To schedule a showing of 5138 Fairway Oaks Dr, Windermere, Florida, Call David Shippey at 863-521-4517 TODAY!
$5,500,000 | 4 beds | 5 full baths | N/A half baths | 4,330 sqft
Windermere, FL 34786
- 4Beds
- 5.00Total Baths
- 5 Full, 0 HalfBaths
- 4,330SqFt
- 1994Year Built
- 0.50Acres
- MLS# O6401757
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market1 month, 25 days
- Area34786 - Windermere
- CountyOrange
- Subdivision Isleworth
Overview
Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Clubrecognized 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 appliancesincluding a striking black range with matching hood, refrigerator, and microwaveall 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 Floridas premier shopping, dining, and entertainment destinations.
Agriculture / Farm
Association Fees / Info
Community Features: BoatFacilities, CommunityMailbox, GolfCartsOk, Playground, WaterAccess, Gated, StreetLights
Pets Allowed: BreedRestrictions
Hoa Frequency Rate: 3672
Association: Yes
Association Amenities: Gated, Playground, Security, CableTv
Hoa Fees Frequency: Quarterly
Association Fee Includes: CableTv, Internet, MaintenanceGrounds, ReserveFund, RoadMaintenance, Security
Bathroom Info
Total Baths: 5.00
Fullbaths: 5
Building Info
Roof: Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: Traditional
Pool Features: Heated, InGround
Patio: RearPorch, Covered
Pool Private: Yes
Exterior Features: FrenchPatioDoors, Lighting, RainGutters
Fees / Restrictions
Financial
Original Price: $5,500,000
Fencing: Other
Garage / Parking
Parking Features: CircularDriveway, Garage, GarageDoorOpener, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: FamilyRoom
Fireplace: Yes
Floors: PorcelainTile
Levels: One
Spa: Yes
Laundry Features: Inside, LaundryRoom
Interior Features: BuiltInFeatures, CeilingFans, CrownMolding, EatInKitchen, KitchenFamilyRoomCombo, LivingDiningRoom, StoneCounters, SolidSurfaceCounters, WalkInClosets
Appliances: BarFridge, Dryer, Dishwasher, ExhaustFan, ElectricWaterHeater, Freezer, Disposal, IceMaker, Microwave, Range, Refrigerator, RangeHood, WineRefrigerator, Washer
Spa Features: Heated, InGround
Lot Info
Direction Remarks: From Apopka Vineland Road to West on Conroy Windermere to Left into Isleworth (Isleworth Country Club Drive) to Right on Fairway Oaks.
Lot Size Units: Acres
Lot Size Acres: 0.5
Lot Sqft: 21,939
Lot Desc: Landscaped, OnGolfCourse, OversizedLot, BuyerApprovalRequired
Misc
Other
Special Conditions: None
Security Features: SecurityGate, GatedWithGuard, GatedCommunity
Other Rooms Info
Property Info
Section: 16
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 1
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 13
Sqft Info
Sqft: 4,330
Bulding Area Sqft: 5,911
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 108
Tax Legal Description: ISLEWORTH 16/118 LOT 108
Tax Block: 01
Tax Annual Amount: 19599.37
Tax Book Number: 16/118
Unit Info
Utilities / Hvac
Heating: Electric, NaturalGas
Water Source: Public
Sewer: SepticTank
Cool System: CentralAir, Zoned, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableConnected, ElectricityConnected, FiberOpticAvailable, NaturalGasConnected, WaterConnected
Waterfront / Water
View: Yes
Water Body Name: LAKE BRENDA AKA HOURGLASS POND
View: GolfCourse, Lake, Pond, Water
Directions
From Apopka Vineland Road to West on Conroy Windermere to Left into Isleworth (Isleworth Country Club Drive) to Right on Fairway Oaks.This listing courtesy of Isleworth Realty Llc
MLS# S5144942 
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MLS IDX data last updated on 06-19-2026 11:45 AM EST.
If you have any questions on 5138 Fairway Oaks Dr, Windermere, Florida, please call David Shippey at 863-521-4517.
MLS# O6401757 located at 5138 Fairway Oaks Dr, Windermere, Florida is brought to you by David Shippey REALTOR®
5138 Fairway Oaks Dr, Windermere, Florida has 4 Beds, 5 Full Bath, and 0 Half Bath.
The MLS Number for 5138 Fairway Oaks Dr, Windermere, Florida is O6401757.
The price for 5138 Fairway Oaks Dr, Windermere, Florida is $5,500,000.
The status of 5138 Fairway Oaks Dr, Windermere, Florida is Active.
The subdivision of 5138 Fairway Oaks Dr, Windermere, Florida is Isleworth.
The home located at 5138 Fairway Oaks Dr, Windermere, Florida was built in 2026.