9725 Chestnut Ridge Drive, WINDERMERE, FL

$5,975,000

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7

Beds

7

Baths

8,000

Square feet

0.56

Acres

Summary of 9725 Chestnut Ridge Drive

9725 Chestnut Ridge Drive is in WINDERMERE, FL. This Residential property for sale is currently being offered at $5,975,000. Built in 1999, this 7 bedroom, 7 bathroom Orange Residential property has been listed on RealtyInOrlando.com for 251 days. 9725 Chestnut Ridge Drive is priced at $746.88 Per Square Foot, and is situated on 0.56 acres of land. Please contact your local Realtor® for more information on 9725 Chestnut Ridge Drive, WINDERMERE, FL 34786-8945. Property Listing Reference: MLS number: O6370294.

About 9725 Chestnut Ridge Drive

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.

Features of 9725 Chestnut Ridge Drive

MLS® # O6370294
Price $5,975,000
Bedrooms 7
Bathrooms 7.00
Full Baths 5
Half Baths 2
Square Footage 8,000
Acres 0.56
Year Built 1999
Type Residential
Sub-Type Single Family Residence
Status Active
HOA $3,129
Taxes $29,046

Community Information

Address 9725 Chestnut Ridge Drive
Area Windermere
Subdivision ISLEWORTH
City WINDERMERE
County Orange
State FL
Zip Code 34786-8945

Amenities

Amenities Clubhouse, Elevator(s), Fitness Center, Gated, Golf Course, Maintenance, Park, Pickleball Court(s), Playground, Pool, Racquetball, Recreation Facilities, Sauna, Security, Spa/Hot Tub, Storage, Tennis Court(s)
Parking Driveway, Garage Faces Side
# of Garages 3
View Garden, Pool, Water
Is Waterfront Yes
Waterfront Waterfront, Pond
Has Pool Yes
Community Features Private Boat Ramp, Water Access, Waterfront, Buyer Approval Required, Clubhouse, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, No Truck/RV/Motorcycle Parking, Playground, Pool, Racquetball, Restaurant, Tennis Court(s)
Gated Community - Guard Yes

Interior

Interior Features Built-in Features, Ceiling Fan(s), Elevator, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
Main Bedroom Downstairs Yes
Appliances Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
Heating Central
Cooling Central Air, Zoned
Fireplace Yes
Fireplaces Gas, Living Room, Master Bedroom
# of Stories 2

Exterior

Exterior Features Fire Pit, French Doors, Outdoor Kitchen
Lot Description Landscaped, Near Golf Course
Roof Tile
Foundation Slab

School Information

Elementary Windermere Elem
Middle Chain of Lakes Middle
High Olympia High

Other Information

Date Listed January 2nd, 2026
Days on Market 251
Zoning P-D
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeDOUGLAS ELLIMAN

Listing Map

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