Homes for sale in
Winter Garden, Florida
Historic downtown charm meets fast-growing West Orange living
740
Homes for sale
$589,945
Median list price
$282
Avg price / sqft
31
Median days on market
Winter Garden pairs a walkable brick-street downtown with the newer, master-planned neighborhoods spreading west toward the Lake County line. The character ranges from established communities like Stoneybrook West and Avalon to the still-building energy of Hamlin, and the mix of single-family homes, townhomes and condos keeps the area appealing across life stages. It's firmly Orange County suburban, with schools like Horizon High and Water Spring Elementary anchoring the family-heavy west side.
For buyers today, there are 740 active listings with a median list price of $589,945, and homes are moving at a median 30.5 days on market — brisk but not frantic. Prices run the full spectrum, from entry points near $150,000 up past $5.9 million, so you can browse by price or lean into new construction where 111 listings are currently available. Expect to pay around $282 per square foot on a typical 2,174-square-foot home.
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
Fresh on the market
Newest homes in Winter Garden
View all 740 homes →
$899,000
346 CRYSTAL WOOD DRIVE, WINTER GARDEN
4 bd · 3 ba · 3,147 sqft
$365,000
14501 GROVE RESORT AVENUE UNIT 3227, WINTER GARDEN
3 bd · 3 ba · 1,544 sqft
$325,000
14501 GROVE RESORT AVENUE UNIT 1614, WINTER GARDEN
3 bd · 3 ba · 1,544 sqft
$715,000
12248 Encore at Ovation Way, Winter Garden FL 34787, WINTER GARDEN
4 bd · 3 ba · 2,346 sqft
$800,000
214 S WOODLAND STREET, WINTER GARDEN
4 bd · 2 ba · 2,868 sqft
$715,000
2025 WINTERMERE POINTE DRIVE, WINTER GARDEN
5 bd · 4 ba · 2,655 sqft
$350,000
14501 GROVE RESORT AVENUE UNIT 3737, WINTER GARDEN
3 bd · 2 ba · 1,396 sqft
$689,000
1743 FULLERS OAK LOOP, WINTER GARDEN
4 bd · 2.5 ba · 2,536 sqft
$525,000
132 ZACHARY WADE STREET, WINTER GARDEN
3 bd · 2 ba · 1,708 sqft
$180,000
14501 GROVE RESORT AVENUE UNIT 1439, WINTER GARDEN
2 bd · 2 ba · 1,265 sqft
$460,000
9078 WADING WALK LANE, WINTER GARDEN
3 bd · 2.5 ba · 1,814 sqft
$275,000
1300 EASTERN PECAN PLACE UNIT 102, WINTER GARDEN
2 bd · 2 ba · 1,152 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.
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
106 homes · $582K median
Village I
80 homes · $646K median
Village F
75 homes · $790K median
Hamlin
44 homes · $591K median
Stoneybrook West
12 homes · $545K median
Avalon
7 homes · $2.0M median
Isles Of Lake Hancock
6 homes · $777K median
East Winter Garden
5 homes · $373K median
Lakeview Reserve
5 homes · $1.3M median
Stone Crest
5 homes · $645K median
Island Pointe
3 homes · $600K median
Carriage Pointe
3 homes · $725K median
Crown Point Springs
2 homes · $454K median
Belle Meade
2 homes · $775K median
Wintermere Pointe
2 homes · $733K median
Village Grove Of Winter Garden
2 homes · $240K median
Park Avenue Estates Of Winter
2 homes · $325K median
Westfield Lakes
2 homes · $919K 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
A downtown you actually walk
Winter Garden's historic brick-street core gives the area a genuine town center, a rarity among West Orange suburbs.
New construction at scale
With 111 new-construction listings active, buyers who want a builder-fresh home have real choice here.
Gated and pool options aplenty
There are 141 gated-community listings and 102 homes with a pool among current active inventory.
Water on the west side
48 waterfront listings reflect the lakes woven through the Hamlin and Lake Hancock areas.
Strong assigned schools
Newer west-side campuses like Horizon High, Water Spring Middle and Water Spring Elementary draw families to the area.
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.
On the calendar
Near Winter Garden
Jul
11
Sat
Walt Disney World Park Meetup
The Orlando Social Network (OSN) is a vibrant community that facilitates adults in meeting, connecting, and building friendships through a variety of fun events, includin…
Jul
11
Sat
Marrakech Nights
6:00pm
Immerse yourself in the vibrant Moroccan culture with traditional music, belly dancing, and a menu brimming with authentic Moroccan flavors. Marrakech Nights offers a uni…
Jul
11
Sat
Bands, Brew, and BBQ
Bands, Brew, and BBQ brings together live country and rock music with delicious food and refreshing drinks for a lively summer experience at SeaWorld Orlando. You can enj…
Jul
11
Sat
Blue Man Group
Since 1987, the unique performance act of Blue Man Group has mesmerized its audience with music and art from both mainstream and obscure genres. This trio of men painted…
Jul
11
Sat
Cirque du Soleil: Drawn to Life
8:00pm
Drawn to Life is a Cirque du Soleil and Disney collaboration featuring acrobatics, animation, and theatrical magic. The show brings classic Disney drawings to life in a d…
Jul
12
Sun
Blue Man Group
Since 1987, the unique performance act of Blue Man Group has mesmerized its audience with music and art from both mainstream and obscure genres. This trio of men painted…
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 one of West Orange County's most livable spots, combining a walkable historic downtown with newer master-planned neighborhoods like Hamlin and Stoneybrook West. Families are drawn to assigned schools including Horizon High and Water Spring Elementary, and the housing mix spans single-family homes, townhomes and condos.
Is Winter Garden expensive?+
It sits above the regional midpoint, with a median list price of $589,945 and about $282 per square foot. There's genuine range, though — listings start near $150,000 and run past $5.9 million, and 107 homes are priced at $1 million or more for the luxury end.
What do homes cost in Winter Garden?+
The median list price is $589,945 on a typical 2,174-square-foot home, working out to roughly $282 per square foot. Single-family homes make up the bulk of inventory at 505 listings, with 103 townhomes and a mix of condos for lower entry points — you can browse by price to narrow the field.
How is the Winter Garden housing market right now?+
There are 740 active listings and homes are selling at a median 30.5 days on market, a steady but competitive pace. With 111 new-construction homes and 141 gated-community listings available, buyers have solid selection — check just reduced listings for negotiating room.
What about HOA fees and property taxes in Winter Garden?+
The median HOA runs about $223 per month, common in the area's master-planned and gated communities. Median property taxes are around $6,709 per year, and if you're weighing renting first, the median rent is $2,895 per month.
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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