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Leona Decastro
Five Star, REALTOR®, SRES
(904) 710-2163
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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 $2,272,000 102
Winter Park Albert Lee Ridge 1st 1 $470,000 32
Winter Park Albert Lee Ridge First 1 $490,000 69
Winter Park Aloma 3 $564,500 167
Winter Park Aloma Park 1 $295,000 9
Winter Park Aloma Trails 1 $390,000 33
Winter Park Aragon Condo 1 $209,999 146
Winter Park Autumn Glen 1 $535,000 17
Winter Park Banks Colonial Estates 1 $1,200,000 2
Winter Park Bear Gully Forest 1 $524,900 127
Winter Park Bldg 6 1 $155,000 89
Winter Park Bridgewater 1 $425,000 20
Winter Park Brookshire Heights 2 $1,237,500 47
Winter Park Brookshire Heights 1st 3 $1,231,333 39
Winter Park Brookshire Heights 2nd 1 $595,000 4
Winter Park Brookshire Heights 4th 2 $899,500 17
Winter Park Campo Bello 1 $649,800 27
Winter Park Camwood 1 $4,995,000 209
Winter Park Capens 3 $649,667 244
Winter Park Carolyn Estates 1 $439,995 19
Winter Park Carver Town 2 $462,500 37
Winter Park Casa Aloma 4 $467,475 156
Winter Park Cedarwood Village 1 5 $273,580 79
Winter Park Charmont 8 $2,467,250 68
Winter Park Chateaux Du Lac 4 $240,125 112
Winter Park Cinnamon Shores 1 $2,200,000 68
Winter Park Cloister Grove 3 $3,996,667 155
Winter Park Cloisters Condo 4 $1,380,750 112
Winter Park College Place Rep 1 $2,200,000 47
Winter Park Colonies 10 $124,580 158
Winter Park Comstock Park 6 $2,321,500 102
Winter Park Conwill Estates 3 $2,049,000 32
Winter Park Coronado Twnhms 1 $339,900 28
Winter Park Coronation 2 $284,500 105
Winter Park Cortland Park 1 $950,000 40
Winter Park Country Lane 1 $475,000 22
Winter Park Dixie Terrace 2 $2,924,450 58
Winter Park Dubsdread Heights 3 $501,333 66
Winter Park Eastbrook 12 $396,516 85
Winter Park Eastgate 4 $659,700 40
Winter Park Ellno Willo 2 $2,572,500 46
Winter Park Enclave At Aloma 1 $599,000 15
Winter Park Enclave At Hawks Crest 1 $435,000 155
Winter Park Fairbanks Park 1 $899,000 145
Winter Park Fairbanks Shores 5th 1 $459,000 49
Winter Park Fernbrook Trails 3 $261,333 66
Winter Park Fontainebleau 2 $1,891,500 122
Winter Park Forest Hills 5 $2,461,000 89
Winter Park Four Seasons 1 $169,000 89
Winter Park Four Seasons Condo 5 $186,800 75
Winter Park Fremar 2 $1,299,000 28
Winter Park Garden Acres Rep 02 Blk E 1 $485,000 26
Winter Park Garden Lake Estates 3 $528,000 104
Winter Park Georgetown Estates 2 $484,995 82
Winter Park Glencoe 6 $553,333 83
Winter Park Goldenrod Villas Condo 4 $233,700 233
Winter Park Golfside 3 $647,967 44
Winter Park Golfside Villas Condo 2 $148,845 68
Winter Park Golfview 2 $432,000 83
Winter Park Golfview Heights 2 $810,000 128
Winter Park Grand Pines 1 $280,000 14
Winter Park Grayson Square 3 $436,300 261
Winter Park Green Oaks Rep 2 $3,422,500 55
Winter Park Green Oaks Rep 02 2 $2,785,000 185
Winter Park Green Oaks Rep 03 1 $1,425,000 126
Winter Park Green Terrace 1 $1,005,000 16
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,890,000 54
Winter Park Greenview At Winter Pines 1 $899,000 41
Winter Park H Vanwies 1 $899,000 72
Winter Park Hamilton Place 1 $1,349,000 26
Winter Park Hawks Crest 1 $845,000 49
Winter Park Hidden Oaks Condo 9 $187,267 89
Winter Park Hidden Oaks Condominium Association, Inc 1 $169,500 13
Winter Park Howell Branch Woods 1 $405,000 44
Winter Park Howell Estates 1st 1 $470,000 109
Winter Park Howell Estates Rep 3 $473,000 17
Winter Park Howell Heights 1 $439,000 61
Winter Park Hyde Park 1 $470,000 0
Winter Park J Kronenberger 3 $3,616,000 61
Winter Park Karolina On Killarney 5 $970,778 47
Winter Park Kawilla Crest 1 $899,999 12
Winter Park Kenilworth Estates 1st 1 $490,000 12
Winter Park Kenilworth Shores 6 $1,376,967 66
Winter Park Killarney Bay Condo 2 $410,000 202
Winter Park Killarney Circle 4 $632,000 269
Winter Park Killarney Estates 3 $2,026,697 119
Winter Park Kings Cove 1 $824,000 5
Winter Park La Casas De Indiana 1 $524,000 9
Winter Park Lake Bell Terrace 3 $786,333 165
Winter Park Lake Florence Preserve 2 $894,000 257
Winter Park Lake Forest Park 4 $1,648,450 35
Winter Park Lake Killarney Condo 1 $298,000 162
Winter Park Lake Killarney Shores 1 $1,499,900 204
Winter Park Lake Knowles Terrace 4 $2,325,000 35
Winter Park Lake Monte 1 $1,689,000 106
Winter Park Lake Virginia 1 $999,000 96
Winter Park Lake Virginia Pt Rep 1 $1,875,000 34
Winter Park Lake Waunatta Village 1 $457,000 112
Winter Park Lakeside Estates 2 $1,172,500 72
Winter Park Lakeside Manor 7 $184,486 161
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 461
Winter Park Lakeview Terrace 3 $1,182,333 74
Winter Park Lancelot/winter Park 2 $169,500 39
Winter Park Landings At Hawks Crest 2 $774,950 85
Winter Park Las Casas De Indiana 1 $545,000 91
Winter Park Laurel Spgs 2 $418,750 18
Winter Park Lawndale 8 $1,122,713 76
Winter Park Lazy Oaks Condo 3 $268,333 47
Winter Park Lords 2 $1,372,500 319
Winter Park Lost Creek 3 $592,967 32
Winter Park Lugano Terrace 1 $2,265,000 182
Winter Park Lyman Ave Villas 1 1 $1,375,000 4
Winter Park Maitland Shores 2 $3,725,000 257
Winter Park Maitland Shores First 2 $2,786,500 95
Winter Park Mead Garden 1 $240,000 20
Winter Park Meadows At Hawks Crest 4 $786,250 40
Winter Park Metzingers 1 $589,900 69
Winter Park Mondrian/winder Park Twnhms 2 $1,247,000 65
Winter Park Morseland 1 $1,185,999 14
Winter Park New England Bldg 1 $425,000 2
Winter Park None 4 $1,350,500 146
Winter Park Northwood Terrace 1 $659,000 201
Winter Park Oakcrest-516 1 $200,000 37
Winter Park Orange Terrace 1 $484,000 279
Winter Park Orwin Manor Stratford 1 $725,000 13
Winter Park Orwin Manor Westminster 5 $1,081,800 106
Winter Park Osceola Place 1 $6,495,000 203
Winter Park Osceola Shores 2 $2,049,500 52
Winter Park Park Aire Condo 1 $450,000 146
Winter Park Park Grove 1 $2,895,000 7
Winter Park Park Grove W/125 Lot 10 Blk D 1 $2,200,000 48
Winter Park Park Manor 2 $1,037,000 95
Winter Park Park North 1 $2,495,000 48
Winter Park Parklando 3 $1,378,000 81
Winter Park Parklando #3 1 $1,690,000 70
Winter Park Parklando 03 1 $1,949,500 388
Winter Park Parkview Village 4 $183,850 535
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 63
Winter Park Pervis Survey For R E 1 $1,850,000 93
Winter Park Phillips Circle Rep 3 $319,600 228
Winter Park Pinewood 2 $415,000 138
Winter Park Preserve At Hawks Crest 2 $694,450 260
Winter Park Quail Hollow 1 $1,295,000 20
Winter Park Quail Run 1 $649,900 26
Winter Park Quarters At Winter Park Condo 1 $625,000 170
Winter Park Replat Of Lts 1 2 & 3 Brookside 1 $510,000 20
Winter Park Robert Dhu Macdonald Park 3 $3,316,667 72
Winter Park Sanctuary At Aloma 1 $665,000 103
Winter Park Sandlewood Creek Condo 1 $314,000 95
Winter Park Sevilla 2 $2,175,000 147
Winter Park Seville Park 1 $510,000 89
Winter Park Shores Lake Killarney 1 $750,000 8
Winter Park Sicilian Shores 3 $4,360,667 42
Winter Park Sicilian Shores Rep 02 1 $4,650,000 47
Winter Park Slovak Village 1 $317,500 203
Winter Park Sorensen Heights 1 $3,250,000 163
Winter Park South Lakemont Shores 2 $1,350,000 34
Winter Park Stratford A Winter Park Condo 7 $172,984 118
Winter Park Stratford Winter Park 1 $144,000 86
Winter Park Suburban Homes 2 $470,000 25
Winter Park Suburban Homes First 1 $375,000 97
Winter Park Swoope Park 1 $695,000 112
Winter Park Sylvan Heights 3 $1,818,000 95
Winter Park Sylvan Hgts 1 $739,000 13
Winter Park Sylvan Lake Shores 2 $1,745,000 59
Winter Park Sylvan Park 2 $1,022,000 44
Winter Park Tanglewood 2 $518,500 515
Winter Park Temple Estates 1 $2,385,000 58
Winter Park Temple Terrace 2 $1,149,500 43
Winter Park Terazzo Del Sol Condo Assn Inc 1 $549,000 119
Winter Park Terrazo Del Sol 1 $550,000 57
Winter Park The Enclave Winter Park 4 $1,702,500 54
Winter Park Timberlane 1 $850,000 57
Winter Park Timberlane Shores 2 $1,520,000 63
Winter Park Town Of Winter Park 1 $450,000 26
Winter Park Townhomes/harper Place 1 $539,000 23
Winter Park Trotters Rep 1 $745,000 5
Winter Park Tuscania 3 $2,731,667 71
Winter Park Tuscany Terrace 1 $1,595,000 96
Winter Park Twin Acres 2 $2,045,000 78
Winter Park Valencia Terrace 1 $4,200,000 265
Winter Park Villa View Park 1 $1,925,000 55
Winter Park Village Green 2 $442,500 29
Winter Park Village Winterset Inc 1 $619,000 64
Winter Park Village/whisperwood 1 $236,800 76
Winter Park Villas Of Casselberry 4 $369,975 38
Winter Park Virginia Heights 3 $4,463,333 86
Winter Park Virginia Heights Rep 2 $1,242,500 20
Winter Park Vistas At Lake Howell 1 $355,000 78
Winter Park Waterfall Cove 3 $124,663 84
Winter Park Waterfall Cove At Winter Park 1 $205,000 435
Winter Park Waterfall Cove At Winter Park Condo 1 $120,000 50
Winter Park Waterfall Cove Winter Park 1 $139,990 47
Winter Park Waterfall Cove/winter Park 1 $125,000 9
Winter Park Whispering Waters/phillips Circle Rep 2 $2,087,500 67
Winter Park Whisperwood Condo 3 $213,000 117
Winter Park Windsong Elizabeths Walk 43/81 1 $2,195,000 40
Winter Park Windsong Lakeside 1 $2,795,000 42
Winter Park Windsong-knowles Place 1 $1,995,000 12
Winter Park Windsong-preserve Point 1 $8,950,000 219
Winter Park Windward Square 3 $268,333 109
Winter Park Winflor Court Pt Rep 1 $4,285,000 28
Winter Park Winter Green 1 $300,000 69
Winter Park Winter Park 4 $2,948,750 142
Winter Park Winter Park Estates 6 $469,667 212
Winter Park Winter Park Manor 1 $399,500 22
Winter Park Winter Park Oaks 1 $285,000 34
Winter Park Winter Park Pines 6 $658,167 101
Winter Park Winter Park Pines Merrie Oaks 2 $652,450 68
Winter Park Winter Park Pines Patio Homes 1 $318,985 42
Winter Park Winter Park Pines Rep 2 $700,000 58
Winter Park Winter Park Pines Ut 5 1 $729,000 48
Winter Park Winter Park Residential 1 $1,450,000 48
Winter Park Winter Park Rev 1 $1,795,000 43
Winter Park Winter Park Village 4 $1,608,625 59
Winter Park Winter Park Villas 1 $199,900 17
Winter Park Winter Park Woods Condo 3 $119,633 132
Winter Park Winter Woods 2 $447,500 79
Winter Park Wrenwood 1 $435,000 42
Winter Park Wrenwood Condo 5 $197,779 64
Winter Park Wrenwood Heights 2 $407,450 23
Leona Decastro
Leona Decastro Office: (904) 641-9522 Cell: (904) 710-2163 Fax: (904) 641-1992 Work Phone: (904) 641-9522 Direct Phone: (904) 710-2163 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 05/13/2026. The listing information on this page last changed on 05/13/2026. 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 Wed 05/13/2026 12:01:56 AM EST) or GAMLS (last updated Tue 05/12/2026 11:15:11 PM EST) or Stellar MLS (last updated Tue 05/12/2026 11:44:10 PM EST) or SPC MLS (last updated Tue 05/12/2026 11:21:18 PM EST) or Martin MLS (last updated Tue 05/12/2026 11:38:09 PM EST) or Indian River MLS (last updated Tue 05/12/2026 11:30:17 PM EST) or Daytona MLS (last updated Tue 05/12/2026 11:36:45 PM EST) or Northeast Florida MLS (last updated Tue 05/12/2026 11:59:08 PM EST) or Beaches MLS (last updated Tue 05/12/2026 11:58:38 PM EST) or BORMLS (last updated Tue 05/12/2026 11:15:23 PM EST) or Golden Isles MLS (last updated Tue 05/12/2026 11:26:35 PM EST) or Amelia/Nassau MLS (last updated Tue 05/12/2026 11:25:12 PM EST) or Dixie Gilchrist Levy MLS (last updated Tue 05/12/2026 11:42:15 PM EST) or NFLMLS (last updated Tue 05/12/2026 9:04:59 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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