Winter Springs neighborhoods with the market data that actually moves a decision.
131 Winter Springs community guides, each with real pricing, HOA/CDD reality, and flood/insurance posture. Below: the Winter Springs market snapshot, then every community we cover.
Winter Springs market snapshot
$437,470Median sale price
$247.9Median $/sq ft
36Median days on market
-3.1%Year over year
+94.5%10-yr appreciation
160Communities with sales data
Median sale price by year
Aggregated from MLS closed-sale records across 160 Winter Springs communities; latest data 2026. Aggregate statistics only, deemed reliable but not guaranteed; not an appraisal. Refreshes with each MLS data update.
All Winter Springs communities (131)
AmherstAmherst in Winter Springs, FL: Median sale $439K (2026), 69 homes, built 1984-1986, median 0 days on market. Live Stellar MLS data and public records.Arrowhead At TuscawillaArrowhead At Tuscawilla in Winter Springs, FL: 298 homes, built 1973-2016. Live Stellar MLS data and public records.Bahama RanchesBahama Ranches in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Barclay ReserveBarclay Reserve in Winter Springs, FL: 18 homes built 2005–2006, ~1,558 sq ft, 3 bd/2.5 ba. ZIP 32708 median $411K, 38 for sale.Barclay Reserve TownhomesBarclay Reserve Townhomes in Winter Springs, FL: 70 homes built 2005–2006, ~1,558 sq ft, 3 bd/2.5 ba. ZIP 32708 median $411K, 38 for sale.Barrington EstatesBarrington Estates in Winter Springs, FL: Median sale $728K (2026), 110 homes, built 2003-2006, median 100 days on market.Bay TreeBay Tree in Winter Springs, FL: a condo community, 2,167 homes for sale in Seminole County (29% under contract), 9 MLS sales on record since 2016.Baytree VillageBaytree Village in Winter Springs, FL: Median sale $180K (2026), median 71 days on market. Live Stellar MLS data and public records.Bear Creek EstatesBear Creek Estates in Winter Springs, FL: 43 homes built 1983–1993, ~3,722 sq ft, 5 bd/4 ba. ZIP 32708 median $411K, 38 for sale.Bentley Club At Bentley GreenBentley Club At Bentley Green in Winter Springs, FL: 24 homes built 1991–1995, ~2,648 sq ft, 4 bd/3 ba. ZIP 32708 median $411K, 38 for sale.Bentley GreenBentley Green in Winter Springs, FL: Recent sales median $508K (2025), $259/sq ft, 9 sales since 2012. Live Stellar MLS data and public records.Carrington WoodsCarrington Woods in Winter Springs, FL: 82 homes, built 1989-2001. Live Stellar MLS data and public records.Casa Park VillasCasa Park Villas in Winter Springs, FL: Median sale $240K (2026), 235 homes, built 1984-1986, median 38 days on market.Chelsea Parc At TuscawillaChelsea Parc At Tuscawilla in Winter Springs, FL: 96 homes, built 1988-2006. Live Stellar MLS data and public records.Chestnut EstatesChestnut Estates in Winter Springs, FL: 48 homes, built 1995-1998. Live Stellar MLS data and public records.Chestnut RidgeChestnut Ridge in Winter Springs, FL: 51 homes, built 1992-2001. Live Stellar MLS data and public records.Chestnut Ridge in TuscawillaChestnut Ridge in Tuscawilla in Winter Springs, FL: 150 homes for sale in ZIP 32708 (33% under contract), 1 MLS sale on record since 2026.Citrus OaksCitrus Oaks in Winter Springs, FL: Median sale $676K (2026), median 5 days on market. Live Stellar MLS data and public records.Country Club VillageCountry Club Village in Winter Springs, FL: Median sale $411K (2026), 244 homes, built 1979-2013, median 37 days on market.Cypress ClubCypress Club in Winter Springs, FL: Recent sales median $264K (2024), $199/sq ft, 39 sales since 2012, 75 homes, built 1986-1995.Cypress VillageCypress Village in Winter Springs, FL: 13 homes built 1981–1985, ~1,344 sq ft, 2 bd/2.5 ba. ZIP 32708 median $411K, 38 for sale.Davenport GlenDavenport Glen in Winter Springs, FL: Recent sales median $615K (2025), $251/sq ft, 28 sales since 2006, 98 homes, built 1989-1999.Deer RunDeer Run in Winter Springs, FL: Median sale $480K (2026), median 5 days on market. Live Stellar MLS data and public records.DeersongDeersong in Winter Springs, FL: 174 homes, built 1973-1996. Live Stellar MLS data and public records.Dougs Unit 1Dougs Unit 1 in Winter Springs, FL: 2,167 homes for sale in Seminole County (29% under contract). Live Stellar MLS data and public records.Dunmar Estates 5 Acre DevDunmar Estates 5 Acre Dev in Winter Springs, FL: 150 homes for sale in ZIP 32708 (33% under contract), 3 MLS sales on record since 2022.Eagles PointEagles Point in Winter Springs, FL: Median sale $664K (2026), 158 homes, built 1964-2012, median 49 days on market.Eagles WatchEagles Watch in Winter Springs, FL: Median sale $490K (2026), 110 homes, built 1995-1998, median 54 days on market.Entzminger FarmsEntzminger Farms in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Fairway OaksFairway Oaks in Winter Springs, FL: Recent sales median $450K (2025), $225/sq ft, 27 sales since 2011, 71 homes, built 1980-2018.Flamingo SpringsFlamingo Springs in Winter Springs, FL: 17 homes built 1952–2015, ~1,422 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Fox Glen at Chelsea Parc TuscawillaFox Glen at Chelsea Parc Tuscawilla in Winter Springs, FL: Recent sales median $422K (2025), $261/sq ft, 36 sales since 2006, 196 homes, built…FoxmoorFoxmoor in Winter Springs, FL: Median sale $325K (2026), 474 homes, built 1958-2023, median 31 days on market. Live Stellar MLS data and public…Foxmoor EastFoxmoor East in Winter Springs, FL: 17 homes built 1990–2006, ~1,817 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Fruitwood LakeFruitwood Lake in Winter Springs, FL: Recent sales median $388K (2025), $307/sq ft, 7 sales since 2012. Live Stellar MLS data and public records.GeorgetowneGeorgetowne in Winter Springs, FL: Median sale $425K (2026), 226 homes, built 1987-2019, median 13 days on market.Glen EagleGlen Eagle in Winter Springs, FL: Median sale $821K (2026), 256 homes, built 1989-2023, median 9 days on market. Live Stellar MLS data and public…Golfside VillasGolfside Villas in Winter Springs, FL: 16 homes built 2001–2001, ~1,237 sq ft, 2 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Greenbriar SubdGreenbriar Subd in Winter Springs, FL: 152 homes, built 1986-2001. Live Stellar MLS data and public records.Greenbriar/ TuscawillaGreenbriar/ Tuscawilla in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Greens At TuscawillaGreens At Tuscawilla in Winter Springs, FL: Median sale $446K (2026), 60 homes, built 2012-2016, median 13 days on market.Greens At Tuscawilla BuildingGreens At Tuscawilla Building in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.GreenspointeGreenspointe in Winter Springs, FL: Median sale $385K (2026), 56 homes, built 1984-2021, median 24 days on market.Harbor WindsHarbor Winds in Winter Springs, FL: Median sale $336K (2026), median 47 days on market. Live Stellar MLS data and public records.Heritage CommonsHeritage Commons in Winter Springs, FL: Median sale $330K (2026), 41 homes, built 2008-2010, median 100 days on market.Heritage ParkHeritage Park in Winter Springs, FL: 158 homes for sale in ZIP 32708 (34% under contract), 1 MLS sale on record since 2026.Heritage Park TownhomesHeritage Park Townhomes in Winter Springs, FL: Median sale $285K (2026), 156 homes, built 2004-2006, median 56 days on market.Hickory GroveHickory Grove in Winter Springs, FL: Median sale $401K (2026), 31 homes, built 2016-2024, median 79 days on market.Hickory Grove TownhomesHickory Grove Townhomes in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Hickory Grove TownhomesHickory Grove Townhomes in Winter Springs, FL: 2 homes for sale from $399K to $512K. Live Stellar MLS data and public records.Hickory Grove TownhomesHickory Grove Townhomes in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Highland LakeHighland Lake in Winter Springs, FL: 16 homes built 1994–1998, ~2,216 sq ft, 3 bd/2.5 ba. ZIP 32708 median $411K, 38 for sale.Highland Patio HomesHighland Patio Homes in Winter Springs, FL: Recent sales median $276K (2025), $185/sq ft, 11 sales since 2015. Live Stellar MLS data and public…Highland Patio HomesHighland Patio Homes in Winter Springs, FL: 18 homes built 1974–1975, ~1,443 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Highland VillageHighland Village in Winter Springs, FL: Median sale $374K (2026), 32 homes, built 1989-1991, median 25 days on market.HighlandsHighlands in Winter Springs, FL: Median sale $407K (2026), 552 homes, built 1972-2006, median 75 days on market. Live Stellar MLS data and public…HighlandsHighlands in Winter Springs, FL: 193 homes built 1972–2003, ~1,607 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Highlands GlenHighlands Glen in Winter Springs, FL: 21 homes built 1985–2000, ~1,171 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.HollowbrookHollowbrook in Winter Springs, FL: Recent sales median $425K (2025), $203/sq ft, 44 sales since 2004, 220 homes, built 1985-1990.Howell Creek ReserveHowell Creek Reserve in Winter Springs, FL: 115 homes, built 1995-2000. Live Stellar MLS data and public records.Indian RidgeIndian Ridge in Winter Springs, FL: Median sale $219K (2026), median 17 days on market. Live Stellar MLS data and public records.Jesups LandingJesups Landing in Winter Springs, FL: Median sale $397K (2026), 80 homes, built 1945-2023, median 37 days on market. Live Stellar MLS data and public…Jesups Reserve TownhomesJesups Reserve Townhomes in Winter Springs, FL: Median sale $347K (2026), 103 homes, built 2007-2013, median 47 days on market.Lake JessupLake Jessup is a master-planned community in Sanford, FL recorded as 3 villages and sections in the MLS: 1 home for sale or pending across them today…Lake TuskawillaLake Tuskawilla in Winter Springs, FL: Median sale $737K (2026), 107 homes, built 1986-2014, median 11 days on market.Lori Anne AcresLori Anne Acres in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Lori Anne AcresLori Anne Acres in Winter Springs, FL: a townhome community, 2,167 homes for sale in Seminole County (29% under contract).Moss CoveMoss Cove in Winter Springs, FL: 16 homes built 1986–1986, ~896 sq ft, 2 bd/1.5 ba. ZIP 32708 median $411K, 38 for sale.Moss PlaceMoss Place in Winter Springs, FL: 16 homes built 1986–1986, ~898 sq ft, 2 bd/1.5 ba. ZIP 32708 median $411K, 38 for sale.Mount GreenwoodMount Greenwood in Winter Springs, FL: Median sale $355K (2026), 170 homes, built 1989-1996, median 0 days on market. Live Stellar MLS data and…Mount GreenwoodMount Greenwood in Winter Springs, FL: Median sale $385K (2026), 302 homes, built 1986-1998, median 13 days on market.North OrlandoNorth Orlando in Winter Springs, FL: Median sale $300K (2026), 501 homes, built 1958-2021, median 46 days on market.North OrlandoNorth Orlando in Winter Springs, FL: Median sale $280K (2026), 344 homes, built 1958-2021, median 32 days on market.North OrlandoNorth Orlando in Winter Springs, FL: Median sale $330K (2026), 293 homes, built 1958-2021, median 80 days on market.North Orlando RanchesNorth Orlando Ranches in Winter Springs, FL: Median sale $484K (2026), 926 homes, built 1959-2024, median 50 days on market.North Orlando TerraceNorth Orlando Terrace in Winter Springs, FL: Median sale $330K (2026), 675 homes, built 1958-2021, median 19 days on market.North Orlando TownsiteNorth Orlando Townsite in Winter Springs, FL: Median sale $292K (2026), 109 homes, built 1960-1972, median 8 days on market.North Orlandoamp;North Orlandoamp; in Winter Springs, FL: 202 homes built 1958–1997, ~1,248 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Northern OaksNorthern Oaks in Winter Springs, FL: Recent sales median $810K (2025), $236/sq ft, 16 sales since 2021, 34 homes, built 2019-2022.Oak ForestOak Forest in Winter Springs, FL: Median sale $485K (2026), 990 homes, built 1973-2021, median 34 days on market. Live Stellar MLS data and public…Oak Hill EstatesOak Hill Estates in Winter Springs, FL: 2,201 homes for sale in Seminole County (27% under contract). Live Stellar MLS data and public records.Parc Du LacParc Du Lac in Winter Springs, FL: 13 homes built 2000–2001, ~2,793 sq ft, 4 bd/3 ba. ZIP 32708 median $411K, 38 for sale.ParkstoneParkstone in Winter Springs, FL: Median sale $520K (2026), 256 homes, built 2000-2004, median 37 days on market. Live Stellar MLS data and public…Reserve At TuscawillaReserve At Tuscawilla in Winter Springs, FL: Recent sales median $900K (2024), $235/sq ft, 22 sales since 2006, 82 homes, built 1995-2018.SeasonsSeasons in Winter Springs, FL: Median sale $288K (2026), 130 homes, built 1996-2000, median 164 days on market. Live Stellar MLS data and public…Seminole Crossing TownhomesSeminole Crossing Townhomes in Winter Springs, FL: Recent sales median $461K (2024), $205/sq ft, 56 sales since 2021, 109 homes, built 2021-2024.Seminole Crossing TownhomesSeminole Crossing Townhomes in Winter Springs, FL: Median sale $488K (2026), 114 homes, built 2021-2024, median 51 days on market.Seven OaksSeven Oaks in Winter Springs, FL: Median sale $600K (2026), 139 homes, built 2014-2017, median 23 days on market. Live Stellar MLS data and public…Seven Oaks TwoSeven Oaks Two in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Seville ChaseSeville Chase in Winter Springs, FL: Median sale $726K (2026), 52 homes, built 1997-2002, median 28 days on market.SheoahSheoah A Condo in Winter Springs, FL: Recent sales median $195K (2024), $137/sq ft, 13 sales since 2016. Live Stellar MLS data and public records.SheoahSheoah in Winter Springs, FL: Recent sales median $158K (2025), $189/sq ft, 42 sales since 2012. Live Stellar MLS data and public records.Stone GableStone Gable in Winter Springs, FL: 48 homes, built 1998-2000. Live Stellar MLS data and public records.SunriseSunrise in Winter Springs, FL: Recent sales median $460K (2025), $218/sq ft, 18 sales since 2008, 31 homes, built 1979-1988.SunriseSunrise in Winter Springs, FL: Median sale $412K (2026), 231 homes, built 1978-1999, median 6 days on market. Live Stellar MLS data and public…SunriseSunrise in Winter Springs, FL: 133 homes built 1978–1989, ~1,551 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.SunriseSunrise in Winter Springs, FL: Recent sales median $360K (2024), $257/sq ft, 18 sales since 2007, 98 homes, built 1980-2000.Sunrise EstatesSunrise Estates in Winter Springs, FL: Median sale $450K (2026), 254 homes, built 1982-1990, median 17 days on market.Sunrise Unit 2C Pb 28 PgSunrise Unit 2C Pb 28 Pg in Winter Springs, FL: a single-family community, 2,167 homes for sale in Seminole County (29% under contract), 1 MLS saleSunrise VillageSunrise Village in Winter Springs, FL: 166 homes, built 1983-1986. Live Stellar MLS data and public records.Susan WoodsSusan Woods in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Talis CrossingTalis Crossing in Winter Springs, FL: 2,206 homes for sale in Seminole County (28% under contract). Live Stellar MLS data and public records.Talmo SubTalmo Sub in Winter Springs, FL: 7 homes built 1958–2007, ~2,038 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.The HighlandsThe Highlands in Winter Springs, FL: 19 homes built 1977–1989, ~1,829 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.the Highlands Sections Seven Eightthe Highlands Sections Seven Eight in Winter Springs, FL: Recent sales median $378K (2024), $237/sq ft, 11 sales since 2016.The Landings At ParkstoneThe Landings At Parkstone in Winter Springs, FL: Recent sales median $375K (2025), $206/sq ft, 38 sales since 2014, 105 homes, built 2006-2007.the Oaksthe Oaks in Winter Springs, FL: 14 homes built 1998–2001, ~2,216 sq ft, 4 bd/2.5 ba. ZIP 32708 median $411K, 38 for sale.Tusca OaksTusca Oaks in Winter Springs, FL: Recent sales median $495K (2025), $287/sq ft, 39 sales since 2013, 136 homes, built 1995-1998.Tuscany PlaceTuscany Place in Winter Springs, FL: Median sale $285K (2026), median 37 days on market. Live Stellar MLS data and public records.TuscawillaTuscawilla Parcel 90 is a master-planned community in Winter Springs, FL recorded as 15 villages and sections in the MLS: 7 homes for sale or pending…TuscawillaTuscawilla in Winter Springs, FL: Recent sales median $692K (2025), $293/sq ft, 33 sales since 2009, 277 homes, built 1977-2016.TuscawillaTuscawilla in Winter Springs, FL: 524 homes built 1972–2000, ~2,530 sq ft, 4 bd/2.5 ba. ZIP 32708 median $411K, 38 for sale.TuscawillaTuscawilla in Winter Springs, FL: Median sale $650K (2026), 1,893 homes, built 1924-2022, median 13 days on market.Tuscawilla BraewickTuscawilla Braewick in Winter Springs, FL: 128 homes, built 1988-2006. Live Stellar MLS data and public records.Tuscawilla RidgeTuscawilla Ridge in Winter Springs, FL: Median sale $415K (2026), median 23 days on market. Live Stellar MLS data and public records.TuskabayTuskabay in Winter Springs, FL: Median sale $750K (2026), 55 homes, built 1983-2019, median 2 days on market. Live Stellar MLS data and public…Tuskawilla CrossingsTuskawilla Crossings in Winter Springs, FL: Median sale $669K (2026), 365 homes, built 2019-2021, median 15 days on market.Tuskawilla CrossingsTuskawilla Crossings in Winter Springs, FL: 150 homes for sale in ZIP 32708 (33% under contract), 4 MLS sales on record since 2021.Tuskawilla Office ParkTuskawilla Office Park in Winter Springs, FL: 3 homes, built 2004-2006. Live Stellar MLS data and public records.Tuskawilla PointTuskawilla Point in Winter Springs, FL: Median sale $445K (2026), 123 homes, built 1964-2012, median 51 days on market.Tuskawilla Trail SubdTuskawilla Trail Subd in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Tuskawilla/Wedgewood Golf VillasTuskawilla/Wedgewood Golf Villas in Winter Springs, FL: ZIP 32708 median $411K, 38 for sale. Schools, HOA & nearby homes for sale.Walden TerraceWalden Terrace in Winter Springs, FL: 34 homes built 1973–1977, ~1,406 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.WedgewoodWedgewood in Winter Springs, FL: Median sale $359K (2026), 158 homes, built 1973-1980, median 10 days on market. Live Stellar MLS data and public…Wedgewood Tennis VillasWedgewood Tennis Villas in Winter Springs, FL: Median sale $375K (2026), 78 homes, built 1983-1991, median 22 days on market.Wicklow Greens At TuscawillaWicklow Greens At Tuscawilla in Winter Springs, FL: 33 homes built 1999–2004, ~3,738 sq ft, 5 bd/4 ba. ZIP 32708 median $411K, 38 for sale.Williamson HeightsWilliamson Heights in Winter Springs, FL: 14 homes built 1959–1979, ~1,240 sq ft, 3 bd/2 ba. ZIP 32708 median $411K, 38 for sale.Willow RunWillow Run in Winter Springs, FL: 104 homes, built 1974-2003. Live Stellar MLS data and public records.Winding HollowWinding Hollow in Winter Springs, FL: Median sale $600K (2026), 387 homes, built 1994-2000, median 21 days on market.Winter SpringsWinter Springs in Winter Springs, FL: Median sale $570K (2026), 1,008 homes, built 1964-2023, median 8 days on market.Winter Springs VillageWinter Springs Village in Winter Springs, FL: Median sale $485K (2026), 255 homes, built 1964-2019, median 59 days on market.