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ActivePrice improved $500,500137 days on market
$4,999,500$5,500,000

5138 FAIRWAY OAKS DRWINDERMERE, FL 34786ISLEWORTH · Single Family Residence

4Beds
5Baths
4,330Sq ft
0.5 acLot
3-carGarage
1994Built
YesPool

About this home

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 conversati…

Description as provided by the listing brokerage.

Highlights

  • Heated saltwater pool
  • 3-car garage
  • Lighting
  • Rain Gutters
  • Built-in Features
  • Ceiling Fans(s)
  • Crown Molding
  • Eat-in Kitchen
  • Kitchen/Family Room Combo

Open houses

No open houses scheduled.

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The details

StatusActive
MLS #MFRO6401757
Property typeSingle Family Residence
Year built1994
Lot size0.5 ac
Living area4,330 sq ft
Price per sq ft$1155
HOA$3,672 / quarterly
CDDNo
Taxes$19,599 (2025)
Garage3-car
StoriesOne
Days on market137
CountyOrange
Flood zoneX (verify)
FurnishedFurnished
ListedApr 22, 2026

Features & property details

Interior

Full baths5
Half baths0
Rooms13
FlooringTile
AppliancesBar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Interior featuresBuilt-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
LaundryCorridor Access, Inside, Laundry Room
FireplaceYes
Fireplace featuresFamily Room
CoolingCentral Air, Zoned
HeatingElectric, Natural Gas
In-law suite0

Exterior & lot

Exterior featuresLighting, Rain Gutters
Patio & porchCovered, Rear Porch
FencingOther
ViewGolf Course, Water
Lot featuresLandscaped, On Golf Course, Oversized Lot
FacesNortheast
Road surfacePaved

Construction

StyleTraditional
ConstructionBlock, Stucco
FoundationSlab
RoofTile
Living area sourcePublic Records
Building area (sq ft)5,911

Parking

GarageYes
Attached garageYes
CarportNo
Parking featuresCircular Driveway, Garage Door Opener, Garage Faces Side

Pool & water

PoolDeck, Heated, In Ground
SpaYes
Spa featuresHeated, In Ground
Water bodyLAKE BRENDA AKA HOURGLASS POND
Water viewLake,Pond
Waterfront feet0
Dock0

Community & HOA

AssociationDan O’Connell
HOA fee$3,672
HOA frequencyQuarterly
Fee includesGuard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Private Road, Security
AmenitiesCable TV, Gated, Playground, Security
Fee requirementRequired
Approval required1
Total monthly fees$1,224
Total annual fees$14,688
Community featuresBuyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Playground, Street Lights
55+ communityNo
PetsBreed Restrictions
Pet restrictionsPer Orange County breed restrictions, number limits and leash laws.
Minimum lease8-12 Months
Lease restrictions0
Lease notesPer Isleworth Community Association (ICA)

Utilities & efficiency

UtilitiesCable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected
SewerSeptic Tank
Water sourcePublic

Financial & terms

CDD0
Tax year2,025
Homestead0
Listing termsCash, Conventional
OwnershipFee Simple
Special conditionsNone
ZoningP-D
OccupantVacant
MLS area34786 - Windermere

Where it sits

Approximate location shown. Exact address available on request per listing brokerage.

Schools

ElementaryWindermere ElemOrange County
MiddleChain of Lakes MiddleOrange County
HighOlympia HighOrange County

School assignments change; verify with the district before relying on them.

Where you'd be
ISLEWORTH, Florida

WINDERMERE · Orange County

MLS# MFRO6401757Listing courtesy of ISLEWORTH REALTY LLCLast updated Sep 16, 2026, 12:50 PM
$4,999,5005138 FAIRWAY OAKS DR · WINDERMERE
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