Source: Stellar MLS via the Bridge RESO feed, pulled 2026-09-10. Updated weekly.
321 of the 630 Winter Garden homes on the market (51%) are asking less than they did on day one, and 303 (48%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 59 days in who has already cut once is a different negotiation than one of the 327 listings still inside its first 60 days.
Across the 321 Winter Garden listings that have already come down, the typical reduction is 4.47% off the original asking price. That is the size of a first concession, not a final one.
Every Winter Garden subdivision with an active listing or its own page here, ranked by inventory. A subdivision showing 0 still appears: this is a live MLS feed and inventory changes daily. The 628 homes in named subdivisions are 100% of the Winter Garden market; the rest are on unplatted land or were listed without a subdivision name.
Grove Residence & Spa Hotel Condo Ii16 active$260,000
Southern Pines Condo12 active$277,450
Grove Resort And Spa Hotel Condominium11 active$249,500
Grove Residence & Spa Hotel Condo 310 active$267,250
Del Webb Oasis10 active$770,000
Grove Resort9 active$225,000
Encore/Ovation7 active$595,000
Summerlake Pd7 active$584,900
Townhomes Winter Garden6 active$212,000
Grove Residence & Spa Hotel Condo I5 active$249,000
Grove Resort And Spa Hotel Condominium 15 active$379,000
Twinwaters5 active$1,046,000
Silverleaf Reserve/Hamlin5 active$950,000
Highland Rdg5 active$499,000
Hickory Hammock5 active$699,995
Oakland Park5 active$1,195,000
Waterside/Johns Lake5 active$660,000
Windtree Gardens Condo4 active$216,000
Palisades4 active$234,500
Lake Avalon Groves Rep4 active$2,162,500
Highlands/Summerlake Grvs4 active$757,249
Grove Resort And Spa Hotel Condo 14 active$267,000
Lakeview Village Estates4 active$1,018,455
Winter Grove4 active$957,480
Stoneybrook West4 active$662,000
Grove Resort And Spa3 active$239,500*
Northlake/Ovation3 active$975,000*
Winter Garden Shores Rep3 active$719,500*
Grove Resort And Spa Hotel Condominium 33 active$335,000*
Stoneybrook West I3 active$369,900*
Tucker Oaks3 active$328,000*
Bronsons Lndgs F & M3 active$860,000*
Carriage Pointe A-I & L3 active$775,000*
Stone Crk3 active$393,000*
Stoneybrook West D3 active$619,900*
Westchester Place2 active$313,500*
Overstreet Crate2 active$437,500*
Sunset Lakes2 active$2,394,450*
Arrowhead Lakes2 active$602,500*
Covington Chase2 active$642,000*
Loveless J S2 active$286,249*
Tilden Place/Winter Garden2 active$802,495*
Avalon Ridge2 active$1,574,500*
Park Place/Winter Garden2 active$844,000*
Park Place At Winter Garden2 active$882,500*
Highland Ridge2 active$552,250*
Grove Residence & Spa Hotel Condo Li2 active$201,950*
Orchard A1-A26 B1 B2 C D1-D42 active$360,000*
Twin City Dev Co2 active$361,500*
Sanctuary/Twin Waters2 active$1,475,000*
Wintermere Pointe2 active$860,000*
Village Grove2 active$232,450*
Black Lake Park2 active$789,000*
Alexander Ridge2 active$544,500*
Grove Resort & Spa Hotel Condominium2 active$174,975*
Waterside/Johns Lk2 active$1,037,499*
Grove Residence & Spa Hotel1 active$359,000*
Grove Resort And Spa Hotel Condominium Ii1 active$325,000*
Grove Resort & Spa Hotel Condo Iv1 active$150,000*
Winter Grv1 active$1,600,000*
Lake Forest1 active$825,000*
Regency Oaks F1 active$595,000*
Grova Residence & Spa Hotel Condo 31 active$480,000*
Bradford Crk1 active$640,000*
Grove Residence & Spa Hotel Condo1 active$299,000*
Lakeview Reserve 46/1491 active$1,300,000*
Grove Residence & Spa Hotel Condo 21 active$299,900*
Grove Resort And Water Park1 active$304,000*
Signature Lks-Pcl 01D1 active$575,000*
Cambridge Crossing1 active$839,000*
Joe Louis Park First1 active$289,000*
Oakland Hills1 active$2,325,000*
Grove Resort And Spa Hotel Condo Ii1 active$165,000*
Grove Resort And Spa Hotel1 active$325,000*
Borders & Woosley1 active$440,000*
Grove Residence & Spa Hotel Condo 11 active$179,000*
30 North Park1 active$1,095,000*
Daniels Lndg A-J1 active$325,000*
Hull Island/Oakland1 active$1,500,000*
Covington Park1 active$800,000*
Wincey Grvs1 active$859,500*
Grove Resort And Waterpark1 active$290,000*
Storey Grv1 active$445,000*
Grove Resort And Spa Hotel Condo1 active$215,000*
Southern Pines1 active$290,000*
Grove Pk/Stone Crest A-E1 active$619,000*
Grove Resort And Spa Hotel Condomimium Building 21 active$275,000*
Fries Winter Garden1 active$800,000*
Black Lake Preserve1 active$640,000*
M C Britt1 active$479,900*
Grove Resort & Spa1 active$239,000*
Grove Resort & Spa Hotel Condo I1 active$290,000*
Grove Resort And Spa Condominium 21 active$244,990*
Bradford Creek1 active$1,060,000*
Joe Louis Park1 active$275,000*
Grove Residence & Spa Hotel Condo Il1 active$194,900*
Highlands/Summerlake Grove1 active$775,000*
East Garden Manor1 active$338,000*
Belle Meade1 active$669,900*
Lakeview Reserve1 active$1,675,000*
Stoneybrook West 47/781 active$439,000*
Park Ave Estates1 active$325,000*
J L Dillard1 active$1,499,999*
Winter Oaks1 active$749,995*
Valencia Shores1 active$750,000*
Winter Garden Shores1 active$849,900*
Grove Resort And Spa Hotel Condominium 21 active$274,900*
Grove Resort And Spa Hote Condominium 31 active$350,000*
Glynwood 51 321 active$850,000*
Walkers Grove Twnhms1 active$540,000*
Reserve/Carriage Point1 active$699,000*
Lake Cove Pointe 46/581 active$849,988*
Oxford Chase1 active$925,000*
Grove Resort And Spa Hotel Condominium 220190396151 active$205,000*
Canopy Oaks1 active$1,225,000*
Vinings Add Winter Garden1 active$545,000*
Woodbridge On Green1 active$699,000*
Serenade/Ovation1 active$529,900*
Lake Star/Ovation1 active$1,639,900*
Amberleigh1 active$600,000*
Block Q Summerlake Pd1 active$735,000*
Orange Cove1 active$489,000*
Winter Garden Shores First1 active$1,020,000*
Johns Lake Pointe1 active$702,500*
Roper Reserve1 active$729,900*
Tilden Place1 active$789,000*
Crown Point Spgs1 active$475,000*
Fullers Crossing1 active$474,990*
Johns Landing1 active$569,000*
Stoneybrook West Ut 4``1 active$859,000*
Oakglen Estates1 active$660,000*
Windtree Gardens1 active$199,999*
Bay Isle 48 171 active$870,000*
Country Lakes1 active$969,000*
Cypress Reserve1 active$970,000*
Oak Park At Winter Garden1 active$455,000*
Wintermere Harbor1 active$730,000*
Stone Creek 48 1401 active$415,000*
Mcallister Lndg1 active$1,349,000*
Harbor1 active$499,900*
Rep Pt Pleasant Park1 active$495,000*
Teacup Spgs Cove1 active$857,000*
John Lake Pointe1 active$520,000*
Winter Garden Shores 2Nd1 active$1,465,000*
Villas/Tucker Oaks1 active$379,000*
Oakland Park B-21 active$1,725,000*
Grovehurst A-D1 active$599,000*
Island Pointe1 active$625,000*
Burchshire1 active$749,999*
Fullers Oak1 active$839,000*
Crown Point Springs1 active$475,000*
Subdivision names come from the MLS as agents entered them. Active count and median list price as of 2026-09-10. * Medians on rows with fewer than 4 listings are indicative only. Open a subdivision for days on market, price per square foot and sales history.
Winter Garden is a city in western Orange County, 46,964 residents at the 2020 census, about 14 miles west of downtown Orlando.
The recorded history is layered and contested. Historians cannot say with confidence whether the people here before Europeans were Timucua, Jororo or Mayaca. Those cultures were gone by the end of the eighteenth century, and Seminole communities later formed along the south shore of Lake Apopka.
The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Winter Garden listing on this page.
