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
MLS #:
O6336655
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Aug 16, 2025
Finished Sq Ft:
4,877
Total Sq Ft:
6,151
Lot Size:
23,624 sqft / 0.54 acres (approx)
Year Built:
1986
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
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
Bathrooms
4 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Marble, Travertine
Heating
Central, Electric, Natural Gas
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
Two
Exterior
Association Amenities
Cable TV, Playground, Security
Attached Garage YN
1
Community Features
Community Boat Ramp, Water Access, Community Mailbox, Gated Community – No Guard, Golf Carts OK, Golf, Playground
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
Northeast
Exterior Features
Balcony, Irrigation System, Outdoor Grill, Rain Gutters
Garage Spaces
2
Lot Features
Landscaped, Near Golf Course
Open Parking YN
1
Parking Features
Circular Driveway, Golf Cart Garage
Roof
Tile
Security Features
Gated Community, Security Lights, Security System, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Pool
Financial
HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2024
Taxes
$19,867
Map
Community
- Address9731 CHESTNUT RIDGE DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ALADAR ON LAKE BUTLER
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BALMORAL
- BELLARIA
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G3 48 70
- BELMERE VILLAGE G5
- BUTLER BAY
- CARRINGTON
- CASA DEL LAGO
- CASA DEL LAGO REP
- CASA DEL LAGO-REPLAT
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- DAVIS SHORES
- DIAMONDHEAD
- DOWN POINT SUB
- EDEN ISLE
- EDEN ISLE 52/9 LOT 173
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTANCIA/WINDERMERE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS/ISLEWORTH
- GARDENS/ISLEWORTH UN #2
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLES WINDERMERE
- ISLEWORTH
- ISLEWORTH WEST
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UT 04 SEC 29 48 82
- KEENES POINTE UT 04 SEC 31 48 82
- KELSO ON LAKE BUTLER
- KELSO ON LAKE BUTLER 5/48 LOT 59
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BURDEN SOUTH PHASE 1
- LAKE BUTLER ESTATES
- LAKE BUTLER PARK PT REP
- LAKE BUYNAK ESTATES
- LAKE CAWOOD COVE
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE DOWN CREST
- LAKE DOWN ESTATES
- LAKE DOWN POINTE 50 42
- LAKE DOWN SHORES
- LAKE DOWN SHORES REP
- LAKE OLIVIA RESERVE
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMER LAKE REAMS TWNHM
- LAKES/WINDERMERE
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE VILLAS CONDO
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 3
- LAKESIDE/LKS/WINDERMERE PH 9
- LEGADO
- LEGADO 95/47 LOT 100
- MAGNOLIA PARK WINDERMERE
- MANORS AT BUTLER BAY
- MANORS AT BUTLER BAY PH 01
- MERRICK LANDING
- METCALF PARK REP
- OASIS COVE
- OASIS COVE 2 AT LAKESIDE VILLAGE CONDO PH 1
- OASIS COVE AT LAKE SIDE
- OASIS COVE AT LAKESIDE VILLAGE
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE #XI
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- RESERVE AT BELMERE
- RESERVE AT BELMERE 48 23
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS
- SILVER WOODS PH 01
- SILVER WOODS PH 03
- SILVER WOODS PH 05
- STILLWATER XINGS PRCL SC-13 PH
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- SUMMERPORT PH 3
- SUMMERPORT PH 5
- SUMMERPORT PHASE 1
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TILDENS GROVE PH 02
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERFORD POINTE PH 02 REP
- WATERSTONE
- WEATHERSTONE ON LAKE OLIVIA
- WESTOVER CLUB PH 01 44/139
- WESTOVER CLUB PH 1 REP
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 01
- WILLOWS AT LAKE RHEA PH 02
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE ISLE-PH 2
- WINDERMERE LANDINGS PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE OAKS
- WINDERMERE POINTE
- WINDERMERE REP
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5B
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of May 19, 2026
279
Single Family Listed
97
Avg DOM
482
Avg $ / SqFt
$2,461,163
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 9731 CHESTNUT RIDGE DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $3,400,000 and features 4 beds, 4 baths, and has approximately 4,877 square feet of living space, and was originally constructed in 1986. The current price per square foot is $697. The average price per square foot for Single Family listings in WINDERMERE is $482. The average listing price for Single Family in WINDERMERE is $2,461,163. To schedule a showing of MLS#o6336655 at 9731 CHESTNUT RIDGE DRIVE in WINDERMERE, FL, contact your LPT Realty agent at 813.694.8061.
Similar Listings Nearby
Courtesy of ISLEWORTH REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than LPT Realty include the name of the listing broker. Neither the listing company nor LPT Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 9731 CHESTNUT RIDGE DRIVE
WINDERMERE, FL
