Neighborhood · Winter Park, Florida
Windsong Estates
Rarely-traded luxury living minutes from downtown
Windsong Estates is a small, high-end enclave in Winter Park, the tree-lined city just north of downtown Orlando known for its lakes and walkable charm. Homes here trade infrequently and at the top of the market, with easy access to nearby communities like Lake Killarney and Winter Park Pines. Families are drawn to the assigned schools — Winter Park High, Glenridge Middle, and Brookshire Elementary — and the sub-15-minute drive into downtown Orlando.
This is a low-inventory, low-turnover market: there are currently no active listings, and only four homes sold here over the past 12 months. Those sales closed at a median of $2,415,000, with sellers collecting 98% of asking on average. Buyers should be patient, well-prepared, and ready to move when the right home in the area — or in neighbors like Eastbrook — comes to market.
Windsong Estates is a community in Winter Park, Florida.
Quick facts
4 sold in 12 months
Drive times
On the market now
Homes for sale in Windsong Estates
Nothing active right now.
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Every active listing inside the Windsong Estates boundary
Open full map search →The numbers that matter
The Windsong Estates market
4
Sold, last 12 months
$2,415,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
2 days
Median time to sell
Windsong Estates vs Winter Park
Live Stellar MLS data — every listing and closed sale inside the Windsong Estates boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsong Estates is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
115
Median age
59
Median income
$149,784
Median home value
$1,078,300
Beyond the listings
Living in Windsong Estates
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.
Lifestyles
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.
Culture
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.
Appearance oriented
Fitness Fashion
Workout clothes aren't just for working out anymore. This population enjoys wearing name-brand athletic apparel for fashion and functional purposes.
Hobbies & Interests
Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Active
Outdoor Adventures
Appreciating the outdoors, this population wants to actively engage with nature. Whether it's finding a new hiking trail or looking for the perfect spot to catch the sunset, they seek to explore the world around them.
People who close here
Our Winter Park experts
Straight answers
Windsong Estates FAQs
Is Windsong Estates a good place to live?+
It's a quiet, upscale pocket of Winter Park with strong school assignments — Winter Park High, Glenridge Middle, and Brookshire Elementary. You're about 11 minutes from downtown Orlando and 28 from the airport, so you get seclusion without sacrificing access. Nearby Winter Park Pines rounds out the area's residential feel.
Is Windsong Estates expensive?+
Yes — this is one of Winter Park's higher-priced neighborhoods, with homes selling at a median of $2,415,000 over the past 12 months. It's a luxury market, so budget accordingly and expect to compete for the few homes that trade. Buyers exploring Winter Park homes for sale more broadly will find a range of price points.
What do homes cost in Windsong Estates?+
The four homes that sold here in the last year closed at a median of $2,415,000. With no active listings at the moment, pricing is best gauged from those recent sales. Comparable homes in surrounding communities like Lake Killarney can help calibrate expectations.
How is the market in Windsong Estates?+
It's a low-inventory, low-turnover market — zero active listings right now and just four sales over the past 12 months. When homes do sell, they command 98% of asking on average, which points to steady demand. Buyers should be ready to act quickly and may also want to watch nearby Eastbrook.
What about HOA fees and property taxes?+
Specific HOA and property tax figures for Windsong Estates aren't available in the current data, which is common given how rarely homes here trade. Your agent can pull exact carrying costs on any individual property before you make an offer. Costs will reflect the neighborhood's luxury price point.
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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