Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda – also known as Hourglass Pond – a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.
Property Details
Price:
$5,500,000
MLS #:
O6401757
Status:
Active
Beds:
4
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Apr 25, 2026
Finished Sq Ft:
4,330
Total Sq Ft:
5,911
Lot Size:
21,939 sqft / 0.50 acres (approx)
Year Built:
1994
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Bathrooms
5 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Porcelain Tile
Heating
Electric, Natural Gas
Interior Features
Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Corridor Access, Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Traditional
Association Amenities
Cable TV, Gated, Playground, Security
Attached Garage YN
1
Community Features
Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community – Guard, Golf Carts OK, Playground
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
Northeast
Exterior Features
French Doors, Lighting, Rain Gutters
Fencing
Other
Garage Spaces
3
Lot Features
Landscaped, On Golf Course, Oversized Lot
Open Parking YN
1
Parking Features
Circular Driveway, Garage Door Opener, Garage Faces Side
Patio And Porch Features
Covered, Rear Porch
Roof
Tile
Security Features
Gated Community, Security Gate
Spa Features
Heated, In Ground
View
Golf Course, Water
Financial
HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Private Road, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2025
Taxes
$19,599
Map
Community
- Address5138 FAIRWAY OAKS DR WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLA VITA ESTATES
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G4 50 58
- BELMERE VLG G2
- BUTLER BAY
- BUTLER BAY / LAKE CRESCENT RESERVE
- BUTLER RIDGE
- CARRINGTON
- CASA DEL LAGO REP
- CASA DEL LAGO-REPLAT
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DOWN ACRES ESTATES
- DOWN POINT SUB
- DOWNS COVE CAMP SITES
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT WINDERMERE LANDING
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTATES AT WINDERMERE
- FARMS
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLEWORTH
- ISLEWORTH 01 AMD
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 06 50 95
- LAKE BURDEN
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #79/32 LOT 223
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE CRESENT RESERVE
- LAKE DAVIS ESTATES
- LAKE DOWN ESTATES
- LAKE DOWN RESERVE
- LAKE HANCOCK SHORES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 3
- LAKE SAWYER SOUTH PH 5
- LAKES
- LAKES OF WINDERMERE PH 1
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE PH 3
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 3
- LAKESIDE VILLAGE TWNHMS
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 10
- LAKESIDE/LKS/WINDERMERE PH 3
- LAKESIDE/LKS/WINDERMERE PH 4
- LAKESIDE/LKS/WINDERMERE PH 9
- LEGADO
- LES TERRACES
- MARINA BAY ESTATES
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE PH
- OASIS COVE II/LAKESIDE VILLAGE UN
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- PROVIDENCE PH 2
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND 45/120
- RESERVE AT LAKE BUTLER SOUND UNIT 02
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- RESERVE/BELMERE PH 04
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SOUND
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03A
- SILVER WOODS PH 04
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT PH 02
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT PH 5
- SUMMERPORT PHASE 1
- SUMMERPORT TRAIL PH 2
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST LAKE BUTLER ESTATES
- WEST POINT COMMONS
- WESTOVER CLUB
- WESTOVER CLUB PH 02 REP
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WINDEMERE SOUND PH 2
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE DOWNS PH 03
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE LNDGS PH 02
- WINDERMERE POINTE
- WINDERMERE POINTE AT LAKE ROPER
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PH 3B
- WINDERMERE TRAILS PHASE 1C 80/15 LOT 113
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH IA
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Apr 29, 2026
290
Single Family Listed
96
Avg DOM
462
Avg $ / SqFt
$2,247,345
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 5138 FAIRWAY OAKS DR WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $5,500,000 and features 4 beds, 5 baths, and has approximately 4,330 square feet of living space, and was originally constructed in 1994. The current price per square foot is $1,270. The average price per square foot for Single Family listings in WINDERMERE is $462. The average listing price for Single Family in WINDERMERE is $2,247,345. To schedule a showing of MLS#o6401757 at 5138 FAIRWAY OAKS DR in WINDERMERE, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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 Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty 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. 5138 FAIRWAY OAKS DR
WINDERMERE, FL

