$3,400,000

9731 CHESTNUT RIDGE DRIVE, WINDERMERE

4

Beds

4

Baths

4,877 ft2

Property Size

O6336655

MLS #

About The 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.

Listing updated: August 17, 2025 at 10:47am

Listed by Realtor: Monica Lochmandy

Listed by office:  ISLEWORTH REALTY LLC

Source: Stellar MLS

Property Details

Listing Id: O6336655
Price: $3,400,000
Property Size: 4,877 ft2
Property Lot Size: 1 ft2
Rooms: 10
Bedrooms: 4
Bathrooms: 4
Association Amenities: Cable TV, Playground, Security
Association Fee: 3129
Association Fee Frequency: Quarterly
Bathrooms Full: 4
Modification Timestamp: August 17, 2025 at 10:50am
Building Area Total: 6151
Community Features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - No Guard, Golf Carts OK, Golf, Playground
Construction Materials: Block, Stucco
Cooling: Central Air, Zoned
CoveredSpaces: 2
CumulativeDaysOnMarket: 19
DaysOnMarket: 19
DirectionFaces: Northeast
ElementarySchool: Windermere Elem
Flooring: Marble, Travertine
FoundationDetails: Block, Slab
GarageSpaces: 2
HighSchool: Olympia High
Laundry Features: Laundry Room
Levels: Two
List AOR: Orlando Regional
List Agent AOR: Orlando Regional
List Agent Email: mlochmandy@isleworth.com
List Agent Full Name: Monica Lochmandy
List Agent MlsId: 261067417
ListOfficeMlsId: 261013260
List Office Name: ISLEWORTH REALTY LLC
ListOfficePhone: 407-909-9000
Listing Terms: Cash, Conventional
Living Area Source: Public Records
Lot Features: Landscaped, Near Golf Course
LotSizeArea: 23624
LotSizeSquareFeet: 23624
MLS Area Major: 34786 - Windermere
MiddleOrJuniorSchool: Chain of Lakes Middle
MlsStatus: Active
ModificationTimestamp: August 17, 2025 at 10:47am
OnMarketDate: 2025-08-16
Originating System Name: Stellar MLS
Ownership: Fee Simple
Parcel Number: 162328389900070
Parking Features: Circular Driveway, Golf Cart Garage
Pets Allowed: Breed Restrictions
Pool Features: Heated, In Ground, Lighting, Self Cleaning
Roof: Tile
Security Features: Gated Community, Security Lights, Security System, Smoke Detector(s)
Sewer: Septic Tank
Spa Features: Heated, In Ground
State Or Province: FL
Status Change Timestamp: August 16, 2025 at 10:25pm
Stories Total: 2
Street Name: CHESTNUT RIDGE
Street Number: 9731
Street Number Numeric: 9731
Street Suffix: DRIVE
Tax Annual Amount: 19866.86
Tax Block: 3899
Tax Book Number: 16-118
Tax Year: 2024
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Street Lights, Water Connected
View: Pool
Water Source: Public
Year Built: 1986
Zoning: P-D
FeedTypes: IDX
Source System Key: 767595455
OriginalEntryTimestamp: August 16, 2025 at 10:25pm
OriginalListPrice: 3400000

Amenities and Features

Outdoor Details
Garage Attached
Other Features
Balcony
Bar Fridge
Built-In Oven
Cathedral Ceiling(s)
Ceiling Fan(s)
Dishwasher
Disposal
Dryer
Exhaust Fan
Gas Water Heater
Has a View
Has Cooling System
Has Garage
Has Heating System
Has Pool
Home Owners Association
Ice Maker
Irrigation System
Kitchen/Family Room Combo
Microwave
Open Parking
Outdoor Grill
Primary Bedroom Main Floor
Rain Gutters
Range
Range Hood
Refrigerator
Stone Counters
Thermostat
Trash Compactor
Walk-In Closet(s)
Washer
Water Filtration System
Water Purifier
Water Softener

Schedule a tour

Fri 22 May
Sat 23 May
Sun 24 May
Mon 25 May
Tue 26 May
Wed 27 May
Thu 28 May
Fri 29 May
Sat 30 May
Sun 31 May
In Person
Video Chat
Your information

Map Location

Property Map

Mortgage Calculator

Payment Calculator

$17,432.47
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 13,182.47

Image Gallery

Similar Listings

Similar Listings

2506 WILKINSON ROAD, SARASOTA
Residential
Active
$750,000

2506 WILKINSON ROAD, SARASOTA

MLS #
A4658952
Size
954 ft2
Beds:
2
Baths:
2
mls_logo
18339 OLIVER TWIST WAY, WINTER GARDEN
Residential
Active
$748,000

18339 OLIVER TWIST WAY, WINTER GARDEN

MLS #
O6280496
Size
2,931 ft2
Beds:
4
Baths:
3
mls_logo
1461 MARLIN STREET, NOKOMIS
Residential
Active
$1,050,000

1461 MARLIN STREET, NOKOMIS

MLS #
N6141707
Size
2,006 ft2
Beds:
3
Baths:
2
mls_logo

Disclaimer

Property ID - | 743252

All listings featuring of Stellar MLS are provided by Stellar MLS. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by MLS.

©2026 Stellar MLS All rights reserved.

Compare Listings

Janet Richmond