by Global Lifestyle Properties

Check Availability
$4,999,500
↓ $501K (9.1%)
● House - For Sale

5138 FAIRWAY OAKS DR

WINDERMERE, FL 34786
bedrooms
4 Beds
bathrooms
5 Baths
square feet
4,330 Ft²
$29,854
Est. Monthly
$3,672
HOA / Fees

About This Property

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.
Unit Size
4,330 Ft²
Days on Market
163 days
Land Size
0.50 acres
Price per sqft
$1,155
Property Type
House
Property Taxes
$1,633
HOA Dues
$3,672
Year Built
1994

Listed By

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Last updated: 2 months ago (Stellar MLS #O6401757)

Price History

Date / Event Date Event Price
Aug 15, 2026 Price Decreased $4,999,500
↓ $501K (9.1%)
Price Decreased
Apr 23, 2026 Listed by ISLEWORTH REALTY LLC $5,500,000
Listed by ISLEWORTH REALTY LLC
Sep 24, 2025 Sold
Sold
Aug 18, 2025 In contract -
In contract
Jul 2, 2025 Relisted $2,900,000
Relisted
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Property Highlights

Garage
Air Conditioning
Fireplace
With View
Parking Details
Has Garage
Attached Garage
Has Open Parking
Parking Features: Circular Driveway, Garage Door Opener, Garage Faces Side
Garage Spaces: 3
Interior Details
Full Bathrooms: 5
Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Stone Counters, Walk-In Closet(s), Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Thermostat
Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Flooring Type: Porcelain Tile
Door Features: French Doors
Laundry Features: Inside, Laundry Room, Corridor Access
Rooms: 13
Has Fireplace
Fireplace Features: Family Room
Exterior Details
Square Footage: 4330
Square Footage Source: $0
Security Features: Gated Community, Security Gate
Architectural Style: Traditional
Year Built: 1994
Waterbody Name: LAKE BRENDA AKA HOURGLASS POND
Building Area Total: 5911
Levels: One
Building Area Units: Square Feet
Construction Materials: Block, Stucco
Patio and Porch Features: Covered, Rear Porch
Pool Features: Heated, In Ground, Deck
Pool is Private
Lot Features: Landscaped, On Golf Course, Oversized Lot
Lot Size Area: 21939
Lot Size Units: Square Feet
Lot Size Acres: 0.5
Lot Size Square Feet: 21939
Tax Lot: 108
Water Source: Public
Financial Details
Tax Annual Amount: $19,599
Lease Considered: Yes
Utilities Details
Cooling Type: Central Air, Zoned
Heating Type: Electric, Natural Gas
Sewer : Septic Tank
Location Details
HOA/Condo/Coop Fee Includes: Security, Cable TV, Internet, Maintenance Grounds, Escrow Reserves Fund, Private Road
HOA/Condo/Coop Amenities: Cable TV, Gated, Playground, Security
HOA Fee: $3,672
HOA Fee Frequency: Quarterly

Building Info

Overview

    General

  • Year Built: 1994
  • Effective Year Built: 1997
  • Building Count: 1
  • Bedroom Count: 4
  • Bathroom Count: 5
  • Full Bathrooms: 4
  • Partial Bathrooms: 5
  • Building Condition: 3
  • Building Quality: 9
  • Construction Type: 0
  • Building Style: 25
  • Exterior Walls Type: 7
  • Interior Walls Type: 14
  • Roof Shape Type: 7
  • Roof Cover Type: 4
  • Floor Count: 100
  • Living Units: 1
  • Floor Cover: 11
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 719
  • Parking Space Count: 2
  • Patio Type: 55
  • Porch Type: 35
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 21,939
  • Total Building Area: 5,560
  • Gross Building Area: 5,560
  • Building Area: 4,077
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 1
  • Heating: 4
  • Heated Square Feet: 4,077
  • Heating Fuel Type: 2

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: ISLEWORTH
  • Land Acres: 0000000504
  • Standard Land Use Code: 1001
  • County Land Use Code: 0104
  • State Land Use Code: 001
  • Legal Description 1: ISLEWORTH 16/118 LOT 108

Neighborhood

  • School District Name: Orange County School District
  • School Tax School District: 0332
  • Census Tract: 014809

Zoning

  • Zoning: P-D

Geography

  • Assessors Map Reference: 72B
  • Subdivision Tract Number: 3899
  • Parcel: 16-23-28-3899-01-080
  • Block: 1
  • Lot: 108
  • Meridian: SEC 16 TWN 23S RNG 28E
  • Municipality: UN-INCORPORATED
  • Latitude: 28.4843
  • Longitude: -81.5305

    Address

  • Full Address: 5138 Fairway Oaks Dr
  • Address - House Number: 5138
  • Address - Street Name: Fairway Oaks
  • Address - Suffix Type: Dr
  • State: FL
  • City Name: Windermere
  • Carrier Code: R010
  • 4-Digit Zip Code: 8933
  • Zip Code: 34786

Valuation

    Tax

  • Total Area: 4,689
  • Tax Year: 2023
  • Tax Amount: $1,768,694
  • Tax Rate Code Area: 75-ORG

    Appraisal Valuation

  • Standard Deviation: 0.123
  • Valuation Date: Jan 03, 2024
  • Confidence Score: 86
  • Final Value: 2,155,656
  • High Value: 2,420,981
  • Low Value: 1,890,332

    Market Valuation

  • Market Total Value: $1,859,774
  • Market Land Value: $835,000
  • Market Improvement Value: $1,024,774

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $1,143,584

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Recording Date: Sep 10, 1997
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Previous Sale Recording Date: Mar 06, 1996
  • Previous Sale Amount: $669,000
  • Previous Sale Document Type: 71
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Isleworth


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Frequently Asked Questions

When was property at 5138 Fairway Oaks Drive built and last sold?
The property at 5138 Fairway Oaks Drive was built in 1994 and last sold on Jan 1, 1970 for $860,000.
How much is this home worth?
The estimated value of the home located at 5138 Fairway Oaks Drive is $5,007,979.
What are some comparable homes to 5138 Fairway Oaks Drive?
There are currently no comparable homes to 5138 Fairway Oaks Drive.