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Andrenia Green
Broker Associate
REALTOR®, LeadingRE Marketing Specialist, LeadingRE Relocation Specialist, LeadingRE Sales Specialist, REALTOR®
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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 $2,150,000 130
Winter Park Acreage 1 $399,900 20
Winter Park Alabama Condo 1 $1,250,000 2
Winter Park Albert Lee Ridge 2 $699,000 19
Winter Park Albert Lee Ridge 1st 1 $460,000 60
Winter Park Aloma 3 $564,500 195
Winter Park Aloma Park 1 $289,000 37
Winter Park Aloma Trails 2 $375,000 39
Winter Park Aragon Condo 1 $209,999 174
Winter Park Autumn Glen 1 $535,000 45
Winter Park Banks Colonial Estates 1 $1,200,000 30
Winter Park Bear Gully Forest 1 $499,900 155
Winter Park Bel-aire Pines, 1 $465,000 235
Winter Park Bldg 6 1 $155,000 117
Winter Park Brookshire Heights 1 $1,825,000 71
Winter Park Brookshire Heights 1st 3 $1,231,333 67
Winter Park Brookshire Heights 4th 1 $1,115,000 37
Winter Park Campo Bello 1 $639,900 55
Winter Park Capens 3 $649,667 272
Winter Park Carver Town 1 $399,999 33
Winter Park Casa Aloma 3 $479,967 198
Winter Park Cedar Ridge 1 $370,000 7
Winter Park Cedarwood Village 1 6 $266,317 92
Winter Park Charmont 9 $2,415,100 86
Winter Park Chateaux Du Lac 4 $236,850 127
Winter Park Cinnamon Shores 1 $2,200,000 96
Winter Park Cloister Grove 2 $5,095,000 232
Winter Park Cloisters Condo 4 $1,343,225 140
Winter Park College Place Rep 1 $1,980,000 75
Winter Park Colonies 4 $136,975 170
Winter Park Comstock Park 5 $3,448,000 136
Winter Park Conwill Estates 3 $2,698,333 43
Winter Park Coronation 1 $269,000 145
Winter Park Cortland Park 1 $950,000 68
Winter Park Country Lane 3 $451,633 27
Winter Park Dixie Terrace 2 $2,889,450 86
Winter Park Dubsdread Heights 2 $562,000 88
Winter Park Eastbrook 13 $403,245 97
Winter Park Eastgate 2 $949,500 70
Winter Park Ellno Willo 2 $2,521,500 74
Winter Park Enclave At Hawks Crest 1 $415,000 27
Winter Park Fairbanks Park 1 $899,000 173
Winter Park Fairbanks Shores 5th 1 $455,000 77
Winter Park Fernbrook Trails 1 $199,000 34
Winter Park Flamingo Shores 1 $865,000 11
Winter Park Fontainebleau 2 $1,891,500 150
Winter Park Forest Hills 5 $2,441,000 117
Winter Park Four Seasons Condo 3 $186,666 53
Winter Park Fremar 2 $1,299,000 56
Winter Park Garden Lake Estates 6 $448,167 11
Winter Park Georgetown Estates 2 $482,450 110
Winter Park Glencoe 7 $581,143 81
Winter Park Goldenrod Villas Condo 2 $222,450 327
Winter Park Golfside 2 $697,450 79
Winter Park Golfside Villas Condo 1 $122,990 110
Winter Park Golfview 2 $431,400 111
Winter Park Golfview Heights 1 $625,000 83
Winter Park Grand Pines 1 $280,000 42
Winter Park Grayson Square 4 $433,475 188
Winter Park Green Oaks Rep 1 $2,295,000 112
Winter Park Green Oaks Rep 02 1 $2,300,000 63
Winter Park Green Terrace 1 $1,005,000 44
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,820,000 82
Winter Park Greenview At Winter Pines 1 $899,000 69
Winter Park H Vanwies 2 $899,000 64
Winter Park Hamilton Place 1 $1,324,000 54
Winter Park Henkel 1 $1,095,000 15
Winter Park Hidden Oaks Condo 8 $183,231 127
Winter Park Hidden Oaks Condominium Association, Inc 1 $159,000 41
Winter Park Horton Aaron 1 $2,000,000 13
Winter Park Howell Branch Woods 2 $427,500 17
Winter Park Howell Estates 1st 1 $460,000 137
Winter Park Howell Estates Rep 1 $470,000 33
Winter Park Howell Heights 2 $403,440 58
Winter Park J Kronenberger 2 $4,299,500 84
Winter Park Karolina On Killarney 4 $1,038,722 54
Winter Park Kawilla Crest 1 $890,000 40
Winter Park Kenilworth Estates 1st 2 $604,500 34
Winter Park Kenilworth Shores 13 $1,258,276 49
Winter Park Killarney Bay Condo 3 $395,000 162
Winter Park Killarney Circle 4 $622,000 297
Winter Park Killarney Estates 5 $1,938,000 82
Winter Park Killarney Point 1 $689,000 11
Winter Park Kings Cove 1 $824,000 33
Winter Park La Casas De Indiana 1 $524,000 37
Winter Park Lake Bell Terrace 3 $786,333 193
Winter Park Lake Florence Preserve 3 $995,667 194
Winter Park Lake Forest Park 6 $1,823,800 49
Winter Park Lake Killarney Condo 2 $268,500 105
Winter Park Lake Killarney Shores 1 $1,449,900 232
Winter Park Lake Knowles Terrace 5 $1,802,800 30
Winter Park Lake Monte 1 $1,095,000 19
Winter Park Lake Virginia 1 $999,000 124
Winter Park Lake Waunatta Village 1 $457,000 140
Winter Park Lakeside Manor 6 $177,050 182
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 489
Winter Park Lakeview Terrace 4 $999,000 80
Winter Park Lancelot/winter Park 1 $159,000 50
Winter Park Landings At Hawks Crest 2 $774,950 113
Winter Park Las Casas De Indiana 1 $545,000 119
Winter Park Laurel Spgs 2 $410,000 46
Winter Park Laurel Springs 2 $394,995 18
Winter Park Lawndale 10 $1,111,950 86
Winter Park Lazy Oaks Condo 1 $280,000 57
Winter Park Lords 1 $1,050,000 592
Winter Park Lost Creek 3 $598,300 47
Winter Park Lugano Terrace 1 $2,225,000 210
Winter Park Lyman Ave Villas 1 1 $1,375,000 32
Winter Park Magnolia Gardens 1 $724,900 9
Winter Park Maitland Shores 2 $3,700,000 285
Winter Park Maitland Shores 1st 1 $3,500,000 5
Winter Park Maitland Shores First 2 $2,786,500 123
Winter Park Meadows At Hawks Crest 5 $756,400 56
Winter Park Metzingers 1 $589,900 97
Winter Park Mondrian/winder Park Twnhms 1 $1,099,000 96
Winter Park Morseland 1 $1,185,999 42
Winter Park New England Bldg 1 $425,000 30
Winter Park None 4 $614,725 89
Winter Park Northwood Terrace 1 $649,000 229
Winter Park Oakcrest-516 1 $325,000 65
Winter Park Orange Terrace 1 $479,900 307
Winter Park Orangewood Park 1 $735,000 3
Winter Park Orwin Manor Westminster 3 $1,066,333 41
Winter Park Osceola Heights 1 $1,299,000 89
Winter Park Osceola Place 1 $6,495,000 231
Winter Park Osceola Shores 2 $2,049,500 80
Winter Park Park Grove 1 $2,895,000 35
Winter Park Park Hill 2 $3,897,500 18
Winter Park Park Manor 2 $1,024,000 123
Winter Park Park North 1 $2,495,000 76
Winter Park Park West Condo 2 $744,500 13
Winter Park Parklando 1 $1,139,750 61
Winter Park Parklando #3 1 $1,649,000 98
Winter Park Parklando 03 1 $1,924,450 416
Winter Park Parkview Village 4 $175,600 333
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 91
Winter Park Pennsylvania Place Rep 1 $1,895,000 20
Winter Park Pervis Survey For R E 1 $1,799,999 121
Winter Park Phillips Circle Rep 4 $304,475 194
Winter Park Preserve At Hawks Crest 1 $764,900 308
Winter Park Quail Hollow 1 $1,245,000 48
Winter Park Quail Run 1 $629,900 54
Winter Park Replat Of Lts 1 2 & 3 Brookside 1 $510,000 48
Winter Park Robert Dhu Macdonald Park 1 $6,950,000 121
Winter Park Sandlewood Creek Condo 1 $314,000 123
Winter Park Sevilla 2 $2,167,500 175
Winter Park Seville Park 2 $549,950 72
Winter Park Shores Lake Killarney 1 $750,000 36
Winter Park Sicilian Shores 1 $2,690,000 62
Winter Park Slovak Village 1 $317,500 231
Winter Park South Lakemont Shores 3 $1,450,000 46
Winter Park Stansbury Estates 1 $338,000 8
Winter Park Stratford A Winter Park Condo 6 $179,282 90
Winter Park Stratford Winter Park 1 $144,000 114
Winter Park Suburban Homes 3 $460,000 44
Winter Park Swoope Park 1 $695,000 140
Winter Park Sylvan Heights 3 $1,266,667 101
Winter Park Sylvan Hgts 1 $709,000 41
Winter Park Sylvan Lake Shores 3 $2,230,000 66
Winter Park Sylvan Park 2 $1,022,000 72
Winter Park Tanglewood 2 $506,000 543
Winter Park Temple Estates 1 $2,385,000 86
Winter Park Temple Heights 1 $2,695,000 75
Winter Park Temple Terrace 1 $1,000,000 86
Winter Park Terazzo Del Sol Condo Assn Inc 1 $549,000 147
Winter Park Terrazo Del Sol 1 $525,000 85
Winter Park The Enclave Winter Park 11 $1,962,545 42
Winter Park Timberlane Shores 2 $1,520,000 91
Winter Park Town Of Winter Park 1 $2,695,000 4
Winter Park Town/winter Park 1 $509,000 1
Winter Park Townhomes/harper Place 1 $534,900 51
Winter Park Trinity Bay 2 $487,500 6
Winter Park Trotters Rep 1 $745,000 33
Winter Park Tuscania 2 $2,000,000 121
Winter Park Tuscany Terrace 1 $1,595,000 124
Winter Park Twin Acres 1 $1,695,000 84
Winter Park Urban Green 12 1 $560,000 7
Winter Park Valencia Terrace 1 $3,995,000 293
Winter Park Villa View Park 1 $1,925,000 83
Winter Park Village Green 1 $549,000 51
Winter Park Village Winterset Inc 2 $804,250 56
Winter Park Village/whisperwood 1 $236,800 104
Winter Park Villas Of Casselberry 4 $371,225 37
Winter Park Virginia Heights 2 $2,650,000 19
Winter Park Virginia Heights Rep 2 $3,345,000 22
Winter Park Vistas At Lake Howell 2 $345,000 62
Winter Park Waterfall Cove 3 $120,997 112
Winter Park Waterfall Cove At Winter Park 1 $205,000 463
Winter Park Waterfall Cove At Winter Park Condo 1 $120,000 78
Winter Park Waterfall Cove Winter Park 1 $134,900 75
Winter Park Waterfall Cove/winter Park 2 $112,000 50
Winter Park Whispering Waters/phillips Circle Rep 1 $1,995,000 33
Winter Park Whisperwood Condo 4 $221,225 161
Winter Park Windsong - Knowles Place 1 $1,875,000 40
Winter Park Windsong Elizabeths Walk 1 $1,395,000 26
Winter Park Windsong Elizabeths Walk 43/81 1 $2,195,000 68
Winter Park Windsong Lakeside 1 $2,699,000 70
Winter Park Windsong-preserve Point 1 $8,950,000 247
Winter Park Windward Square 4 $294,750 79
Winter Park Winflor Court Pt Rep 2 $4,267,500 40
Winter Park Winter Green 1 $300,000 97
Winter Park Winter Park 5 $3,094,778 84
Winter Park Winter Park Estates 7 $459,571 207
Winter Park Winter Park Gardens Condo 3 $308,333 13
Winter Park Winter Park Gdns Condo 1 $235,900 5
Winter Park Winter Park Manor 2 $462,500 27
Winter Park Winter Park Oaks 1 $285,000 62
Winter Park Winter Park Oasis 1 $1,795,000 2
Winter Park Winter Park Pines 10 $617,200 107
Winter Park Winter Park Pines Merrie Oaks 2 $499,950 75
Winter Park Winter Park Pines Patio Homes 1 $318,985 70
Winter Park Winter Park Pines Rep 3 $634,933 57
Winter Park Winter Park Pines Ut 5 1 $710,000 76
Winter Park Winter Park Rev 1 $1,795,000 71
Winter Park Winter Park Village 6 $1,548,917 65
Winter Park Winter Park Villas 1 $199,900 45
Winter Park Winter Park Woods Condo 2 $129,950 198
Winter Park Winter Woods 2 $447,500 107
Winter Park Woodcrest 1 $370,000 8
Winter Park Wrenwood 1 $489,000 27
Winter Park Wrenwood Condo 4 $193,225 60
Winter Park Wrenwood Heights 2 $454,995 39
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 06/10/2026. The listing information on this page last changed on 06/10/2026. 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 06/10/2026 12:13:57 AM EST) or GAMLS (last updated Tue 06/09/2026 11:15:11 PM EST) or Stellar MLS (last updated Tue 06/09/2026 11:58:59 PM EST) or SPC MLS (last updated Tue 06/09/2026 11:20:57 PM EST) or Martin MLS (last updated Tue 06/09/2026 11:38:11 PM EST) or Indian River MLS (last updated Tue 06/09/2026 11:30:13 PM EST) or Daytona MLS (last updated Tue 06/09/2026 11:36:47 PM EST) or Northeast Florida MLS (last updated Wed 06/10/2026 12:08:54 AM EST) or Beaches MLS (last updated Wed 06/10/2026 12:10:51 AM EST) or BORMLS (last updated Tue 06/09/2026 11:15:33 PM EST) or Amelia/Nassau MLS (last updated Tue 06/09/2026 11:25:13 PM EST) or Dixie Gilchrist Levy MLS (last updated Tue 06/09/2026 11:42:17 PM EST) or NFLMLS (last updated Tue 06/09/2026 9:05:20 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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