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.
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
See this Listing
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
- Address13858 CAYWOOD POND DRIVE WINDERMERE FL
- SubdivisionSUMMERPORT PH 1
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLARIA
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G5
- BUTLER BAY
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DIAMONDHEAD
- DOWN POINT SUB
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT BERKSHIRE PARK
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTANCIA/WINDERMERE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS OF ISLEWORTH
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLEWORTH
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 9
- KEENES POINTE UT 06 50 95
- KELSO ON LAKE BUTLER
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUTLER PARK PT REP
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE DOWN ESTATES
- LAKE DOWN RESERVE
- LAKE DOWN SHORES REP
- LAKE REAMS TOWNHOMES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE LAKE REAMS
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 03 P & Q
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 3
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE A CONDO
- LAKESIDE/LKS/WINDERMERE PH 3
- LEGADO
- MARINA BAY ESTATES
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE 2 AT LAKESIDE VILAGE
- OASIS COVE AT LAKE SIDE
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PH 03 51 01
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROYAL ESTATE
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS PH 02
- SILVER WOODS PH 03
- SILVER WOODS PH 04
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1A
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST POINT COMMONS
- WESTOVER CLUB PH 01 44/139
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 02
- WILLOWS AT LAKE RHEA PH 03
- WINDEMERE SOUND PH 2
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE DOWNS PH 03
- WINDERMERE ISLE
- WINDERMERE ISLE-PH 2
- WINDERMERE LANDINGS
- WINDERMERE LANDINGS PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE POINTE
- WINDERMERE REP
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PHASE 5A 80/102 LOT 39
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
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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Courtesy of SPRING REALTY ONE LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 13858 CAYWOOD POND DRIVE
WINDERMERE, FL





