Gated Communities in Winter Garden, FL: Homes for Sale
This page tracks every Winter Garden listing whose MLS record reports a gated community (manned gate, unmanned gate or security gate), by community, with live counts and asking prices, and the fee questions that come with the gate.
177 homes in gated communities are for sale or pending in Winter Garden, FL today across 81 communities. The median asking price is $351,450, from $150,000 to $2,099,000. Listings in Winter Garden without that feature have a median of $989,900. Most listings right now: Grove Residence & Spa Hotel Condo Ii (13), Grove Resort And Spa Hotel Condominium (12), Southern Pines Condo (11). Updated September 9, 2026 from the MLS.
Winter Garden gated community homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most gated community homes listed are tabled; the rest follow.
| Community | Gated Community Homes | New build | Median list | From |
|---|---|---|---|---|
| 13 | 0 | $250,000 | $185,000 | |
| 12 | 0 | $249,250 | $169,900 | |
| 11 | 0 | $259,000 | $212,000 | |
| Lake Star At Ovation | 7 | 7 | $814,990 | $669,990 |
| Del Webb Oasis | 6 | 2 | $899,000 | $595,000 |
| Winter Grove | 6 | 6 | $889,325 | $872,000 |
| 6 | 0 | $285,445 | $190,000 | |
| 6 | 0 | $240,000 | $179,000 | |
| 5 | 0 | $379,000 | $235,100 | |
| 4 | 0 | $745,000 | $575,000 | |
| 4 | 0 | $304,500 | $209,000 | |
| 4 | 0 | $249,000 | $210,000 | |
| 3 | 0 | $1,249,990 | $1,159,000 | |
| Bronsons Lndgs F & M | 3 | 0 | $860,000 | $749,000 |
| 3 | 0 | $825,000 | $815,000 | |
| Stoneybrook West | 3 | 0 | $625,000 | $615,000 |
| Del Webb Oasis Ph 3 | 3 | 0 | $419,000 | $400,000 |
| 3 | 0 | $335,000 | $250,000 | |
| Tucker Oaks | 3 | 0 | $319,500 | $310,000 |
| Hickory Hammock Ph 1D | 2 | 0 | $1,579,500 | $1,060,000 |
| Stoneybrook West D | 2 | 0 | $563,500 | $438,000 |
| Hickory Hammock Ph 1C | 2 | 0 | $490,000 | $465,000 |
| Orchard A1-A26 B1 B2 C D1-D4 | 2 | 0 | $360,000 | $355,000 |
| Daniels Lndg A-J | 2 | 0 | $317,000 | $309,000 |
| 2 | 0 | $255,250 | $239,500 | |
| 2 | 0 | $217,500 | $210,000 | |
| 2 | 0 | $201,950 | $184,900 | |
| 2 | 0 | $194,999 | $174,999 | |
| 2 | 0 | $174,975 | $169,950 | |
| Lake Avalon Groves Rep | 1 | 0 | $1,775,000 | $1,775,000 |
| Lakeview Reserve | 1 | 0 | $1,675,000 | $1,675,000 |
| Winter Grv | 1 | 0 | $1,600,000 | $1,600,000 |
| 1 | 0 | $1,225,000 | $1,225,000 | |
| Lake Roberts Lndg E | 1 | 0 | $1,200,000 | $1,200,000 |
| Lakeview Village Estates | 1 | 1 | $1,137,150 | $1,137,150 |
| Estates At Lakeview Preserve | 1 | 0 | $1,089,000 | $1,089,000 |
| Johns Cove 43/104 | 1 | 0 | $1,075,000 | $1,075,000 |
| Bradford Creek Phase Ii | 1 | 0 | $1,060,000 | $1,060,000 |
| 1 | 0 | $925,000 | $925,000 | |
| Bay Isle 48 17 | 1 | 0 | $870,000 | $870,000 |
| Glynwood 51 32 | 1 | 0 | $850,000 | $850,000 |
| Lake Cove Pointe 46/58 | 1 | 0 | $849,988 | $849,988 |
| Winter Garden Shores Add 02 | 1 | 0 | $849,900 | $849,900 |
| 1 | 0 | $849,000 | $849,000 | |
| Stoneybrook West Un 06 | 1 | 0 | $829,900 | $829,900 |
| Roper Reserve | 1 | 0 | $775,000 | $775,000 |
| Bradford Creek | 1 | 1 | $759,900 | $759,900 |
| 1 | 0 | $730,000 | $730,000 | |
| Hickory Hammock Ph 2A | 1 | 0 | $699,995 | $699,995 |
| Del Webb Oasis Phase 2 | 1 | 0 | $699,000 | $699,000 |
| 1 | 0 | $669,900 | $669,900 | |
| Black Lake Preserve | 1 | 0 | $640,000 | $640,000 |
| 1 | 0 | $569,000 | $569,000 | |
| Waterleigh Ph 1A | 1 | 0 | $550,000 | $550,000 |
| 1 | 0 | $525,000 | $525,000 | |
| Lakeview Reserve 46/149 | 1 | 0 | $510,000 | $510,000 |
| 1 | 0 | $489,000 | $489,000 | |
| Emerald Ridge | 1 | 0 | $465,000 | $465,000 |
| Stoneybrook West 47/78 | 1 | 0 | $439,000 | $439,000 |
| 1 | 0 | $438,000 | $438,000 |
Also with gated community homes for sale: Del Webb Oasis Ph 2 (1), Hickory Hammock Phase 2B (1), Villas/Tucker Oaks (1), (1), Tucker Oaks Bldg 5 (1), Tucker Oaks Ph 8 (1), (1), (1), (1), (1), (1), (1), Southern Pines (1), (1), (1), (1), (1), (1), (1), (1), (1).
What the gate costs and what it actually does
A gate is an HOA amenity, so it shows up in dues: an unmanned keypad or transponder gate adds little; a 24-hour manned gate is a six-figure annual staffing line shared by the homeowners, and the roads behind it are usually private, which means the association, not the county, pays to repave them. Ask for the current HOA budget and reserve study, whether the roads are private, and whether a gate or road assessment is pending. The MLS field records the gate, not its staffing, so confirm which kind it is before you value it. Our true cost of ownership calculator puts HOA dues, taxes and insurance into one monthly number.
Questions to ask about any gated-community listing
Is the gate manned, and during what hours? Are the roads private, and what do the reserves look like for repaving? What are the HOA dues today and what did they run three years ago? Is there a CDD or a special assessment on the books? What are the guest-access and delivery rules? A local agent who works the community will know which gates are staffed and which associations are underfunded.
Common questions
How many homes in gated communities are for sale in Winter Garden?
What do gated community homes cost in Winter Garden?
Which Winter Garden community has the most gated community homes for sale?
Are gated communities more expensive to own?
Keep exploring Winter Garden
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Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Winter Garden, FL whose MLS record reports a gated community. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.