Neighborhood · Winter Garden, Florida
Winter Oaks
Family-Sized Homes Minutes From West Orange Life
2
Homes for sale
$684,998
Median list price
$255
Avg price / sqft
11
Median days on market
Winter Oaks sits in the fast-growing western corner of Winter Garden, where full-sized homes on generous lots feel a world away from the theme-park crowds — yet Downtown Orlando is about 28 minutes out and Walt Disney World roughly 38. Homes here average around 3,102 square feet, so you get the kind of space families come to West Orange for. Nearby communities like Hickory Hut, Village I and Hamlin round out the area with schools, shopping and the easy suburban rhythm buyers keep asking for.
The market reality is tight. With just one active listing at $775,995 and only four sales in the past year, inventory moves fast — the current home is priced at $250 per square foot, and homes that sold recently traded at a median of $677,500 with sellers getting 100% of asking on average. Median days on market sits at one, so serious buyers should be ready to act.
Winter Oaks is a community in Winter Garden, Florida.
Quick facts
$620,000 – $750K price range
2,705 sqft median home
$146/mo median HOA
4 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Oaks
$620,000
880 SUMMER OAKS ROAD, WINTER GARDEN
4 bd · 3 ba · 2,308 sqft
$749,995$759,995
644 AUTUMN OAKS LOOP, WINTER GARDEN
5 bd · 3 ba · 3,102 sqft
Every active listing inside the Winter Oaks boundary
Open full map search →Find your fit
Browse Winter Oaks
By feature — on the live map
The numbers that matter
The Winter Oaks market
4
Sold, last 12 months
$677,500
Median sold price
100%
Sale-to-list ratio
What sellers actually get vs asking
32 days
Median time to sell
Winter Oaks vs Winter Garden
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 36.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Oaks boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Oaks is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winter Oaks home
≈ $4,641/mo
$684,998 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$146/mo
Median HOA
From current listings inside the boundary
Population
267
Median age
40
Median income
$69,779
Median home value
$446,100
Beyond the listings
Living in Winter Oaks
Hobbies & Interests
Top 3% 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 9% in the U.S.Wine Lovers
It's all about the grape. This population enjoys a trip to the vineyard to learn about wine and sharing a good bottle with friends and family.
Lifestyles
Top 11% 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.
Entertainment
Top 11% in the U.S.Party Life
The party don't stop until the sun comes up. Loud music, crowds, and shots are a recipe for a great night out for these people.
Entertainment
Top 12% in the U.S.Late-night Leisure
Ready to turn up when the sun goes down, this population is looking for nighttime entertainment at home or out on the town.
Culture
Top 15% in the U.S.Dance Devotion
Some dance for fitness, others for fun, and a few turn it into a profession. No matter how these people groove to the music, their love for dance is what bonds them.
Straight answers
Winter Oaks FAQs
Is Winter Oaks a good place to live?+
It's a solid pick for families who want space and a suburban feel with quick access to the whole metro. Homes here average around 3,102 square feet, feed into West Orange High, and put you about 28 minutes from Downtown Orlando. Neighboring Hamlin adds shopping and dining just minutes away.
Is Winter Oaks expensive?+
It sits in the upper-middle range for Winter Garden. The one active listing is priced at $775,995, while homes sold over the past year came in at a median of $677,500 — reflecting larger floor plans rather than luxury extras.
What do homes cost in Winter Oaks?+
Right now the single active listing is $775,995, or about $250 per square foot for roughly 3,102 square feet. Over the last 12 months four homes sold at a median price of $677,500, so pricing depends heavily on timing and inventory. Comparing nearby Village F can help you gauge value.
How is the market in Winter Oaks?+
It's fast and seller-friendly. With only one active listing and four sales in the past year, homes move at a median of one day on market and sellers are collecting 100% of asking on average — buyers need to be prepared to move quickly.
What are the HOA fees and property taxes?+
The median HOA runs about $146 per month, which covers community upkeep at a reasonable rate. Property taxes come in around $8,987 per year, in line with homes of this size in Orange County.
Keep exploring
More Winter Garden neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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.
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