Neighborhood · Winter Garden, Florida
Winter Oaks
Established West Orange living close to everything
1
Homes for sale
$749,995
Median list price
$242
Avg price / sqft
21
Median days on market
Winter Oaks sits in the heart of Winter Garden, an established West Orange County pocket where mature streets and roomy floor plans define the day-to-day. Homes here run large — a median of 2,705 square feet — and you're within easy reach of nearby communities like Hickory Hut, Village I, and the newer development around Hamlin. Commutes are reasonable in every direction: downtown Orlando is about 28 minutes, Universal roughly 29, and Walt Disney World around 38.
The market here is tight and moves fast. With just two active listings and a median list price of $684,998, buyers are working with limited inventory — and homes are selling in a median of 10.5 days at 100% of asking. If you're comparing options across Winter Garden homes for sale, expect to act decisively when the right property in Winter Oaks comes up.
Winter Oaks is a community in Winter Garden, Florida.
Quick facts
$749,995 – $750K price range
3,102 sqft median home
$146/mo median HOA
4 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Oaks
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
≈ $5,057/mo
$749,995 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 an established Winter Garden neighborhood with large homes — a median of 2,705 square feet — and easy access to Orlando's major job and entertainment centers. Downtown Orlando is about 28 minutes out and Walt Disney World roughly 38. Assigned schools include West Orange High, Lakeview Middle, and Tildenville Elementary.
Is Winter Oaks expensive?+
It sits in the mid-to-upper range for Winter Garden, with a median list price of $684,998 and active listings running from $620,000 to $749,995. At an average of $255 per square foot, you're paying for size and location rather than luxury extras. There are no $1M+ homes currently active in the neighborhood.
What do homes cost in Winter Oaks?+
Current active listings range from $620,000 to $749,995 with a median of $684,998. Over the past 12 months, four homes sold at a median price of $677,500. You can compare pricing against nearby options like Village F to gauge value.
How is the market in Winter Oaks?+
It's fast and competitive, with only two active listings and a median of just 10.5 days on market. Sellers are getting 100% of their asking price on average, so buyers should be prepared to move quickly and offer strong.
What are the HOA fees and property taxes?+
The median HOA runs about $146 per month, which is modest for a neighborhood of this size. Property taxes come in around $8,107 per year, in line with homes in this price range across 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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