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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 4572 Palmetto Condo 1 $3,200,000 8
Winter Park Acreage & Unrec 1 $3,750,000 19
Winter Park Alabama Oaks 1 $5,900,000 8
Winter Park Albert Lee Ridge 2 $482,450 54
Winter Park Albert Lee Ridge 1st 1 $439,000 171
Winter Park Albert Lee Ridge Annex 1 $1,600,000 33
Winter Park Alexander Place 1 $4,250,000 78
Winter Park Aloma 4 $499,000 167
Winter Park Aloma Trails 3 $366,300 56
Winter Park Amberwood Unit 3 1 $775,000 32
Winter Park Arrowhead Cove 1 $575,000 40
Winter Park Attilio G Panacciones 1 $586,567 19
Winter Park Banks Colonial Estates 1 $1,150,000 141
Winter Park Bear Gully Forest 1 $599,000 8
Winter Park Bear Gully Pointe 1 $1,395,000 21
Winter Park Bel Aire Pines 1 $449,900 6
Winter Park Bridgewater 1 $410,500 3
Winter Park Brookshire Heights 2 $774,500 16
Winter Park Brookshire Heights 2nd 2 $737,000 10
Winter Park Brookshire Heights 4th 1 $895,000 13
Winter Park Canton Ave Cottages 1 1 $849,000 106
Winter Park Capens 4 $625,000 235
Winter Park Casa Aloma 2 $489,450 109
Winter Park Casa Jardin Condo 2 $874,500 22
Winter Park Cedar Ridge 1 $475,000 106
Winter Park Cedarwood Village 3 $256,267 50
Winter Park Cedarwood Village 1 5 $267,400 122
Winter Park Charmont 7 $2,040,857 93
Winter Park Chateaux Du Lac 3 $214,833 132
Winter Park Cloister Grove 1 $3,750,000 458
Winter Park Cloisters Condo 2 $1,547,000 83
Winter Park Colonies 5 $139,580 226
Winter Park Comstock Park 2 $3,797,500 156
Winter Park Conwill Estates 3 $1,800,000 40
Winter Park Conwill Ests 1 $700,000 25
Winter Park Coronation 2 $271,925 144
Winter Park Country Lane 2 $435,000 104
Winter Park Cranes Creek 1 $365,000 27
Winter Park Cranes Crk 1 $309,900 29
Winter Park Detmar Terrace Winter Park 1 $3,600,000 35
Winter Park Dixie Terrace 1 $1,950,000 34
Winter Park Dubsdread Heights 1 $349,000 166
Winter Park Eastbrook 15 $400,653 88
Winter Park Eastgate 4 $1,037,250 68
Winter Park Edgewood 1 $1,095,000 24
Winter Park Elizabeth Heights 1 $1,350,000 26
Winter Park Ellno Willo 1 $3,275,000 201
Winter Park Enclave At Aloma 1 $585,000 6
Winter Park Enclave At Hawks Crest 2 $424,950 23
Winter Park Ethel Park 2 $960,000 14
Winter Park Fairbanks Park 1 $899,000 284
Winter Park Fairshores Place 1 $525,000 81
Winter Park Fairview Heights Rep 1 $315,000 55
Winter Park Flamingo Shores 2 $667,950 91
Winter Park Fontainebleau 2 $1,687,500 48
Winter Park Forest Hills 3 $3,723,333 168
Winter Park Forrest Hills 1 $4,325,000 16
Winter Park Fremar 1 $1,599,000 151
Winter Park Garden Grove 1 $395,000 48
Winter Park Garden Lake Estates 6 $444,940 83
Winter Park Georgetown Estates 1 $419,000 200
Winter Park Glencoe 8 $560,393 167
Winter Park Golfside 2 $709,950 23
Winter Park Golfside Villas Condo 5 $126,800 81
Winter Park Golfview 1 $459,900 282
Winter Park Golfview Terrace 1 $6,995,000 11
Winter Park Grand Pines 1 $550,000 66
Winter Park Grayson Square 4 $394,474 76
Winter Park Green Oaks Rep 02 1 $3,265,000 34
Winter Park Green Terrace V/140 Lot 3 Blk B 1 $1,750,000 193
Winter Park Greens/pk 1 $6,195,000 5
Winter Park Hamilton Place 1 $1,295,000 165
Winter Park Harbor East 1 $1,000,000 25
Winter Park Henkel 1 $999,000 126
Winter Park Hidden Oaks Condo 10 $186,769 137
Winter Park Horton Aaron 1 $1,700,000 124
Winter Park Howell Branch Woods 2 $404,950 93
Winter Park Howell Estates Rep 1 $450,000 40
Winter Park J Kronenberger 3 $4,763,633 80
Winter Park Justamere Camp Rep 2 $2,347,000 55
Winter Park Karolina On Killarney 3 $922,666 169
Winter Park Kenilworth Estates 1st 1 $675,000 12
Winter Park Kenilworth Shores 11 $1,884,045 83
Winter Park Killarney Bay Condo 2 $432,000 128
Winter Park Killarney Circle 4 $804,725 347
Winter Park Killarney Estates 7 $1,488,571 48
Winter Park Killarney Point 1 $689,000 122
Winter Park Kings Cove 1 $599,900 96
Winter Park Lake Ann Estates 2 $805,000 49
Winter Park Lake Bell Terrace 2 $615,000 139
Winter Park Lake Florence Preserve 2 $1,387,450 114
Winter Park Lake Forest Park 4 $1,796,000 59
Winter Park Lake Killarney Condo 3 $284,666 276
Winter Park Lake Killarney Condominium Assn Inc. 1 $199,900 103
Winter Park Lake Killarney Shores 1 $1,599,000 7
Winter Park Lake Knowles Terrace 10 $1,405,800 51
Winter Park Lake Knowles Terrace 2nd 1 $1,829,000 35
Winter Park Lake Maitland 2 $2,874,750 48
Winter Park Lake Spier Xing 1 $925,000 20
Winter Park Lake Sylvan Shores 1 $2,200,000 81
Winter Park Lake Virgina Shores 1 $2,095,000 5
Winter Park Lake Waunatta Wods 1 $599,000 56
Winter Park Lake Waunatta Woods 2 $654,389 41
Winter Park Lakeside Estates 2 $1,135,000 50
Winter Park Lakeside Manor 5 $181,140 134
Winter Park Lakeview Terrace 3 $1,025,000 42
Winter Park Lancelot/winter Park 2 $162,450 24
Winter Park Landings At Hawks Crest 3 $733,167 120
Winter Park Landmark Winter Park Condo 1 $2,350,000 104
Winter Park Lawndale 4 $1,334,925 65
Winter Park Lazy Oaks Condo 4 $274,725 85
Winter Park Lords 1 $1,050,000 703
Winter Park Lugano Terrace 1 $2,195,000 321
Winter Park Mack Peter Rev 1 $650,000 70
Winter Park Magnolia Gardens 3 $650,967 59
Winter Park Maitland Shores 1st 1 $3,500,000 116
Winter Park Maitland Shores First 4 $3,467,485 37
Winter Park Mead Garden 2 $255,000 13
Winter Park Mead Garden Condominium 1 $245,000 35
Winter Park Meadows At Hawks Crest 4 $767,500 118
Winter Park Metzingers 2 $524,950 107
Winter Park Monroe 1 $530,000 12
Winter Park Morse & Pennsylvania Twnhms 1 $2,800,000 96
Winter Park Morseland 1 $1,185,999 153
Winter Park Mrs L A Dennis 1 $1,050,000 18
Winter Park New England Bldg 1 $425,000 141
Winter Park None 7 $1,499,186 82
Winter Park Northwood Terrace 2 $1,722,500 73
Winter Park Not On The List 2 $552,000 63
Winter Park Oakcrest-516 3 $345,000 77
Winter Park Olympia Heights 1 $340,000 39
Winter Park Olympia Heights Annex 1 $489,000 46
Winter Park Orange Grove 1 $2,569,999 83
Winter Park Orange Terrace 1 $449,900 95
Winter Park Orangewood Park 2 $632,000 67
Winter Park Orwin Manor Westminster 4 $714,225 82
Winter Park Osceola Or Lakeview Deed 2 $850,000 1
Winter Park Osceola Shores 2 $2,150,000 111
Winter Park Palmer Ave Lakeside Prop 2 $4,950,000 13
Winter Park Park Grove 2 $4,072,500 31
Winter Park Park Manor First 1 $1,449,000 66
Winter Park Park Pointe Rep 1 $985,000 57
Winter Park Park West Condo 3 $716,000 62
Winter Park Parklando 1 $1,049,000 172
Winter Park Parklando #3 1 $1,649,000 209
Winter Park Parklando 03 1 $1,890,000 6
Winter Park Parkview Village 3 $152,833 66
Winter Park Parkview Village Condo 1 $150,000 387
Winter Park Parkview Village Condo Blvd 2918 1 $189,000 202
Winter Park Phillips Circle Rep 4 $1,001,000 143
Winter Park Pines 1 $439,900 82
Winter Park Preserve At Hawks Crest 1 $770,000 46
Winter Park Quail Run 1 $675,000 13
Winter Park Ridge High 3 $341,333 28
Winter Park Ridge High 1st 2 $359,495 41
Winter Park Sanctuary At Aloma 1 $659,000 7
Winter Park Sandlewood Creek 1 $285,000 36
Winter Park Seville Park 4 $597,500 55
Winter Park Sharon Place 2 $1,774,500 20
Winter Park Sherbrooke 1 $789,000 16
Winter Park Slovak Village 1 $235,000 98
Winter Park South Interlachen Place 2 $3,522,500 61
Winter Park South Lakemont Shores 4 $1,597,000 121
Winter Park Stansbury Estates 2 $388,500 88
Winter Park Stratford A Winter Park Condo 4 $192,175 115
Winter Park Suburban Homes 2 $407,450 82
Winter Park Suburban Homes First 1 $380,000 13
Winter Park Swoope Park 1 $680,000 251
Winter Park Sylvan Heights 3 $1,726,667 203
Winter Park Sylvan Lake Shores 2 $2,624,750 94
Winter Park Sylvan Park 2 $3,625,000 94
Winter Park Tanglewood 2 $458,500 572
Winter Park Tanglewood Rep 1 $439,900 11
Winter Park Tantum 3 $1,057,667 90
Winter Park Temple Estates 1 $1,795,000 32
Winter Park Temple Terrace 1 $950,000 197
Winter Park Temple Terrace Annex 1 $299,900 47
Winter Park Terrazo Del Sol 1 $499,000 196
Winter Park The Enclave Winter Park 7 $2,085,000 158
Winter Park Timberlane Shores 1 $3,890,000 47
Winter Park Town Of Winter Park 1 $2,625,000 115
Winter Park Townhomes/harper Place 2 $557,500 96
Winter Park Trinity Bay 1 $455,000 108
Winter Park Trotters Rep 1 $745,000 144
Winter Park Tuscany Terrace 2 $1,595,000 173
Winter Park Twin Acres 1 $1,649,000 195
Winter Park Urban Green 12 1 $535,000 118
Winter Park Versailles Winter Park Condo 1 $2,350,000 21
Winter Park Via Lago/hanging Moss Condo 1 $335,000 75
Winter Park Vilasa Twnhms 2 $1,349,500 58
Winter Park Villa View Park 2 $1,842,500 43
Winter Park Village Condos 1 $349,500 26
Winter Park Village Green 2 $489,000 104
Winter Park Village Winterset Inc 1 $989,500 131
Winter Park Villas Of Aragon Condo 1 $510,000 61
Winter Park Villas Of Casselberry 3 $369,967 121
Winter Park Virginia Heights Condo 1 $359,000 9
Winter Park Virginia Heights Rep 2 $1,262,000 124
Winter Park Virginia Hgts Rep 1 $810,000 110
Winter Park Vistas At Lake Howell 1 $315,000 129
Winter Park Waterbridge 1 $660,000 43
Winter Park Waterfall Cove 4 $129,725 76
Winter Park Waterfall Cove At Winter Park 1 $205,000 574
Winter Park Waterfall Cove At Winter Park Condominium D107 1 $180,000 55
Winter Park Waterfall Cove/winter Park 1 $102,500 174
Winter Park Waters Edge At Hawks Crest 2 $1,462,500 27
Winter Park Whispering Waters/phillips Circle Rep 1 $1,825,000 144
Winter Park Whisperwood 1 $134,900 12
Winter Park Whisperwood Condo 3 $194,300 166
Winter Park Windsong Elizabeths Walk 43/81 1 $1,377,500 109
Winter Park Windward Square 6 $284,998 74
Winter Park Winflor Court Pt Rep 1 $3,995,000 167
Winter Park Winter Park 8 $2,265,625 109
Winter Park Winter Park Estates 4 $483,725 29
Winter Park Winter Park Forest 1 $474,900 6
Winter Park Winter Park Gardens Condo 1 $350,000 130
Winter Park Winter Park Oasis 2 $1,397,000 70
Winter Park Winter Park Pines 10 $685,220 130
Winter Park Winter Park Pines Merrie Oaks 2 $529,950 153
Winter Park Winter Park Pines Rep 4 $563,350 107
Winter Park Winter Park Pointe 02 1 $319,000 6
Winter Park Winter Park Residential 2 $1,612,500 55
Winter Park Winter Park Rev 1 $1,770,000 182
Winter Park Winter Park Village 8 $1,438,813 80
Winter Park Winter Park Villas Condo 2 $210,950 24
Winter Park Winter Park Woods Condo 2 $104,700 169
Winter Park Winter Woods 3 $463,000 134
Winter Park Woodcrest 2 $487,450 42
Winter Park Woodmere Terrace Rep 1 $1,649,000 18
Winter Park Wrenwood 1 $495,000 20
Winter Park Wrenwood Condo 1 $175,000 117
Winter Park Wrenwood Heights 1 $460,000 162
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 09/29/2026. The listing information on this page last changed on 09/29/2026. 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 Tue 09/29/2026 2:05:04 AM EST) or GAMLS (last updated Mon 09/28/2026 11:15:08 PM EST) or Stellar MLS (last updated Tue 09/29/2026 1:54:35 AM EST) or SPC MLS (last updated Mon 09/28/2026 11:20:18 PM EST) or Martin MLS (last updated Mon 09/28/2026 11:38:12 PM EST) or Indian River MLS (last updated Mon 09/28/2026 11:30:06 PM EST) or Daytona MLS (last updated Mon 09/28/2026 11:36:44 PM EST) or Northeast Florida MLS (last updated Tue 09/29/2026 12:18:53 AM EST) or Beaches MLS (last updated Mon 09/28/2026 5:19:06 PM EST) or BORMLS (last updated Mon 09/28/2026 11:15:44 PM EST) or Scout MLS (Golden Isles) (last updated Mon 09/28/2026 7:06:18 AM EST) or Amelia/Nassau MLS (last updated Mon 09/28/2026 11:25:13 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 09/28/2026 11:42:17 PM EST) or NFLMLS (last updated Mon 09/28/2026 9:06:15 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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