5138 FAIRWAY OAKS DR, Windermere, FL, 34786 | $5,500,000

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.

Features

  • Amenities: Cable TV, Gated, Playground, Security
  • Rooms: 13
  • Bedrooms: 4
  • Baths: 5 full
  • Laundry: Corridor Access, Inside, Laundry Room
  • Style: Traditional
  • Year Built: 1994
  • Garage: 3-car Circular Driveway, Garage Door Opener, Garage Faces Side
  • Heating: Electric, Natural Gas
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 4,330
  • Acreage: 0.5
  • Est. Taxes: $19,599
  • HOA Fee: $3,672 Quarterly
  • Lot Desc: Landscaped, On Golf Course, Oversized Lot
  • View: Golf Course, Water
  • Elem. School: Windermere Elem
  • Middle School: Chain of Lakes Middle
  • High School: Olympia High
  • Pool: Deck, Heated, In Ground
  • Pet Policy: Breed Restrictions
  • Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • MLS#: O6401757
  • Days on Market: 10 days
  • Website: https://www.raveis.com
    /eprop/O6401757/5138fairwayoaksdr_windermere_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 5/12/2026 8:47:09 AM)
Listing courtesy of ISLEWORTH REALTY LLC   Phone: 407-909-9000

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

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5138 FAIRWAY OAKS DR, Windermere, FL, 34786

$5,500,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $4,400,000 $4,400,000 $4,400,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.875% 6.125% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.300% 6.235% 6.164%
Monthly Tax Payment $1,633 $1,633 $1,633
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $26,028 $26,735 $37,130
Total Monthly Payment $27,786 $28,493 $38,888

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.