Property Search/WINDERMERE/ISLEWORTH

Showing 0 of 51 photos — the full gallery is being added and will appear here shortly.

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.

Can't make it? Request a private showing.

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

Open in Maps

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

Homes in WINDERMERE

More like this

WaterfrontPool6-car garage

Listing courtesy of THE SIMON SIMAAN GROUP · MLS# MFRO6446042

Listing courtesy of SOUTHERN REALTY GROUP LLC · MLS# MFRO6445244

Stellar MLSMLS# MFRO6401757Listing courtesy of ISLEWORTH REALTY LLCLast updated Sep 16, 2026, 12:50 PM

$4,999,5005138 FAIRWAY OAKS DR · WINDERMERE

Tour Ask