Ad #6529003
MLS #O6336655
Nestled within the gates of the renowned Isleworth Golf &
9731 CHESTNUT RIDGE DR, Windermere, FL 34786
$3,400,000
4Beds
4Baths
4,877Sqft
0.54Acres
About this property
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 closetspleting 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.
Property Features
4 Beds
4 Baths
4,877 Sqft
Built in 1986
0.54 Acres
Isleworth Golf and Country Club
On Golf Course
Driveway, Garage, Garage - Attached, Golf Cart
Siding: Block, Stucco
Tile Roof
Has Swimming Pool
Central, Electric (Heating), Natural Gas
$19,867 / yr property tax
Orange County
$14,688 / yr HOA
ISLEWORTH Community
Additional Photos
Contact Information
Monica Lochmandy
Isleworth Realty, LLC
407-230-6888
Location
Listing Agent: Monica Lochmandy (License #: 3237911) 407-230-6888
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
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.
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
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.
GolfHomes.com
Printed Aug 11, 2026
Photo Gallery
$3,400,000
4
Beds
4
Baths
4,877
Sqft
9731 CHESTNUT RIDGE DR, Windermere, FL 34786
By contacting this agent you agree to these Terms and Conditions.
MLS# O6336655
Nestled within the gates of the renowned Isleworth Golf &
$3,400,000
9731 CHESTNUT RIDGE DR, Windermere, FL 34786
4
Beds
4
Baths
4,877
Sqft
0.54
Acres
$3,400,000
9731 CHESTNUT RIDGE DR, Windermere, FL 34786
4 Beds
4 Baths
4,877 Sqft
0.54 Acres
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 closetspleting 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.
360 days
on GolfHomes.com
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Property Details
HOME DETAILS
4 Beds
4 Baths
4,877 Sqft
Built in 1986
0.54 Acres
GOLF COURSE & VIEW
Isleworth Golf and Country Club
On Golf Course
EXTERIOR
Driveway, Garage, Garage - Attached, Golf Cart
Siding: Block, Stucco
Tile Roof
Has Swimming Pool
INTERIOR
Central, Electric (Heating), Natural Gas
FINANCIAL & COMMUNITY
$19,867 / yr property tax
Orange County
$14,688 / yr HOA
ISLEWORTH Community
See More Details
Location
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Ad Statistics
Ad Number
6529003
Viewed
388 times
Listing Status
Active
Added
Aug 16, 2025
Last Refreshed
Jul 03, 2026 06:17:28 PM
Listing Information
Data Source
Stellar MLS
Source Property ID
O6336655
Listing Agent: Monica Lochmandy (License #: 3237911) 407-230-6888
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
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.
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
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.
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