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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 $2,170,000 121
Winter Park Acreage 1 $399,900 11
Winter Park Albert Lee Ridge 2 $699,000 10
Winter Park Albert Lee Ridge 1st 1 $470,000 51
Winter Park Aloma 3 $564,500 186
Winter Park Aloma Park 1 $289,000 28
Winter Park Aloma Trails 2 $375,000 30
Winter Park Aragon Condo 1 $209,999 165
Winter Park Autumn Glen 1 $535,000 36
Winter Park Banks Colonial Estates 1 $1,200,000 21
Winter Park Bear Gully Forest 1 $499,900 146
Winter Park Bldg 6 1 $155,000 108
Winter Park Brookshire Heights 2 $1,237,500 66
Winter Park Brookshire Heights 1st 3 $1,231,333 58
Winter Park Brookshire Heights 2nd 1 $595,000 23
Winter Park Brookshire Heights 4th 1 $1,115,000 28
Winter Park Campo Bello 1 $639,900 46
Winter Park Capens 3 $649,667 263
Winter Park Carolyn Estates 1 $439,995 38
Winter Park Carver Town 1 $399,999 24
Winter Park Casa Aloma 3 $481,667 189
Winter Park Cedarwood Village 1 6 $267,983 83
Winter Park Charmont 8 $2,443,363 87
Winter Park Chateaux Du Lac 4 $237,850 118
Winter Park Cinnamon Shores 1 $2,200,000 87
Winter Park Cloister Grove 3 $3,996,667 174
Winter Park Cloisters Condo 4 $1,372,000 131
Winter Park College Place Rep 1 $2,200,000 66
Winter Park Colonies 6 $136,650 173
Winter Park Comstock Park 5 $3,465,800 127
Winter Park Conwill Estates 2 $2,500,000 53
Winter Park Coronado Twnhms 1 $339,900 47
Winter Park Coronation 1 $269,000 136
Winter Park Cortland Park 1 $950,000 59
Winter Park Country Lane 2 $477,500 29
Winter Park Dixie Terrace 2 $2,889,450 77
Winter Park Dubsdread Heights 2 $562,000 79
Winter Park Eastbrook 13 $394,861 90
Winter Park Eastgate 2 $949,500 61
Winter Park Ellno Willo 2 $2,521,500 65
Winter Park Enclave At Hawks Crest 1 $415,000 18
Winter Park Fairbanks Park 1 $899,000 164
Winter Park Fairbanks Shores 5th 1 $455,000 68
Winter Park Fernbrook Trails 1 $199,000 25
Winter Park Flamingo Shores 1 $865,000 2
Winter Park Fontainebleau 2 $1,891,500 141
Winter Park Forest Hills 5 $2,461,000 108
Winter Park Four Seasons 1 $169,000 108
Winter Park Four Seasons Condo 4 $182,250 60
Winter Park Fremar 2 $1,299,000 47
Winter Park Garden Acres Rep 02 Blk E 1 $485,000 45
Winter Park Garden Lake Estates 5 $468,800 49
Winter Park Georgetown Estates 2 $482,450 101
Winter Park Glencoe 8 $603,500 79
Winter Park Goldenrod Villas Condo 4 $232,975 252
Winter Park Golfside 2 $697,450 70
Winter Park Golfside Villas Condo 2 $148,845 87
Winter Park Golfview 2 $431,400 102
Winter Park Golfview Heights 2 $810,000 147
Winter Park Grand Pines 1 $280,000 33
Winter Park Grayson Square 4 $433,475 179
Winter Park Green Oaks Rep 2 $3,422,500 74
Winter Park Green Oaks Rep 02 2 $2,785,000 204
Winter Park Green Terrace 1 $1,005,000 35
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,820,000 73
Winter Park Greenview At Winter Pines 1 $899,000 60
Winter Park H Vanwies 2 $899,000 55
Winter Park Hamilton Place 1 $1,349,000 45
Winter Park Henkel 1 $1,095,000 6
Winter Park Hidden Oaks Condo 9 $185,983 108
Winter Park Hidden Oaks Condominium Association, Inc 1 $159,000 32
Winter Park Horton Aaron 1 $2,000,000 4
Winter Park Howell Branch Woods 1 $450,000 17
Winter Park Howell Estates 1st 1 $460,000 128
Winter Park Howell Estates Rep 2 $509,500 28
Winter Park Howell Heights 2 $403,440 49
Winter Park Hyde Park 1 $470,000 19
Winter Park J Kronenberger 3 $3,599,000 80
Winter Park Karolina On Killarney 7 $836,270 49
Winter Park Kawilla Crest 1 $890,000 31
Winter Park Kenilworth Estates 1st 2 $604,500 25
Winter Park Kenilworth Shores 9 $1,206,089 60
Winter Park Killarney Bay Condo 3 $405,000 153
Winter Park Killarney Circle 4 $622,000 288
Winter Park Killarney Estates 4 $2,122,500 91
Winter Park Killarney Point 1 $689,000 2
Winter Park Kings Cove 1 $824,000 24
Winter Park La Casas De Indiana 1 $524,000 28
Winter Park Lake Bell Terrace 3 $786,333 184
Winter Park Lake Florence Preserve 3 $995,667 185
Winter Park Lake Forest Park 6 $1,823,800 40
Winter Park Lake Killarney Condo 2 $268,500 96
Winter Park Lake Killarney Shores 1 $1,449,900 223
Winter Park Lake Knowles Terrace 5 $1,802,800 21
Winter Park Lake Monte 1 $1,095,000 10
Winter Park Lake Virginia 1 $999,000 115
Winter Park Lake Virginia Pt Rep 1 $1,875,000 53
Winter Park Lake Waunatta Village 1 $457,000 131
Winter Park Lakeside Estates 1 $995,000 53
Winter Park Lakeside Manor 7 $183,771 180
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 480
Winter Park Lakeview Terrace 4 $999,000 71
Winter Park Lancelot/winter Park 2 $169,000 58
Winter Park Landings At Hawks Crest 2 $774,950 104
Winter Park Las Casas De Indiana 1 $545,000 110
Winter Park Laurel Spgs 2 $410,000 37
Winter Park Laurel Springs 2 $399,995 9
Winter Park Lawndale 9 $1,064,178 85
Winter Park Lazy Oaks Condo 2 $255,000 69
Winter Park Lords 1 $1,050,000 583
Winter Park Lost Creek 3 $604,967 38
Winter Park Lugano Terrace 1 $2,265,000 201
Winter Park Lyman Ave Villas 1 1 $1,375,000 23
Winter Park Maitland Shores 2 $3,700,000 276
Winter Park Maitland Shores First 2 $2,786,500 114
Winter Park Mead Garden 1 $240,000 39
Winter Park Meadows At Hawks Crest 4 $786,250 59
Winter Park Metzingers 1 $589,900 88
Winter Park Mondrian/winder Park Twnhms 1 $1,099,000 87
Winter Park Morseland 1 $1,185,999 33
Winter Park New England Bldg 1 $425,000 21
Winter Park None 5 $1,180,400 132
Winter Park Northwood Terrace 1 $649,000 220
Winter Park Oakcrest-516 1 $200,000 56
Winter Park Orange Terrace 1 $480,000 298
Winter Park Orwin Manor Stratford 1 $725,000 32
Winter Park Orwin Manor Westminster 5 $1,081,800 125
Winter Park Osceola Heights 1 $1,299,000 80
Winter Park Osceola Place 1 $6,495,000 222
Winter Park Osceola Shores 2 $2,049,500 71
Winter Park Park Grove 1 $2,895,000 26
Winter Park Park Hill 1 $4,295,000 18
Winter Park Park Manor 2 $1,024,000 114
Winter Park Park North 1 $2,495,000 67
Winter Park Park West Condo 1 $750,000 10
Winter Park Parklando 2 $904,875 52
Winter Park Parklando #3 1 $1,649,000 89
Winter Park Parklando 03 1 $1,924,450 407
Winter Park Parkview Village 4 $176,600 324
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 82
Winter Park Pennsylvania Place Rep 1 $1,895,000 11
Winter Park Pervis Survey For R E 1 $1,799,999 112
Winter Park Phillips Circle Rep 3 $314,300 247
Winter Park Preserve At Hawks Crest 2 $694,450 279
Winter Park Quail Hollow 1 $1,295,000 39
Winter Park Quail Run 1 $649,900 45
Winter Park Replat Of Lts 1 2 & 3 Brookside 1 $510,000 39
Winter Park Robert Dhu Macdonald Park 1 $6,950,000 112
Winter Park Sanctuary At Aloma 1 $665,000 122
Winter Park Sandlewood Creek Condo 1 $314,000 114
Winter Park Sevilla 2 $2,167,500 166
Winter Park Seville Park 2 $549,950 63
Winter Park Shores Lake Killarney 1 $750,000 27
Winter Park Sicilian Shores 1 $2,790,000 53
Winter Park Sicilian Shores Rep 02 1 $4,650,000 66
Winter Park Slovak Village 1 $317,500 222
Winter Park South Lakemont Shores 3 $1,450,000 37
Winter Park Stratford A Winter Park Condo 7 $185,684 121
Winter Park Stratford Winter Park 1 $144,000 105
Winter Park Suburban Homes 3 $460,000 35
Winter Park Swoope Park 1 $695,000 131
Winter Park Sylvan Heights 4 $1,519,750 90
Winter Park Sylvan Hgts 1 $739,000 32
Winter Park Sylvan Lake Shores 3 $2,230,000 57
Winter Park Sylvan Park 2 $1,022,000 63
Winter Park Tanglewood 2 $506,000 534
Winter Park Temple Estates 1 $2,385,000 77
Winter Park Temple Terrace 2 $1,099,500 62
Winter Park Terazzo Del Sol Condo Assn Inc 1 $549,000 138
Winter Park Terrazo Del Sol 1 $525,000 76
Winter Park The Enclave Winter Park 11 $1,962,545 33
Winter Park Timberlane Shores 2 $1,520,000 82
Winter Park Townhomes/harper Place 1 $539,000 42
Winter Park Trotters Rep 1 $745,000 24
Winter Park Tuscania 2 $2,000,000 112
Winter Park Tuscany Terrace 1 $1,595,000 115
Winter Park Twin Acres 2 $1,995,000 97
Winter Park Valencia Terrace 1 $3,995,000 284
Winter Park Villa View Park 1 $1,925,000 74
Winter Park Village Green 1 $549,000 42
Winter Park Village Winterset Inc 2 $804,250 47
Winter Park Village/whisperwood 1 $236,800 95
Winter Park Villas Of Casselberry 4 $371,225 28
Winter Park Virginia Heights 3 $4,463,333 105
Winter Park Virginia Heights Rep 1 $1,695,000 32
Winter Park Vistas At Lake Howell 2 $345,000 53
Winter Park Waterfall Cove 3 $121,330 103
Winter Park Waterfall Cove At Winter Park 1 $205,000 454
Winter Park Waterfall Cove At Winter Park Condo 1 $120,000 69
Winter Park Waterfall Cove Winter Park 1 $134,900 66
Winter Park Waterfall Cove/winter Park 1 $125,000 28
Winter Park Whispering Waters/phillips Circle Rep 1 $1,995,000 24
Winter Park Whisperwood Condo 4 $221,975 152
Winter Park Windsong - Knowles Place 1 $1,875,000 31
Winter Park Windsong Elizabeths Walk 1 $1,395,000 17
Winter Park Windsong Elizabeths Walk 43/81 1 $2,195,000 59
Winter Park Windsong Lakeside 1 $2,699,000 61
Winter Park Windsong-preserve Point 1 $8,950,000 238
Winter Park Windward Square 4 $294,750 70
Winter Park Winflor Court Pt Rep 2 $4,267,500 31
Winter Park Winter Green 1 $300,000 88
Winter Park Winter Park 5 $3,736,778 132
Winter Park Winter Park Estates 7 $459,571 198
Winter Park Winter Park Gardens Condo 2 $340,000 10
Winter Park Winter Park Manor 1 $399,500 41
Winter Park Winter Park Oaks 1 $285,000 53
Winter Park Winter Park Pines 9 $632,667 76
Winter Park Winter Park Pines Merrie Oaks 2 $502,450 66
Winter Park Winter Park Pines Patio Homes 1 $318,985 61
Winter Park Winter Park Pines Rep 2 $692,450 77
Winter Park Winter Park Pines Ut 5 1 $719,000 67
Winter Park Winter Park Rev 1 $1,795,000 62
Winter Park Winter Park Village 6 $1,549,917 56
Winter Park Winter Park Villas 1 $199,900 36
Winter Park Winter Park Woods Condo 3 $119,633 151
Winter Park Winter Woods 2 $447,500 98
Winter Park Wrenwood 1 $489,000 18
Winter Park Wrenwood Condo 3 $195,967 68
Winter Park Wrenwood Heights 2 $454,995 30
Kelly Kinney
Kelly Kinney Cell: (904) 477-4425 Email Me
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 06/01/2026. The listing information on this page last changed on 06/01/2026. 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 Mon 06/01/2026 12:04:13 AM EST) or GAMLS (last updated Sun 05/31/2026 11:15:04 PM EST) or Stellar MLS (last updated Sun 05/31/2026 11:58:52 PM EST) or SPC MLS (last updated Sun 05/31/2026 11:20:58 PM EST) or Martin MLS (last updated Sun 05/31/2026 11:38:09 PM EST) or Indian River MLS (last updated Sun 05/31/2026 11:30:15 PM EST) or Daytona MLS (last updated Sun 05/31/2026 11:36:47 PM EST) or Northeast Florida MLS (last updated Sun 05/31/2026 11:58:51 PM EST) or Beaches MLS (last updated Sun 05/31/2026 11:57:34 PM EST) or BORMLS (last updated Sun 05/31/2026 11:15:26 PM EST) or Golden Isles MLS (last updated Sun 05/31/2026 7:04:45 AM EST) or Amelia/Nassau MLS (last updated Sun 05/31/2026 11:25:11 PM EST) or Dixie Gilchrist Levy MLS (last updated Sun 05/31/2026 11:42:15 PM EST) or NFLMLS (last updated Sun 05/31/2026 9:05:10 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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