Neighborhood · Ocoee, Florida
Windsor Landing
West Orange living with a straight shot to everything
3
Homes for sale
$699,900
Median list price
$275
Avg price / sqft
24
Median days on market
Windsor Landing is a pool-friendly pocket of Ocoee that leans into the quiet, family-scaled side of West Orange County. Homes here run larger than the county norm — a median of around 2,631 square feet — and a couple of the streets sit behind gates. It shares the neighborhood with well-known Ocoee communities like Wesmere, Westyn Bay, and Silver Bend, and the location does a lot of the work: Universal Orlando is about 21 minutes out, downtown Orlando roughly 23, and Walt Disney World around 32.
For a buyer, this is a small, tightly held market — only three homes are active right now, with a median list price of $699,900. Over the past year just six homes sold, at a median of $742,000, and sellers walked away with about 99% of asking on average. With a median 24 days on market, well-priced listings don't sit long, so being ready to move matters more than waiting for a wave of inventory.
Windsor Landing is a community in Ocoee, Florida.
Quick facts
$690,000 – $899K price range
2,631 sqft median home
$107/mo median HOA
6 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor Landing
$699,900$739,000
3426 KENTSHIRE BOULEVARD, OCOEE
4 bd · 3 ba · 2,631 sqft
$899,000$906,500
173 CALLIOPE STREET, OCOEE
5 bd · 5.5 ba · 3,668 sqft
$690,000$700,000
65 CALLIOPE STREET, OCOEE
4 bd · 3 ba · 2,192 sqft
Every active listing inside the Windsor Landing boundary
Open full map search →Find your fit
Browse Windsor Landing
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor Landing market
6
Sold, last 12 months
$742,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
16 days
Median time to sell
Windsor Landing vs Ocoee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 0.6% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsor Landing boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor Landing is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor Landing home
≈ $4,409/mo
$699,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$107/mo
Median HOA
From current listings inside the boundary
Population
533
Median age
51
Median income
$200,500
Median home value
$716,700
Beyond the listings
Living in Windsor Landing
Lifestyles
Top 5% 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 6% in the U.S.Spiritual Practices
Making it to church on Sunday, this population is drawn together by their devotion to, primarily Christian, religion. Common activities include worship services and bible studies.
Beliefs
Top 13% 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.
Appearance oriented
Top 16% in the U.S.All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
Active
Top 18% in the U.S.Yoga Advocates
Improving flexibility, strength, and overall well-being is the yogi's aim. This population is looking for the right community, instruction, and accessories.
Emotional
Top 18% 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.
On the calendar
Near Windsor Landing
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
Vibe, Sip, and Make Jewelry
Wanda Taylor, a seasoned craftswoman, invites the community to a workshop where she'll share her expertise in creating a wide range of handcrafted items. Attendees will h…
Jul
12
Sun
Bite30
Bite30 in Orlando, FL, USA, is a culinary celebration that spotlights the creativity and talent of Central Florida’s top chefs and restaurants. For a set price, diners ca…
Jul
12
Sun
Bands, Brew, and BBQ
Bands, Brew, and BBQ brings together live country and rock music with delicious food and refreshing drinks for a lively summer experience at SeaWorld Orlando. You can enj…
Jul
12
Sun
Cirque du Soleil: Drawn to Life
1:30pm
Drawn to Life is a Cirque du Soleil and Disney collaboration featuring acrobatics, animation, and theatrical magic. The show brings classic Disney drawings to life in a d…
People who close here
Our Ocoee experts
Straight answers
Windsor Landing FAQs
Is Windsor Landing a good place to live?+
It's a good fit if you want larger, pool-friendly homes in a calm West Orange setting with fast access to jobs and attractions. The neighborhood sits near established Ocoee communities like Towns Of Westyn Bay, and it's zoned for Olympia High, Gotha Middle, and Thornebrooke Elementary. Commutes are easy too — about 23 minutes to downtown Orlando.
Is Windsor Landing expensive?+
It sits in the upper-mid range for Ocoee, with a median list price of $699,900 and homes ranging from $690,000 up to $899,000. At an average of $275 per square foot, you're paying for size — the median home is around 2,631 square feet. Compared with entry-level Ocoee homes for sale, this is a step up.
What do homes cost in Windsor Landing?+
Right now the three active listings are priced from $690,000 to $899,000, with a median of $699,900. Over the past 12 months, six homes sold at a median price of $742,000. Expect roughly $275 per square foot on a typical 2,600-plus-square-foot home.
How is the market here?+
It's small and moves quickly — only three homes are active, and the median time on market is 24 days. Sellers averaged about 99% of asking over the last year, so there isn't much room to lowball. With just six sales in the past 12 months, inventory is limited and you'll want to act when the right home appears.
What are the HOA fees and property taxes?+
The median HOA runs about $107 per month, which is modest for a neighborhood with gated sections. Property taxes come in around $4,846 per year at current values. Both are worth confirming per listing, since gated and non-gated streets can differ.
Keep exploring
More Ocoee 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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