Neighborhood · Kissimmee, Florida
Windsor Oaks
A quiet Kissimmee pocket close to everything
1
Homes for sale
$245,000
Median list price
$178
Avg price / sqft
353
Median days on market
Windsor Oaks is a small residential enclave in Osceola County, the kind of place where a modest, gated community sits within easy reach of Central Florida's biggest draws. It's an easy fit for buyers who want the theme-park proximity without living in a tourist corridor — Walt Disney World is about 33 minutes out, Universal Orlando roughly 28, and Orlando International Airport a quick 24-minute drive. Nearby you'll find a mix of established and resort-style neighborhoods among Kissimmee homes for sale, from Lake Marion Village to newer builds at Storey Lake and Solara.
The market here is genuinely small and slow-moving, so timing and patience matter. With just two active listings and a median list price of $260,000, inventory is tight and homes tend to sit — the median days on market runs around 170. That's a buyer's pace, and it can leave room to negotiate, especially set against neighboring options like Windsor at Westside.
Windsor Oaks is a community in Kissimmee, Florida.
Quick facts
$245,000 – $245K price range
1,380 sqft median home
$185/mo median HOA
2 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor Oaks
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
2
Sold, last 12 months
$247,750
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
7 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
≈ $1,894/mo
$245,000 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 suits buyers who want a quiet, gated residential feel with quick access to Central Florida's attractions — Walt Disney World is about 33 minutes away and Orlando International Airport roughly 24. It's assigned to schools including Osceola County School for the Arts and Mill Creek Elementary. The trade-off is a very small community with limited listings at any given time.
Is Windsor Oaks expensive?+
No — it's one of the more attainable pockets in the area, with a median list price of $260,000 and an average of about $188 per square foot. For comparison, you can browse the broader range of Kissimmee homes for sale to see how it stacks up against resort-style communities nearby.
What do homes cost in Windsor Oaks?+
Current active listings run from $245,000 to $275,000, with a median around $260,000 on homes near 1,380 square feet. Over the past year, two homes sold at a median price of $257,750, so pricing is consistent and predictable in this small neighborhood.
How is the market in Windsor Oaks?+
It's a slow, tight market with just two active listings and only two sales in the past 12 months. Homes take a median of about 170 days to sell, and sellers are getting roughly 96% of asking on average — which points to real negotiating room for a patient buyer.
What about HOA fees and property taxes?+
The median HOA runs about $185 per month, and median property taxes are around $2,932 per year. Those are typical figures for a gated Osceola County community and worth budgeting alongside your mortgage.
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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