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For sale
    • Price cut: $150K (5/2)
    $6,000,000

    9725 Chestnut Ridge Dr, Windermere, FL 34786

    7beds
    8,000sqft
    : 
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    Single Family Residence
    Built in 1999
    0.56 Acres Lot
    $-- Zestimate®
    $750/sqft
    $1,043/mo HOA

    What's special

    Newly renovatedFull privacySix bedroomsDedicated officeSummer kitchenTaj mahal quartzite countertopsWine cellar
    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.
    200 days
    |
    911
    |
    72
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Dianna Desboyaux 407-920-4601,

    DOUGLAS ELLIMAN 561-655-8600,

    Adriana Morris 407-920-4600,

    DOUGLAS ELLIMAN

    Source: Stellar MLS,MLS#: O6370294MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 7
      • Full bathrooms: 5
      • 1/2 bathrooms: 2
      Rooms
      • Room types: Den/Library/Office, Family Room, Living Room, Media Room
      Primary bedroom
      • Features: Breakfast Bar, Walk-In Closet(s)
      • Level: First
      Dining room
      • Level: First
      • Area: 300 Square Feet
      • Dimensions: 20x15
      Family room
      • Features: Bar
      • Level: First
      • Area: 441 Square Feet
      • Dimensions: 21x21
      Kitchen
      • Features: Pantry
      • Level: First
      • Area: 320 Square Feet
      • Dimensions: 20x16
      Living room
      • Level: First
      • Area: 260 Square Feet
      • Dimensions: 20x13
      Heating
      • Central
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Bar Fridge, Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
      • Laundry: Laundry Room
      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, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar, In-Law Floorplan
      • Flooring: Porcelain Tile, Travertine, Hardwood
      • Doors: French Doors, Outdoor Kitchen
      • Windows: Skylight(s)
      • Has fireplace: Yes
      • Fireplace features: Gas, Living Room, Master Bedroom
      Interior area
      • Total structure area: 11,952
      • Total interior livable area: 8,000 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Driveway, Garage Faces Side
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: Three Or More
      • Stories: 3
      • Patio & porch: Covered, Enclosed, Rear Porch, Screened
      • Exterior features: Fire Pit, Outdoor Kitchen
      • Has private pool: Yes
      • Pool features: Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
      • Has spa: Yes
      • Spa features: Heated, In Ground
      • Has view: Yes
      • View description: Garden, Pool, Water, Pond
      • Has water view: Yes
      • Water view: Water,Pond
      • Waterfront features: Waterfront, Pond, Lake Privileges, Pond Access
      Lot
      • Size: 0.56 Acres
      • Features: Landscaped, Near Golf Course
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Parcel number: 162328389900060
      • Zoning: P-D
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1999

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Electricity Connected, Water Connected

      Community & HOA

      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)
      • Security: Gated Community, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: ISLEWORTH
      HOA
      • Has HOA: Yes
      • Amenities included: 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)
      • Services included: 24-Hour Guard, Community Pool, Maintenance Grounds, Manager, Pool Maintenance, Security
      • HOA fee: $1,043 monthly
      • HOA name: Dan O'Connell
      • HOA phone: 407-909-2071
      Location
      • Region: Windermere

      Financial & listing details

      • Price per square foot: $750/sqft
      • Tax assessed value: $2,495,801
      • Annual tax amount: $29,046
      • Date on market: 1/2/2026
      • Cumulative days on market: 200 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/2/2026Price change$6,000,000-2.4%$750/sqft
        Source: Stellar MLS #O6370294 Report a problem
        4/15/2026Price change$6,150,000-11.5%$769/sqft
        Source: Stellar MLS #O6370294 Report a problem
        1/2/2026Listed for sale$6,950,000+75.1%$869/sqft
        Source: Stellar MLS #O6370294 Report a problem
        8/9/2024Listing removed--
        Source: Stellar MLS #O6192766 Report a problem
        6/28/2024Price change$3,969,000-0.7%$496/sqft
        Source: Stellar MLS #O6192766 Report a problem
        5/1/2024Price change$3,995,000-7.8%$499/sqft
        Source: Stellar MLS #O6192766 Report a problem
        4/5/2024Listed for sale$4,335,000+8.5%$542/sqft
        Source: Stellar MLS #O6192766 Report a problem
        1/11/2024Listing removed--
        Source: Stellar MLS #O6128678 Report a problem
        10/10/2023Price change$3,995,000-6%$499/sqft
        Source: Stellar MLS #O6128678 Report a problem
        7/25/2023Listed for sale$4,249,000-1.2%$531/sqft
        Source: Stellar MLS #O6128678 Report a problem
        7/18/2023Listing removed--
        Source: Stellar MLS #S5085670 Report a problem
        5/30/2023Listed for sale$4,299,000$537/sqft
        Source: Stellar MLS #S5085670 Report a problem
        5/16/2023Listing removed--
        Source: Stellar MLS #O6098611 Report a problem
        5/3/2023Price change$4,299,000-2.3%$537/sqft
        Source: Stellar MLS #O6098611 Report a problem
        3/27/2023Listed for sale$4,399,000+282.5%$550/sqft
        Source: Stellar MLS #O6098611 Report a problem
        11/9/1999Sold$1,150,000+318.2%$144/sqft
        Source: Public Record Report a problem
        10/2/1998Sold$275,000$34/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$29,046 +7.2%$1,792,498 +3%
        2023$27,092 +2.9%$1,740,289 +3%
        2022$26,331 +1.2%$1,689,601 +3%
        2021$26,031 +0.5%$1,640,389 +1.3%
        2020$25,896 +0.8%$1,619,460 +2.3%
        2019$25,701 +0.7%$1,583,050 +1.9%
        2018$25,526 $1,553,533 -3.2%
        2017$25,526 +1%$1,605,397 +2%
        2016$25,262 +0.1%$1,574,569 +2.2%
        2015$25,243 -2.6%$1,540,282 +4.9%
        2014$25,929 +22.8%$1,468,180 +20.6%
        2013$21,118 +1%$1,217,832 +2.7%
        2012$20,912 -10.6%$1,185,861 -10.1%
        2011$23,396 -1.8%$1,318,419 -4.3%
        2010$23,825 $1,376,989 -17.4%
        2009-- $1,667,624 -7.4%
        2008$22,991 +2.4%$1,800,734 +7.8%
        2007$22,455 -6.4%$1,670,004 +9.7%
        2006$23,986 -0.1%$1,522,014 +18.1%
        2005$24,005 +4.2%$1,289,162 +4.1%
        2004$23,026 +8.4%$1,238,960 +12.8%
        2003$21,236 +4.9%$1,098,702 +3.9%
        2002$20,242 +3.2%$1,057,076 +6.2%
        2001$19,615 $995,032
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34786

        Getting around

        18 / 100
        Car-Dependent
        23 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Windermere Elem
        • Middle: Chain of Lakes Middle
        • High: Olympia High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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