Neighborhood · Winter Garden, Florida
Deer Island
A rare enclave where seven figures buys space
Deer Island sits within Winter Garden in west Orange County, a pocket of large-lot homes that trade hands quietly rather than often. This is estate-scale living close to the everyday conveniences of West Orange — with downtown Orlando about 24 minutes out and Walt Disney World roughly 38 — while nearby communities like Hamlin and Village I offer their own distinct character just down the road.
The market reality here is scarcity: there are no active Deer Island listings on the MLS right now, so buyers set on this address should be ready to move when one surfaces. Over the last 12 months just five homes sold, at a median of $1,700,000, which tells you exactly what tier this is. If timing matters, it's worth watching adjacent options in Village F and Hickory Hut while you wait for the right Deer Island home.
Deer Island is a community in Winter Garden, Florida.
Quick facts
5 sold in 12 months
Drive times
On the market now
Homes for sale in Deer Island
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Deer Island boundary
Open full map search →The numbers that matter
The Deer Island market
5
Sold, last 12 months
$1,700,000
Median sold price
91%
Sale-to-list ratio
What sellers actually get vs asking
184 days
Median time to sell
Deer Island vs Winter Garden
Median sold price — 3-yr, 3-mo rolling
▲ 100.0% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Deer Island boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Deer Island is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
284
Median age
36
Median income
$186,838
Median home value
$675,900
Beyond the listings
Living in Deer Island
Hobbies & Interests
Top 1% 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.
Relationships
Top 3% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Lifestyles
Top 4% 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.
Beliefs
Top 4% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Hobbies & Interests
Top 5% 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.
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.
On the calendar
Near Deer Island
Jul
13
Mon
Sunset Saturday Artisan Market
Visitors will revel in the lively Sunset Saturday Artisan Market, teeming with local crafters and unique vendors from Central Florida. Event-goers can enjoy rhythm-filled…
Jul
13
Mon
Sunset Craft, Food, and Drink Market
This market is a bubbling hub of creativity with over 20 artisan vendors from across Florida. Attendees can indulge in hand-crafted food and beverages while dancing to th…
Jul
13
Mon
Dockside Dueling Pianos
Tap your toes during this electrifying evening of musical entertainment. Watch as talented pianists engage in a friendly yet fierce battle of skills, taking song requests…
Jul
13
Mon
Promenade Racing Car and Truck Show
The Promenade Racing Car and Truck event is a thrilling spectacle where car enthusiasts can marvel at an array of various makes and models you won't often find elsewhere…
Jul
13
Mon
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
13
Mon
Promenade Second Sunday Car and Truck Show
The Second Sunday Car and Truck Show is a monthly gathering of classic to modern vehicles of all makes and models, complete with a DJ spinning a mix of classic rock and t…
Straight answers
Deer Island FAQs
Is Deer Island a good place to live?+
It's a low-density, high-price enclave in Winter Garden that suits buyers who want space and stability over quick turnover. Homes here are assigned to Tildenville Elementary, Lakeview Middle, and West Orange High, and the location keeps you about 24 minutes from downtown Orlando. For a broader sense of the area, it helps to browse Winter Garden homes for sale alongside it.
Is Deer Island expensive?+
Yes — it's one of Winter Garden's upper-end pockets. The five homes sold over the past year came in at a median of $1,700,000, so this is a seven-figure neighborhood rather than an entry-level one.
What do homes cost in Deer Island?+
There are no active listings at the moment, so the clearest guide is recent sales: five homes closed in the last 12 months at a median of $1,700,000. Buyers comparing options might also look at nearby Village F, where the surrounding market offers more available inventory.
How is the market in Deer Island?+
It's tight and seller-friendly. With zero active listings and only five sales in the past year, supply is thin, and sellers have averaged 91% of their asking price at closing. Buyers should be prepared to act when a home does list.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available in the current data for Deer Island, which is common when there are no active listings to reference. Because this is an estate-scale neighborhood, budget for costs consistent with $1M-plus homes, and confirm exact figures on any individual property with your agent.
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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