$5,500,000
5138 Fairway Oaks Dr
Windermere, FL 34786
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
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 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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history10 days on market
- Status: ActiveApr 25, 2026
- Listed$5,500,000Apr 25, 2026
- Price increased$5,500,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 10
- Subdivision
- Isleworth
- County
- Orange
- Year built
- 1994
- Living area
- 4,330 sq ft
- Price/sq ft
- $1,270
- Building area
- 5,911 sq ft (Public Records)
- Lot size
- 21,939 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $19,599 (2025)
- Parcel #
- 16-23-28-3899-01-080
- Zoning
- P-D
- MLS #
- O6401757
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 5
- Flooring
- Tile
- Appliances
- Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- 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)
- Laundry
- Corridor Access, Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- Northeast
- Fireplace
- Yes
Heating & Cooling
- Heating
- Electric, Natural Gas
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Circular Driveway, Garage Door Opener, Garage Faces Side
HOA & Financial
- HOA fee
- $3,672 / Quarterly
- Monthly HOA
- $1,224/mo
- Total monthly fees
- $1,224/mo
- Total annual fees
- $14,688
- HOA name
- Dan O’Connell
- CDD
- No
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Per Isleworth Community Association (ICA)
- Approval process
- Per Isleworth Community Association (ICA)
Exterior & Construction
- Exterior features
- French Doors, Lighting, Rain Gutters
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected
Community
- Pets allowed
- Breed Restrictions
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Primary Bathroom | First | |
| Bedroom 2 | First | |
| Bathroom 2 | First | |
| Bedroom 3 | First | |
| Bathroom 3 | First | |
| Bedroom 4 | First | |
| Bathroom 4 | First | |
| Kitchen | First | |
| Family Room | First | |
| Living Room | First | |
| Dining Room | First | |
| Office | First |
Listing Details
- Listing date
- 2026-04-23
- On market date
- 2026-04-25
- Original list price
- $5,500,000
- Occupant type
- Vacant
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2026-04-25
- Tax legal description
- ISLEWORTH 16/118 LOT 108
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Apopka Vineland Road to West on Conroy Windermere to Left into Isleworth (Isleworth Country Club Drive) to Right on Fairway Oaks.
Property sale history
Public records5138 FAIRWAY OAKS DR, Windermere 34786
- Sep 2025$2,500,000
4,077 sq ft · Built 1994 · 0.5037 acres
Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 5, 2026 at 2:46 PM ET. All data is obtained from various sources and may not have been verified by 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.
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