9725 Chestnut Ridge DriveWindermere, FL 34786Price: $6,000,000

  • Price: $6,000,000
  • Est. Mortgage of $/month
  • 178 Days on Market
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Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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9725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 347869725 Chestnut Ridge Drive Windermere FL 34786
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  • 7Bedrooms
  • 0.56Acreage
  • 7Bathrooms
  • 1999Year Built
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. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.
Listing Courtesy of DOUGLAS ELLIMAN

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More Info

Location Information

  • Road Frontage DescriptionAsphalt

School Information

  • Elementary SchoolWindermere Elem
  • High SchoolOlympia High
  • Junior HighChain of Lakes Middle

Parking

  • Parking Features Driveway, Garage Faces Side

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential
  • Virtual TourView Tour

Building

  • Bathroom7
  • Construction Materials Block, Stucco
  • FireplaceGas, Living Room, Primary Bedroom
  • Fireplace YN Yes
  • Foundation Details Slab
  • GarageYes
  • Garage Spaces3
  • Levels Three Or More
  • Patio And Porch Features Covered, Enclosed, Rear Porch, Screened
  • RoofTile
  • Rooms5
  • Stories2
  • Window Features Skylight(s), ENERGY STAR Qualified Windows
  • Year Built1999

Water Body

  • MFR Water Access YN Yes
  • MFR Water Frontage Feet Pond 113
  • MFR Waterfront Feet Total 113
  • Pool Private YN Yes
  • Water AccessLake - Chain of Lakes, Pond
  • Water FeaturesPond
  • Water ViewYes
  • WaterfrontYes

Other

  • Building Area Source Builder
  • Date Listed01/02/2026
  • MFR Additional Lease Restrictions Per Isleworth Community Association
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Flood Zone Date 2009-09-25
  • MFR Minimum Lease 8-12 Months
  • Status Change Timestamp2026-01-02T05:14:07
  • Vegetation Mature Landscaping, Trees/Landscaped
  • View Garden, Pool, Water
  • View Count5

Basic Information

  • List Price$6,000,000
  • ListingContractDate2026-01-02
  • MLS NumberO6370294
  • Mls Status Active
  • OriginalListPrice6950000
  • PostalCodePlus48945
  • PublicSurveyRange28
  • StatusACT

Rooms

  • Bedrooms7
  • Full Bath5
  • Half Baths2
  • MFR Additional Rooms Den/Library/Office, Family Room, Formal Living Room Separate, Interior In-Law Suite w/Private Entry, Media Room

Property

  • ZoningP-D

Interior

  • Flooring Tile, Travertine, Wood

Utilities

  • Cooling Central Air, Zoned
  • Heating Central
  • Laundry Features Laundry Room
  • Sewer Septic Tank
  • Utilities Electricity Connected, Water Connected
  • Water Source Public

Amenities

  • Appliances IncludedBar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
  • Association Amenities
    • Clubhouse
    • Elevators
    • Fitness Center
    • Gated
    • Golf Course
    • Maintenance
    • Park
    • Pickleball Court(s)
    • Playground
    • Pool
    • Racquetball
    • Recreation Facilities
    • Sauna
    • Security
    • Spa/Hot Tub
    • Storage
    • Tennis Court(s)
  • Association Fee Includes Guard - 24 Hour, Pool, Maintenance Grounds, Management, Security
  • Association YN Yes
  • Community Features
    • Buyer Approval Required
    • Clubhouse
    • Fitness Center
    • Gated Community - Guard
    • Golf
    • Golf Carts OK
    • No Truck/RV/Motorcycle Parking
    • Playground
    • Pool
    • Racquetball
    • Restaurant
    • Tennis Court(s)
  • MFR Amenities Additional Fees Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
  • MFR Pet Restrictions Please call the association
  • Other Amenities
    • Fireplace
    • Golf
    • Pool
    • Tennis
    • Water View
    • Waterfront
  • Other Equipment Fire Pit
  • PetsYes
  • Pool Features
    • Heated
    • In Ground
    • Indoor
    • Lap
    • Outside Bath Access
    • Screen Enclosure
    • Tile
  • Security Features Gated Community, Smoke Detector(s)
  • Spa Features Heated, In Ground

Tax Information

  • Association Fee $3,129
  • Association Fee Frequency Quarterly
  • Fees$12,516
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $1,043
  • Tax Year 2024
  • Taxes$29,046
  • Total Monthly Fees $1,043

Location

  • Address9725 Chestnut Ridge Drive
  • AreaWindermere
  • CountyOrange
  • Exterior Features Fire Pit, French Doors, Outdoor Kitchen
  • MFR Water View Pond
  • StateFL
  • SubdivisionIsleworth
  • TownWindermere
  • Township 23
  • Zip34786

Property Information

  • Acreage0.56
  • Attached Garage YN Yes
  • Building Area Total 11,952
  • BuildingAreaUnitsSquare Feet
  • LivingAreaUnitsSquare Feet
  • Lot DescriptionLandscaped, Near Golf Course, Paved
  • Lot Size Square Feet 24,349
  • MFR Living Area Meters 743
  • MFR Lot Size Square Meters 2262
  • MFR Total Acreage 1/2 to less than 1
  • Square Feet8,000
Fusilier Realty Group
Fusilier Realty Group
Office: 407-281-8455
10016 Wellness Way
Orlando, FL 32832

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of June 28, 2026 10:31 PM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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