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Haley Woodard
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 $2,170,000 113
Winter Park Acreage 1 $399,900 3
Winter Park Albert Lee Ridge 2 $699,000 2
Winter Park Albert Lee Ridge 1st 1 $470,000 43
Winter Park Albert Lee Ridge First 1 $490,000 80
Winter Park Aloma 3 $564,500 178
Winter Park Aloma Park 1 $295,000 20
Winter Park Aloma Trails 1 $375,000 44
Winter Park Aragon Condo 1 $209,999 157
Winter Park Autumn Glen 1 $535,000 28
Winter Park Banks Colonial Estates 1 $1,200,000 13
Winter Park Bear Gully Forest 1 $524,900 138
Winter Park Bldg 6 1 $155,000 100
Winter Park Brookshire Heights 2 $1,237,500 58
Winter Park Brookshire Heights 1st 3 $1,231,333 50
Winter Park Brookshire Heights 2nd 1 $595,000 15
Winter Park Brookshire Heights 4th 1 $1,115,000 20
Winter Park Campo Bello 1 $649,800 38
Winter Park Capens 3 $649,667 255
Winter Park Carolyn Estates 1 $439,995 30
Winter Park Carver Town 2 $462,500 48
Winter Park Casa Aloma 4 $467,475 167
Winter Park Cedarwood Village 1 6 $269,650 75
Winter Park Charmont 8 $2,455,863 79
Winter Park Chateaux Du Lac 4 $237,850 110
Winter Park Cinnamon Shores 1 $2,200,000 79
Winter Park Cloister Grove 3 $3,996,667 166
Winter Park Cloisters Condo 4 $1,372,000 123
Winter Park College Place Rep 1 $2,200,000 58
Winter Park Colonies 9 $130,089 185
Winter Park Comstock Park 4 $2,832,250 150
Winter Park Conwill Estates 3 $2,049,000 43
Winter Park Coronado Twnhms 1 $339,900 39
Winter Park Coronation 1 $269,000 128
Winter Park Cortland Park 1 $950,000 51
Winter Park Country Lane 2 $482,500 21
Winter Park Dixie Terrace 2 $2,889,450 69
Winter Park Dubsdread Heights 2 $562,000 71
Winter Park Eastbrook 13 $396,091 82
Winter Park Eastgate 4 $659,700 51
Winter Park Ellno Willo 2 $2,521,500 57
Winter Park Enclave At Aloma 1 $599,000 26
Winter Park Enclave At Hawks Crest 2 $425,000 88
Winter Park Fairbanks Park 1 $899,000 156
Winter Park Fairbanks Shores 5th 1 $455,000 60
Winter Park Fernbrook Trails 2 $247,000 83
Winter Park Fontainebleau 2 $1,891,500 133
Winter Park Forest Hills 5 $2,461,000 100
Winter Park Four Seasons 1 $169,000 100
Winter Park Four Seasons Condo 3 $188,000 71
Winter Park Fremar 2 $1,299,000 39
Winter Park Garden Acres Rep 02 Blk E 1 $485,000 37
Winter Park Garden Lake Estates 3 $494,667 71
Winter Park Georgetown Estates 2 $482,450 93
Winter Park Glencoe 7 $577,000 82
Winter Park Goldenrod Villas Condo 4 $233,350 244
Winter Park Golfside 2 $697,450 62
Winter Park Golfside Villas Condo 2 $148,845 79
Winter Park Golfview 2 $431,550 94
Winter Park Golfview Heights 2 $810,000 139
Winter Park Grand Pines 1 $280,000 25
Winter Park Grayson Square 4 $433,475 206
Winter Park Green Oaks Rep 2 $3,422,500 66
Winter Park Green Oaks Rep 02 2 $2,785,000 196
Winter Park Green Terrace 1 $1,005,000 27
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,890,000 65
Winter Park Greenview At Winter Pines 1 $899,000 52
Winter Park H Vanwies 2 $899,000 47
Winter Park Hamilton Place 1 $1,349,000 37
Winter Park Hawks Crest 1 $845,000 60
Winter Park Hidden Oaks Condo 9 $185,983 100
Winter Park Hidden Oaks Condominium Association, Inc 1 $169,500 24
Winter Park Howell Branch Woods 2 $427,500 32
Winter Park Howell Estates 1st 1 $470,000 120
Winter Park Howell Estates Rep 3 $473,000 28
Winter Park Howell Heights 2 $408,440 41
Winter Park Hyde Park 1 $470,000 11
Winter Park J Kronenberger 3 $3,599,000 72
Winter Park Karolina On Killarney 5 $970,778 58
Winter Park Kawilla Crest 1 $890,000 23
Winter Park Kenilworth Estates 1st 2 $604,500 17
Winter Park Kenilworth Shores 8 $1,272,475 59
Winter Park Killarney Bay Condo 3 $410,000 145
Winter Park Killarney Circle 4 $622,000 280
Winter Park Killarney Estates 4 $2,122,500 83
Winter Park Kings Cove 1 $824,000 16
Winter Park La Casas De Indiana 1 $524,000 20
Winter Park Lake Bell Terrace 3 $786,333 176
Winter Park Lake Florence Preserve 2 $894,000 268
Winter Park Lake Forest Park 5 $1,796,760 39
Winter Park Lake Killarney Condo 2 $268,500 88
Winter Park Lake Killarney Shores 1 $1,449,900 215
Winter Park Lake Knowles Terrace 4 $2,325,000 46
Winter Park Lake Monte 1 $1,095,000 2
Winter Park Lake Virginia 1 $999,000 107
Winter Park Lake Virginia Pt Rep 1 $1,875,000 45
Winter Park Lake Waunatta Village 1 $457,000 123
Winter Park Lakeside Estates 2 $1,172,500 83
Winter Park Lakeside Manor 7 $183,771 172
Winter Park Lakeside Manor Condominium Association, Inc. 1 $224,999 472
Winter Park Lakeview Terrace 3 $1,165,667 85
Winter Park Lancelot/winter Park 2 $169,500 50
Winter Park Landings At Hawks Crest 2 $774,950 96
Winter Park Las Casas De Indiana 1 $545,000 102
Winter Park Laurel Spgs 2 $410,000 29
Winter Park Laurel Springs 1 $400,000 6
Winter Park Lawndale 9 $1,064,178 77
Winter Park Lazy Oaks Condo 3 $268,333 58
Winter Park Lords 1 $1,050,000 575
Winter Park Lost Creek 3 $604,967 30
Winter Park Lugano Terrace 1 $2,265,000 193
Winter Park Lyman Ave Villas 1 1 $1,375,000 15
Winter Park Maitland Shores 2 $3,725,000 268
Winter Park Maitland Shores First 2 $2,786,500 106
Winter Park Mead Garden 1 $240,000 31
Winter Park Meadows At Hawks Crest 4 $786,250 51
Winter Park Metzingers 1 $589,900 80
Winter Park Mondrian/winder Park Twnhms 2 $1,247,000 76
Winter Park Morseland 1 $1,185,999 25
Winter Park New England Bldg 1 $425,000 13
Winter Park None 4 $1,350,500 157
Winter Park Northwood Terrace 1 $649,000 212
Winter Park Oakcrest-516 1 $200,000 48
Winter Park Orange Terrace 1 $480,000 290
Winter Park Orwin Manor Stratford 1 $725,000 24
Winter Park Orwin Manor Westminster 5 $1,081,800 117
Winter Park Osceola Heights 1 $1,399,000 72
Winter Park Osceola Place 1 $6,495,000 214
Winter Park Osceola Shores 2 $2,049,500 63
Winter Park Park Grove 1 $2,895,000 18
Winter Park Park Grove W/125 Lot 10 Blk D 1 $2,200,000 59
Winter Park Park Hill 1 $4,295,000 10
Winter Park Park Manor 2 $1,024,000 106
Winter Park Park North 1 $2,495,000 59
Winter Park Park West Condo 1 $750,000 2
Winter Park Parklando 2 $904,875 44
Winter Park Parklando #3 1 $1,649,000 81
Winter Park Parklando 03 1 $1,949,000 399
Winter Park Parkview Village 4 $176,600 316
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 74
Winter Park Pennsylvania Place Rep 1 $1,895,000 3
Winter Park Pervis Survey For R E 1 $1,799,999 104
Winter Park Phillips Circle Rep 3 $317,933 239
Winter Park Preserve At Hawks Crest 2 $694,450 271
Winter Park Quail Hollow 1 $1,295,000 31
Winter Park Quail Run 1 $649,900 37
Winter Park Replat Of Lts 1 2 & 3 Brookside 1 $510,000 31
Winter Park Robert Dhu Macdonald Park 1 $6,950,000 104
Winter Park Sanctuary At Aloma 1 $665,000 114
Winter Park Sandlewood Creek Condo 1 $314,000 106
Winter Park Sevilla 2 $2,175,000 158
Winter Park Seville Park 2 $549,950 55
Winter Park Shores Lake Killarney 1 $750,000 19
Winter Park Sicilian Shores 1 $2,790,000 45
Winter Park Sicilian Shores Rep 02 1 $4,650,000 58
Winter Park Slovak Village 1 $317,500 214
Winter Park South Lakemont Shores 2 $1,350,000 45
Winter Park Stratford A Winter Park Condo 6 $175,148 132
Winter Park Stratford Winter Park 1 $144,000 97
Winter Park Suburban Homes 3 $461,667 27
Winter Park Swoope Park 1 $695,000 123
Winter Park Sylvan Heights 4 $1,519,750 82
Winter Park Sylvan Hgts 1 $739,000 24
Winter Park Sylvan Lake Shores 3 $2,263,333 49
Winter Park Sylvan Park 2 $1,022,000 55
Winter Park Tanglewood 2 $506,000 526
Winter Park Temple Estates 1 $2,385,000 69
Winter Park Temple Terrace 2 $1,099,500 54
Winter Park Terazzo Del Sol Condo Assn Inc 1 $549,000 130
Winter Park Terrazo Del Sol 1 $525,000 68
Winter Park The Enclave Winter Park 8 $1,886,625 36
Winter Park Timberlane Shores 2 $1,520,000 74
Winter Park Townhomes/harper Place 1 $539,000 34
Winter Park Trotters Rep 1 $745,000 16
Winter Park Tuscania 2 $2,000,000 104
Winter Park Tuscany Terrace 1 $1,595,000 107
Winter Park Twin Acres 2 $1,995,000 89
Winter Park Valencia Terrace 1 $4,075,000 276
Winter Park Villa View Park 1 $1,925,000 66
Winter Park Village Green 1 $549,000 34
Winter Park Village Winterset Inc 2 $804,250 39
Winter Park Village/whisperwood 1 $236,800 87
Winter Park Villas Of Casselberry 5 $353,980 40
Winter Park Virginia Heights 3 $4,463,333 97
Winter Park Virginia Heights Rep 2 $1,242,500 31
Winter Park Vistas At Lake Howell 2 $345,000 45
Winter Park Waterfall Cove 3 $122,997 95
Winter Park Waterfall Cove At Winter Park 1 $205,000 446
Winter Park Waterfall Cove At Winter Park Condo 1 $120,000 61
Winter Park Waterfall Cove Winter Park 1 $137,900 58
Winter Park Waterfall Cove/winter Park 1 $125,000 20
Winter Park Whispering Waters/phillips Circle Rep 1 $2,075,000 16
Winter Park Whisperwood Condo 4 $221,975 144
Winter Park Windsong Elizabeths Walk 1 $1,395,000 9
Winter Park Windsong Elizabeths Walk 43/81 1 $2,195,000 51
Winter Park Windsong Lakeside 1 $2,699,000 53
Winter Park Windsong-knowles Place 1 $1,995,000 23
Winter Park Windsong-preserve Point 1 $8,950,000 230
Winter Park Windward Square 3 $268,333 120
Winter Park Winflor Court Pt Rep 2 $4,267,500 23
Winter Park Winter Green 1 $300,000 80
Winter Park Winter Park 5 $3,736,778 124
Winter Park Winter Park Estates 6 $469,667 223
Winter Park Winter Park Gardens Condo 2 $340,000 2
Winter Park Winter Park Manor 1 $399,500 33
Winter Park Winter Park Oaks 1 $285,000 45
Winter Park Winter Park Pines 8 $649,875 77
Winter Park Winter Park Pines Merrie Oaks 1 $554,900 119
Winter Park Winter Park Pines Patio Homes 1 $318,985 53
Winter Park Winter Park Pines Rep 2 $697,450 69
Winter Park Winter Park Pines Ut 5 1 $719,000 59
Winter Park Winter Park Rev 1 $1,795,000 54
Winter Park Winter Park Village 5 $1,619,900 58
Winter Park Winter Park Villas 1 $199,900 28
Winter Park Winter Park Woods Condo 3 $119,633 143
Winter Park Winter Woods 1 $375,000 17
Winter Park Wrenwood 1 $489,000 10
Winter Park Wrenwood Condo 4 $195,724 70
Winter Park Wrenwood Heights 2 $454,995 22
Haley Woodard
Haley Woodard Office: (352) 377-8899 ext. 7294 Cell: (352) 339-3142 Work Phone: (352) 224-2694 Email Me
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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 05/24/2026. The listing information on this page last changed on 05/24/2026. 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 Sun 05/24/2026 12:00:22 AM EST) or GAMLS (last updated Sat 05/23/2026 11:15:08 PM EST) or Stellar MLS (last updated Sat 05/23/2026 11:44:13 PM EST) or SPC MLS (last updated Sat 05/23/2026 11:21:03 PM EST) or Martin MLS (last updated Sat 05/23/2026 11:38:08 PM EST) or Indian River MLS (last updated Sat 05/23/2026 11:30:15 PM EST) or Daytona MLS (last updated Sat 05/23/2026 11:36:46 PM EST) or Northeast Florida MLS (last updated Sat 05/23/2026 11:58:51 PM EST) or Beaches MLS (last updated Sat 05/23/2026 2:39:39 AM EST) or BORMLS (last updated Sat 05/23/2026 11:15:35 PM EST) or Golden Isles MLS (last updated Sat 05/23/2026 11:26:36 PM EST) or Amelia/Nassau MLS (last updated Sat 05/23/2026 11:25:15 PM EST) or Dixie Gilchrist Levy MLS (last updated Sat 05/23/2026 11:42:16 PM EST) or NFLMLS (last updated Sat 05/23/2026 9:04:42 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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