Neighborhood · Winter Springs, Florida
Winding Hollow
Roomy homes and easy access in Seminole County
2
Homes for sale
$717,500
Median list price
$236
Avg price / sqft
5
Median days on market
Winding Hollow sits in Winter Springs, a quiet Seminole County suburb where lots run generous and the pace stays residential. Homes here trend large — the typical property is around 3,660 square feet — and neighbors are drawn to the same things that anchor nearby Tuscawilla, Deer Run, and Oak Forest: space, mature landscaping, and a short hop to central Orlando. Downtown Orlando is about 27 minutes out and MCO roughly 35, so commuting and travel don't dominate your day.
For buyers, this is a tight, fast-moving market. There's just one active listing right now at $785,000, while 13 homes sold over the past year at a median of $590,000 — and sellers pulled in 99% of asking on average. With a median of one day on market, well-priced homes move quickly, so coming in prepared matters more than waiting for options to pile up. Explore more Winter Springs homes for sale if the timing isn't right in Winding Hollow itself.
Winding Hollow is a community in Winter Springs, Florida.
Quick facts
$650,000 – $785K price range
3,097 sqft median home
$45/mo median HOA
13 sold in 12 months
Drive times
On the market now
Homes for sale in Winding Hollow
$650,000
1105 SHADOWBROOK TRAIL, WINTER SPRINGS
4 bd · 3.5 ba · 2,533 sqft
$785,000
337 TWELVE OAKS DRIVE, WINTER SPRINGS
5 bd · 3.5 ba · 3,660 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
Where the market lives
The numbers that matter
The Winding Hollow market
13
Sold, last 12 months
$600,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
6 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
▼ 2.5% 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
≈ $4,649/mo
$717,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$45/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 settled, family-oriented pocket of Winter Springs with generously sized homes and low HOA dues around $48 a month. You get suburban quiet with Orlando about 27 minutes down the road, plus assigned schools including Winter Springs High School. Nearby established communities like Oak Forest share the same residential character.
Is Winding Hollow expensive?+
It sits in the upper-middle range for the area — the median sold price over the past year was $590,000, and the single active listing is priced at $785,000. Homes here are large, averaging about $214 per square foot, so you're paying for square footage. Compared with nearby North Orlando Ranches, pricing reflects the bigger footprints.
What do homes cost in Winding Hollow?+
Thirteen homes sold in the last 12 months at a median of $590,000, while the current listing is at $785,000 for a roughly 3,660-square-foot home. Average pricing works out to about $214 per square foot. Because inventory is thin, expect the mix to shift with whatever comes on the market.
How is the market in Winding Hollow?+
It's fast and competitive — the median days on market is just one, and sellers are getting 99% of asking on average. With only one active listing against 13 sales in the past year, well-priced homes move almost immediately. Buyers should be financing-ready and prepared to act quickly.
What are the HOA fees and property taxes like?+
The HOA is light at a median of $48 per month, which keeps ongoing costs down. Property taxes are the bigger line item, with a median of $9,512 per year, reflecting the larger home values here. Budget for both when you compare monthly carrying costs against nearby Deer Run.
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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