Neighborhood · Winter Springs, Florida
Winding Hollow
A family-scaled pocket of Winter Springs
2
Homes for sale
$712,500
Median list price
$207
Avg price / sqft
12
Median days on market
Winding Hollow sits in the heart of Seminole County's Winter Springs, a quiet residential enclave built around larger single-family homes and shaded streets. It's the kind of neighborhood where kids feed into Winter Springs High School and the daily commute to downtown Orlando runs about 27 minutes, with Orlando International Airport roughly 35 minutes out. Neighbors here look to nearby communities like Tuscawilla, Deer Run and the Highlands for the same suburban rhythm.
For buyers today, this is a tight, low-inventory market. There's just one active listing at $685,000, while the 12 homes sold over the past year closed at a median of $600,000 — and sellers collected 99% of asking on average. Homes here move in about 16 days, so when the right one lands, you'll want to be ready.
Winding Hollow is a community in Winter Springs, Florida.
Quick facts
$685,000 – $740K price range
3,452 sqft median home
$46/mo median HOA
12 sold in 12 months
Drive times
On the market now
Homes for sale in Winding Hollow
$740,000
340 TWELVE OAKS DRIVE, WINTER SPRINGS
5 bd · 3.5 ba · 3,657 sqft
$685,000
525 SADDLEWOOD LANE, WINTER SPRINGS
4 bd · 3 ba · 3,246 sqft
Every active listing inside the Winding Hollow boundary
Open full map search →Find your fit
Browse Winding Hollow
By feature — on the live map
The numbers that matter
The Winding Hollow market
12
Sold, last 12 months
$600,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
17 days
Median time to sell
Winding Hollow vs Winter Springs
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 4.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winding Hollow boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winding Hollow is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winding Hollow home
≈ $4,383/mo
$712,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$46/mo
Median HOA
From current listings inside the boundary
Population
1,252
Median age
46
Median income
$97,519
Median home value
$350,921
Beyond the listings
Living in Winding Hollow
Relationships
Top 2% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Active
Top 3% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
Active
Top 3% 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.
Appearance oriented
Top 6% in the U.S.Fitness Fashion
Workout clothes aren't just for working out anymore. This population enjoys wearing name-brand athletic apparel for fashion and functional purposes.
Active
Top 7% in the U.S.Organized Sports
From tryouts and casual pick-up games, to varsity tournaments and intramural matches, this population includes people who participate in organized athletics. Often through schools or public recreational areas.
Entertainment
Top 7% in the U.S.Competitive Nature
These folks have their head in the game. Whether it's creating a card game tournament with friends or cheering on the home team, these people want to win.
Straight answers
Winding Hollow FAQs
Is Winding Hollow a good place to live?+
It's a quiet, family-oriented neighborhood in Winter Springs with larger homes and an easy 27-minute drive to downtown Orlando. Assigned schools include Layer Elementary, Indian Trails Middle and Winter Springs High School, and neighbors sit close to established communities like Tuscawilla. It suits buyers who want suburban space without giving up city access.
Is Winding Hollow expensive?+
It's a mid-to-upper price point for the area, with the median home sold over the past year at $600,000 and the single current listing at $685,000. At roughly $211 per square foot, you're paying for size — the median home is around 3,246 square feet. Compared with nearby Deer Run, it lands solidly in family-home territory.
What do homes cost in Winding Hollow?+
Twelve homes sold in the last 12 months at a median of $600,000, while the current active listing is priced at $685,000. Expect around $211 per square foot for homes near the 3,246-square-foot median size. Pricing here reflects the neighborhood's larger floor plans.
How is the market in Winding Hollow?+
It's tight and fast-moving, with just one active listing and a median 16 days on market. Sellers have been getting 99% of their asking price on average, so well-priced homes don't linger. Buyers should be prepared to act quickly when inventory appears across Winter Springs.
What about HOA fees and property taxes?+
The HOA runs a modest median of about $42 per month, which is low for the region. Property taxes come in around $4,016 per year at current values. Both keep ongoing carrying costs reasonable relative to the home sizes here.
Keep exploring
More Winter Springs 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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