9731 CHESTNUT RIDGE DRIVE Windermere, FL $ 3,400,000
9731 CHESTNUT RIDGE DRIVE
$ 3,400,000
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9731 CHESTNUT RIDGE DRIVE

Windermere, FL, 34786
$ 3,400,000
Bedrooms4 Baths4.0 Sq 4,877

Monthly Estimate*

$ 21,212

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Single Family Home for sale in Windermere, FL

for $3,400,000 with 4 bedrooms and 4 full baths. This 4,877 square foot home was built in 1986 on a lot size of 0.54.

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.

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Single Family Active

Price

$ 3,400,000

Bedrooms

4

Full Bath

4

Property Type

Single Family

Taxes

$ 19,866

Style

Single Family Residence

Lot Size

0.54

Year Built

1986

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6336655

Features
Interior
Interior Amenities cathedral ceiling(s) ceiling fan(s) kitchen/family room combo primary bedroom main floor stone counters thermostat walk-in closet(s)
Flooring marble travertine
Total Stories 2
Air Conditioning Y/N yes
Heating Y/N yes
Fireplace Y/N no
Half Baths 0
Laundry Features laundry room
Total Bedrooms 4
Total Baths 4
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General
Sewer septic tank
Heating central electric natural gas
Cooling central air zoned
Utilities bb/hs internet available cable connected electricity connected natural gas connected street lights water connected
Roof tile
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 s
Zoning p-d
HOA Fee 3129
Garage Spaces 2
Association Fee Includes 24-hour guard cable tv escrow reserves fund internet maintenance grounds maintenance repairs security
Pool Features heated in ground lighting self cleaning
Security Features gated community security lights security system smoke detector(s)
Construction Materials block stucco
Pets Allowed breed restrictions
Year Built 1986
View pool
Levels two
Property Subtype single family residence
Tax Year 2024
Ownership fee simple
Community Features community boat ramp water access community mailbox gated community - no guard golf carts ok golf playground
Assoc Fee Paid Per quarterly
County orange
New Construction no
Property Type residential
Association Amenities cable tv playground security
HOA Y
Attached Garage yes
Subdivision Name isleworth
Facing Direction northeast
Garage Y/N yes
Total Rooms 10
Full Baths 4
Status active
Directions i-4 to conroy windermere road west to isleworth subdivision. stay straight on isleworth country club drive. turn right on latrobe turn right on chestnut ridge drive. estate will be on the right.
High School olympia high
City windermere
Body of Water lake butler chain of lakes
Association Name dan o'connell
Senior Community Y/N no
MLS Area 34786 - windermere
Lot Size Units square feet
Lot Size Square Feet 23624
Carport Y/N no
Listing Terms cash conventional
Spa Features heated in ground
Elementary School windermere elem
Land Lease Y/N no
Tax Annual Amount 19866.86
Middle/Junior High School chain of lakes middle
Additional Parcels Y/N no
Lease Considered Y/N yes
Building Area Units square feet
Living Area Units square feet
Standard Status active
Occupancy Type owner
Tax Lot 7
Legal Description isleworth 16/118 lot 7
Water Access Type lake - chain of lakes
Minimum Lease no minimum
Water Access Y/N yes
Monthly HOA Amount 1043
Water View Y/N no
Flood Zone Code x
DockY/N no
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Exterior
Exterior Amenities balcony irrigation system outdoor grill rain gutters
Parking Features circular driveway golf cart garage
Lot Features landscaped near golf course
Water Source public
Lot Size Area 23624
Foundation Details block slab
Building Area Total 6151
Lot Size Acres 0.54
Road Surface Type paved
Private Pool yes
Waterfront Y/N no
Covered Spaces 2
Road Frontage Type street paved
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Internal Only
Street Number 1 9731
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* Excluded Features
List By
Isleworth Realty Llc

Broker

mlochmandy@isleworth.com

Email

Affordability Calculator

$22,867
Per Month
93%
7%
0%
Monthly Principal & Interest
$21,212
Monthly Property Taxes
$1,656
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3324044 Elementary School
3220805 Middle School
Olympia High High School
Pricing History
DatePricePrice ChangeDescription
8/17/2025$3,400,000 Listed Price

Map


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9731 CHESTNUT RIDGE DRIVE, Windermere, FL, 34786 is a Single Family Home for sale at $3,400,000 with 4,877 sqft and a lot size of 0.54. 9731 CHESTNUT RIDGE DRIVE has 4 bedrooms, 4.0 baths, and was built in 1986. The property's zip code is 34786 which is in Windermere, FL