Neighborhood · Kissimmee, Florida
Windsong
An easygoing pocket of Kissimmee close to it all
Windsong is a small, low-key residential enclave in Osceola County, the kind of Kissimmee neighborhood where modest single-family homes sit on quiet streets and daily life stays uncomplicated. You're roughly 22 minutes from Orlando International Airport and about a half hour from both Universal Orlando and Walt Disney World, so theme-park days and travel are genuinely easy from here. It's a practical spot for buyers who want central Florida access without living inside a resort-scale master plan like Storey Lake or Solara.
The market here is tight and small, which shapes what a buyer should expect. Right now there's essentially one active listing among the broader Kissimmee homes for sale, priced at $359,000, and only three homes sold in the past year at a $280,000 median. Homes that are priced right move — median days on market sit at 18 — so when something in Windsong comes up, you'll want to be ready to act.
Windsong is a community in Kissimmee, Florida.
Quick facts
4 sold in 12 months
Drive times
On the market now
Homes for sale in Windsong
Nothing active right now.
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Every active listing inside the Windsong boundary
Open full map search →The numbers that matter
The Windsong market
4
Sold, last 12 months
$285,500
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
15 days
Median time to sell
Windsong vs Kissimmee
Live Stellar MLS data — every listing and closed sale inside the Windsong boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsong is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
470
Median age
40
Median income
$69,875
Median home value
$233,400
Beyond the listings
Living in Windsong
Hobbies & Interests
Top 1% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
Appearance oriented
Top 8% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Food & Drink
Top 10% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Active
Top 15% in the U.S.Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Relationships
Top 21% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Attitudes
Top 24% in the U.S.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
Windsong FAQs
Is Windsong a good place to live?+
It's a quiet, small residential neighborhood that trades resort-style amenities for easy access — MCO is about 22 minutes and Disney around 31. Assigned schools include Osceola County School for the Arts and Osceola High School. If you want a calmer base in Kissimmee rather than a busy vacation-home community, it fits well.
Is Windsong expensive?+
It's relatively attainable for the area, with the current active listing at $359,000 and last year's three sales landing at a $280,000 median. Compared to larger nearby communities like Windsor at Westside, the smaller home sizes here keep entry prices lower.
What do homes cost in Windsong?+
The single active listing is priced at $359,000, and average price per square foot runs about $306 on a median home size near 1,173 square feet. Recent sold prices came in lower, with a $280,000 median over the past 12 months, so what's for sale can price above what's actually closed.
How is the market in Windsong?+
It's small and moves quickly when priced correctly — median days on market is 18, and sellers have been getting about 94% of asking. With only one active listing and three sales in the past year, inventory is thin, so buyers should be prepared to move fast.
What about HOA and property taxes?+
The HOA here is modest at a median of about $31 a month, well below many master-planned Kissimmee communities. Median property taxes run around $3,885 a year, which is typical for Osceola County homes in this price range.
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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