Homes for sale in
Winter Garden, Florida
Small-town charm on the edge of the theme parks
687
Homes for sale
$595,000
Median list price
$276
Avg price / sqft
60
Median days on market
Winter Garden sits on the west side of Orange County, where a walkable historic downtown and the West Orange Trail share space with fast-growing master-planned neighborhoods like Hamlin and Stoneybrook West. It's a genuinely commutable base — Walt Disney World is about 28 minutes out, downtown Orlando roughly 30, and Orlando International around 40 — which makes it popular with families and hospitality-industry professionals alike. The mix runs from older enclaves like Village I to brand-new builds, so you can pick your era.
For buyers, the market is active but not frantic: 740 homes are listed right now against 1,898 sales in the past year, and the median list price sits at $589,945. Homes typically move in about a month, and sellers are getting 98% of asking on average, so well-priced listings hold their value. If your budget is tighter, it's worth watching just reduced listings and using the browse by price tools, since the range starts around $150,000 and runs all the way to nearly $6M.
Winter Garden is in Orange County, Florida.
Quick facts
$149,900 – $6.0M price range
2,117 sqft median home
$2,950/mo median rent
Leans seller right now
Drive times
Fresh on the market
Newest homes in Winter Garden
View all 687 homes →
$1,895,000
16143 BARKLY RIDGE COURT, WINTER GARDEN
6 bd · 6 ba · 5,247 sqft
$535,000
15066 MARBLED GODWIT DRIVE, WINTER GARDEN
3 bd · 2.5 ba · 2,156 sqft
$515,000
9662 WATERWAY PASSAGE DRIVE, WINTER GARDEN
3 bd · 2.5 ba · 1,918 sqft
$520,000
324 E FULLERS CROSS ROAD, WINTER GARDEN
3 bd · 2 ba · 1,924 sqft
$175,000
14501 GROVE RESORT AVENUE UNIT 3636, WINTER GARDEN
2 bd · 2 ba · 1,434 sqft
$344,900
14501 GROVE RESORT UNIT 1723, WINTER GARDEN
3 bd · 3 ba · 1,544 sqft
$164,900
14501 GROVE RESORT AVENUE UNIT 3631, WINTER GARDEN
2 bd · 2 ba · 1,375 sqft
$1,049,000
13541 PARKFIELD WAY, WINTER GARDEN
5 bd · 4 ba · 3,688 sqft
$235,000
14501 GROVE RESORT AVENUE UNIT 1218, WINTER GARDEN
2 bd · 2 ba · 1,265 sqft
$635,572
14775 FIELD DAISY DRIVE, WINTER GARDEN
4 bd · 4.5 ba · 2,618 sqft
$610,000
923 COLIE ALLEY, WINTER GARDEN
3 bd · 2.5 ba · 1,786 sqft
$495,000
9356 TYRELLA PINE TRAIL, WINTER GARDEN
4 bd · 2.5 ba · 1,838 sqft
250 of 687 active listings shown
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Property features
The numbers that matter
The Winter Garden market
Leans seller
4.3 months of inventory
Demand still outpaces supply, but buyers have a little more room.
1,938
Sold, last 12 months
$599,900
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
29 days
Median time to sell
Winter Garden vs Orange County
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 5.3% yr/yr
Homes on the market
▼ 2.0% yr/yr
Homes sold per month
Live Stellar MLS data — listings and closed sales in Winter Garden, FL. Rolling medians smooth single-month swings in thin markets.
Where to look
Winter Garden neighborhoods
Hickory Hut
103 homes · $620K median
Village I
79 homes · $640K median
Village F
60 homes · $740K median
Hamlin
41 homes · $531K median
Stoneybrook West
14 homes · $455K median
East Winter Garden
10 homes · $352K median
Stone Crest
7 homes · $790K median
Avalon
4 homes · $1.9M median
Lakeview Reserve
4 homes · $1.4M median
Stone Creek
4 homes · $427K median
Wintermere Pointe
3 homes · $790K median
Isles Of Lake Hancock
3 homes · $610K median
Amberleigh
2 homes · $564K median
Winter Oaks
2 homes · $715K median
Orange Cove
2 homes · $449K median
Lake Cove Pointe
2 homes · $887K median
Black Lake Park
2 homes · $879K median
Carriage Pointe
2 homes · $800K median
Show all 38 Winter Garden neighborhoods A–ZHide the full neighborhood list+
Neighborhood boundaries by edgeAI — listings matched to the actual polygon, not agent-entered subdivision names.
For the school run
School zones with homes for sale
Homes matched to official attendance boundaries — always verify zoning with the district.
Beyond the listings
Living in Winter Garden
Commuter-friendly location
Disney is about 28 minutes away, downtown Orlando 30, Universal 31, and MCO airport roughly 40 — hard to beat for a west-Orlando base.
Wide price spectrum
Listings run from $150,000 to $5,995,000, with 107 homes above $1M for buyers shopping the luxury tier.
Room for new-build buyers
With 98 [new construction](/area/winter-garden-fl/new-construction) listings active, there's real inventory for buyers who want a fresh floor plan.
Pools and gated options
Buyers will find 102 [homes with a pool](/area/winter-garden-fl/homes-with-pool) and 141 in [gated communities](/area/winter-garden-fl/gated-communities) across the area.
Mostly single-family stock
Of the active mix, 505 are [single-family homes](/area/winter-garden-fl/single-family-homes), with townhomes and condos rounding out the options.
What it really costs
Owning here
Owning the median Winter Garden home
≈ $4,129/mo
$595,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
3%
In a FEMA flood zone
Most homes here sit outside high-risk zones
$2,950/mo
Median rent
196 homes for rent right now
Straight answers
Winter Garden real estate FAQs
Is Winter Garden a good place to live?+
It's a strong pick for families and commuters, with a walkable historic downtown, the West Orange Trail, and quick access to the theme parks — Disney is about 28 minutes away and downtown Orlando around 30. Assigned schools include Horizon High, Water Spring Elementary and Middle, and West Orange High. Neighborhoods range from established Village F to newer master-planned communities.
Is Winter Garden expensive?+
It sits on the higher side of the Orlando metro, with a median list price of $589,945 and an average of $282 per square foot. That said, listings start around $150,000, so there's still an entry point — the browse by price tool helps you find it. At the top end, 107 homes are currently listed above $1M.
What do homes cost in Winter Garden?+
The median sold price over the past year was $580,000, and the median list price today is $589,945 for a home around 2,174 square feet. Prices vary widely by segment — waterfront and gated stock trends higher, while townhomes and condos offer more affordable options. There are 48 waterfront homes on the market for buyers chasing a water view.
How is the Winter Garden housing market right now?+
It's active and reasonably balanced: 740 homes are listed against 1,898 sales in the last 12 months, and the median home sells in about 30 days. Sellers are averaging 98% of asking price, so sharp pricing matters. Watching just reduced listings can help you spot motivated sellers.
What about HOA fees and property taxes?+
The median HOA runs about $223 per month, common in the area's newer master-planned communities like Stone Crest. Median property tax is roughly $6,709 per year. Older neighborhoods and non-gated single-family homes may carry lower or no HOA dues, so it's worth comparing by community.
Keep exploring
Nearby areas
IDX information is provided exclusively 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS. Market statistics are computed from listing and sold data and change as the market moves.
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