9731 Chestnut Ridge DriveWindermere, FL 34786Price: $3,400,000

  • Price: $3,400,000
  • Est. Mortgage of $/month
  • 317 Days on Market
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Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
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9731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 347869731 Chestnut Ridge Drive Windermere FL 34786
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  • 4Bedrooms
  • 0.54Acreage
  • 4Bathrooms
  • 1986Year Built
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.
Listing Courtesy of ISLEWORTH REALTY LLC

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More Info

Location Information

  • Road Frontage DescriptionPaved

School Information

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

Parking

  • Parking Features Circular Driveway, Golf Cart Garage

Basic Information

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

Property

  • ZoningP-D

Interior

  • Flooring Marble, Travertine

Utilities

  • Cooling Central Air, Zoned
  • Heating Central, Electric, Natural Gas
  • Laundry Features Laundry Room
  • Sewer Septic Tank
  • Utilities BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected
  • Water Source Public

Water Body

  • MFR Additional Water Information The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
  • MFR Water Access YN Yes
  • Pool Private YN Yes
  • Water AccessLake - Chain of Lakes
  • Water Body Name LAKE BUTLER CHAIN OF LAKES
  • Water ViewNo

Other

  • Building Area Source Public Records
  • Date Listed08/16/2025
  • MFR Additional Lease Restrictions Per Isleworth Community Association (ICA)
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Flood Zone Date 2009-09-25
  • MFR Minimum Lease No Minimum
  • Status Change Timestamp2025-08-16T22:25:06
  • View Pool
  • View Count6

Basic Information

  • List Price$3,400,000
  • ListingContractDate2025-07-30
  • MLS NumberO6336655
  • Mls Status Active
  • OriginalListPrice3400000
  • PostalCodePlus48945
  • PublicSurveyRange28
  • StatusACT

Rooms

  • Bedrooms4
  • Full Bath4

Building

  • Bathroom4
  • Construction Materials Block, Stucco
  • Foundation Details Block, Slab
  • GarageYes
  • Garage Spaces2
  • Levels Two
  • RoofTile
  • Rooms10
  • Stories2
  • Year Built1986

Amenities

  • Appliances IncludedBar 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
  • Association Amenities Cable TV, Playground, Security
  • Association Fee Includes
    • Cable TV
    • Escrow Reserves Fund
    • Guard - 24 Hour
    • Internet
    • Maintenance
    • Maintenance Grounds
    • Security
  • Association YN Yes
  • Community Features
    • Community Mailbox
    • Gated Community - No Guard
    • Golf
    • Golf Carts OK
    • Playground
    • Street Lights
  • 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 Per Orange County breed restrictions, number limits and leash laws.
  • Other AmenitiesPool, Golf
  • Other Equipment Irrigation Equipment
  • PetsBreed Restrictions
  • Pool Features Heated, In Ground, Lighting, Self Cleaning
  • Security Features Gated Community, Security Lights, Security System, Smoke Detector(s)
  • Spa Features Heated, In Ground

Tax Information

  • Association Fee $3,672
  • Association Fee Frequency Quarterly
  • Fees$14,688
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $1,224
  • Tax Year 2024
  • Taxes$19,866
  • Total Monthly Fees $1,224

Location

  • Address9731 Chestnut Ridge Drive
  • AreaWindermere
  • CountyOrange
  • Exterior Features Balcony, Outdoor Grill, Rain Gutters
  • StateFL
  • SubdivisionIsleworth
  • TownWindermere
  • Township 23
  • Zip34786

Property Information

  • Acreage0.54
  • Attached Garage YN Yes
  • Building Area Total 6,151
  • BuildingAreaUnitsSquare Feet
  • LivingAreaUnitsSquare Feet
  • Lot DescriptionLandscaped, Near Golf Course, Paved
  • Lot Size Square Feet 23,624
  • MFR Living Area Meters 453
  • MFR Lot Size Square Meters 2195
  • MFR Total Acreage 1/2 to less than 1
  • Square Feet4,877
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 9:32 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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