Neighborhood · Kissimmee, Florida
Windsor Oaks
Compact Kissimmee living close to the theme parks
2
Homes for sale
$260,000
Median list price
$188
Avg price / sqft
168
Median days on market
Windsor Oaks is a small residential pocket of Kissimmee where the appeal is straightforward: single-family homes at an approachable size, sitting a short drive from Central Florida's biggest draws. Orlando International Airport is about 24 minutes away, Universal Orlando around 28, and Walt Disney World roughly 33 — close enough to be convenient without living in the tourist crush. It's the kind of neighborhood that reads as everyday Kissimmee rather than a resort address like nearby Storey Lake or Windsor at Westside.
For buyers, the market here is genuinely thin — there's currently one active listing at $275,000, so options are limited and timing matters. Three homes sold in the past year at a median of $264,000, with sellers collecting about 96% of asking, which points to steady but unhurried demand. If you're comparing this to other Kissimmee options like Solara or Lake Marion Village, expect to move decisively when the right home appears.
Windsor Oaks is a community in Kissimmee, Florida.
Quick facts
$245,000 – $275K price range
1,380 sqft median home
$185/mo median HOA
3 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor Oaks
$275,000
1622 Windsor Oak Court, Kissimmee FL 34744, KISSIMMEE
3 bd · 2.5 ba · 1,380 sqft
$245,000$247,000
1647 WINDSOR OAK COURT, KISSIMMEE
3 bd · 2.5 ba · 1,380 sqft
Every active listing inside the Windsor Oaks boundary
Open full map search →Find your fit
Browse Windsor Oaks
By feature — on the live map
The numbers that matter
The Windsor Oaks market
3
Sold, last 12 months
$264,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
23 days
Median time to sell
Windsor Oaks vs Kissimmee
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Windsor Oaks boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor Oaks is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor Oaks home
≈ $2,009/mo
$260,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$185/mo
Median HOA
From current listings inside the boundary
Population
688
Median age
48
Median income
$72,436
Median home value
$290,600
Beyond the listings
Living in Windsor Oaks
Emotional
Top 7% in the U.S.Memory Lane
Intentionally preserving memories of lost loved ones, joyful times, or reflecting on painful experiences in the past.
Lifestyles
Top 16% in the U.S.Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Relationships
Top 19% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
Beliefs
Top 21% 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.
Entertainment
Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Attitudes
Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Windsor Oaks FAQs
Is Windsor Oaks a good place to live?+
It's a quiet residential corner of Kissimmee that trades resort flash for practicality, with major destinations like Walt Disney World about 33 minutes out and Orlando International Airport around 24. Assigned schools include Osceola County School for the Arts and Mill Creek Elementary. It suits buyers who want to be near the action without living in it.
Is Windsor Oaks expensive?+
No — it sits at the accessible end of the Kissimmee market, with the current listing priced at $275,000 and last year's homes selling at a median of $264,000. At roughly $199 per square foot, it's more affordable than the resort-oriented communities like Solara nearby.
What do homes cost in Windsor Oaks?+
The one active listing is priced at $275,000, and the median sold price over the past 12 months was $264,000. With a median home size around 1,380 square feet, you're looking at compact single-family homes rather than large estates.
How is the market in Windsor Oaks?+
It's a small, slow-turning market — just three homes sold in the past year and one currently active. Homes take a median of 62 days to sell and close at about 96% of asking, so pricing tends to be realistic and buyers should be ready to act when inventory appears.
What about HOA fees and property taxes?+
Median property tax runs about $3,372 per year based on recent data, while HOA figures aren't currently reported for the neighborhood. Always confirm any HOA dues and current tax figures for a specific home before you write an offer.
Keep exploring
More Kissimmee 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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