Neighborhood · Kissimmee, Florida
Windsor Pines
Small-scale Kissimmee living with room to grow
1
Homes for sale
$175,000
Median list price
$136
Avg price / sqft
57
Median days on market
Windsor Pines is a compact residential pocket in Osceola County, part of the wider Kissimmee landscape where established neighborhoods sit close to the region's theme-park and tourism corridor. It's the kind of place where homes are modest in size — the median here is around 1,290 square feet — and the pace feels neighborly rather than resort-driven. Families are zoned for schools including Osceola County School for the Arts and Osceola High School, and you're within easy reach of larger communities like Storey Lake and Windsor at Westside.
For buyers today, this is a thin, quiet market. There's just one active listing at $175,000, and only two homes have sold here in the past twelve months at a median of $181,500. That scarcity means opportunities come up rarely, so when a home in Windsor Pines or a nearby community like Solara hits the market, it pays to be ready to move.
Windsor Pines is a community in Kissimmee, Florida.
Quick facts
$175,000 – $175K price range
1,290 sqft median home
$375/mo median HOA
2 sold in 12 months
On the market now
Homes for sale in Windsor Pines
Every active listing inside the Windsor Pines boundary
Open full map search →Find your fit
Browse Windsor Pines
By feature — on the live map
The numbers that matter
The Windsor Pines market
2
Sold, last 12 months
$181,500
Median sold price
91%
Sale-to-list ratio
What sellers actually get vs asking
74 days
Median time to sell
Windsor Pines vs Kissimmee
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Windsor Pines boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor Pines is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor Pines home
≈ $1,590/mo
$175,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$375/mo
Median HOA
From current listings inside the boundary
Population
2,043
Median age
30
Median income
$38,838
Median home value
$226,500
Beyond the listings
Living in Windsor Pines
Relationships
Top 1% in the U.S.Dating Life
With dating comes highs, lows, and lots of questions. You can find this population talking about dating advice, breakups and how to express their feelings.
Emotional
Top 1% 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.
Appearance oriented
Top 1% in the U.S.Men's Style
This population is all about finding the latest in men's style - from fashion to grooming. Captures guys looking to stay on trend and significant others assisting with shopping.
Relationships
Top 1% in the U.S.My Crew
Family, and friends who are like family - that's what this population is all about. These people love celebrating and nurturing their closest relationships.
Lifestyles
Top 2% 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.
Lifestyles
Top 2% in the U.S.Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
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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