YOUR NEIGHBORHOOD GUIDE · OAKLAND, FL
Get to know
Winters Landing.
Explore Winters Landing in Oakland, FL: nearby homes, schools and everyday places.
LIFE IN WINTERS LANDING
Get a feel for Winters Landing.
Winters Landing is a neighborhood in Oakland, 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 Winters Landing
Ranked FastExpert agents serving Oakland, FL. Rankings are citywide, not specific to Winters Landing.
A LOOK AT THE MARKET
Homes & housing in Winters Landing
Asking prices come from active listings. Recorded sales cover to . A dash means that figure was not available.
What kinds of homes are here?
39 residential property records give a broader picture of Winters Landing, including homes that aren’t for sale.
Updated 2026-10-14. 1 land or other records are excluded from this housing mix. These are property classifications, not a census of individual homes.
How does Winters Landing compare?
Compare median asking prices across Oakland neighborhoods.
| Neighborhood | Median asking price | Compared with Winters Landing | Sale price / sq ft | Recorded sales |
|---|---|---|---|---|
| Winters Landing This neighborhood | $394,900 | — | — | 2 |
| Johns Landing | $342,450 | 13% lower | — | 2 |
| Trailside Station | $244,950 | 38% lower | — | 2 |
| Johns Cove | $530,000 | 34% higher | — | 0 |
| Oakland Town | $229,000 | 42% lower | — | 1 |
| Hull Island Estates | $139,900 | 65% lower | — | 0 |
Median asking price and price per square foot come from the same listing sample as the neighborhood cards. Recorded sales cover 2025-10-14 to 2026-10-14. A dash means that figure was not available.
Explore nearby neighborhoods in Oakland
Johns Landing ↗
- Median asking price
- $342,450
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 130
CNearby schools · estimated
5.3/10 · 3 schools
Trailside Station ↗
- Median asking price
- $244,950
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 28
CNearby schools · estimated
5.3/10 · 3 schools
Johns Cove ↗
- Median asking price
- $530,000
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 21
CNearby schools · estimated
5.3/10 · 3 schools
Oakland Town ↗
- Median asking price
- $229,000
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 20
CNearby schools · estimated
5.3/10 · 3 schools
Hull Island Estates ↗
- Median asking price
- $139,900
- / sq ft
- —
- Active listings
- Not available
- properties in discovery sample
- 3
CNearby schools · estimated
5.3/10 · 3 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 Oakland 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 Winters Landing’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 Winters Landing.
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 Winters Landing’s center, without live traffic. Nearby results may extend beyond neighborhood boundaries.
LEARNING CLOSE TO HOME
Nearby schools
Public schools returned for sampled Winters Landing properties. Attendance depends on the specific address.
W marks Winters Landing’s center. Shading shows a half-mile radius around that point, not a neighborhood boundary. Numbered pins match the places below.
School ratings · 2026-10-14. Grade methodology is below.
THE CITY AROUND YOU
Oakland demographics & households
Citywide context for a move to Winters Landing. These figures describe Oakland as a whole.
Explore Oakland’s age distribution
From FastExpert’s existing Oakland city-data source, retrieved 2026-10-14; source year was not supplied. Explore all Oakland city data →
FIND YOUR PLACE HERE
Homes for sale in Winters Landing
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 Oakland.
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 2025-10-14 to 2026-10-14. 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 Winters Landing 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.
Oakland demographics come from the existing FastExpert city-data source. The city’s source year was not supplied. Top agents use FastExpert’s existing Oakland ranking; a Winters Landing-specific ranking is not available yet.