Neighborhood · Winter Garden, Florida
Wintermere Pointe
A gated pocket near the heart of West Orange
2
Homes for sale
$732,500
Median list price
$259
Avg price / sqft
4
Median days on market
Wintermere Pointe is a small gated community in Winter Garden, the kind of quiet enclave that keeps you close to everything West Orange has to offer while feeling a step removed from the traffic. Homes here run large — the median is 2,833 square feet — and families are drawn to the assigned schools of Lake Whitney Elementary, Sunridge Middle, and West Orange High. It sits comfortably among other established Winter Garden neighborhoods like Hickory Hut, Village I, and the newer builds out in Hamlin.
For a buyer today, this is a tight market with real momentum. Just two homes are active right now, both gated and both with pools, priced from $715,000 to $750,000 with a median list of $732,500. Homes that hit the market move fast — median days on market is under four — so if you want in, be ready to act. Browse the full picture across Winter Garden homes for sale to see how this pocket compares.
Wintermere Pointe is a community in Winter Garden, Florida.
Quick facts
$715,000 – $750K price range
2,833 sqft median home
$91/mo median HOA
$3,500/mo median rent
9 sold in 12 months
On the market now
Homes for sale in Wintermere Pointe
$715,000
2025 WINTERMERE POINTE DRIVE, WINTER GARDEN
5 bd · 4 ba · 2,655 sqft
$750,000
2006 WINTERMERE POINTE DRIVE, WINTER GARDEN
5 bd · 4 ba · 3,011 sqft
Every active listing inside the Wintermere Pointe boundary
Open full map search →Find your fit
Browse Wintermere Pointe
By feature — on the live map
Where the market lives
The numbers that matter
The Wintermere Pointe market
9
Sold, last 12 months
$539,900
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
18 days
Median time to sell
Wintermere Pointe vs Winter Garden
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 37.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Wintermere Pointe boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Wintermere Pointe is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Wintermere Pointe home
≈ $4,491/mo
$732,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$91/mo
Median HOA
From current listings inside the boundary
$3,500/mo
Median rent
Homes for rent inside the boundary
Population
300
Median age
31
Median income
$127,292
Median home value
$462,800
Beyond the listings
Living in Wintermere Pointe
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.
Emotional
Top 4% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Culture
Top 9% 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.
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.
Relationships
Top 10% 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.
Food & Drink
Top 11% 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 Wintermere Pointe
Jul
12
Sun
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
12
Sun
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
12
Sun
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
12
Sun
Rumba Brunch
11:30am
Every Sunday, attendees have the opportunity to immerse themselves in the authentic rumba music played live by wandering guitarists and vocalists. To accompany the riveti…
Jul
12
Sun
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
12
Sun
Sunday-Latin-Sunday
Sunday-Latin-Sunday is a vibrant event featuring Central Florida's top DJs, including DJ Gabriel, DJ J Quezt, DJ Elie, and DJ K1X, who will be spinning the best Merengue,…
Straight answers
Wintermere Pointe FAQs
Is Wintermere Pointe a good place to live?+
It's a good fit if you want a gated, family-oriented community with larger homes near the heart of Winter Garden. The median home runs 2,833 square feet, and residents are zoned for well-regarded schools including West Orange High. Nearby established neighborhoods like Village F round out the area's appeal.
Is Wintermere Pointe expensive?+
It sits in the upper-middle range for Winter Garden, with active listings priced from $715,000 to $750,000 and a median list of $732,500. That said, the 9 homes sold over the last year had a lower median sold price of $539,900, so pricing depends heavily on the specific home and timing.
What do homes cost in Wintermere Pointe?+
Right now the two active listings are priced between $715,000 and $750,000, averaging about $259 per square foot. Over the past 12 months, nine sales closed at a median of $539,900, and sellers typically got 99% of their asking price.
How is the market in Wintermere Pointe?+
It's fast and low-inventory — only two homes are active and the median days on market is about 3.5. With sellers averaging 99% of asking, buyers should come prepared to move quickly and offer close to list.
What about HOA fees and property taxes?+
The median HOA runs about $91 per month, which is modest for a gated community. Median annual property tax is around $3,974, and if you're weighing renting, the median rent in the area is about $3,500 per month.
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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