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Single family home for sale at 9725 Chestnut Ridge Dr, Windermere, FL 34786 | MLS# O6370294 | Listing updated on 2026-09-22
Photo 1 of Single family home for sale at 9725 Chestnut Ridge Dr, Windermere, FL 34786 | MLS# O6370294 | Listing updated on 2026-09-22
Photo 2 of Single family home for sale at 9725 Chestnut Ridge Dr, Windermere, FL 34786 | MLS# O6370294 | Listing updated on 2026-09-22
Photo 3 of Single family home for sale at 9725 Chestnut Ridge Dr, Windermere, FL 34786 | MLS# O6370294 | Listing updated on 2026-09-22
Photo 4 of Single family home for sale at 9725 Chestnut Ridge Dr, Windermere, FL 34786 | MLS# O6370294 | Listing updated on 2026-09-22
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$5,975,000

Monthly Est:$29,740

  • Beds Icon7 Beds
  • Beds Icon
    7 Baths
  • Beds Icon8,000sqft

9725 Chestnut Ridge Dr, Windermere, FL 34786

$29,740/moEst:

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  • Single Family Residence

  • Built in 1999

  • $1,043/mo HOA

  • 24,349 sqft lot

  • $747/sq.ft

Description

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.

  • Houzeo last checked: 2 hours ago
  • Listing updated: September 22, 2026 at 7:52 pm
  • Listing Provided by: Dianna Desboyaux (407) 920-4601 , Adriana Morris | DOUGLAS ELLIMAN (561) 655-8600
  • Source: Stellar MLS-FL | MLS#: O6370294 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Orange County

  • City

    Windermere

  • Neighborhood

    --

  • Year Built

    1999

  • HOA Fees

    $1043/mo

  • Finished Area

    8,000 sqft

  • Lot Size

    24,349 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6370294

  • MLS Status

    Active

  • Days on Market

    299

  • Cumulative Days on Market

    263

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Location

HOA Management

Dan O'Connell

HOA Fees

$3,129/ Quarterly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Elevator Elevator

Security Gate Security Gate

Club House Club House

Golf Golf

Tennis Tennis

Spa Spa

Security Guard Security Guard

Pool Pool

Maintenance Maintenance

Gym Gym

Storage Storage

Park Playground Park Playground

Sports Court Sports Court

Recreation Facilities Recreation Facilities

Management Management

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 7

    Bathrooms: 7

  • Family Room

    Level: First

    Area: 441.00 Square Feet

    Dimensions: 21x21

  • Kitchen

    Level: First

    Area: 320.00 Square Feet

    Dimensions: 20x16

  • Dining Room

    Level: First

    Area: 300.00 Square Feet

    Dimensions: 20x15

  • Living Room

    Level: First

    Area: 260.00 Square Feet

    Dimensions: 20x13

  • Primary Bedroom

    Level: First

Interior

  • Sewer

    Septic Tank

  • Flooring

    Tile, Travertine, Wood

  • Appliances

    Bar Fridge, Built In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer

  • Cooling

    Central Air, Zoned

  • Window Features

    Skylight(s), Energy Star Qualified Windows

  • Exterior Features

    Fire Pit, Outdoor Kitchen

  • Heating

    Central

  • Interior Features

    Built In Features, Ceiling Fans(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

Construction

  • Year Built

    Year Built: 1999

  • Home type

    Single Family Residence

  • Foundation Details

    Slab

  • Construction Materials

    Block, Stucco

  • Roof

    Tile

Utilities & Energy

  • Parking Features

    Driveway, Garage Faces Side

  • Utilities

    Electricity Connected, Water Connected

  • Laundry Features

    Laundry Room

  • Pool Features

    Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile

  • Security Features

    Gated Community, Smoke Detector(s)

  • 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)

  • Water Source

    Public

  • Fireplace Features

    Gas, Living Room, Primary Bedroom

Other Features

  • Community Features

    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)

  • Patio And Porch Features

    Covered, Enclosed, Rear Porch, Screened

  • Lot Features

    Landscaped, Near Golf Course, Paved

  • Subdivision Name

    Isleworth

  • Vegetation

    Mature Landscaping, Trees/landscaped

Price History

DateEventPrice

08/22/2026

Source: mls_logoStellar MLS-FL #MFRO6370294

Price Decreased

$5,975,000 -0.42%

$747/sqft

05/02/2026

Source: mls_logoStellar MLS-FL #MFRO6370294

Price Decreased

$6,000,000 -2.44%

$750/sqft

04/15/2026

Source: mls_logoStellar MLS-FL #MFRO6370294

Price Increased

$6,150,000 +2.93%

$769/sqft

01/02/2026

Source: mls_logoStellar MLS-FL #MFRO6370294

Listed for Sale

$5,975,000 -14.03%

$747/sqft

01/02/2026

Source: mls_logoStellar MLS-FL #MFRO6370294

Price Increased

$6,950,000 +75.11%

$869/sqft

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Nearby Homes

Based on information from Stellar MLS® through Oct 28, 2026, 02:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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 non-commercial use. It 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 prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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