9731 CHESTNUT RIDGE DRIVE, Windermere, FL, 34786 | $3,400,000

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5, 000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

Features

  • Amenities: Cable TV, Playground, Security
  • Rooms: 10
  • Bedrooms: 4
  • Baths: 4 full
  • Laundry: Laundry Room
  • Year Built: 1986
  • Garage: 2-car Circular Driveway, Golf Cart Garage
  • Heating: Central, Electric, Natural Gas
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 4,877
  • Acreage: 0.54
  • Est. Taxes: $19,867
  • HOA Fee: $3,129 Quarterly
  • Lot Desc: Landscaped, Near Golf Course
  • View: Pool
  • Elem. School: Windermere Elem
  • Middle School: Chain of Lakes Middle
  • High School: Olympia High
  • Pool: Heated, In Ground, Lighting, Self Cleaning
  • Pet Policy: Breed Restrictions
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Trash Compactor, Washer, Water Filtration System, Water Purifier, Water Softener
  • MLS#: O6336655
  • Days on Market: 1 day
  • Website: https://www.raveis.com
    /eprop/O6336655/9731chestnutridgedrive_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 12/8/2025 4:47:08 PM)
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

Melissa.Cohn@raveis.com

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9731 CHESTNUT RIDGE DRIVE, Windermere, FL, 34786

$3,400,000

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 $2,720,000 $2,720,000 $2,720,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.000% 5.875%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.477% 6.133% 6.038%
Monthly Tax Payment $1,656 $1,656 $1,656
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $15,873 $16,308 $22,770
Total Monthly Payment $17,654 $18,089 $24,551

* 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.