Virtual TourMap

For SaleSingle Family ResidenceActive

9725 Chestnut Ridge Drive

Windermere, FL 34786

$5,975,000

307 Days On Site

  • 7Beds
  • 7Baths5 full, 2 half
  • 8,000Sq Ft
  • $747Per Sq Ft
  • 0.56Acres
  • 1999Built
Subdivision
Isleworth
County
Orange
MLS®
O6370294

Overview

Virtually Staged. Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed.

The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.

Listing Snapshot

Price
$5,975,000
Days On Site
307 Days
Bedrooms
7
Inside Area (SqFt)
8,000 sqft
Total Baths
7
Full Baths
5
Partial Baths
2
Lot Size
0.56 Acres
Year Built
1999
MLS® Number
O6370294
Status
Active
Property Tax
$29,046.23 (2024)
HOA/Condo/Coop Fees
$1,043 monthly
Sq Ft Source
Builder

Property Details

General Features

17 items
Acres
0.56
Attached Garage
Yes
Direction Faces
West
Foundation
Slab
Garage
Yes
Garage Spaces
3
Levels
Three Or More
Number Of Stories
2
Parking
Driveway, Garage Faces Side, Attached
Pets
Yes
Property Sub Type
Single Family Residence
Security
Gated Community, Smoke Detector(s)
Sewer
Septic Tank
SqFt Total
11,952
Utilities
Electricity Connected, Water Connected
Water Source
Public
Zoning
P-D

Interior Features

15 items
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
Cooling
Central Air, Zoned
Fireplace
Yes
Fireplace Features
Gas, Living Room
Flooring
Tile, Wood
Heating
Central
Interior
Built-in Features, Elevator, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s), Wet Bar
Laundry Features
Laundry Room
Spa
Yes
Window Features
Skylight(s), ENERGY STAR Qualified Windows

Rooms

RoomDimensionsLevelFeatures
Dining Room20x15First
Family Room21x21FirstBar
Kitchen20x16First
Living Room20x13First
Master BedroomFirstBreakfast Bar

Exterior Features

14 items
Construction Details
Block, Stucco
Exterior
Fire Pit, Outdoor Kitchen
Lot Features
Landscaped, Near Golf Course, Paved, Waterfront
Patio And Porch
Covered, Enclosed, Rear Porch, Screened
Pool Features
Heated, In Ground, Indoor, Lap, Screen Enclosure, Tile, Private
Private Pool
Yes
Roof
Tile
Spa
Yes
Spa Features
Heated, In Ground
View
Pond, Water, Garden, Pool
Waterfront
Yes
Waterfront Features
Lake Privileges, Pond
Waterview
Pond, Water, Garden, Pool
Windows/Doors
Skylight(s), ENERGY STAR Qualified Windows

Community Features

8 items
Association Amenities
Clubhouse, Elevator(s), Fitness Center, Gated, Golf Course, Maintenance, Park, Playground, Pool, Racquetball, Recreation Facilities, Sauna, Security, Spa/Hot Tub, Storage, Tennis Court(s)
Association Fee
$3129.0
Association Fee Frequency
Quarterly
Community Features
Gated, Clubhouse, Fitness Center, Golf, Playground, Pool, Racquetball, Restaurant, Tennis Court(s)
MLS Area
34786 - Windermere
Township
23
Financing Terms Available
Cash, Conventional
Roads
Asphalt

Location

9725 Chestnut Ridge Drive, Windermere, FL 34786 · 34786 - Windermere

Neighborhood & Commute

ZIP Code 34786

Median household income
$127,371
Income per person
$64,053
Households
17,419
Average household size
2.82
Median age
38.9

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Schools

Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Price changed to $5,975,000
  3. Listing first seen on site
  4. Status changed to Active

Friends & Family

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Listing courtesy of DOUGLAS ELLIMAN (407) 920-4601

Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.

Last checked: 2026-11-05 09:54 PM EST

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