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Windermere › Windermere Gated Homes

Windermere Gated Homes

If the privacy and security of a gated neighborhood is important to you - Windermere offers a variety of housing options set behind a gate. Below is a list of residential home listings that have been listed as either being located in a gated neighborhood or having a private gate.

Windermere Gated Homes for Sale

9508 Windy Ridge Road, Windermere image
9508 Windy Ridge Road, Windermere $24,995,000 ▼

Perfectly positioned on 18 acres of lakefront property with meticulously manicured grounds, this walled and gated compound includes apprx 614 feet of pristine lake fronta...

  • 7 Beds
  • 14.5 Baths
  • Acreage & Unrec SubDv.
  • 34786 Zip Code
9306 Blanche Cove Drive Drive, Windermere image
9306 Blanche Cove Drive Drive, Windermere $17,500,000

Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured man...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11301 Bridge House Road, Windermere image
11301 Bridge House Road, Windermere $11,995,000

Stunning modern masterpiece situated in Windermere's Reserve on Lake Butler Sound's most coveted waterfront lot. Known as "Overjoy" for its location on the sparkling wate...

  • 5 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
11205 Bridge House Road, Windermere image
11205 Bridge House Road, Windermere $7,900,000

A home designed for entertaining and intimate gatherings focused on comfort, convenience, and functionality. Welcome to the guarded gated community of Reserve at Lake But...

  • 6 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound 45/120 SubDv.
  • 34786 Zip Code
5139 Isleworth Country Club Dr, Windermere image
5139 Isleworth Country Club Dr, Windermere $7,500,000

With a fabulous location along the front nine of Isleworth’s renowned championship golf course overlooking Hole 3, this expansive estate showcases just under 14,000 squar...

  • 7 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9736 Chestnut Ridge Drive, Windermere image
9736 Chestnut Ridge Drive, Windermere $7,388,000

Pre-Construction. To be built. Featuring an exceptional setting along the shores of beautiful Lake Bessie with gorgeous sunset views, this five-bedroom estate will be bui...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9832 Laurel Valley Drive, Windermere image
9832 Laurel Valley Drive, Windermere $7,250,000 ▼

Stunning water views and **captivating sunsets** will take your breath away at this exquisite lakefront Estate. Perfectly situated on the shores of Lake Butler and the 1...

  • 6 Beds
  • 7.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9838 Laurel Valley Drive, Windermere image
9838 Laurel Valley Drive, Windermere $7,000,000

Majestic Lake Butler lakefront, Sunset views, Disney fireworks and the 15th hole of Isleworth's renowned championship golf course. As far as location goes, this home has ...

  • 5 Beds
  • 6.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
9520 Windy Ridge Road, Windermere image
9520 Windy Ridge Road, Windermere $6,995,000 ▼

Exceptional Windermere "Chain of Lakes" opportunity to purchase a "6-acre" parcel of land encompassed by a walled double row of mature live oak trees perimeter and gated ...

  • Acreage & Unrec SubDv.
  • 34786 Zip Code
9139 Tibet Pointe Circle, Windermere image
9139 Tibet Pointe Circle, Windermere $6,500,000

Windermere Lakefront on Butler Chain of Lakes in guard-gated Keene’s Pointe Neighborhood. Entertainer’s paradise featuring over 10,000 square feet of Mediterranean luxury...

  • 6 Beds
  • 6.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
9718 Green Island Cove, Windermere image
9718 Green Island Cove, Windermere $5,999,999

Beautiful lakefront views of Lake Louise set along the renowned Butler Chain of Lakes provide the backdrop for the stunning, modern, newer golf villa. This open concept f...

  • 4 Beds
  • 4.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11049 Bridge House Road, Windermere image
11049 Bridge House Road, Windermere $5,995,000 ▼

Exquisite Mediterranean masterpiece, located in the 24-hour guard-gated community of Lake Butler Sound. This stunning residence features over 10,000 square feet of luxury...

  • 5 Beds
  • 5.5 Baths
  • Reserve At Lake Butler Sound 45/120 SubDv.
  • 34786 Zip Code
6474 Deacon Circle, Windermere image
6474 Deacon Circle, Windermere $4,950,000 ▼

New Price. Step into this updated waterfront estate situated along the shores of the famed Butler Chain of Lakes. The airy Mediterranean-style two-story is an ideal lak...

  • 6 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
6117 Louise Cove Drive, Windermere image
6117 Louise Cove Drive, Windermere $4,200,000

Stunning Lake Louise views abound from this perfectly-sized Isleworth lakefront residence, perched above a protected cove on the famed Butler Chain of Lakes. Just unveile...

  • 4 Beds
  • 4.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11006 Bridge House Road, Windermere image
11006 Bridge House Road, Windermere $3,500,000

Welcome home to your magnificent custom estate poised on an acre lot on one of the most prominent streets in Central Florida. Nicknamed Moon Shadow, by the award-winning ...

  • 5 Beds
  • 5.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
6839 Valhalla Way, Windermere image
6839 Valhalla Way, Windermere $3,199,000 ▼

Keene's Pointe, highly desired gated/24-hour attended community featuring The Golden Bear Club, a private/member's only club with 18-hole golf course designed by Jack Nic...

  • 5 Beds
  • 5.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
6024 Greatwater Drive, Windermere image
6024 Greatwater Drive, Windermere $2,900,000

Spectacular and captivating custom-built courtyard-style home on the 17th hole of the Golden Bear Golf Course in exclusive guard-gated Keene’s Pointe. Style, elegance, an...

  • 5 Beds
  • 5.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
6234 Greatwater Drive, Windermere image
6234 Greatwater Drive, Windermere $2,799,000 ▼

Fabulous casually elegant French country estate in Keene's Pointe. Situated on the 18th fairway of The Golden Bear Club. This six bedroom, five bath home has unmatched cu...

  • 6 Beds
  • 5 Baths
  • Keenes Pointe Unit 2 SubDv.
  • 34786 Zip Code
1238 Lake Whitney Drive, Windermere image
1238 Lake Whitney Drive, Windermere $2,475,000 ▼

$25K PRICE REDUCTION - VERY MOTIVATED SELLERS!! Welcome to the exquisite and elegant Reserve At Belmere. A true luxury Tuscan style luxury home with spectacular views of ...

  • 4 Beds
  • 5.5 Baths
  • Reserve At Belmere Ph 02 48 144 SubDv.
  • 34786 Zip Code
11155 Coniston Way, Windermere image
11155 Coniston Way, Windermere $2,475,000 ▼

Lake Butler Sound, 24 hour gated/attended community - From the moment you enter through the stunning 12 ft arched glass and iron doors you will be impressed with this cus...

  • 5 Beds
  • 5.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
3426 Cocard Court, Windermere image
3426 Cocard Court, Windermere $2,399,000 ▼

One or more photo(s) has been virtually staged. Luxurious custom built estate in the beautifully gated Chaine du Lac community, built by Tom Coudriet, and featured on CNB...

  • 4 Beds
  • 4.5 Baths
  • Chaine Du Lac SubDv.
  • 34786 Zip Code
11423 Waterstone Loop, Windermere image
11423 Waterstone Loop, Windermere $2,300,000 ▼

BEAUTIFUL CUSTOM HOME , WATERSTONE SUBDIVISION WITH SECURITY GUARD , AMAZING FLOOR PLAN. an amazing oversized kitchen with island, huge laundry downstairs , top of t...

  • 4 Beds
  • 4.5 Baths
  • Waterstone SubDv.
  • 34786 Zip Code
12012 Waterstone Loop Drive, Windermere image
12012 Waterstone Loop Drive, Windermere $2,199,000 ▼

This beautiful David Weekley Custom Classic home is a MUST-SEE! You will fall in love when you see this beautiful landscape in the front yard. As you walk into the foyer,...

  • 5 Beds
  • 5.5 Baths
  • Waterstone SubDv.
  • 34786 Zip Code
8254 Tibet Butler Drive, Windermere image
8254 Tibet Butler Drive, Windermere $1,975,000

Captivating custom home elegance with transitional updates within the highly sought-after and 24-hour guard gated Keene’s Pointe community. The grand Porte Cochere entran...

  • 4 Beds
  • 5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
2229 Butler Bay Drive N, Windermere image
2229 Butler Bay Drive N, Windermere $1,899,000

Welcome Home to this beautiful 5/4 lakefront home situated on private spring fed Lake Crescent. This home features a triple split floor plan for added privacy, and an o...

  • 5 Beds
  • 4 Baths
  • Butler Bay SubDv.
  • 34786 Zip Code
2241 Lake Crescent Court, Windermere image
2241 Lake Crescent Court, Windermere $1,850,000

Schedule your personal tour for this captivating stunning Lakefront Home! Enjoy a gorgeous morning Sunrise or Evening Disney Fireworks with Expansive Panoramic Lakefront ...

  • 4 Beds
  • 3.5 Baths
  • Butler Bay SubDv.
  • 34786 Zip Code
11936 Provincial Way, Windermere image
11936 Provincial Way, Windermere $1,840,000 ▼

Nestled on the shores of Lake Whitney, this **LAKEFRONT** property is immaculately presented and ideally situated on a quiet peninsula within the guard gated community of...

  • 4 Beds
  • 4 Baths
  • Reserve At Belmere Ph 4 SubDv.
  • 34786 Zip Code
11948 Provincial Way, Windermere image
11948 Provincial Way, Windermere $1,750,000 ▼

HUGE PRICE REDUCED TO SELL!!!Exquisite Arthur Rutenberg customized Calais model home is sought after in Reserve at Belmere. This lakefront, 4bed/5bath/den/bonus room hous...

  • 4 Beds
  • 5 Baths
  • Reserve At Belmere Ph4 SubDv.
  • 34786 Zip Code
12715 Jacob Grace Court, Windermere image
12715 Jacob Grace Court, Windermere $1,499,000 ▼

One or more photo(s) has been virtually staged. ** TROPICAL OASIS. STUNNING CUSTOM BUILT ESTATE POOL HOME in the highly sought after TILDENS GROVE, Windermere’s exclusiv...

  • 7 Beds
  • 4.5 Baths
  • Tildens Grove Ph 01 47/65 SubDv.
  • 34786 Zip Code
11402 Camden Loop Way, Windermere image
11402 Camden Loop Way, Windermere $1,400,000 ▼

One or more photo(s) has been virtually staged. If you are looking for a turn-key home that has been renovated top to bottom in Windermere, then this is your home. From ...

  • 5 Beds
  • 4.5 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
5933 Oxford Moor Boulevard, Windermere image
5933 Oxford Moor Boulevard, Windermere $1,359,000

One or more photo(s) has been virtually staged. Welcome to Luxury Living in Windermere's gated Oxford Moor neighborhood! Nestled among pristine freshwater lakes and a sho...

  • 5 Beds
  • 4 Baths
  • Oxford Moor SubDv.
  • 34786 Zip Code
5915 Caymus Loop, Windermere image
5915 Caymus Loop, Windermere $1,349,000

KEENE’S POINTE GOLF COURSE HOME - Enjoy country club living at its finest with this home on Caymus Loop privately situated between the 14th and 15th holes of The Golden B...

  • 5 Beds
  • 4 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
9119 Balmoral Mews Sq, Windermere image
9119 Balmoral Mews Sq, Windermere $1,225,000 ▼

MARCH MADNESS MOVING SALE - PRICE IMPROVEMENT for a home in Balmoral and your new highly sought after Windermere address! An exclusive gated community containing only 32 ...

  • 4 Beds
  • 4 Baths
  • Balmoral SubDv.
  • 34786 Zip Code
11237 Camden Park Drive, Windermere image
11237 Camden Park Drive, Windermere $1,200,000

Welcome to your dream home located in the desirable Keene's Pointe community! This updated and upgraded 4 bedroom, 4 bath pool home boasts 3,492 square feet of luxurious ...

  • 4 Beds
  • 4 Baths
  • Keenes Pointe Unit 7 SubDv.
  • 34786 Zip Code
1907 Westover Reserve Boulevard, Windermere image
1907 Westover Reserve Boulevard, Windermere $1,195,000 ▼

Tucked inside Windermere is this incredible estate that underwent a complete renovation in 2020 and is now ready for new homeowners. Step inside to soaring ceilings, a ne...

  • 4 Beds
  • 3 Baths
  • Westover Reserve Ph 02 SubDv.
  • 34786 Zip Code
8429 Woburn Court, Windermere image
8429 Woburn Court, Windermere $935,000

Welcome to Keene’s Pointe, a Jack Nicklaus Golden Bear Golf community, with two 24-hour manned gate entries, in Windermere, conveniently located to Disney, Universal, Win...

  • 4 Beds
  • 3 Baths
  • Keenes Pointe Unit 1 SubDv.
  • 34786 Zip Code
1439 Whitney Isles Drive, Windermere image
1439 Whitney Isles Drive, Windermere $782,000

Location, Location, Location.... where this beautiful home is perfectly situated in the Windermere gated community of Whitney Isles of Belmere! The welcoming 2 story home...

  • 5 Beds
  • 4 Baths
  • Whitney Isles/Belmere Ph 02 SubDv.
  • 34786 Zip Code
11410 Rapallo Lane, Windermere image
11410 Rapallo Lane, Windermere $778,900 ▼

Welcome Home. This beautiful home built by Park Square will take your breath away upon entering. From its turret-style architectural exterior design to the beautiful wi...

  • 6 Beds
  • 5.5 Baths
  • Belmere Village G2 48 65 SubDv.
  • 34786 Zip Code
1348 Lake Olivia, Windermere image
1348 Lake Olivia, Windermere $699,000

Welcome to the gated community of Lake Olivia Reserve, your next step to luxury lakefront living. Located within the sought-after Windermere region of Southwest Orange Co...

  • Lake Olivia Reserve Rep SubDv.
  • 34786 Zip Code
11015 Belmere Isles Court, Windermere image
11015 Belmere Isles Court, Windermere $650,000

Beautiful house! Fully renovated. This three-bedroom, two-bath home is located in the guard-gated community, The Reserve at Belmere. As you enter through the double doors...

  • 3 Beds
  • 2 Baths
  • Reserve At Belmere Ph 02 48 144 SubDv.
  • 34786 Zip Code
1372 Lake Olivia, Windermere image
1372 Lake Olivia, Windermere $650,000

Welcome to the gated community of Lake Olivia Reserve, your next step to luxury lakefront living. Located within the sought-after Windermere region of Southwest Orange Co...

  • Lake Olivia Reserve Rep SubDv.
  • 34786 Zip Code
11225 Via Andiamo, Windermere image
11225 Via Andiamo, Windermere $629,000 ▼

Check out this stunner! This home has updated flooring in some rooms as well as fresh interior and exterior paint. Windows create a light filled interior with well placed...

  • 4 Beds
  • 3 Baths
  • Belmere Village G2 48 65 SubDv.
  • 34786 Zip Code
1028 Lascala Drive, Windermere image
1028 Lascala Drive, Windermere $619,000 ▼

One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has fresh interior paint and partial flooring replacement in some areas. A s...

  • 4 Beds
  • 2.5 Baths
  • Belmere Village G2 SubDv.
  • 34786 Zip Code
11564 Mizzon Drive Unit 304, Windermere image
11564 Mizzon Drive Unit 304, Windermere — 927 $369,000 ▼

This 3 bedroom Windermere Condo is situated in a beautiful residential complex that offers its residents a comfortable and spacious living experience together with luxuri...

  • 3 Beds
  • 2 Baths
  • Lakeside/Lks/Windermere Ph 9 SubDv.
  • 34786 Zip Code
11446 Jasper Kay Ter Unit 309, Windermere image
11446 Jasper Kay Ter Unit 309, Windermere — 11446/Bldg 10 $325,000 ▼

Welcome to Lakeside! This well maintained 2 bedroom/2 bath unit is located on the third floor and features updated low maintenance wood-look tile, updated bathrooms and ...

  • 2 Beds
  • 2 Baths
  • Lakeside/Lks/Windermere Condo SubDv.
  • 34786 Zip Code
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