Gated Communities in Winter Garden, FL
Looking for gated communities in Winter Garden, FL? Momentum tracks 38 Winter Garden communities with evidence of gated community living, each with MLS-derived pricing and market pace below — plus the local questions worth asking before you buy, and a direct line to an agent who works these communities.
Winter Garden gated communities at a glance
The communities, by recent sales activity
| Community | City | Median price | 1-yr change | Days on mkt |
|---|---|---|---|---|
| LAKE STAR AT OVATION · agent | Winter Garden | $550,000 | – | 62 d |
| Stoneybrook West · agent | Winter Garden | $652,000 | – | 36 d |
| HICKORY HAMMOCK · agent | Winter Garden | $908,000 | – | 26 d |
| DEL WEBB OASIS · agent | Winter Garden | $419,000 | – | 35 d |
| WEST LAKE HANCOCK ESTATES · agent | Winter Garden | $705,000 | – | 16 d |
| TUCKER OAKS · agent | Winter Garden | $291,000 | – | 82 d |
| STONEYBROOK WEST 44/134 · agent | Winter Garden | $640,000 | – | 94 d |
| STONEYBROOK WEST D · agent | Winter Garden | $568,000 | – | – |
| WINTER GROVE · agent | Winter Garden | $983,000 | – | 18 d |
| BLACK LAKE PRESERVE · agent | Winter Garden | $732,000 | – | 55 d |
| LAKE COVE POINTE · agent | Winter Garden | $842,000 | – | – |
| WINTERMERE POINTE · agent | Winter Garden | $534,000 | – | – |
| DANIELS LNDG A-J · agent | Winter Garden | $288,000 | – | 24 d |
| VILLAS/TUCKER OAKS · agent | Winter Garden | $350,000 | – | – |
| ROPER RESERVE · agent | Winter Garden | $708,000 | – | 101 d |
| WATERSIDE ON JOHNS LAKE · agent | Winter Garden | $810,000 | – | – |
| LAKEVIEW RESERVE 46/149 · agent | Winter Garden | $594,000 | – | 137 d |
| TILDEN PLACE/WINTER GARDEN · agent | Winter Garden | $885,000 | – | 237 d |
| DANIELS LANDING A-J · agent | Winter Garden | $324,000 | – | – |
| WINDWARD CAY 48 125 · agent | Winter Garden | $775,000 | – | – |
| BRONSONS LNDGS F & M · agent | Winter Garden | $985,000 | – | 23 d |
| BAY ISLE 48 17 · agent | Winter Garden | $890,000 | – | 49 d |
| LAKE ROBERTS LNDG E · agent | Winter Garden | $960,000 | – | – |
| LAKE AVALON GROVES · agent | Winter Garden | $750,000 | – | 255 d |
| BRANDY CREEK · agent | Winter Garden | $492,000 | – | – |
Communities are listed by recent closing volume in Momentum’s MLS data. Figures are aggregates, change over time, and are deemed reliable but not guaranteed.
Every other tracked gated communities in Winter Garden
- WINTER GRV
- ARROWHEAD LAKES
- EMERALD RIDGE
- BRADFORD CREEK
- BRADFORD CRK PH I
- ORCHARD A1-A26 B1 B2 C D1-D4
- LAKEVIEW RESERVE
- ISLES OF LAKE HANCOCK
- STONEYBROOK WEST 47/78
- LAKEVIEW VILLAGE ESTATES
- GLYNWOOD 51 32
- ISLES LAKE HANCOCK
- TUCKER OAKS BLDG 5
What gates change about ownership
Controlled access typically comes with a manned gate, a transponder system, or both — funded through HOA dues. Expect guest-access procedures, delivery and contractor rules, and in some communities rental restrictions. Review the HOA budget for how the gate and any roving patrol are funded, and whether roads are private (the HOA maintains them — another line in the dues) or public.
Due diligence before you buy behind a gate
Request the HOA documents early: budget, reserves, rules, and the last two years of meeting minutes. Private roads, gates and common areas are owner-funded, so thin reserves become special assessments. Our buyer closing costs calculator helps you model dues and assessments into the real monthly cost.
What it costs to own here
At Orange County’s typical combined millage of 16.67 mills, a purchase at $705,000 (the median across these Winter Garden gated communities) generates roughly $11,755 a year in property tax before exemptions — about $980 a month. Florida resets the assessed value to roughly your purchase price, so the seller’s current bill is not a preview of yours; a homesteaded owner then gets the $25,000–$50,000 exemption and the 3% Save Our Homes cap going forward. Citizens Property Insurance policies in Orange County average about $1,409 a year ($117 a month) — private-market quotes vary with roof age and wind mitigation, so price coverage before your inspection window closes. All-in, our county model puts the typical monthly cost of ownership in Orange County near $2,402 (principal and interest on the typical home, tax, and insurance).
Run your exact numbers: the property tax after purchase calculator uses Orange County’s verified millage, and the buyer closing costs calculator builds the full cash-to-close.
Demand and supply in Orange County right now
In the most recent IRS migration data (2022-2023), Orange County lost a net 9,037 people to relocation, with the largest inbound flows from NY, CA, NJ. Households moving IN reported average incomes of $66,457 versus $61,323 for those leaving — the income mix of demand, straight from tax filings. Population is up about 9.0% over the recent multi-year window. On the supply side, builders pulled 13,140 residential permits in Orange County in 2025 (4,221 single-family), up 63.2% year over year. Permits are tomorrow’s inventory: a shrinking pipeline supports prices, a swelling one hands buyers leverage. Our valuation model reads the county as overvalued by about 6.9% versus its income-and-rent fundamentals.
Explore more of Winter Garden
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Run the numbers in Orange County
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- Get a cash offer in Orange County
- Orange County housing scorecard
- What would selling net you
- Buyer closing costs calculator
Common questions
How many gated communities does Winter Garden, FL have?
What do homes in Winter Garden gated communities cost?
How does Momentum classify a community as one of the gated communities?
How much is home insurance in Orange County?
What are property taxes like in Orange County?
Community classifications are compiled from MLS-reported amenities, verified amenity records and MLS build-year data, as of 2026-06-16; they are informational, change over time, and are deemed reliable but not guaranteed — verify details with each association. Not an offer of housing to any protected class to the exclusion of others. Equal Housing Opportunity.