Neighborhood · Winter Park, Florida
Windsong
Gated lakeside living minutes from downtown Winter Park
2
Homes for sale
$5,200,000
Median list price
$600
Avg price / sqft
100
Median days on market
Windsong is one of Winter Park's most established lakeside enclaves, built around chain-of-lakes access and a scale of home you don't find in many close-in Orlando neighborhoods. Median homes here run past 7,400 square feet, and the community sits within easy reach of the shops and restaurants that give Winter Park homes for sale their appeal. It also puts you near neighboring pockets like Lake Killarney and the walkable energy of Hannibal Square.
For a buyer today, this is a thin, high-end market. There are just two active listings with a median list price of $5.2 million, while the nine homes sold over the past year closed at a median of $1.85 million — a wide spread that reflects how much size, waterfront, and finish level swing the number. Homes take time to trade here, with a median of about 100 days on market, so patience and precise pricing both matter. If Windsong's inventory is tight, comparing options in nearby Kenilworth and Winter Park Pines is a smart move.
Windsong is a community in Winter Park, Florida.
Quick facts
$1,450,000 – $8.9M price range
7,417 sqft median home
$265/mo median HOA
9 sold in 12 months
Drive times
On the market now
Homes for sale in Windsong
$1,450,000$1,550,000
1421 CHAPMAN CIRCLE, WINTER PARK
4 bd · 3.5 ba · 3,578 sqft
$8,950,000
1120 PRESERVE POINT DRIVE, WINTER PARK
7 bd · 10 ba · 11,255 sqft
Every active listing inside the Windsong boundary
Open full map search →Find your fit
Browse Windsong
By feature — on the live map
Where the market lives
The numbers that matter
The Windsong market
9
Sold, last 12 months
$1,850,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
29 days
Median time to sell
Windsong vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 15.1% 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.
What it really costs
Owning here
Owning the median Windsong home
≈ $31,016/mo
$5,200,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$265/mo
Median HOA
From current listings inside the boundary
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.
On the calendar
Near Windsong
Jul
13
Mon
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
14
Tue
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Jul
14
Tue
The Captivating Unknown
The event, The Captivating Unknown, is an art exhibition that explores humanity's fascination with the cosmos through various artistic mediums. The works on display aim t…
Jul
14
Tue
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
14
Tue
Pathways
This exhibition, a collaboration between the Rollins Museum of Art and the UCF Art Gallery, showcases the diverse works of emerging Florida artists, handpicked by a panel…
Jul
16
Thu
Thursday Thinks Trivia
7:30pm
This challenging trivia night promises a wide range of engaging questions, ensuring something new and exciting for everyone - from pop culture, geography, and history, to…
People who close here
Our Winter Park experts
Straight answers
Windsong FAQs
Is Windsong a good place to live?+
Windsong suits buyers who want large, gated-feel lakeside homes with quick access to Winter Park's dining and shopping. The neighborhood feeds well-regarded schools — Brookshire Elementary, Glenridge Middle, and Winter Park High — and downtown Orlando is only about 20 minutes away. It's a quieter, estate-scale alternative to the walkable density of Hannibal Square.
Is Windsong expensive?+
Yes — it's one of the higher-end pockets in the area. The two active listings carry a median list price of $5.2 million, ranging from $1.45 million to $8.95 million, and pricing averages around $600 per square foot. Recent closings were more grounded, with a median sold price of $1.85 million over the past 12 months.
What do homes cost in Windsong?+
Over the last year, nine homes sold at a median of $1.85 million, though the current listings sit much higher because of size and waterfront. Expect roughly $600 per square foot on homes that median around 7,400 square feet. Buyers watching value should also track nearby Winter Park Pines, where the price ceiling is lower.
How is the market in Windsong?+
It's a low-volume, high-value market with just two active listings and nine sales over the past year. Homes take time to move — the median is about 100 days on market — but sellers still capture around 97% of asking. Well-priced, move-in-ready homes tend to draw the most serious interest.
What about HOA fees and property taxes?+
The median HOA here runs about $265 per month, which is reasonable for a gated-feel lakeside community. Property taxes are the bigger line item, with a median of roughly $37,714 per year reflecting the neighborhood's high home values. Both figures scale with the size and price of the specific home you buy.
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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