Homes for sale in
Winter Garden, Florida
Small-town charm on the edge of the theme parks
740
Homes for sale
$589,945
Median list price
$282
Avg price / sqft
31
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.
Within a 30-minute drive
Quick facts
$150,000 – $6.0M price range
2,174 sqft median home
$2,895/mo median rent
Balanced right now
Drive times
Fresh on the market
Newest homes in Winter Garden
View all 740 homes →
$1,800,000
16945 W PHIL C PETERS ROAD, WINTER GARDEN
6 bd · 4 ba · 4,396 sqft
$295,000
14501 GROVE RESORT AVENUE UNIT 3706, WINTER GARDEN
2 bd · 2 ba · 1,265 sqft
$799,000
16736 GULLFLOSS TERRACE, WINTER GARDEN
4 bd · 3.5 ba · 2,806 sqft
$800,000
214 S WOODLAND STREET, WINTER GARDEN
4 bd · 2 ba · 2,868 sqft
$988,539
15280 MARITIME PINE DRIVE, WINTER GARDEN
5 bd · 3 ba · 3,550 sqft
$325,000
14501 GROVE RESORT AVENUE UNIT 1614, WINTER GARDEN
3 bd · 3 ba · 1,544 sqft
$899,000
346 CRYSTAL WOOD DRIVE, WINTER GARDEN
4 bd · 3 ba · 3,147 sqft
$350,000
14501 GROVE RESORT AVENUE UNIT 3737, WINTER GARDEN
3 bd · 2 ba · 1,396 sqft
$275,000
1300 EASTERN PECAN PLACE UNIT 102, WINTER GARDEN
2 bd · 2 ba · 1,152 sqft
$170,000
14501 GROVE RESORT AVENUE UNIT 1527, WINTER GARDEN
2 bd · 2 ba · 1,265 sqft
$275,000
14501 GROVE RESORT AVENUE UNIT 2530, WINTER GARDEN
2 bd · 2 ba · 1,265 sqft
$725,000
3447 CURRENT, WINTER GARDEN
4 bd · 3.5 ba · 2,741 sqft
250 of 740 active listings shown
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Property features
The numbers that matter
The Winter Garden market
Balanced
5.5 months of inventory
Supply and demand are roughly even — negotiation cuts both ways.
1,898
Sold, last 12 months
$580,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
31 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
▼ 1.7% yr/yr
Homes on the market
▲ 5.5% 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
107 homes · $575K median
Village I
78 homes · $649K median
Village F
74 homes · $802K median
Hamlin
43 homes · $610K median
Stoneybrook West
9 homes · $525K median
Stone Crest
7 homes · $645K median
Avalon
7 homes · $1.8M median
Lakeview Reserve
5 homes · $1.3M median
Isles Of Lake Hancock
5 homes · $766K median
East Winter Garden
5 homes · $373K median
Carriage Pointe
4 homes · $745K median
Island Pointe
3 homes · $600K median
Village Grove Of Winter Garden
2 homes · $239K median
Westfield Lakes
2 homes · $914K median
Belle Meade
2 homes · $765K median
Stone Creek
2 homes · $451K median
Fullers Crossing
2 homes · $507K median
Sunset Lakes Of Windermere
2 homes · $2.4M 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.
Population
47,182
Median age
39.2
Median income
$106,371
Median home value
$428,200
What people here are into
Hobbies & Interests
Top 2% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Food & Drink
Top 5% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Lifestyles
Top 10% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Food & Drink
Top 13% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Food & Drink
Top 13% in the U.S.Asian Food & Culture
Asian culture has a lot to offer, but the Asian cuisine tends to be the most frequently referenced. This population is talking about Asian dishes, holidays, and drinks.
Hobbies & Interests
Top 14% in the U.S.Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
What it really costs
Owning here
Owning the median Winter Garden home
≈ $4,100/mo
$589,945 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
4%
In a FEMA flood zone
Most homes here sit outside high-risk zones
$2,895/mo
Median rent
190 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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