Under contract-accepting backup offers. Located along the 2nd tee of Isleworth’s renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-bedroom home features offers a spacious and open floor plan of more than 5,900 square feet overlooking the serene golf and water vistas. .
Property Details
Price:
$3,600,000
MLS #:
O6427447
Status:
Active Under Contract
Beds:
5
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Jul 30, 2026
Finished Sq Ft:
5,972
Total Sq Ft:
8,281
Lot Size:
22,076 sqft / 0.51 acres (approx)
Year Built:
1989
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Bathrooms
5 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Carpet, Marble, Hardwood
Heating
Central, Zoned
Interior Features
Built-in Features, Primary Bedroom Main Floor, Walk-In Closet(s)
Laundry Features
Inside
Levels
Two
Exterior
Association Amenities
Cable TV, Gated, Playground
Attached Garage YN
1
Community Features
Lake, Private Boat Ramp, Water Access, Waterfront, Community Mailbox, Deed Restrictions, Gated Community – Guard, Golf, Playground
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
Northwest
Exterior Features
Irrigation System
Garage Spaces
3
Roof
Tile
Spa Features
In Ground
View
Golf Course, Water
Waterfront Features
Lake, Waterfront
Financial
HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Repairs, Private Road, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2025
Taxes
$45,808
Map
Community
- Address5237 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ALADAR ON LAKE BUTLER
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BALMORAL
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BUTLER BAY
- BUTLER BAY,WINDERMERE CLUB
- CARRINGTON
- CASA DEL LAGO
- CASA DEL LAGO REP
- CASABELLA
- CHAIN DU LAC
- CHAINE DU LAC
- DAVIS SHORES
- DOWN ACRES ESTATES
- DOWN POINT SUB
- EDEN ISLE
- EDEN ISLE BOAT RAMP
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTANCIA/WINDERMERE
- ESTATES AT LAKE CLARICE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS/ISLEWORTH UN #2
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLES WINDERMERE
- ISLEWORTH
- ISLEWORTH 5TH AMD
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINT
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 03 46/104
- 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 BUYNAK ESTATES
- LAKE CAWOOD COVE
- LAKE CRESCENT RESERVE
- LAKE DOWN CREST
- LAKE DOWN ESTATES
- LAKE DOWN POINTE 50 42
- LAKE DOWN RESERVE
- LAKE DOWN SHORES
- LAKE DOWN SHORES REP
- LAKE HANCOCK SHORES
- LAKE OLIVIA RESERVE
- LAKE ROPER POINTE
- LAKE SAWYER
- LAKE SAWYER SOUTH
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 04
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 2
- LAKE SAWYER SOUTH PH 3
- LAKE SAWYER SOUTH PH 5
- LAKES
- LAKES OF WINDERMERE PEACHTREE
- LAKES OF WINDERMERE PH 2A
- LAKES OF WINDERMERE-PEACHTREE
- LAKES WINDERMERE PH 01 49 108
- 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
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 1
- LAKESIDE AT LAKES OF WINDERMERE CONDOMINIUM
- LAKESIDE/LKS
- LAKESIDE/LKS/WINDERMERE
- LEGADO
- LEGADO 95/47 LOT 100
- LEGADO 95/47 LOT 99
- LES TERRACES
- MAGNOLIA PARK WINDERMERE
- MANORS AT BUTLER BAY PH 01
- MANORS AT BUTLER BAY PH 02
- MARINA BAY ESTATES
- MERRICK LANDING
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- OASIS COVE/LAKESIDE VILLAGE PH VII
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY AT LAKES OF WINDERMERE
- SANDY SHORES
- SAWYER SHORES SUB
- SILVER WOODS
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03
- SILVER WOODS PH 05
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 PH
- SUMMERPORT
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT PH 5
- SUMMERPORT PHASE 1
- SUMMERPORT PHASE4
- SUMMERPORT TRAIL PH 2
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE PH 02 REP
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WESTSIDE VILLAGE
- WHICKHAM PARK
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA
- WILLOWS AT LAKE RHEA PH 03
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PHASE 1C
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PH 5B
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Sep 17, 2026
238
Single Family Listed
113
Avg DOM
465
Avg $ / SqFt
$2,363,329
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 5237 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $3,600,000 and features 5 beds, 5 baths, and has approximately 5,972 square feet of living space, and was originally constructed in 1989. The current price per square foot is $603. The average price per square foot for Single Family listings in WINDERMERE is $465. The average listing price for Single Family in WINDERMERE is $2,363,329. To schedule a showing of MLS#o6427447 at 5237 ISLEWORTH COUNTRY CLUB DRIVE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of ISLEWORTH REALTY 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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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. 5237 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL