9731 Chestnut Ridge Drive, Windermere, FL 34786
For Sale $3,400,000
Request Club Info by Email
Calculate Your Payment
Like this listing?
Contact the Listing Agent directly:
Listing Agent: Monica Lochmandy
Agent Phone:
407-230-6888
Agent Email:
mlochmandy@isleworth.com
Share Property
Save 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 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.
Cathedral Ceiling(s)
Ceiling Fans(s)
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Stone Counters
Thermostat
Walk-In Closet(s)
Cable TV
Playground
Security
Taxes: $19.00
Tax Year: 2024
HOA Fee 1: $3,129.00
HOA Frequency 1: Quarterly
Condo Fee Frequency: Quarterly
Balcony
Outdoor Grill
Rain Gutters
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
Pool
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
MLS Area: 34786 - Windermere
Price per Square Feet: $697.15
Total Floors: 2
Water: Public
Lot Desc.: Landscaped, Near Golf Course, Paved
Construction: Block, Stucco
Date Listed: 2025-08-16 22:25:06
Pool: Yes
Pool Type: Heated, In Ground, Lighting, Self Cleaning
Parking: Circular Driveway, Golf Cart Garage
Garage Spaces: 2
Flooring: Marble, Travertine
Roof: Tile
Heating: Central, Electric, Natural Gas
Cooling: Central Air, Zoned
Pets: Breed Restrictions
Sewer: Septic Tank
Amenities: Cable Tv, Playground, Security
Listing Courtesy Of: Isleworth Realty Llc
mlochmandy@isleworth.com
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.
Property Details
Price: $3,400,000
Sq Ft: 4,877
($697 per sqft)
Bedrooms: 4
Bathrooms: 4
City: Windermere
County: Orange
Type: Single Family Reside
Development: Isleworth
Acres: 0.54
Year Built: 1986
Listing Number: O6336655
Status Code: A-Active
Taxes: $19.00
Tax Year: 2024
Garage:
2
Pets Allowed: Breed Restrictions
Interior Features:
Cathedral Ceiling(s)
Ceiling Fans(s)
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Stone Counters
Thermostat
Walk-In Closet(s)
Amenities:
Cable TV
Playground
Security
Financial Information:
Taxes: $19.00
Tax Year: 2024
HOA Fee 1: $3,129.00
HOA Frequency 1: Quarterly
Condo Fee Frequency: Quarterly
Exterior Features:
Balcony
Outdoor Grill
Rain Gutters
Equipment:
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
View:
Pool
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
Additional Information:
MLS Area: 34786 - Windermere
Price per Square Feet: $697.15
Total Floors: 2
Water: Public
Lot Desc.: Landscaped, Near Golf Course, Paved
Construction: Block, Stucco
Date Listed: 2025-08-16 22:25:06
Pool: Yes
Pool Type: Heated, In Ground, Lighting, Self Cleaning
Parking: Circular Driveway, Golf Cart Garage
Garage Spaces: 2
Flooring: Marble, Travertine
Roof: Tile
Heating: Central, Electric, Natural Gas
Cooling: Central Air, Zoned
Pets: Breed Restrictions
Sewer: Septic Tank
Amenities: Cable Tv, Playground, Security
Map of 9731 Chestnut Ridge Drive, Windermere, FL 34786
Listing Courtesy Of: Isleworth Realty Llc
mlochmandy@isleworth.com