Communities Windermere, Winter Garden & Dr. Phillips, FL
Explore Central Florida Communities
Browse the communities below to explore what makes each area unique. Whether you are seeking waterfront living, gated privacy, golf communities, or modern master-planned neighborhoods, this guide will help you navigate the options with confidence, backed by the local insight of Infinity Realty Group.
Dr. Phillips Communities
Windermere Communities
Winter Garden Communities
Compare Communities: Gated, Lake and Golf
Windermere
| Community | Gated community | Lakefront / lake access | On-site golf course | Homes | Median sale price, single-family |
|---|---|---|---|---|---|
| Bellaria | Yes: guard-gated | Yes: Lake Burden frontage | — | 64 | — |
| Berkshire Park & Enclave at Berkshire Park | Partly: Berkshire Park no, Enclave yes | — | — | — | — |
| Casa Del Lago | Yes | Yes: Lake Burden frontage | — | 88 | — |
| Casabella | Yes | Pond / water views | — | 79 | $3,097,500 |
| Chaine Du Lac | Yes | Yes: Lake Butler frontage | — | 32 | $2,400,000 |
| Glenmuir | Yes | — | — | 227 | $880,000 |
| Isleworth | Yes: guard-gated | Yes | Yes | 292 | $4,365,000 |
| Keene's Pointe | Yes: guard-gated | Yes | Yes | 887 | $1,525,000 |
| Kelso on Lake Butler | No community gate | Yes | — | 59 | $1,865,000 |
| Lake Burden South | No | Yes: some Lake Burden frontage | — | 332 (225 townhomes) | $1,385,000 |
| Lake Sawyer South | No | — | — | 554 (140 townhomes) | $682,500 |
| Lakes of Windermere | No | Yes: Lake Sawyer | — | 1,167 (382 townhomes) | $570,000 |
| Marina Bay | No | Yes: Lake Down frontage | — | 29 | — |
| Oxford Moor | Yes | — | — | 83 | — |
| Providence | No | Yes: Little Lake Sawyer access | — | 216 | $774,500 |
| Summerport | No | — | — | 999 (171 townhomes) | $595,000 |
| The Estates at Windermere | Yes | — | — | 66 | — |
| The Manors | No | Yes: Lake Crescent access | — | 94 | — |
| The Reserve at Lake Butler | Yes: guard-gated | Yes | — | 213 | $2,200,000 |
| Tildens Grove | Yes | — | — | 138 | $1,170,000 |
| Vineyards | No | — | — | 283 (192 townhomes) | $637,500 |
| Waterford Pointe | Yes: guard-gated | Yes: Lake Roberts | — | 76 | $2,075,000 |
| Waterstone | Yes: 24-hour guard gate | Yes: Lake Butler | — | 120 | $1,517,500 |
| Westover Club | Yes | — | — | 160 | $831,250 |
| Westover Reserve | Yes | — | — | 78 | — |
| Wickham Park | No | — | — | 301 (245 townhomes) | $495,000 |
| Willows at Lake Rhea | No | Nearby | — | 141 | — |
| Windermere Club | Yes | Yes: Lakes Crescent / Roberts | Former course (closed) | 148 | — |
| Windermere Downs | No | Yes: deeded Lake Down access | — | 204 | $750,000 |
| Windermere Isle | No | — | — | 116 | $1,140,000 |
| Windermere Landing & Enclave | Partly: Landing no, Enclave yes | — | — | — | — |
| Windermere Trails | No | — | — | 767 (120 townhomes) | $716,250 |
Winter Garden
| Community | Gated community | Lakefront / lake access | On-site golf course | Homes | Median sale price, single-family |
|---|---|---|---|---|---|
| Alexander Ridge | No | — | — | 196 | $546,000 |
| Avalon Cove | Ask us (being confirmed) | Yes: Hickorynut Lake frontage | — | 49 | $2,254,000 |
| Banana Bay | No | Yes: Lake Luntz frontage | — | 28 | — |
| Bronson's Landing | Yes | Lakefront homes / nearby lake | — | 123 | $825,000 |
| Carriage Pointe & Reserve at Carriage Pointe | Yes: both gated | — | — | 275 | $772,500 |
| Del Webb Oasis | Yes (55+) | — | — | 370 | $607,500 |
| Hawksmoor | No | — | — | 459 (187 townhomes) | $630,000 |
| Hickory Hammock | Yes | Yes: lake access | — | 485 (100 townhomes) | $1,118,400 |
| Highlands at Summerlake Groves | No | — | — | 355 (52 townhomes) | $739,000 |
| Independence and Signature Lakes | No | Yes | — | — | — |
| Isles of Lake Hancock | Yes | Yes: lake access | — | 71 | — |
| Johns Lake Pointe | No | Nearby | — | 312 | $740,000 |
| Johns Landing | Yes | Yes: Johns Lake access | — | 261 | $600,000 |
| Lakeview Pointe | No | — | — | 314 (70 townhomes) | $538,750 |
| Latham Park | No | — | — | 340 | $845,000 |
| Oakland Park | No | — | — | 719 | $994,950 |
| Orchard Hills | No | — | — | 644 (67 townhomes) | $595,000 |
| Orchard Park | No | — | — | 196 | $595,000 |
| Overlook at Hamlin | No | Yes: Lake Hancock | — | 381 (planned) | — |
| Stoneybrook West | Yes: 24-hour guard gate | Yes: Black Lake access | Yes | 1,393 (184 townhomes) | $622,500 |
| Storey Grove | No | — | — | 888 (333 townhomes) | $530,000 |
| Summerlake | No | — | — | 1,119 (178 townhomes) | $584,000 |
| Sunset Lakes | No | Yes: lakefront lots | — | 104 | $992,500 |
| The Enclave at Hamlin | Ask us (being confirmed) | Lake Hartley views / frontage | — | 93 | $635,000 |
| The Enclave at Ovation | Ask us (being confirmed) | — | — | — | — |
| Waterleigh | No | — | — | 2,377 (472 townhomes) | $692,000 |
| Watermark | No | — | — | 848 (119 townhomes) | $700,000 |
| Windermere Crossing | Yes | — | — | 153 | $755,000 |
| Winding Bay Preserve | No | — | — | 85 (85 townhomes) | Townhomes: $410,000 |
| Wintermere Harbor | Yes | Yes: lakefront | — | 91 | $800,000 |
| Wintermere Pointe | Yes | — | — | 201 | $559,950 |
Dr. Phillips
| Community | Gated community | Lakefront / lake access | On-site golf course | Homes | Median sale price, single-family |
|---|---|---|---|---|---|
| Bay Hill | Partly: varies by subdivision | Yes | Yes | — | — |
| Cypress Point | Yes: guard-gated | Yes | — | 129 | $1,970,000 |
| Isle of Osprey | Yes: guard-gated | Yes | Nearby | 21 | — |
| Millionaire's Row & Kilgore Road | No community gate; some estate gates | Yes | — | — | — |
| Orange Tree | Yes | Yes | Yes | 514 | — |
| Phillips Landing | Yes: guard-gated | Yes | — | 298 | $1,195,500 |
| Sand Lake Point | No | Yes | — | 430 | $675,000 |
| South Bay | No | Yes | Nearby | 170 | $1,065,000 |
| Turtle Creek | Yes: guard-gated | Yes | — | 277 | — |
| Vizcaya | Yes: guard-gated | Yes | — | — | — |
Guides: Home prices by neighborhood (2026) · Orange County property taxes for home buyers · Gated communities in Windermere, FL · Isleworth vs Keene's Pointe vs Lake Butler Sound · Windermere vs Winter Garden · Horizon West communities compared · Dr. Phillips communities compared · Homes on the Butler Chain of Lakes · Golf communities in Windermere, Winter Garden and Dr. Phillips · Townhomes and condos in Windermere and Winter Garden · All real estate guides
Schools: Zoned schools by neighborhood (2026–27): the elementary, middle and high school for each community, from the OCPS zone map.
“Gated” means a controlled entrance gate for the neighborhood, not a gate on one estate. “Partly” means gate rules differ by subdivision or enclave. A dash means it is not a main feature, or we have not confirmed it. Homes and prices come from the Florida Department of Revenue 2026 county tax roll: homes include townhomes and condos; the median price uses qualified single-family sales from July 2025 to June 2026 and is shown only with 3 or more sales. Gate rules and amenities can change, so we confirm them for every buyer. Last reviewed October 2026.