Neighborhood · Winter Garden, Florida
Winter Oaks
An established West Orange address near everything
Winter Oaks sits in the heart of Winter Garden, a pocket of West Orange County where mature streets and a settled, residential feel win out over the churn of new-build sprawl. You're close to the neighboring communities that define this side of town — Hickory Hut, Village I, and Village F — with the growing Hamlin district and its shops and dining a short drive away. Downtown Orlando is about 28 minutes out, Universal roughly 29, and Walt Disney World around 38, so you're central without living on top of the tourist corridor.
The market reality here is scarcity: there are zero active listings right now, and only three homes changed hands over the past 12 months. Those sales carried a median price of $715,000, and sellers averaged 101% of asking — meaning when a home does come up, it moves at or above list. For a buyer, this is a neighborhood you watch and act on quickly rather than shop at leisure.
Winter Oaks is a community in Winter Garden, Florida.
Quick facts
3 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Oaks
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Winter Oaks boundary
Open full map search →The numbers that matter
The Winter Oaks market
3
Sold, last 12 months
$715,000
Median sold price
101%
Sale-to-list ratio
What sellers actually get vs asking
42 days
Median time to sell
Winter Oaks vs Winter Garden
Median sold price — 3-yr, 3-mo rolling
▲ 22.6% 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.
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.
On the calendar
Near Winter Oaks
Jul
17
Fri
Ride the Cyclone
19:30
Ride the Cyclone is a musical about a Canadian chamber choir whose members die in a roller coaster accident and find themselves in limbo. A mechanical fortune teller invi…
Jul
24
Fri
Adam Ray
8:00pm
Adam Ray is an American comedian and actor who has appeared in many movies and TV shows including "Ghostbusters," "Spy," "Arrested Development," and "American Vandal." No…
Jul
25
Sat
Kaliente Fest
1:00 PM
The First Annual Kaliente 103.1 FM Fest, presented by Norsan Media and Sunwave Energy, promises a vibrant celebration of Latin culture, complete with live performances fr…
Jul
25
Sat
B.E.L.A.C. Childhood Cancer 5K
8:00 AM
The B.E.L.A.C. Foundation's annual Childhood Cancer 5K is a community-driven event that combines physical activity with philanthropy, aiming to raise awareness and funds…
Jul
29
Wed
Mumford & Sons
Mumford & Sons are a Grammy Award-winning British band that brought a modern edge to folk rock. With their signature blend of soaring harmonies and acoustic instrumentati…
Aug
9
Sun
Mon Laferte
8:00pm
Mon Laferte is a singer, songwriter, and musician from Chile who composes songs combining many genres like pop, bolero, rock, salsa, and cumbia. She is the biggest Chilea…
Straight answers
Winter Oaks FAQs
Is Winter Oaks a good place to live?+
It's an established West Orange neighborhood with a settled, low-turnover feel and quick access to downtown Orlando (about 28 minutes) and the theme parks. Homes are zoned for West Orange High, Lakeview Middle, and Tildenville Elementary. If you value being central without living in the middle of the tourist corridor, it fits.
Is Winter Oaks expensive?+
It sits in the upper-mid range for the area — the median sold price over the last 12 months was $715,000. There are no active listings at the moment, so pricing is best judged off recent closings rather than what's currently on the market.
What do homes cost in Winter Oaks?+
Over the past year, three homes sold here at a median price of $715,000. With no active inventory right now, buyers should be ready to move when a listing appears, since comparable neighborhoods like Hamlin offer a broader picture of nearby pricing.
How is the market in Winter Oaks?+
It's a low-supply, seller-favored market — just three sales in the last 12 months and zero homes currently active. Those sellers averaged 101% of asking, so homes here tend to sell at or above list when they hit the market.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available in the current data for Winter Oaks. Because inventory is so limited, it's worth confirming these details on any individual home before you write an offer.
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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