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13858 CAYWOOD POND DRIVE
WINDERMERE, FL, 34786
$963,000
5 Beds
4 Baths
3,070 SqFt
0.52 Acres
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MLS #O6382987 image #0
Under contract-accepting backup offers. 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 positioned between downtown Windermere and Winter Garden Village, this exceptional property is nestled within the highly desirable Summerport community and features pristine waterfront views. This is more than a home-it’s a lifestyle.
From the moment you arrive, the home’s curb appeal impresses with a beautiful stone façade, charming arbor detail, spacious covered front porch, and a 3-car split garage. Inside, you are welcomed by a dramatic 20-foot ceiling in the formal living room, highlighted by elegant arched openings, a sweeping staircase, and a curved balcony overlooking the space below. Fresh updates throughout create a bright, modern feel, making this home truly move-in ready. Major improvements include a recently updated roof in last 6 years, brand-new AC system, and new water heater, new pool pump, new spa gas heater — offering comfort and peace of mind for years to come.
Step outside to your private screened-in pool oasis. Cool off in the sparkling pool while enjoying serene lake views, mature landscaping, and added privacy from lush greenery — the perfect setting for relaxing or entertaining.
Residents of Summerport enjoy resort-style amenities including a community pool, fitness center, basketball and tennis courts — all just minutes from shopping, dining, and entertainment at Winter Garden Village, and zoned for top-rated Windermere schools.
Experience luxury lakefront living with privacy, elegance, and timeless charm — all in one of Central Florida’s most sought-after communities. Information deemed reliable but not guaranteed.

Property Details

Price:
$963,000
MLS #:
O6382987
Status:
Pending
Beds:
5
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
SUMMERPORT PH 1
Neighborhood:
34786windermere
Listed Date:
Feb 24, 2026
Finished Sq Ft:
3,070
Total Sq Ft:
4,246
Lot Size:
22,621 sqft / 0.52 acres (approx)
Year Built:
2004
WaterfrontLakefrontPoolCommunity Club House34786 – Windermere34786windermereSummerport Ph 1Keene Crossing ElementaryBridgewater MiddleWindermere High SchoolCaywood PondWaterBuyer To Verify With Hoa1-2 YearsPets Allowed

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Schools

Elementary School:
Keene Crossing Elementary
Middle School:
Bridgewater Middle
High School:
Windermere High School

Interior

Appliances
Dishwasher, Microwave, Range, Refrigerator
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Engineered Hardwood, Tile
Heating
Central
Interior Features
High Ceilings, PrimaryBedroom Upstairs, Thermostat, Window Treatments
Laundry Features
Inside
Levels
Two

Exterior

Attached Garage YN
1
Community Features
Fishing, Clubhouse, Fitness Center, Playground, Pool, Sidewalks
Construction Materials
Stucco
Covered Spaces
3
Direction Faces
Northeast
Exterior Features
Irrigation System, Lighting, Private Mailbox, Sidewalk, Sliding Doors
Garage Spaces
3
Roof
Shingle
View
Water
Waterfront Features
Lake Front

Financial

HOA Fee
$391
HOA Fee Frequency
Quarterly
HOA Name
Summerport HOA
HOA Phone
407-656-6501
Tax Year
2025
Taxes
$12,050

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Apr 23, 2026
289
Single Family Listed
96
Avg DOM
458
Avg $ / SqFt
$2,232,330
Avg List Price

Property Summary

    Located in the SUMMERPORT PH 1 subdivision, 13858 CAYWOOD POND DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $963,000 and features 5 beds, 4 baths, and has approximately 3,070 square feet of living space, and was originally constructed in 2004. The current price per square foot is $314. The average price per square foot for Single Family listings in WINDERMERE is $458. The average listing price for Single Family in WINDERMERE is $2,232,330. To schedule a showing of MLS#o6382987 at 13858 CAYWOOD POND DRIVE in WINDERMERE, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

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13858 CAYWOOD POND DRIVE
WINDERMERE, FL