125
Winter Park Terrazo Del Sol 1 $550,000 63
Winter Park The Enclave Winter Park 6 $1,793,167 42
Winter Park Timberlane 1 $850,000 63
Winter Park Timberlane Shores 2 $1,520,000 69
Winter Park Townhomes/harper Place 1 $539,000 29
Winter Park Trotters Rep 1 $745,000 11
Winter Park Tuscania 2 $2,000,000 99
Winter Park Tuscany Terrace 1 $1,595,000 102
Winter Park Twin Acres 2 $1,995,000 84
Winter Park Valencia Terrace 1 $4,075,000 271
Winter Park Villa View Park 1 $1,925,000 61
Winter Park Village Green 1 $549,000 29
Winter Park Village Winterset Inc 1 $619,000 70
Winter Park Village/whisperwood 1 $236,800 82
Winter Park Villas Of Casselberry 4 $369,975 44
Winter Park Virginia Heights 3 $4,463,333 92
Winter Park Virginia Heights Rep 2 $1,242,500 26
Winter Park Vistas At Lake Howell 1 $355,000 84
Winter Park Waterfall Cove 3 $124,663 90
Winter Park Waterfall Cove At Winter Park 1 $205,000 441
Winter Park Waterfall Cove At Winter Park Condo 1 $120,000 56
Winter Park Waterfall Cove Winter Park 1 $139,990 53
Winter Park Waterfall Cove/winter Park 1 $125,000 15
Winter Park Whispering Waters/phillips Circle Rep 2 $2,087,500 73
Winter Park Whisperwood Condo 4 $222,225 139
Winter Park Windsong Elizabeths Walk 1 $1,395,000 4
Winter Park Windsong Elizabeths Walk 43/81 1 $2,195,000 46
Winter Park Windsong Lakeside 1 $2,699,000 48
Winter Park Windsong-knowles Place 1 $1,995,000 18
Winter Park Windsong-preserve Point 1 $8,950,000 225
Winter Park Windward Square 3 $268,333 115
Winter Park Winflor Court Pt Rep 2 $4,267,500 18
Winter Park Winter Green 1 $300,000 75
Winter Park Winter Park 5 $3,736,778 119
Winter Park Winter Park Estates 6 $469,667 218
Winter Park Winter Park Manor 1 $399,500 28
Winter Park Winter Park Oaks 1 $285,000 40
Winter Park Winter Park Pines 6 $657,500 97
Winter Park Winter Park Pines Merrie Oaks 2 $652,450 74
Winter Park Winter Park Pines Patio Homes 1 $318,985 48
Winter Park Winter Park Pines Rep 2 $699,750 64
Winter Park Winter Park Pines Ut 5 1 $719,000 54
Winter Park Winter Park Residential 1 $1,450,000 54
Winter Park Winter Park Rev 1 $1,795,000 49
Winter Park Winter Park Village 5 $1,619,900 53
Winter Park Winter Park Villas 1 $199,900 23
Winter Park Winter Park Woods Condo 3 $119,633 138
Winter Park Winter Woods 1 $375,000 12
Winter Park Wrenwood 1 $489,000 5
Winter Park Wrenwood Condo 5 $196,579 70
Winter Park Wrenwood Heights 2 $454,995 17
4194 San Juan Avenue
Jacksonville, FL 32210
(904) 219-5033
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 05/19/2026. The listing information on this page last changed on 05/19/2026. 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 Tue 05/19/2026 12:02:02 AM EST) or GAMLS (last updated Mon 05/18/2026 11:15:10 PM EST) or Stellar MLS (last updated Mon 05/18/2026 11:44:07 PM EST) or SPC MLS (last updated Mon 05/18/2026 11:21:11 PM EST) or Martin MLS (last updated Mon 05/18/2026 11:38:10 PM EST) or Indian River MLS (last updated Mon 05/18/2026 11:30:19 PM EST) or Daytona MLS (last updated Mon 05/18/2026 11:36:42 PM EST) or Northeast Florida MLS (last updated Mon 05/18/2026 11:58:55 PM EST) or Beaches MLS (last updated Mon 05/18/2026 11:52:15 PM EST) or BORMLS (last updated Mon 05/18/2026 11:15:04 PM EST) or Golden Isles MLS (last updated Mon 05/18/2026 11:26:19 PM EST) or Amelia/Nassau MLS (last updated Mon 05/18/2026 11:25:11 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 05/18/2026 11:42:15 PM EST) or NFLMLS (last updated Mon 05/18/2026 9:04:28 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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