Search Gated Communities in Windermere

Windermere is known for its established gated and guard gated communities, offering a range of homes from golf course properties to lakefront estates along the Butler Chain of Lakes. Some Windermere neighborhoods feature 24 hour staffed security entrances. Others offer resident only gate access through private entry systems. Below, explore Windermere’s guard gated communities and private gated neighborhoods separately to compare access levels, property types, and current homes for sale.

Windermere Guard-Gated Communities

Windermere’s guard-gated communities include staffed entrances that monitor visitor access. Many are positioned around golf courses, waterfront settings, or estate-sized properties. Review the guard-gated communities below to explore homes for sale and neighborhood details.


Windermere Gated Communities

Windermere’s gated communities feature private entrances with resident access systems. These neighborhoods range from established residential enclaves to newer communities, offering controlled entry. Explore the gated communities below to compare locations, home styles, and current availability.


Windermere Gated Communities Homes For Sale

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New
8156 Boat Hook Loop 623, WINDERMERE

$327,000

8156 Boat Hook Loop 623, WINDERMERE

3 Beds 2 Baths 1,455 SqFt Residential MLS® # O6439822
New
8142 Tibet Butler Drive, WINDERMERE

$2,685,000

8142 Tibet Butler Drive, WINDERMERE

5 Beds 7 Baths 5,747 SqFt Residential MLS® # O6439814
New
5373 Isleworth Country Club Drive, WINDERMERE

$7,200,000

5373 Isleworth Country Club Drive, WINDERMERE

5 Beds 6 Baths 5,993 SqFt Residential MLS® # O6439156
New
6243 Andreozzi Lane, WINDERMERE

$720,000

6243 Andreozzi Lane, WINDERMERE

4 Beds 2 Baths 2,516 SqFt Residential MLS® # O6439730
New
12417 Cruxbury Drive, WINDERMERE

$360,000

12417 Cruxbury Drive, WINDERMERE

2 Beds 3 Baths 1,311 SqFt Residential MLS® # O6439656
New
5050 Isleworth Country Club Drive, WINDERMERE

$3,189,000

5050 Isleworth Country Club Drive, WINDERMERE

4 Beds 5 Baths 3,365 SqFt Residential MLS® # O6438618
4415 Blue Major Drive, WINDERMERE

$779,900

↓ $25,100

4415 Blue Major Drive, WINDERMERE

5 Beds 3 Baths 3,211 SqFt Residential MLS® # O6359496
5379 Isleworth Country Club Drive, WINDERMERE

$3,400,000

5379 Isleworth Country Club Drive, WINDERMERE

4 Beds 4 Baths 3,872 SqFt Residential MLS® # O6438449
14077 Ancilla Boulevard, WINDERMERE

$399,000

14077 Ancilla Boulevard, WINDERMERE

3 Beds 3 Baths 1,651 SqFt Residential MLS® # O6437694
12264 Montalcino Circle, WINDERMERE

$5,390,000

12264 Montalcino Circle, WINDERMERE

4 Beds 7 Baths 7,872 SqFt Residential MLS® # O6404587
13048 Garridan Avenue, WINDERMERE

$445,000

13048 Garridan Avenue, WINDERMERE

3 Beds 3 Baths 1,748 SqFt Residential MLS® # O6437967
13239 Jervey Street, WINDERMERE

$710,999

13239 Jervey Street, WINDERMERE

4 Beds 4 Baths 2,745 SqFt Residential MLS® # O6436893
13844 Amelia Pond Drive, WINDERMERE

$600,000

13844 Amelia Pond Drive, WINDERMERE

4 Beds 3 Baths 2,670 SqFt Residential MLS® # O6401590
12989 Westside Village Loop, WINDERMERE

$1,159,000

↓ $28,000

12989 Westside Village Loop, WINDERMERE

4 Beds 4 Baths 2,665 SqFt Residential MLS® # O6437718
Open House
4844 Flint Road, WINDERMERE

$529,000

4844 Flint Road, WINDERMERE

3 Beds 2 Baths 2,085 SqFt Residential
Sun, Sep 13th, 2026 @ 1pm - 4pm
MLS® # O6436938