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Jamie Deihl
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(719) 468-9744

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 $160,000 390
Winter Garden 0000 1 $500,000 746
Winter Garden 30 North Park 2 $1,559,000 19
Winter Garden Acreage 3 $1,633,000 174
Winter Garden Acreage & Unrec 3 $1,216,600 173
Winter Garden Alexander Ridge 1 $550,000 4
Winter Garden Amberleigh 1 $625,000 54
Winter Garden Arrowhead Lakes 1 $650,000 508
Winter Garden Avalon Cove 3 $2,250,000 57
Winter Garden Avalon Estates 2 $1,624,500 237
Winter Garden Avalon Hills 1 $1,375,000 622
Winter Garden Avalon Reserve 1 $625,000 35
Winter Garden Avalon Reserve - Village 1 1 $918,000 117
Winter Garden Avalon Reserve Village 1 1 $715,000 233
Winter Garden Avalon Ridge 1 $2,280,000 144
Winter Garden Avalon Woods 59 $852,831 95
Winter Garden Bay Isle 48 17 2 $834,950 299
Winter Garden Bay St Park 1 $244,900 168
Winter Garden Black Lake 1 $409,999 208
Winter Garden Black Lake Park 2 $554,500 38
Winter Garden Black Lake Preserve 4 $861,000 59
Winter Garden Bradford Creek 1 $937,500 87
Winter Garden Bradford Crk 1 $799,000 129
Winter Garden Bray J W F 1 $639,000 67
Winter Garden Bronson's Landing 1 $680,000 104
Winter Garden Bronsons Lndgs F & M 2 $1,587,500 4
Winter Garden Burchshire 4 $547,500 108
Winter Garden Canopy Oaks 1 $1,350,000 1
Winter Garden Carriage Pointe 1 $810,000 47
Winter Garden Carriage Pointe A-i & L 2 $590,000 29
Winter Garden Citrus Cove 1 $749,900 144
Winter Garden Cobblestone/winter Garden 1 $494,000 39
Winter Garden Country Lakes 1 $1,490,000 6
Winter Garden Courtlea Oaks 3 $1,248,333 20
Winter Garden Covington Chase 3 $591,633 31
Winter Garden Covington Park A B D E F G & J 1 $549,900 153
Winter Garden Crown Point Springs Ut 2 1 $425,000 13
Winter Garden Cypress Reserve 4 $799,750 33
Winter Garden Daniels Crossing 2 $325,000 87
Winter Garden Daniels Landing 1 $310,000 7
Winter Garden Daniels Landing A-j 1 $300,000 29
Winter Garden Daniels Lndg A-j 1 $275,000 101
Winter Garden Deer Island 2 $2,017,500 83
Winter Garden Deerfield Place A-g 1 $605,000 157
Winter Garden Del Webb Oasis 15 $605,399 100
Winter Garden East Garden Manor First 1 $305,000 19
Winter Garden Emerald Acres 2 $1,575,000 82
Winter Garden Emerald Ridge 1 $610,000 12
Winter Garden Enclave At Hamlin 1 $599,900 8
Winter Garden Enclave/hamlin 2 $589,945 34
Winter Garden Encore At Ovation 4 $604,973 160
Winter Garden Encore At Ovation-ph 3 1 $715,000 124
Winter Garden Encore/ovation 2 $473,000 24
Winter Garden Encore/ovation-ph 2 1 $725,000 64
Winter Garden Esplanade At Mckinnon Groves 1 $389,999 4
Winter Garden Ests/lakeview Preserve 2 $971,450 182
Winter Garden Fries Winter Garden 1 $2,999,000 333
Winter Garden Fullers Crossing 1 $520,000 40
Winter Garden Fullers Lndg B 1 $630,000 40
Winter Garden Fullers Xing 1 $595,000 83
Winter Garden Garden Heights 1 $585,000 35
Winter Garden Garden West 1 $1,150,000 32
Winter Garden Glenview Estates 2nd 1 $424,000 2
Winter Garden Grove Park At Stone Crest 1 $576,500 7
Winter Garden Grove Pk/stone Crest A-e 1 $644,900 68
Winter Garden Grove Res & Spa Hotel Condo 3 1 $290,000 228
Winter Garden Grove Res & Spa Hotel Condo Iv 1 $345,000 282
Winter Garden Grove Residence & Spa Hotel 1 $359,000 291
Winter Garden Grove Residence & Spa Hotel Condo 2 $227,000 132
Winter Garden Grove Residence & Spa Hotel Condo 1 2 $251,750 59
Winter Garden Grove Residence & Spa Hotel Condo 2 1 $314,900 6
Winter Garden Grove Residence & Spa Hotel Condo 3 11 $289,582 234
Winter Garden Grove Residence & Spa Hotel Condo I 7 $274,271 137
Winter Garden Grove Residence & Spa Hotel Condo Ii 15 $263,673 146
Winter Garden Grove Residence & Spa Hotel Condo Il 2 $280,000 295
Winter Garden Grove Residence Y Spa Hotel Condo Ii 1 $224,000 299
Winter Garden Grove Resort 7 $339,463 338
Winter Garden Grove Resort & Spa 1 $325,000 1350
Winter Garden Grove Resort & Spa Hotel Condo I 1 $300,000 13
Winter Garden Grove Resort & Spa Hotel Condo Iv 1 $150,000 166
Winter Garden Grove Resort And Spa 2 $320,000 164
Winter Garden Grove Resort And Spa Condominium 2 1 $287,990 15
Winter Garden Grove Resort And Spa Hotel 1 $332,500 845
Winter Garden Grove Resort And Spa Hotel Condo 1 5 $355,800 111
Winter Garden Grove Resort And Spa Hotel Condo Ii 1 $184,900 36
Winter Garden Grove Resort And Spa Hotel Condominium 12 $289,650 285
Winter Garden Grove Resort And Spa Hotel Condominium 1 8 $346,362 326
Winter Garden Grove Resort And Spa Hotel Condominium 2 1 $289,500 186
Winter Garden Grove Resort And Spa Hotel Condominium 2 201903961 1 $299,000 119
Winter Garden Grove Resort And Spa Hotel Condominium 3 6 $312,665 399
Winter Garden Grove Resort And Spa Hotel Condominium U 1 $190,000 34
Winter Garden Grove Resort And Water Park 1 $304,000 95
Winter Garden Grovehurst A-d 1 $660,000 34
Winter Garden Hamilton Gardens 6 $568,333 110
Winter Garden Hamlin Meadows 1 $471,735 21
Winter Garden Hamlin Meadows At Hamlin 15 $687,597 14
Winter Garden Hamlin Pointe 1 $575,000 5
Winter Garden Hamlin Rdg 2 $441,950 129
Winter Garden Hamlin Reserve 6 $593,283 238
Winter Garden Harvest At Ovation 8 $685,311 21
Winter Garden Harvest/ovation 2 $569,500 92
Winter Garden Hawksmoor 6 $776,650 109
Winter Garden Hawksmoor-ph 1 2 $692,995 114
Winter Garden Hawksmoor-ph 3 1 $450,000 13
Winter Garden Heritage/plant Street 1 $525,000 12
Winter Garden Hickory Hammock 10 $1,023,999 74
Winter Garden Hickory Hammock Emerald Pointe 1 $2,150,000 116
Winter Garden Hickory Lake Estates 1 $1,150,000 11
Winter Garden Highland Rdg 4 $505,725 204
Winter Garden Highland Ridge 5 $486,580 84
Winter Garden Highland Ridge 110/69 Lot 19 1 $474,500 158
Winter Garden Highlands At Summerlake Groves 2 $1,037,500 72
Winter Garden Highlands/summerlake Grove 2 $825,000 63
Winter Garden Highlands/summerlake Grvs 9 $678,433 70
Winter Garden Highlands/summerlake Grvs #1 1 $416,000 101
Winter Garden Hillcrest 1 $415,000 509
Winter Garden Horizon Isle 1 $669,000 11
Winter Garden Horizon Isles 1 $879,000 90
Winter Garden Independence 1 $359,000 97
Winter Garden Independence Community 1 $575,000 342
Winter Garden Island Pointe 3 $624,666 98
Winter Garden Isles Lake Hancock 1 $3,380,000 29
Winter Garden Isles Of Lake Hancock 1 $1,100,000 35
Winter Garden J L Dillard 1 $1,750,000 141
Winter Garden Joe Louis Park 1 $169,000 43
Winter Garden Joe Louis Park First 1 $278,700 7
Winter Garden Johns Lake Pointe 1 $609,000 259
Winter Garden Johns Lake Pointe A & S 4 $810,998 251
Winter Garden K Hovnanian Winding Bay Preserve 1 $445,000 329
Winter Garden Lake Apopka Sound 3 $824,333 91
Winter Garden Lake Avalon Groves 2 $1,897,500 238
Winter Garden Lake Avalon Groves Rep 6 $1,834,000 225
Winter Garden Lake Avalon Grvs 2nd Rep 1 $2,500,000 404
Winter Garden Lake Avalon Heights 1 $1,150,000 153
Winter Garden Lake Forest 1 $900,000 20
Winter Garden Lake Hancock Preserve 4 $619,950 123
Winter Garden Lake Roberts Lndg E 1 $845,000 33
Winter Garden Lake Star At Ovation 11 $779,083 128
Winter Garden Lakeshore Preserve 11 $1,040,580 134
Winter Garden Lakeside At Hamlin 1 $735,000 135
Winter Garden Lakeside/hamlin 2 $584,500 58
Winter Garden Lakeview Pointe 2 $425,000 13
Winter Garden Lakeview Pointe/horizon West 1 $499,990 170
Winter Garden Lakeview Pointe/horizon West P 2 $475,713 21
Winter Garden Lakeview Preserve 12 $704,742 65
Winter Garden Lakeview Reserve 46/149 3 $965,333 85
Winter Garden Lakeview Village Estates 2 $757,170 7
Winter Garden Latham Park North 3 $715,000 37
Winter Garden Latham Park South 1 $995,000 108
Winter Garden Lift Station/cobblestone/winte 1 $609,900 29
Winter Garden Loveless J S 2 $154,500 193
Winter Garden Magnolia Wood Fifth 1 $625,000 40
Winter Garden Mary Jean 1 $119,000 146
Winter Garden Mcallister Lndg 2 $725,000 62
Winter Garden Merchants 1 $343,000 183
Winter Garden Mezzano 4 $491,225 83
Winter Garden Mt Park Orange Grove 1 $799,000 33
Winter Garden None 9 $1,370,000 341
Winter Garden Northlake At Ovation 7 $716,349 76
Winter Garden Northlake/ovation 8 $796,750 80
Winter Garden Not On The List 1 $625,000 54
Winter Garden Oak Park At Winter Garden 1 $489,900 27
Winter Garden Oakland 1 $1,495,000 18
Winter Garden Oakland Hills 1 $1,850,000 6
Winter Garden Oakland Park 6 $1,183,150 79
Winter Garden Oakland Park Ut 1b - 1a 1 $875,000 20
Winter Garden Oaks/brandy Lake 01 Rep A & B 1 $540,000 120
Winter Garden Oaks/brandy Lake O 2 $499,450 45
Winter Garden Orange Grove 1 $1,650,000 36
Winter Garden Orchard A1-a26 B1 B2 C D1-d4 1 $399,000 40
Winter Garden Orchard Hills 7 $626,000 107
Winter Garden Orchard Pk/stillwater Xing 5 $732,700 105
Winter Garden Osprey Ranch 3 $657,506 55
Winter Garden Osprey Ranch - Phase 1 1 $455,000 187
Winter Garden Osprey Ranch-ph 1 2 $702,500 147
Winter Garden Overlook 2 At Hamlin 1 $1,200,000 33
Winter Garden Overlook 2 Hamlin 1 $635,000 7
Winter Garden Overlook 2/hamlin 5 $987,800 45
Winter Garden Overstreet Crate 5 $720,400 261
Winter Garden Oxford Chase 2 $749,450 22
Winter Garden Palisades 3 $247,000 198
Winter Garden Palisades Condo 1 $259,900 191
Winter Garden Panther View 3 $742,633 116
Winter Garden Park Place 1 $969,000 219
Winter Garden Park Place/winter Garden 1 $895,000 53
Winter Garden Parkview At Hamlin 12 $487,025 46
Winter Garden Parkview/hamlin 3 $492,657 13
Winter Garden Prominent Pointe 1 $810,000 46
Winter Garden Ravenna 4 $517,075 108
Winter Garden Regal Pointe 1 $334,900 13
Winter Garden Regency Oaks F 1 $595,000 165
Winter Garden Reserve At Carriage Pointe 2 $847,450 55
Winter Garden Reserve Carriage Pointe 1 $775,000 27
Winter Garden Roper Reserve 2 $750,000 51
Winter Garden Sanctuary / Twin Waters 1 $900,000 6
Winter Garden Sanctuary/hamlin 2 $885,000 61
Winter Garden Sanctuary/twin Waters 2 $1,465,000 43
Winter Garden Savannah Ridge 1 $3,299,999 257
Winter Garden Serenade At Ovation 18 $583,763 76
Winter Garden Shorefront Cove 2 $3,419,193 167
Winter Garden Showalter Park 2 $462,500 110
Winter Garden Signature Lakes 14 $1,005,607 81
Winter Garden Signature Lakes Parcel 1a 1 $505,000 46
Winter Garden Signature Lakes Parcel 1d 1 $1,246,000 230
Winter Garden Signature Lakes Prcl 01c 1 $3,195,000 22
Winter Garden Signature Lakes, Independence 2 $1,694,950 41
Winter Garden Signature Lakes-pcl 01d 1 $824,900 116
Winter Garden Signature Lks-pcl 01a 2 $339,950 82
Winter Garden Signature Lks-pcl 01b 3 $543,300 40
Winter Garden Signature Lks-pcl 01d 2 $332,495 63
Winter Garden Silverleaf Oaks 2 $754,595 32
Winter Garden Silverleaf Oaks At Hamlin 1 $585,000 149
Winter Garden Silverleaf Oaks/hamlin 1 $455,000 20
Winter Garden Silverleaf Reserve 1 $899,000 104
Winter Garden Silverleaf Reserve/haml 1 $564,900 26
Winter Garden Silverleaf Reserve/hamlin 5 $670,400 55
Winter Garden Siplin Heights 1 $129,900 567
Winter Garden Solomon 1 $285,000 50
Winter Garden Southern Pines 1 $270,000 29
Winter Garden Southern Pines Condo 10 $286,479 105
Winter Garden Southern Pines Condominium 1 $240,000 14
Winter Garden Stanton Estates 1 $1,200,000 5
Winter Garden Stone Creek 1 $389,900 41
Winter Garden Stone Creek 44/131 2 $417,500 34
Winter Garden Stoneybrook West 4 $703,200 152
Winter Garden Stoneybrook West 44/134 2 $685,000 16
Winter Garden Stoneybrook West D 2 $557,495 19
Winter Garden Stoneybrook West I 1 $365,000 204
Winter Garden Stoneybrook West Ut 04 48 48 4 $619,973 57
Winter Garden Stoneybrook West Ut 04 Rep 49 121 1 $549,000 50
Winter Garden Storey Grove 18 $535,933 76
Winter Garden Storey Grove 50 1 $675,000 228
Winter Garden Storey Grv 1 $519,000 155
Winter Garden Summerlake 1 $509,900 48
Winter Garden Summerlake Groves 1 $495,900 5
Winter Garden Summerlake Grvs 6 $672,083 40
Winter Garden Summerlake Pd 19 $723,889 97
Winter Garden Summerlake Pd Phases 2c 1 $505,000 187
Winter Garden Summerlake Reserve 2 $949,000 125
Winter Garden The Grove Resort 2 $337,500 181
Winter Garden The Grove Resort And Spa 1 $215,000 40
Winter Garden Tilden Place 1 $1,399,000 6
Winter Garden Tilden Place/winter Garden 3 $868,300 86
Winter Garden Townhomes Of Winter Garden Condo 1 $225,000 88
Winter Garden Townhomes Winter Garden 2 $169,950 107
Winter Garden Tribute At Ovation Way 1 $459,900 36
Winter Garden Troynelle By Lake Apopka 1 $260,000 151
Winter Garden Tucker Oaks 2 $2,543,500 405
Winter Garden Tuscany 3 $609,930 184
Winter Garden Twinwaters 3 $1,586,300 67
Winter Garden Twinwaters Homeowners' Association, Inc. 1 $1,399,900 36
Winter Garden Valencia Shores 1 $495,000 19
Winter Garden Verde Park 2 $704,500 230
Winter Garden Village Grove 4 $237,475 146
Winter Garden Vinings 1 $775,000 112
Winter Garden Walkers Grove Twnhms 1 $490,000 47
Winter Garden Waterleigh 90 $660,596 94
Winter Garden Watermark 19 $661,189 139
Winter Garden Waterside On Johns Lake 1 $795,000 14
Winter Garden Waterside/johns Lake 4 $578,000 95
Winter Garden Waterside/johns Lk-ph 1 1 $1,590,000 6
Winter Garden Waterside/johns Lk-ph 2a 1 $510,000 83
Winter Garden Waterside/johns Lk-ph 2b 1 $874,500 18
Winter Garden West Lake Hancock Estates 3 $1,278,296 159
Winter Garden Westchester Place 3 $314,000 48
Winter Garden Westfield Lakes 1 $549,000 40
Winter Garden Westhaven At Ovation 11 $716,717 64
Winter Garden Westhaven/ovation 3 $643,333 200
Winter Garden Westlake Manor 1st 1 $765,000 27
Winter Garden Westside Townhomes 1 $212,500 244
Winter Garden Westside Twnhms 1 $229,000 120
Winter Garden Wincey Groves 3 $833,267 193
Winter Garden Wincey Grvs 4 $778,750 31
Winter Garden Winding Bay 14 $717,035 68
Winter Garden Winding Bay Ii Llc 1 $1,175,000 47
Winter Garden Winding Bay Preserve 2 $444,000 196
Winter Garden Windtree Gardens 1 $199,900 94
Winter Garden Windtree Gardens Condo 4 $211,500 79
Winter Garden Windtree Professional Center 1 $399,000 6
Winter Garden Winter Garden Manor 1 $575,000 35
Winter Garden Winter Garden Shores Rep 2 $892,450 92
Winter Garden Winter Garden Trls 01-3 1 $512,000 272
Winter Garden Winter Grove 2 $899,950 9
Winter Garden Wintermere Pointe 3 $823,333 27
Winter Garden Winters Lndg 1 $875,000 57
Jamie Deihl
Jamie Deihl Office: (904) 461-9066 Cell: (719) 468-9744 Fax: (904) 461-9925 Direct Phone: (719) 468-9744 Email Me
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 03/10/2026. The listing information on this page last changed on 03/10/2026. 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 Tue 03/10/2026 12:42:09 AM EST) or GAMLS (last updated Mon 03/09/2026 11:14:58 PM EST) or Stellar MLS (last updated Tue 03/10/2026 12:29:11 AM EST) or SPC MLS (last updated Mon 03/09/2026 11:20:30 PM EST) or Martin MLS (last updated Mon 03/09/2026 11:38:19 PM EST) or Indian River MLS (last updated Mon 03/09/2026 11:30:27 PM EST) or Daytona MLS (last updated Mon 03/09/2026 11:36:51 PM EST) or Northeast Florida MLS (last updated Tue 03/10/2026 12:18:46 AM EST) or Beaches MLS (last updated Tue 03/10/2026 12:35:40 AM EST) or BORMLS (last updated Mon 03/09/2026 11:15:20 PM EST) or Golden Isles MLS (last updated Mon 03/09/2026 11:26:41 PM EST) or Amelia/Nassau MLS (last updated Mon 03/09/2026 11:25:21 PM EST) or Dixie Gilchrist Levy MLS (last updated Mon 03/09/2026 11:42:28 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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