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$4,999,500
Monthly Est:$24,884
4 Beds
- 5 Baths
5 full baths
4,330sqft
5138 Fairway Oaks Dr, Windermere, FL 34786
$4,999,500
$24,884/moEst:
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Single Family Residence
Built in 1994
$1,224/mo HOA
21,939 sqft lot
$1,155/sq.ft
Description
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.
- Houzeo last checked: 2 hours ago
- Listing updated: September 16, 2026 at 4:50 pm
- Listing Provided by: Monica Lochmandy (407) 230-6888 , Sarah Longwell | ISLEWORTH REALTY LLC (407) 909-9000
- Source: Stellar MLS-FL | MLS#: O6401757

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1994
HOA Fees
$1224/mo
Finished Area
4,330 sqft
Lot Size
21,939 sqft lot
Basement Area
- sqft
MLS Name
Stellar MLS
MLS Number
O6401757
MLS Status
Active
Days on Market
186
Cumulative Days on Market
137

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Location
HOA Management
Dan O’Connell
HOA Fees
$3,672/ Quarterly
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Internet
Security Gate
Cable TV
Security Guard
Park Playground
Maintenance
Escrow Reserves Fund
Private Road
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 5
Primary Bedroom
Level: First
Primary Bathroom
Level: First
Bedroom 2
Level: First
Bathroom 2
Level: First
Bedroom 3
Level: First
Bathroom 3
Level: First
Bedroom 4
Level: First
Bathroom 4
Level: First
Kitchen
Level: First
Family Room
Level: First
Living Room
Level: First
Dining Room
Level: First
Office
Level: First
Interior
Exterior Features
Lighting, Rain Gutters
Sewer
Septic Tank
Heating
Electric, Natural Gas
Cooling
Central Air, Zoned
Interior Features
Built 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)
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Flooring
Tile
Construction
Year Built
Year Built: 1994
Home type
Single Family Residence
Foundation Details
Slab
Architectural Style
Traditional
Construction Materials
Block, Stucco
Roof
Tile
Utilities & Energy
Parking Features
Circular Driveway, Garage Door Opener, Garage Faces Side
Security Features
Gated Community, Security Gate
Pool Features
Deck, Heated, In Ground
Association Amenities
Cable Tv, Gated, Playground, Security
Fireplace Features
Family Room
Laundry Features
Corridor Access, Inside, Laundry Room
Utilities
Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected
Water Source
Public
Other Features
Lot Features
Landscaped, On Golf Course, Oversized Lot
Community Features
Buyer Approval Required, Community Mailbox, Gated Community Guard, Golf Carts Ok, Playground, Street Lights
Patio And Porch Features
Covered, Rear Porch
Subdivision Name
Isleworth
Price History
| Date | Event | Price |
|---|---|---|
08/14/2026 Source: | Listing Removed | $4,999,500 -9.10% $1,155/sqft |
04/25/2026 Source: | Listed for Sale | $5,500,000 +89.66% $1,270/sqft |
09/24/2025 Source: | Sold | $2,900,000 +16.00% $670/sqft |
09/24/2025 Source: | Price Decreased | $2,500,000 -13.79% $577/sqft |
08/17/2025 Source: | Pending | $2,900,000 $670/sqft |
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Based on information from Stellar MLS® through Oct 28, 2026, 02:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.
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