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
Laundry Features
Laundry Room
Exterior
Association Amenities
Cable TV, Playground, Security
Community Features
Community Boat Ramp, Water Access, Community Mailbox, Gated Community – No Guard, Golf Carts OK, Golf, Playground
Construction Materials
Block, Stucco
Exterior Features
Balcony, Irrigation System, Outdoor Grill, Rain Gutters
Parking Features
Circular Driveway, Golf Cart Garage
Roof
Tile
Security Features
Gated Community, Security Lights, Security System, Smoke Detector(s)
Financial
HOA Fee
$3,672
HOA Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
HOA Name
Dan O’Connell
Tax Year
2024
Taxes
$19,867
Map
Community
- Address9731 CHESTNUT RIDGE DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- ASHLIN PK PH 2
- BELLARIA
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BUTLER BAY
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DIAMONDHEAD
- DOWN POINT SUB
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT BERKSHIRE PARK
- ESTANCIA/WINDERMERE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS OF ISLEWORTH
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UNIT 1
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLEWORTH
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 01
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 04 SEC 31 48 82
- KEENES POINTE UT 06 50 95
- KELSO ON LAKE BUTLER
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUTLER PARK PT REP
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE DAVIS RESERVE A & B
- LAKE DOWN ESTATES
- LAKE DOWN POINTE 50 42
- LAKE DOWN RESERVE
- LAKE DOWN SHORES REP
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE
- LAKES/WINDERMERE LAKE REAMS
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 03 P & Q
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE A CONDO
- LAKESIDE/LKS/WINDERMERE PH 3
- LANDINGS AT LAKE SAWYER
- LEGADO
- MARINA BAY ESTATES
- MERRICK LANDING
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE 2 AT LAKESIDE VILAGE
- OASIS COVE AT LAKE SIDE
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROSSER RESERVE REP
- ROYAL ESTATE
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS
- SILVER WOODS PH 03
- SILVER WOODS PH 04
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- SUMMERPORT PH 1
- SUMMERPORT PHASE 4
- SUNSET BAY
- THE LAKES
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1A
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WESTOVER CLUB PH 01 44/139
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 02
- WINDEMERE SOUND PH 2
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE ISLE-PH 2
- WINDERMERE LANDINGS
- 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 TRAILS PHASE 5A 80/102 LOT 39
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Mar 19, 2026
257
Single Family Listed
102
Avg DOM
462
Avg $ / SqFt
$2,229,812
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 $462. The average listing price for Single Family in WINDERMERE is $2,229,812. To schedule a showing of MLS#o6336655 at 9731 CHESTNUT RIDGE DRIVE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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
























































