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Details for 13858 Caywood Pond Drive, WINDERMERE, FL 34786

Single Family

Price: $959,900.00
Price sqft: $226.07 / sqft
Previous Price: $999,000
Last Price Change: 03/21/26
Days On Market: 26
Bedrooms: 5
Baths: 4
Garage / Parking Spaces: 3
Bldg sqft: 4246
Acreage: 0.52 acres
Pool: Yes
Community Pool: Yes
Waterfront: Yes
Wateraccess: Yes
Waterfront Type: Lake Front
Year Built: 2004

MLS#: O6382987

County: ORANGE
City: WINDERMERE
Zipcode: 34786
Subdivision: Summerport Ph 1
Elementary School: Keene Crossing
Middle School: Bridgewater
High School: Windermere
Provided by: SPRING REALTY ONE LLC
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JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly p

Listing Details and 90 Additional Pictures

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Single Family

Price: $874,900.00
Price sqft: $240.95 / sqft
Days On Market: 1
Bedrooms: 4
Baths: 3
Garage / Parking Spaces: 2
Bldg sqft: 3631
Acreage: 0.55 acres
Pool: Yes
Spa/HotTub: Yes
Waterfront: Yes
Wateraccess: Yes
Waterfront Type: Lake Front
Year Built: 2006

MLS#: O6392262

County: ORANGE
City: WINDERMERE
Zipcode: 34786
Subdivision: Summerport
Elementary School: Keene Crossing
Middle School: Bridgewater
High School: Windermere
Provided by: RE/MAX PRIME PROPERTIES
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Super Rare Opportunity! Tucked away in one of Windermeres most desirable areas is the beautiful home on over 1 half acre homesite on a corner lot with no rear neighbors and a gorgeous lake view. Don't

4415 Blue Major Drive

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Details for 4415 Blue Major Drive, WINDERMERE, FL 34786

Single Family

Price: $815,000.00
Price sqft: $253.82 / sqft
Days On Market: 131
Bedrooms: 5
Baths: 3
Garage / Parking Spaces: 2
Bldg sqft: 3211
Acreage: 0.15 acres
Pool: No
Waterfront: No
Year Built: 2006

MLS#: O6359496

County: ORANGE
City: WINDERMERE
Zipcode: 34786
Subdivision: Summerport Ph 05
Provided by: M2M REALTY
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This beautiful MOVE IN READY two story home is located in the highly desired community of Summerport in Windermere! The Wow factor begins the moment the front door opens to a towering cathedral ceilin

13609 Ancilla Boulevard

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Details for 13609 Ancilla Boulevard, WINDERMERE, FL 34786

Single Family

Price: $789,000.00
Price sqft: $234.82 / sqft
Previous Price: $799,000
Last Price Change: 03/17/26
Days On Market: 37
Bedrooms: 4
Baths: 4
Garage / Parking Spaces: 3
Bldg sqft: 3360
Acreage: 0.24 acres
Pool: No
Waterfront: No
Year Built: 2005

MLS#: O6381542

County: ORANGE
City: WINDERMERE
Zipcode: 34786
Subdivision: Summerport Ph 03
Elementary School: Keene Crossing
Middle School: Bridgewater
High School: Windermere
Provided by: WRA BUSINESS & REAL ESTATE
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Welcome to this stunning and spacious single family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated livin

5018 River Gem Avenue

Listing Details and 45 Additional Pictures

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Details for 5018 River Gem Avenue, WINDERMERE, FL 34786

Single Family

Price: $785,000.00
Price sqft: $232.11 / sqft
Days On Market: 53
Bedrooms: 3
Baths: 3
Garage / Parking Spaces: 2
Bldg sqft: 3382
Acreage: 0.21 acres
Pool: Yes
Spa/HotTub: Yes
Waterfront: No
Year Built: 2005

MLS#: TB8469061

County: ORANGE
City: WINDERMERE
Zipcode: 34786
Subdivision: Summerport Ph 03
Elementary School: Keene Crossing
Middle School: Bridgewater
High School: Windermere
Provided by: KELLER WILLIAMS SOUTH TAMPA
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Welcome to 5018 River Gem Avenue, an exceptional one story pool estate with serene pond views in the prestigious Summerport community of Windermere, perfectly positioned for luxury living, convenience