YOUR NEIGHBORHOOD GUIDE · WINTER SPRINGS, FL
Get to know
Winding Hollow.
Explore Winding Hollow in Winter Springs, FL: nearby homes, schools and everyday places.
LIFE IN WINDING HOLLOW
Get a feel for Winding Hollow.
Winding Hollow is a neighborhood in Winter Springs, FL. This guide brings together a housing snapshot and places to explore in and around the community.
LOCAL KNOWLEDGE MAKES A DIFFERENCE
Top real estate agents in Winding Hollow
Ranked FastExpert agents serving Winter Springs, FL. Rankings are citywide, not specific to Winding Hollow.
A LOOK AT THE MARKET
Homes & housing in Winding Hollow
Asking prices come from active listings. Recorded sales cover to . A dash means that figure was not available.
What kinds of homes are here?
40 residential property records give a broader picture of Winding Hollow, including homes that aren’t for sale.
Updated 2026-10-09. These are property classifications, not a census of individual homes.
How does Winding Hollow compare?
Compare median asking prices across Winter Springs neighborhoods.
| Neighborhood | Median asking price | Compared with Winding Hollow | Sale price / sq ft | Recorded sales |
|---|---|---|---|---|
| Winding Hollow This neighborhood | $362,950 | — | — | 1 |
| Tuscawilla | $295,000 | 19% lower | $261 | 3 |
| Mount Greenwood | $145,500 | 60% lower | — | 1 |
| North Orlando Terrace | $202,450 | 44% lower | — | 4 |
| Willow Run | $325,000 | 10% lower | — | 0 |
| The Oaks | $249,900 | 31% lower | — | 0 |
Median asking price and price per square foot come from the same listing sample as the neighborhood cards. Recorded sales cover 2025-10-09 to 2026-10-09. A dash means that figure was not available.
Explore nearby neighborhoods in Winter Springs
Tuscawilla ↗
- Median asking price
- $295,000
- / sq ft
- $261
- Active listings
- 28
- properties in discovery sample
- 173
BNearby schools · estimated
7/10 · 6 schools
Mount Greenwood ↗
- Median asking price
- $145,500
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 43
CNearby schools · estimated
5.7/10 · 3 schools
North Orlando Terrace ↗
- Median asking price
- $202,450
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 28
CNearby schools · estimated
5.5/10 · 4 schools
Willow Run ↗
- Median asking price
- $325,000
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 4
CNearby schools · estimated
5.3/10 · 3 schools
The Oaks ↗
- Median asking price
- $249,900
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 2
CNearby schools · estimated
4.8/10 · 4 schools
Median asking price is the midpoint of listing prices in the discovery sample. A dash means that figure was not available. Photos show community or nearby landmarks.
See all featured Winter Springs neighborhoods →MAKE TIME FOR OUTSIDE
Parks, lakes & recreation nearby
Find a place for a walk, a swim or an afternoon in the park. Some pools and lake facilities are private or for association members; check access before visiting.
Data not available for this view yet. Explore on Google Maps ↗
Places, ratings and photos from Google Maps. Saved results come from an approved snapshot. This page does not call Places API while you view it. Drives are estimates from Winding Hollow’s center, without live traffic. Nearby results may extend beyond neighborhood boundaries.
YOUR EVERYDAY STOPS
Shopping & dining nearby
Discover restaurants for dining out and shopping centers in and around Winding Hollow.
Restaurants for dining out, ranked using Google ratings and review counts. Fast-food and convenience-store results are filtered out.
Data not available for this view yet. Explore on Google Maps ↗
Places, ratings and photos from Google Maps. Saved results come from an approved snapshot. This page does not call Places API while you view it. Drives are estimates from Winding Hollow’s center, without live traffic. Nearby results may extend beyond neighborhood boundaries.
LEARNING CLOSE TO HOME
Nearby schools
Public schools returned for sampled Winding Hollow properties. Attendance depends on the specific address.
W marks Winding Hollow’s center. Shading shows a half-mile radius around that point, not a neighborhood boundary. Numbered pins match the places below.
School ratings · 2026-10-09. Grade methodology is below.
THE CITY AROUND YOU
Winter Springs demographics & households
Citywide context for a move to Winding Hollow. These figures describe Winter Springs as a whole.
Explore Winter Springs’s age distribution
From FastExpert’s existing Winter Springs city-data source, retrieved 2026-10-09; source year was not supplied. Explore all Winter Springs city data →
FIND YOUR PLACE HERE
Homes for sale in Winding Hollow
No listings returned by our provider right now. Explore current homes using the link above.
Listing data: Redfin. Photos and listing links: Redfin. Open a listing for its current status and full details.
KEEP EXPLORING
Get to know Winter Springs.
Explore the broader area’s housing and demographic context.
Sources, dates & how we calculate estimates
Nearby places and photos come from an approved snapshot. Viewing this page does not call Google Places. A controlled refresh can still search within 5 km of the center. Recreation combines park, lake, trail and club searches, removes duplicates and keeps results within 5 miles. Restaurant ranking balances star ratings with review counts; fast-food, convenience stores and places marked as not offering dine-in are excluded.
Housing mix uses residential property records, including homes that are not for sale. Market prices use the most recent recorded qualifying sale per property within 2025-10-09 to 2026-10-09. Transfers identified as non-market transactions and records without a positive sale amount are excluded. Medians appear with at least 10 sales; price per square foot also requires a recorded home size. Property classifications and neighborhood definitions may differ from local usage. These are dated snapshots, not a complete transaction history or live inventory feed.
School grades are FastExpert estimates based on the mean available ratings for unique public schools found across 4 Winding Hollow property samples: A = 8–10, B = 6–under 8, C = 4–under 6, D = 2–under 4, F = 1–under 2. Unrated schools are excluded. Grades do not confirm attendance eligibility.
Winter Springs demographics come from the existing FastExpert city-data source. The city’s source year was not supplied. Top agents use FastExpert’s existing Winter Springs ranking; a Winding Hollow-specific ranking is not available yet.