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David Podvia
REALTOR®, U.S. Military on the Move Certified Military Specialist
(904) 333-2016
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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 $2,195,000 105
Winter Park Albert Lee Ridge 1st 1 $470,000 35
Winter Park Albert Lee Ridge First 1 $490,000 72
Winter Park Aloma 3 $564,500 170
Winter Park Aloma Park 1 $295,000 12
Winter Park Aloma Trails 1 $390,000 36
Winter Park Aragon Condo 1 $209,999 149
Winter Park Autumn Glen 1 $535,000 20
Winter Park Banks Colonial Estates 1 $1,200,000 5
Winter Park Bear Gully Forest 1 $524,900 130
Winter Park Bldg 6 1 $155,000 92
Winter Park Bridgewater 1 $425,000 23
Winter Park Brookshire Heights 2 $1,237,500 50
Winter Park Brookshire Heights 1st 3 $1,231,333 42
Winter Park Brookshire Heights 2nd 1 $595,000 7
Winter Park Brookshire Heights 4th 2 $899,500 20
Winter Park Campo Bello 1 $649,800 30
Winter Park Capens 3 $649,667 247
Winter Park Carolyn Estates 1 $439,995 22
Winter Park Carver Town 2 $462,500 40
Winter Park Casa Aloma 4 $467,475 159
Winter Park Cedarwood Village 1 5 $273,580 82
Winter Park Charmont 8 $2,455,863 71
Winter Park Chateaux Du Lac 3 $230,500 136
Winter Park Cinnamon Shores 1 $2,200,000 71
Winter Park Cloister Grove 3 $3,996,667 158
Winter Park Cloisters Condo 4 $1,372,000 115
Winter Park College Place Rep 1 $2,200,000 50
Winter Park Colonies 10 $124,580 161
Winter Park Comstock Park 4 $2,832,250 142
Winter Park Conwill Estates 3 $2,049,000 35
Winter Park Coronado Twnhms 1 $339,900 31
Winter Park Coronation 2 $284,500 108
Winter Park Cortland Park 1 $950,000 43
Winter Park Country Lane 2 $482,500 13
Winter Park Dixie Terrace 2 $2,889,450 61
Winter Park Dubsdread Heights 2 $562,000 63
Winter Park Eastbrook 14 $400,228 76
Winter Park Eastgate 4 $659,700 43
Winter Park Ellno Willo 2 $2,572,500 49
Winter Park Enclave At Aloma 1 $599,000 18
Winter Park Enclave At Hawks Crest 2 $425,000 80
Winter Park Fairbanks Park 1 $899,000 148
Winter Park Fairbanks Shores 5th 1 $459,000 52
Winter Park Fernbrook Trails 3 $261,333 69
Winter Park Fontainebleau 2 $1,891,500 125
Winter Park Forest Hills 5 $2,461,000 92
Winter Park Four Seasons 1 $169,000 92
Winter Park Four Seasons Condo 4 $186,000 66
Winter Park Fremar 2 $1,299,000 31
Winter Park Garden Acres Rep 02 Blk E 1 $485,000 29
Winter Park Garden Lake Estates 4 $495,750 81
Winter Park Georgetown Estates 2 $484,995 85
Winter Park Glencoe 6 $553,333 86
Winter Park Goldenrod Villas Condo 4 $233,700 236
Winter Park Golfside 3 $647,967 47
Winter Park Golfside Villas Condo 2 $148,845 71
Winter Park Golfview 2 $431,900 86
Winter Park Golfview Heights 2 $810,000 131
Winter Park Grand Pines 1 $280,000 17
Winter Park Grayson Square 3 $436,300 264
Winter Park Green Oaks Rep 2 $3,422,500 58
Winter Park Green Oaks Rep 02 2 $2,785,000 188
Winter Park Green Oaks Rep 03 1 $1,425,000 129
Winter Park Green Terrace 1 $1,005,000 19
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,890,000 57
Winter Park Greenview At Winter Pines 1 $899,000 44
Winter Park H Vanwies 2 $899,000 39
Winter Park Hamilton Place 1 $1,349,000 29
Winter Park Hawks Crest 1 $845,000 52
Winter Park Hidden Oaks Condo 9 $187,267 92
Winter Park Hidden Oaks Condominium Association, Inc 1 $169,500 16
Winter Park Howell Branch Woods 2 $427,500 24
Winter Park Howell Estates 1st 1 $470,000 112
Winter Park Howell Estates Rep 3 $473,000 20
Winter Park Howell Heights 2 $408,440 33
Winter Park Hyde Park 1 $470,000 3
Winter Park J Kronenberger 3 $3,616,000 64
Winter Park Karolina On Killarney 5 $970,778 50
Winter Park Kawilla Crest 1 $899,999 15
Winter Park Kenilworth Estates 1st 2 $604,500 9
Winter Park Kenilworth Shores 7 $1,308,686 59
Winter Park Killarney Bay Condo 3 $410,000 137
Winter Park Killarney Circle 4 $622,000 272
Winter Park Killarney Estates 2 $2,795,000 156
Winter Park Kings Cove 1 $824,000 8
Winter Park La Casas De Indiana 1 $524,000 12
Winter Park Lake Bell Terrace 3 $786,333 168
Winter Park Lake Florence Preserve 2 $894,000 260
Winter Park Lake Forest Park 5 $1,796,760 31
Winter Park Lake Killarney Condo 1 $298,000 165
Winter Park Lake Killarney Shores 1 $1,499,900 207
Winter Park Lake Knowles Terrace 4 $2,325,000 38
Winter Park Lake Monte 1 $1,689,000 109
Winter Park Lake Virginia 1 $999,000 99
Winter Park Lake Virginia Pt Rep 1 $1,875,000 37
Winter Park Lake Waunatta Village 1 $457,000 115
Winter Park Lakeside Estates 2 $1,172,500 75
Winter Park Lakeside Manor 7 $183,771 164
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 464
Winter Park Lakeview Terrace 3 $1,165,667 77
Winter Park Lancelot/winter Park 2 $169,500 42
Winter Park Landings At Hawks Crest 2 $774,950 88
Winter Park Las Casas De Indiana 1 $545,000 94
Winter Park Laurel Spgs 2 $410,000 21
Winter Park Lawndale 8 $1,110,325 79
Winter Park Lazy Oaks Condo 3 $268,333 50
Winter Park Lords 1 $1,050,000 567
Winter Park Lost Creek 2 $574,950 36
Winter Park Lugano Terrace 1 $2,265,000 185
Winter Park Lyman Ave Villas 1 1 $1,375,000 7
Winter Park Maitland Shores 2 $3,725,000 260
Winter Park Maitland Shores First 2 $2,786,500 98
Winter Park Mead Garden 1 $240,000 23
Winter Park Meadows At Hawks Crest 4 $786,250 43
Winter Park Metzingers 1 $589,900 72
Winter Park Mondrian/winder Park Twnhms 2 $1,247,000 68
Winter Park Morseland 1 $1,185,999 17
Winter Park New England Bldg 1 $425,000 5
Winter Park None 4 $1,350,500 149
Winter Park Northwood Terrace 1 $659,000 204
Winter Park Oakcrest-516 1 $200,000 40
Winter Park Orange Terrace 1 $484,000 282
Winter Park Orwin Manor Stratford 1 $725,000 16
Winter Park Orwin Manor Westminster 5 $1,081,800 109
Winter Park Osceola Place 1 $6,495,000 206
Winter Park Osceola Shores 2 $2,049,500 55
Winter Park Park Aire Condo 1 $450,000 149
Winter Park Park Grove 1 $2,895,000 10
Winter Park Park Grove W/125 Lot 10 Blk D 1 $2,200,000 51
Winter Park Park Hill 1 $4,295,000 2
Winter Park Park Manor 2 $1,037,000 98
Winter Park Park North 1 $2,495,000 51
Winter Park Parklando 3 $1,378,000 84
Winter Park Parklando #3 1 $1,649,000 73
Winter Park Parklando 03 1 $1,949,500 391
Winter Park Parkview Village 4 $183,850 538
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 66
Winter Park Pervis Survey For R E 1 $1,850,000 96
Winter Park Phillips Circle Rep 3 $319,600 231
Winter Park Pinewood 2 $415,000 141
Winter Park Preserve At Hawks Crest 2 $694,450 263
Winter Park Quail Hollow 1 $1,295,000 23
Winter Park Quail Run 1 $649,900 29
Winter Park Quarters At Winter Park Condo 1 $595,000 173
Winter Park Replat Of Lts 1 2 & 3 Brookside 1 $510,000 23
Winter Park Robert Dhu Macdonald Park 3 $3,316,667 75
Winter Park Sanctuary At Aloma 1 $665,000 106
Winter Park Sandlewood Creek Condo 1 $314,000 98
Winter Park Sevilla 2 $2,175,000 150
Winter Park Seville Park 2 $554,950 47
Winter Park Shores Lake Killarney 1 $750,000 11
Winter Park Sicilian Shores 2 $3,042,500 60
Winter Park Sicilian Shores Rep 02 1 $4,650,000 50
Winter Park Slovak Village 1 $317,500 206
Winter Park Sorensen Heights 1 $3,250,000 166
Winter Park South Lakemont Shores 2 $1,350,000 37
Winter Park Stratford A Winter Park Condo 7 $170,841 121
Winter Park Stratford Winter Park 1 $144,000 89
Winter Park Suburban Homes 3 $461,667 19
Winter Park Swoope Park 1 $695,000 115
Winter Park Sylvan Heights 4 $1,519,750 74
Winter Park Sylvan Hgts 1 $739,000 16
Winter Park Sylvan Lake Shores 2 $1,745,000 62
Winter Park Sylvan Park 2 $1,022,000 47
Winter Park Tanglewood 2 $518,500 518
Winter Park Temple Estates 1 $2,385,000 61
Winter Park Temple Terrace 2 $1,149,500 46
Winter Park Terazzo Del Sol Condo Assn Inc 1 $549,000 122
Winter Park Terrazo Del Sol 1 $550,000 60
Winter Park The Enclave Winter Park 6 $1,793,167 39
Winter Park Timberlane 1 $850,000 60
Winter Park Timberlane Shores 2 $1,520,000 66
Winter Park Townhomes/harper Place 1 $539,000 26
Winter Park Trotters Rep 1 $745,000 8
Winter Park Tuscania 3 $2,731,667 74
Winter Park Tuscany Terrace 1 $1,595,000 99
Winter Park Twin Acres 2 $1,995,000 81
Winter Park Valencia Terrace 1 $4,075,000 268
Winter Park Villa View Park 1 $1,925,000 58
Winter Park Village Green 2 $442,500 32
Winter Park Village Winterset Inc 1 $619,000 67
Winter Park Village/whisperwood 1 $236,800 79
Winter Park Villas Of Casselberry 4 $369,975 41
Winter Park Virginia Heights 3 $4,463,333 89
Winter Park Virginia Heights Rep 2 $1,242,500 23
Winter Park Vistas At Lake Howell 1 $355,000 81
Winter Park Waterfall Cove 3 $124,663 87
Winter Park Waterfall Cove At Winter Park 1 $205,000 438
Winter Park Waterfall Cove At Winter Park Condo 1 $120,000 53
Winter Park Waterfall Cove Winter Park 1 $139,990 50
Winter Park Waterfall Cove/winter Park 1 $125,000 12
Winter Park Whispering Waters/phillips Circle Rep 2 $2,087,500 70
Winter Park Whisperwood Condo 4 $222,225 136
Winter Park Windsong Elizabeths Walk 1 $1,395,000 1
Winter Park Windsong Elizabeths Walk 43/81 1 $2,195,000 43
Winter Park Windsong Lakeside 1 $2,795,000 45
Winter Park Windsong-knowles Place 1 $1,995,000 15
Winter Park Windsong-preserve Point 1 $8,950,000 222
Winter Park Windward Square 3 $268,333 112
Winter Park Winflor Court Pt Rep 1 $4,285,000 31
Winter Park Winter Green 1 $300,000 72
Winter Park Winter Park 4 $2,948,750 145
Winter Park Winter Park Estates 6 $469,667 215
Winter Park Winter Park Manor 1 $399,500 25
Winter Park Winter Park Oaks 1 $285,000 37
Winter Park Winter Park Pines 5 $634,000 113
Winter Park Winter Park Pines Merrie Oaks 2 $652,450 71
Winter Park Winter Park Pines Patio Homes 1 $318,985 45
Winter Park Winter Park Pines Rep 2 $699,750 61
Winter Park Winter Park Pines Ut 5 1 $729,000 51
Winter Park Winter Park Residential 1 $1,450,000 51
Winter Park Winter Park Rev 1 $1,795,000 46
Winter Park Winter Park Village 5 $1,619,900 50
Winter Park Winter Park Villas 1 $199,900 20
Winter Park Winter Park Woods Condo 3 $119,633 135
Winter Park Winter Woods 1 $375,000 9
Winter Park Wrenwood 2 $462,000 24
Winter Park Wrenwood Condo 5 $197,779 67
Winter Park Wrenwood Heights 2 $454,995 14
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 05/16/2026. The listing information on this page last changed on 05/16/2026. 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 05/16/2026 12:01:10 AM EST) or GAMLS (last updated Fri 05/15/2026 11:15:28 PM EST) or Stellar MLS (last updated Fri 05/15/2026 11:45:14 PM EST) or SPC MLS (last updated Fri 05/15/2026 11:21:13 PM EST) or Martin MLS (last updated Fri 05/15/2026 11:38:11 PM EST) or Indian River MLS (last updated Fri 05/15/2026 11:30:19 PM EST) or Daytona MLS (last updated Fri 05/15/2026 11:36:53 PM EST) or Northeast Florida MLS (last updated Fri 05/15/2026 11:59:04 PM EST) or Beaches MLS (last updated Fri 05/15/2026 11:59:28 PM EST) or BORMLS (last updated Fri 05/15/2026 11:16:08 PM EST) or Golden Isles MLS (last updated Fri 05/15/2026 11:26:35 PM EST) or Amelia/Nassau MLS (last updated Fri 05/15/2026 11:25:20 PM EST) or Dixie Gilchrist Levy MLS (last updated Fri 05/15/2026 11:42:16 PM EST) or NFLMLS (last updated Fri 05/15/2026 9:08:02 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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