Neighborhood · Winter Park, Florida
Windsong
Gated Winter Park living close to Park Avenue
Windsong is a well-established gated community in the heart of Winter Park, where mature landscaping, private lakes, and a walkable network of streets set the tone for everyday life. You're minutes from Park Avenue's shops and dining, with the character of nearby Lake Killarney and Hannibal Square close at hand, and assigned schools like Winter Park High and Brookshire Elementary rounding out the appeal for families. Downtown Orlando is roughly 20 minutes away, so the location works whether you're commuting or heading out for the weekend.
This is a low-inventory, high-value pocket, and buyers should plan accordingly. Right now there's a single active listing at $1,450,000, while nine homes have sold over the past year at a median of $1,755,000. Sellers here are getting about 97% of asking on average, so serious offers matter — but with a median of 58 days on market, there's room to negotiate on the right home.
Windsong is a community in Winter Park, Florida.
Quick facts
11 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
11
Sold, last 12 months
$1,755,000
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
67 days
Median time to sell
Windsong vs Winter Park
Median sold price — 3-yr, 3-mo rolling
▲ 19.0% yr/yr
Homes sold per month
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
714
Median age
57
Median income
$139,554
Median home value
$868,200
Beyond the listings
Living in Windsong
Relationships
Top 16% 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.
Culture
Top 22% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Beliefs
Politically Engaged
Politically aware, this population is interested in civic issues on both the local and national level. They often discuss candidates for office, taxes, and political ideologies.
Beliefs
Activism
This population seeks to advocate for a more just world. Common activities include protests, rallies, and spreading awareness to the public about social justice issues.
Entertainment
Late-night Leisure
Ready to turn up when the sun goes down, this population is looking for nighttime entertainment at home or out on the town.
Beliefs
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.
People who close here
Our Winter Park experts
Straight answers
Windsong FAQs
Is Windsong a good place to live?+
Windsong suits buyers who want a gated, family-friendly community with quick access to Park Avenue and the rest of Winter Park. It's assigned to Winter Park High, Glenridge Middle, and Brookshire Elementary, and downtown Orlando sits about 20 minutes away. The setting is quiet and established, which is a big part of the draw.
Is Windsong expensive?+
Yes — this is a seven-figure neighborhood. The lone active listing is priced at $1,450,000, and the median sold price over the past year was $1,755,000. It's one of the more premium pockets around Lake Killarney and central Winter Park.
What do homes cost in Windsong?+
Homes here trade in the $1.45M to $1.75M range, with the current active listing at $1,450,000 and recent sales at a median of $1,755,000. That works out to roughly $405 per square foot on a median home size of about 3,578 square feet. Compared with nearby Winter Park Pines, Windsong sits firmly at the upper end.
How is the market in Windsong?+
It's a low-inventory market with just one active listing right now and nine sales over the past 12 months. Homes take a median of 58 days to sell, and sellers are averaging about 97% of their asking price. That balance means well-priced homes move, but buyers still have negotiating room.
What about HOA fees and property taxes?+
The median HOA runs about $268 per month, which reflects the gated community's shared upkeep. Property taxes come in around $10,592 per year, in line with homes at this price point. Both are worth factoring into your monthly budget alongside the purchase price.
Keep exploring
More Winter Park 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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