Neighborhood · Winter Park, Florida
Windsong Estates
Gated luxury living minutes from downtown Winter Park
Windsong Estates sits inside the larger Windsong community, a quiet, tree-lined enclave in Winter Park built around access to the Winter Park Chain of Lakes. It's the kind of address that trades on privacy and proximity — near Lake Killarney, a short drive from the shops and restaurants of Hannibal Square, and zoned for some of the area's most sought-after schools. Buyers here lean toward move-up and luxury, drawn by lake life and the polish of established neighborhoods like Kenilworth nearby.
The market reality is scarcity. There are zero active listings in Windsong Estates right now, so this is a neighborhood you watch and wait for rather than shop off a long list. Over the last 12 months only 4 homes changed hands, at a median sold price of $2,415,000, and sellers walked away with about 98% of asking — a sign that when a home does hit the market, it commands its price.
Windsong Estates is a community in Winter Park, Florida.
Quick facts
4 sold in 12 months
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 strong fit for buyers who want privacy, lake access, and a premier school assignment — Brookshire Elementary, Glenridge Middle, and Winter Park High. The community is quiet and established, and it's close to the dining and shops around Hannibal Square. It suits move-up and luxury buyers more than first-timers.
Is Windsong Estates expensive?+
Yes — this is one of Winter Park's upper-end neighborhoods, with a median sold price of $2,415,000 over the past year. There's no entry-level product here, so plan for a luxury budget. For a wider range of price points, it's worth also looking at nearby Winter Park Pines.
What do homes cost in Windsong Estates?+
Over the last 12 months, 4 homes sold at a median price of $2,415,000. There are currently no active listings, so pricing on the next home to hit the market will depend heavily on its size, lake access, and condition.
How is the market in Windsong Estates?+
It's tight and seller-favorable. Only 4 homes sold in the past year, there are zero active listings today, and sellers are getting about 98% of their asking price on average. Buyers should be ready to move quickly and expect little negotiating room.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available in the current data for Windsong Estates, and with no active listings there's nothing to pull live numbers from. Because it's a gated, lake-oriented community, budget for an HOA and verify exact dues and tax amounts per property once a home is listed.
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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