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(912) 409-2395 Cell
(912) 409-2395 Cell Email (912) 409-2395
Debby McDermott
REAL ESTATE AGENT
REALTOR®, HEROES, Leading RE Agent
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Winter Garden, FL Real Estate Subdivision Directory

Are you considering moving to a certain Winter Garden, FL subdivision? Select the subdivision from the list below and browse its real estate and homes for sale.

Click any of the Winter Garden Subdivisions below to view real estate listings for sale in that respective Subdivision.

City Subdivision Listings Avg Asking Price Avg Days on Market
Winter Garden . 1 $160,000 541
Winter Garden 0000 1 $500,000 897
Winter Garden 30 North Park 1 $1,095,000 165
Winter Garden Acreage 1 $3,300,000 8
Winter Garden Acreage & Unrec 3 $1,782,967 289
Winter Garden Alexander Rdg 2 $527,000 98
Winter Garden Amberleigh 47/7 1 $730,000 19
Winter Garden Arrowhead Lakes 3 $506,000 236
Winter Garden Avalon Cove 3 $1,907,667 123
Winter Garden Avalon Hills 1 $1,250,000 773
Winter Garden Avalon Ridge 2 $1,574,500 78
Winter Garden Avalon Woods 62 $835,399 154
Winter Garden Bay Isle 48 17 1 $885,000 64
Winter Garden Bay St Park 1 $255,000 53
Winter Garden Belle Meade 1 $821,000 66
Winter Garden Belle Meade-ph I B D & G 1 $689,900 38
Winter Garden Black Lake Park 3 $577,667 115
Winter Garden Black Lake Preserve 2 $704,950 124
Winter Garden Block Q Summerlake Pd 1 $765,900 88
Winter Garden Borders & Woosley 1 $440,000 43
Winter Garden Boyd-lutz 1 $2,190,000 43
Winter Garden Bradford Creek 2 $929,950 55
Winter Garden Bradford Crk 1 $640,000 81
Winter Garden Bray J W F 1 $550,000 218
Winter Garden Bronsons Lndgs F & M 2 $1,247,500 92
Winter Garden Burchshire 1 $699,000 155
Winter Garden Cambridge Crossing 1 $839,000 108
Winter Garden Canopy Oaks 2 $1,347,500 74
Winter Garden Carriage Pointe A-i & L 3 $695,000 37
Winter Garden Chapin Station 1 $515,000 51
Winter Garden Chapin Station A 1 $615,000 8
Winter Garden Citrus Cove 1 $699,500 99
Winter Garden Cooper & Sewell 2 $930,000 51
Winter Garden Country Lakes 1 $975,000 119
Winter Garden Courtlea Oaks 1 $950,000 23
Winter Garden Covington Chase 2 $654,500 37
Winter Garden Covington Park 1 $800,000 106
Winter Garden Covington Park A B D E F G & J 1 $525,000 86
Winter Garden Crown Point Spgs 2 $454,000 72
Winter Garden Crown Point Springs 1 $539,999 74
Winter Garden Cypress Reserve 5 $978,600 25
Winter Garden Daniels Landing 1 $307,000 38
Winter Garden Daniels Lndg A-j 3 $326,333 48
Winter Garden Deerfield Place A-g 1 $498,995 69
Winter Garden Del Webb Oasis 9 $711,544 68
Winter Garden Downtown Winter Garden 1 $1,099,000 17
Winter Garden East Garden Manor 2 $619,500 80
Winter Garden Edgewater Beach 2 $479,000 29
Winter Garden Ellman Park 1 $544,900 82
Winter Garden Emerald Ridge 2 $570,000 74
Winter Garden Enclave At Hamlin 1 $565,000 159
Winter Garden Encore At Ovation 4 $588,745 76
Winter Garden Encore At Ovation-ph 3 1 $715,000 275
Winter Garden Encore/ovation 7 $646,571 69
Winter Garden Encore/ovation-ph 3 2 $729,950 86
Winter Garden Esplanade At Mckinnon Groves 13 $625,064 61
Winter Garden Estates At Lakeview Preserve 1 $1,099,000 30
Winter Garden Ests/lakeview Preserve 2 $969,450 89
Winter Garden Fries Winter Garden 2 $1,899,500 268
Winter Garden Fullers Crossing 2 $502,495 87
Winter Garden Fullers Oak 1 $689,000 29
Winter Garden Glynwood 51 32 1 $850,000 54
Winter Garden Grova Residence & Spa Hotel Condo 3 1 $480,000 61
Winter Garden Grove Pk/stone Crest A-e 1 $619,000 24
Winter Garden Grove Res & Spa Hotel Condo Iv 1 $345,000 433
Winter Garden Grove Residence & Spa Hotel 1 $359,000 442
Winter Garden Grove Residence & Spa Hotel Condo 2 $274,500 208
Winter Garden Grove Residence & Spa Hotel Condo 1 1 $179,000 205
Winter Garden Grove Residence & Spa Hotel Condo 2 1 $299,900 157
Winter Garden Grove Residence & Spa Hotel Condo 3 10 $260,740 157
Winter Garden Grove Residence & Spa Hotel Condo I 3 $315,967 168
Winter Garden Grove Residence & Spa Hotel Condo Ii 16 $261,050 145
Winter Garden Grove Residence & Spa Hotel Condo Il 1 $240,000 215
Winter Garden Grove Residence & Spa Hotel Condo Li 1 $219,000 7
Winter Garden Grove Resort 6 $285,390 442
Winter Garden Grove Resort & Spa Hotel Condo I 1 $290,000 164
Winter Garden Grove Resort & Spa Hotel Condo Iv 1 $150,000 317
Winter Garden Grove Resort & Spa Hotel Condominium 1 $179,950 143
Winter Garden Grove Resort And Spa 2 $255,250 97
Winter Garden Grove Resort And Spa Condominium 2 1 $244,990 166
Winter Garden Grove Resort And Spa Hote Condominium 3 1 $350,000 106
Winter Garden Grove Resort And Spa Hotel 1 $325,000 996
Winter Garden Grove Resort And Spa Hotel Condo 1 $215,000 122
Winter Garden Grove Resort And Spa Hotel Condo 1 5 $306,600 220
Winter Garden Grove Resort And Spa Hotel Condo 3 1 $329,900 110
Winter Garden Grove Resort And Spa Hotel Condo Ii 1 $165,000 187
Winter Garden Grove Resort And Spa Hotel Condomimium Building 2 1 $275,000 147
Winter Garden Grove Resort And Spa Hotel Condominium 11 $265,659 236
Winter Garden Grove Resort And Spa Hotel Condominium 1 6 $344,015 494
Winter Garden Grove Resort And Spa Hotel Condominium 2 1 $289,500 337
Winter Garden Grove Resort And Spa Hotel Condominium 3 6 $309,332 550
Winter Garden Grove Resort And Spa Hotel Condominium Ii 1 $325,000 102
Winter Garden Grove Resort And Water Park 1 $304,000 246
Winter Garden Grove Resort And Waterpark 1 $290,000 148
Winter Garden Grove/oakland 1 $2,210,000 94
Winter Garden Grovehurst A-d 2 $602,500 108
Winter Garden Hamilton Gardens 5 $456,480 137
Winter Garden Hamlin Meadows 10 $471,784 69
Winter Garden Hamlin Meadows At Hamlin 62 $699,541 104
Winter Garden Hamlin Pointe 1 $570,000 17
Winter Garden Hamlin Rdg 1 $449,999 43
Winter Garden Hamlin Reserve 7 $661,284 34
Winter Garden Hamlin Southwest 1 $18,900,000 158
Winter Garden Harvest At Ovation 9 $701,534 91
Winter Garden Harvest/ovation 7 $671,141 52
Winter Garden Hawksmoor 5 $735,996 108
Winter Garden Hawksmoor-ph 1 4 $643,950 149
Winter Garden Hawksmoor-ph 3 1 $419,900 164
Winter Garden Hickory Hammock 8 $882,975 44
Winter Garden Hickory Lake Estates 1 $639,000 11
Winter Garden Highland Rdg 6 $516,317 69
Winter Garden Highland Ridge 3 $529,833 86
Winter Garden Highlands/summerlake Grove 1 $790,000 215
Winter Garden Highlands/summerlake Grvs 10 $746,380 84
Winter Garden Hillcrest 1 $1,390,000 17
Winter Garden Horizon Isle 2 $738,000 108
Winter Garden Hull Island/oakland 2 $1,599,500 38
Winter Garden Independence 1 $1,690,000 23
Winter Garden Island Pointe 3 $604,000 91
Winter Garden Isles Lake Hancock 1 $3,330,000 101
Winter Garden J L Dillard 1 $1,499,999 292
Winter Garden Joe Louis Park First 2 $164,250 36
Winter Garden Joe Louis Park Q162 1 $419,000 37
Winter Garden Johns Cove 43/104 1 $1,075,000 49
Winter Garden Johns Lake Pointe 2 $907,000 37
Winter Garden Johns Lake Pointe A & S 2 $722,450 572
Winter Garden Johns Landing 1 $599,000 22
Winter Garden K Hovnanian Winding Bay Preserve 1 $445,000 480
Winter Garden Lake Apopka Sound 4 $674,475 11
Winter Garden Lake Avalon Groves 1 $2,500,000 571
Winter Garden Lake Avalon Groves Rep 7 $2,085,714 302
Winter Garden Lake Avalon Heights 1 $695,000 78
Winter Garden Lake Avalon Rural Settlement 1 $950,000 50
Winter Garden Lake Cove Pointe 1 $980,000 68
Winter Garden Lake Forest 3 $846,667 34
Winter Garden Lake Hancock Preserve 2 $642,500 210
Winter Garden Lake Roberts Lndg E 1 $1,200,000 58
Winter Garden Lake Star At Ovation 3 $969,993 106
Winter Garden Lake Star/ovation 1 $1,720,000 90
Winter Garden Lakeshore Preserve 28 $1,062,564 91
Winter Garden Lakeside At Hamlin 1 $579,000 38
Winter Garden Lakeside/hamlin 1 $695,990 24
Winter Garden Lakeside/hamlin 60 1 $1,045,000 50
Winter Garden Lakeview Pointe At Horizon West 2 $599,950 47
Winter Garden Lakeview Pointe/horizon West P 4 $530,000 48
Winter Garden Lakeview Preserve 6 $738,983 116
Winter Garden Lakeview Preserve Rep 1 $610,000 10
Winter Garden Lakeview Reserve 2 $1,137,500 78
Winter Garden Lakeview Reserve 46/149 4 $979,750 125
Winter Garden Lakeview Village Estates 4 $951,428 1
Winter Garden Latham Park North 1 $627,000 107
Winter Garden Latham Park South 2 $855,000 21
Winter Garden Lift Station/cobblestone/winte 1 $525,000 7
Winter Garden Longleaf At Oakland 1 $499,900 15
Winter Garden Loveless J S 3 $218,833 278
Winter Garden Magnolia Wood Fifth 1 $443,000 77
Winter Garden Mary Jean 1 $119,000 297
Winter Garden Mcallister Lndg 1 $1,349,000 113
Winter Garden Mezzano 3 $468,000 111
Winter Garden Mt Park Orange Grove 2 $912,500 152
Winter Garden None 7 $1,460,714 536
Winter Garden Northlake At Ovation 12 $827,467 56
Winter Garden Northlake/ovation 4 $892,250 149
Winter Garden Oak Park At Winter Garden 1 $468,000 3
Winter Garden Oakland Hills 1 $2,325,000 24
Winter Garden Oakland Park 7 $1,200,414 63
Winter Garden Oakland Park B-2 1 $1,765,000 188
Winter Garden Oakland Park South 1 $985,000 4
Winter Garden Oakland Parka 1 $890,000 60
Winter Garden Oakland Trls 1 $525,000 69
Winter Garden Oaks/brandy Lake 01 Rep A & B 1 $529,900 92
Winter Garden Orange Cove 2 $445,000 28
Winter Garden Orchard A1-a26 B1 B2 C D1-d4 2 $337,000 40
Winter Garden Orchard Hills 9 $641,211 44
Winter Garden Osprey Ranch 14 $641,916 70
Winter Garden Osprey Ranch-ph 1 2 $725,000 107
Winter Garden Ovation/westhaven 1 $515,000 180
Winter Garden Overlook 2 At Hamlin 1 $1,250,000 19
Winter Garden Overlook 2/hamlin 6 $1,180,991 69
Winter Garden Overlook At Hamlin 1 $2,295,000 109
Winter Garden Overstreet Crate 6 $730,000 341
Winter Garden Oxford Chase 2 $922,000 11
Winter Garden Palisades 3 $245,667 221
Winter Garden Panther View 2 $709,000 43
Winter Garden Panther View 40 1 $610,000 72
Winter Garden Park Ave Estates 2 $324,950 77
Winter Garden Park Place At Winter Garden 2 $882,500 56
Winter Garden Park Place/winter Garden 2 $861,500 122
Winter Garden Parkview At Hamlin 11 $497,796 53
Winter Garden Pleasant Park 1 $450,000 46
Winter Garden Ravenna 1 $799,900 61
Winter Garden Regal Pointe 1 $400,000 8
Winter Garden Regency Oaks 1 $524,500 30
Winter Garden Regency Oaks F 1 $595,000 114
Winter Garden Rep Pt Pleasant Park 1 $500,000 75
Winter Garden Reserve/carriage Point 1 $709,000 30
Winter Garden Reserve/carriage Pointe 1 $765,000 135
Winter Garden Roper Reserve 3 $724,633 113
Winter Garden Sanctuary/twin Waters 2 $998,500 115
Winter Garden Serenade At Ovation 20 $571,018 72
Winter Garden Serenade/ovation 1 $555,000 31
Winter Garden Shorefront Cove At Horizon West 1 $2,985,000 1
Winter Garden Signature Lakes 12 $568,483 60
Winter Garden Signature Lakes Independence 1 $2,860,000 5
Winter Garden Signature Lakes Prcl 01c 1 $440,000 25
Winter Garden Signature Lakes/independence 1 $645,000 37
Winter Garden Signature Lks-pcl 01b 2 $497,450 29
Winter Garden Signature Lks-pcl 01d 4 $1,627,000 57
Winter Garden Silverleaf Oaks 10 $500,030 33
Winter Garden Silverleaf Oaks At Hamlin 1 $585,000 57
Winter Garden Silverleaf Reserve 2 $719,500 155
Winter Garden Silverleaf Reserve At Hamlin 2 $779,950 276
Winter Garden Silverleaf Reserve Bungalows 1 $540,000 121
Winter Garden Silverleaf Reserve/hamlin 4 $940,000 90
Winter Garden Siplin Heights 1 $129,900 718
Winter Garden Southern Pines 1 $290,000 25
Winter Garden Southern Pines Condo 14 $270,975 78
Winter Garden Southern Pines Condominium 1 $225,000 165
Winter Garden Stone Creek 44/131 1 $477,000 67
Winter Garden Stone Crk 2 $417,000 58
Winter Garden Stoneybrook West 5 $667,780 69
Winter Garden Stoneybrook West 44/134 2 $617,500 112
Winter Garden Stoneybrook West 47/78 3 $609,997 71
Winter Garden Stoneybrook West I 3 $373,300 31
Winter Garden Stoneybrook West Ut 04 Rep 49 121 1 $474,000 201
Winter Garden Storey Grove 17 $544,579 136
Winter Garden Storey Grv 1 $445,000 2
Winter Garden Suburban Shores 1 $245,000 129
Winter Garden Suburban Shores Rep Pt Blk 03 1 $425,000 9
Winter Garden Summerlake 3 $491,667 95
Winter Garden Summerlake Groves 1 $640,000 53
Winter Garden Summerlake Grvs 4 $550,225 98
Winter Garden Summerlake Pd 12 $746,050 83
Winter Garden Summerlake Pd Phases 2c 1 $505,000 338
Winter Garden Summerlake Reserve 1 $989,000 393
Winter Garden Sunset Lakes 2 $2,399,450 100
Winter Garden Teacup Spgs Cove 1 $878,000 54
Winter Garden The Grove Resort 4 $278,750 307
Winter Garden The Grove Resort And Spa 2 $195,000 122
Winter Garden Tilden Place 1 $799,000 150
Winter Garden Tilden Place/winter Garden 2 $802,495 250
Winter Garden Timbercreek Pines A B C & D 1 $525,000 79
Winter Garden Townhomes Winter Garden 5 $203,980 71
Winter Garden Traditions 1 $429,975 144
Winter Garden Troynelle By Lake Apopka 1 $252,000 302
Winter Garden Tucker Oaks 5 $334,880 98
Winter Garden Tucker Oaks Bldg 5 1 $347,500 136
Winter Garden Tucker Oaks Condo 1 $350,000 44
Winter Garden Tuscany 1 $479,900 344
Winter Garden Twinwaters 9 $1,051,098 54
Winter Garden Valley View 1 $1,300,000 17
Winter Garden Verde Park 1 $834,999 42
Winter Garden Village Grove 2 $232,450 156
Winter Garden Waterleigh 107 $687,851 87
Winter Garden Watermark 27 $691,296 101
Winter Garden Waterside 90's 1 $2,795,900 58
Winter Garden Waterside At Johns Lake 1 $658,000 66
Winter Garden Waterside/johns Lake 5 $747,780 56
Winter Garden Waterside/johns Lk-ph 2a 2 $592,500 6
Winter Garden West Lake Hancock Estates 4 $1,202,500 42
Winter Garden Westchester Place 2 $313,500 218
Winter Garden Westfield Lakes 3 $974,300 44
Winter Garden Westhaven At Ovation 30 $663,348 118
Winter Garden Westhaven/ovation 1 $468,000 99
Winter Garden Westpoint Townhomes 1 $330,000 29
Winter Garden Westside Townhomes 1 $215,000 61
Winter Garden Wincey Groves 1 $649,900 149
Winter Garden Wincey Grvs 2 $764,750 42
Winter Garden Winding Bay 9 $628,989 88
Winter Garden Winding Bay Preserve 1 $439,000 17
Winter Garden Windtree Gardens 1 $199,999 15
Winter Garden Windtree Gardens Condo 4 $209,200 165
Winter Garden Winter Garden Executive Centre 1 $799,000 67
Winter Garden Winter Garden Shores 2nd 1 $1,495,000 8
Winter Garden Winter Garden Shores First 1 $1,080,000 64
Winter Garden Winter Garden Shores Rep 2 $1,025,000 129
Winter Garden Winter Grove 5 $1,029,078 103
Winter Garden Winter Grv 1 $1,600,000 79
Winter Garden Winter Oaks 1 $775,995 3
Winter Garden Wintermere Pointe 2 $732,500 33
Winter Garden Woodbridge On Green 1 $714,999 137
Debby McDermott Office: (912) 882-5658 ext. 4443 Cell: (912) 409-2395 Fax: (912) 882-1816 Office: (912) 882-5658 Cell: (912) 409-2395 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 08/08/2026. The listing information on this page last changed on 08/08/2026. 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 08/08/2026 10:28:01 AM EST) or GAMLS (last updated Sat 08/08/2026 10:26:01 AM EST) or Stellar MLS (last updated Sat 08/08/2026 10:16:15 AM EST) or SPC MLS (last updated Sat 08/08/2026 10:25:04 AM EST) or Martin MLS (last updated Sat 08/08/2026 10:27:41 AM EST) or Indian River MLS (last updated Sat 08/08/2026 10:24:39 AM EST) or Daytona MLS (last updated Sat 08/08/2026 10:17:34 AM EST) or Northeast Florida MLS (last updated Sat 08/08/2026 10:19:36 AM EST) or Beaches MLS (last updated Sat 08/08/2026 12:35:29 AM EST) or BORMLS (last updated Sat 08/08/2026 10:23:07 AM EST) or Scout MLS (Golden Isles) (last updated Sat 08/08/2026 7:06:08 AM EST) or Amelia/Nassau MLS (last updated Sat 08/08/2026 10:27:35 AM EST) or Dixie Gilchrist Levy MLS (last updated Sat 08/08/2026 10:27:45 AM EST) or NFLMLS (last updated Sat 08/08/2026 9:05:14 AM 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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