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About This Home

This 4-bedroom, 4-bathroom single family at 9731 CHESTNUT RIDGE DRIVE in Windermere, FL is listed for $3,400,000 ($697 per sqft). Built in 1986, the home offers 4,877 sqft of living space on a 0.54 acres lot.

Agent Description

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.

Key Features

  • Built in 1986
  • 0.54 acre lot
  • Private pool

Property Details

4 full
1986

Amenities

Pool

Monthly Cost Estimate

$18,184/mo

20% down · 6.5% · 30 years

Principal$2,459
Interest$14,733
Insurance$992

Estimates only. Actual payments may vary.

Location

9731 CHESTNUT RIDGE DRIVE

Windermere, FL 34786

ISLEWORTH

Features & Amenities

Interior Features

Cathedral Ceiling(s)Ceiling Fans(s)Kitchen/Family Room ComboPrimary Bedroom Main FloorStone CountersThermostatWalk-in Closet(s)

Exterior Features

PavedBalconyOutdoor GrillRain GuttersPoolSecurity Lights

Property Details

Flooring

Marble

Construction

BlockStucco

Parking

DrivewayGarageGarage - AttachedGolf Cart

Heating

CentralElectric (Heating)Natural Gas

Cooling

Central AirZoned

Appliances

DishwasherDryerGarbage DisposerIce MakerMicrowaveRangeRefrigeratorTrash CompactorWasherWater - PurifierWater - Softener

Questions & Answers

This 4-bedroom, 4-bathroom single family at 9731 CHESTNUT RIDGE DRIVE is listed at $3,400,000 ($697/sqft). The estimated monthly payment is $14,733 based on 20% down at 6.5% interest.

Key features include: Built in 1986, 0.54 acre lot, Private pool. Interior Features: Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/Family Room Combo. Exterior Features: Paved, Balcony, Outdoor Grill.

This property is listed by Monica Lochmandy and can be reached at 4072306888 or mlochmandy@isleworth.com.

ML

Monica Lochmandy

Agent at ISLEWORTH REALTY LLC

(407) 230-6888

Listed by ISLEWORTH REALTY LLC · View on Broker Site

MLS# O6336655· Source: listhub· Updated 306 days ago

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

9731 CHESTNUT RIDGE DRIVE, Windermere, FL 34786

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