9725 Chestnut Ridge Dr

Windermere, FL 34786

$6,950,000
Price
7
Beds
8,000 Sq. Ft.
$869 / Sq. Ft.
8,000
Sq. Ft.
$869
per Sq. Ft.
Virtual TourNew
Virtual TourNew
a view of a lake with houses in the back
a living room with furniture potted plant and a fireplace
a living room with furniture a fireplace and a chandelier
a living room with furniture and a large mirror
a view of a dining room with furniture and wooden floor
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a kitchen with stainless steel appliances granite countertop a sink a stove and a wooden floors
a bathroom with a double vanity sink a mirror and a shower
a view of walk in closet with clothes and shoes
a bathroom with a granite countertop sink toilet and shower
a view of an empty room with a window and wooden floor
an empty room with wooden floor closet and windows
a view of an empty room with a ceiling fan and wooden floor
a view of an empty room with wooden floor and a window
a view of a house with a yard and plant
an aerial view of a houses with a lake

Description

Private showings are easily accommodated, including same-day requests. Newly renovated and fully turnkey, 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,...Private showings are easily accommodated, including same-day requests. Newly renovated and fully turnkey, 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.
  1. Listed by Dianna Desboyaux • Brokerage DRE #1020232 • DOUGLAS ELLIMAN
    P: (407)-920-4601 C: (407)-920-4601 diannadesboyaux@gmail.com

Property Details for 9725 Chestnut Ridge Drive

Subdivision Name
ISLEWORTH
Township
23
Garage Spaces
3
View
Garden, Pool, Water
Waterfront
Yes
Water View
Pond
Furnished
Furnished
LISTING UPDATED: 01/02/2026 07:11 AM

Property Details for 9725 Chestnut Ridge Drive

StatusActive
MLS #O6370294
Days on MarketListed Today
Taxes$29,046 / year
HOA Fees$12,516 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1999
Lot Size0.56 AC / 24,349 SF
CountyOrange County

Location

Listing Courtesy of DOUGLAS ELLIMAN, Dianna Desboyaux
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Building Information for 9725 Chestnut Ridge Drive

Stories2Year Built1999Building Size-Lot Size0.56 AC / 24,349 SF

Payment Calculator

$37,806 per month

30 year fixed, 6.28% Interest

Principal and Interest

$34,342

Property Taxes

$2,421

HOA Dues

$1,043

The Payment Calculator is for illustrative purposes only.

Property Information for 9725 Chestnut Ridge Drive

Summary
Location and General Information
  • Building Area Source: Builder
  • Building Area Total: 11952.0
  • Building Area Units: Square Feet
  • 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)
  • Direction Faces: West
  • Directions: I-4 to Conroy Windermere Road west to Isleworth Golf and Country Club which will be on the left, turn right onto Latrobe Drive and next right onto Chestnut Ridge Drive, the home will be situated on the right.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Olympia High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 9725
  • Street Name: CHESTNUT RIDGE
  • Street Suffix: DRIVE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Driveway, Garage Faces Side
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Community Pool, Maintenance Grounds, Manager, Pool Maintenance, Security
  • Association Fee Requirement: Required
  • Association Name: Dan O'Connell
  • Association Phone: 407-909-2071
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Please call the association
  • Tax Block: 00
  • Tax Book Number: 16-118
  • Tax Legal Description: ISLEWORTH 16/118 LOT 6 & BEG NW COR OF SAID LOT 6 TH S 63 DEG E 85 FT N 76 DEG E39.14 FT N 63 DEG W 113.43 FT S 30 DEGW 25.29 FT TO POB & BEG AT WLY MOST COROF LOT 4 TH N33-00-00E ALONG WLY LINE OFLOT 4 10.06 FT TH N63-04-56W 133.88 FTTH S30-16-40W 1 0.02 FT TO NELY LINE OF LANDS DESC IN 5925/4062 TH S63-04-56E 133.40 FT TO POB
  • Tax Lot: 6
  • Tax Year: 2024
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Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Landscaped, Near Golf Course
  • Parcel Number: 162328389900060
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake - Chain of Lakes, Pond
  • Water Access: Yes
  • Water Extras: No
  • Zoning: P-D
  • Living Area: 8000
Property and Assessments
  • Year Built Numeric: 1999
  • 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.
  • Association 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)
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0385F
  • Homestead: No
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 16
  • Dock Description: Clubhouse
Utilities
  • Sewer: Septic Tank
  • Utilities: Electricity Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: Fire Pit, French Doors, Outdoor Kitchen
  • Foundation Details: Slab
  • Levels: Three Or More
  • Patio And Porch Features: Covered, Enclosed, Rear Porch, Screened
  • Pool Features: Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
  • Pool Private: Yes
  • Pool: Private, Community
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community, Smoke Detector(s)
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Features: Waterfront, Pond
  • Waterfront Feet Total: 113
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 7
  • Bathrooms Full: 5
  • Additional Rooms: Den/Library/Office, Family Room, Formal Living Room Separate, Interior In-Law Suite w/Private Entry, Media Room
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
  • Cooling: Central Air, Zoned
  • Fireplace Features: Gas, Living Room, Master Bedroom
  • Fireplace: Yes
  • Flooring: Porcelain Tile, Travertine, Hardwood
  • Heating: Central
  • 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
  • Laundry Features: Laundry Room
  • Living Area Source: Builder
  • Living Area Units: Square Feet
  • Room Count: 5.0
  • Water View: Yes
  • Window Features: ENERGY STAR Qualified Windows
  • Bathrooms Half: 2
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 9725 Chestnut Ridge Drive

DateEvent & SourcePriceAppreciation
Jan 2, 2026

Listed (Active)

MFRMLS #O6370294

$6,950,000—
Dec 6, 2024

Sold (Public Record)

Public Record #1546609458

$3,100,000—
Aug 10, 2024

Withdrawn

MFRMLS #O6192766

$3,969,000—
Apr 5, 2024

Listed (Active)

MFRMLS #O6192766

$4,335,000—
Jan 11, 2024

Withdrawn

MFRMLS #O6128678

$3,995,000—
Jul 25, 2023

Listed (Active)

MFRMLS #O6128678

$4,249,000—
Jul 18, 2023

Withdrawn

MFRMLS #S5085670

$4,299,000—
May 30, 2023

Listed (Active)

MFRMLS #S5085670

$4,299,000—
May 16, 2023

Withdrawn

MFRMLS #O6098611

$4,299,000—
Mar 27, 2023

Listed (Active)

MFRMLS #O6098611

$4,399,000—
DateEvent & SourcePrice
01/02/2026

Listed (Active)

MFRMLS #O6370294

$6,950,000
12/06/2024

Sold (Public Record)

Public Record #1546609458

$3,100,000
08/10/2024

Withdrawn

MFRMLS #O6192766

$3,969,000
04/05/2024

Listed (Active)

MFRMLS #O6192766

$4,335,000
01/11/2024

Withdrawn

MFRMLS #O6128678

$3,995,000
07/25/2023

Listed (Active)

MFRMLS #O6128678

$4,249,000
07/18/2023

Withdrawn

MFRMLS #S5085670

$4,299,000
05/30/2023

Listed (Active)

MFRMLS #S5085670

$4,299,000
05/16/2023

Withdrawn

MFRMLS #O6098611

$4,299,000
03/27/2023

Listed (Active)

MFRMLS #O6098611

$4,399,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 9725 Chestnut Ridge Drive

Taxable ValueLand$725,000Additions$1,863,050Total$2,588,050
Tax Record2024$29,046 ($2,421 / month)
Home Facts
Beds5Total Finished SqFt6,885 SqFtAbove Grade Finished SqFt6,885 SqFtStories2Lot Size25,685 SqFtStyleSingle Family ResidenceYear Built1999ZoningP-DCountyORANGEAPN16-23-28-3899-00-060Fireplace TypeHas Fireplace

Schools near 9725 Chestnut Ridge Drive

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Chain Of Lakes Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Chain Of Lakes Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 9725 Chestnut Ridge Drive, Windermere, FL 34786

9725 Chestnut Ridge Drive is a single family home for sale in Windermere, FL 34786. This property was listed for sale on January 2, 2026 by DOUGLAS ELLIMAN, it's currently listed at $6,950,000. It has been on the market for a total of 0 days and was last sold on December 6, 2024. This listing's school district is Orange County Public Schools. Nearby schools include Windermere Elementary School, Cornerstone Academy Charter and Chain Of Lakes Middle School. 9725 Chestnut Ridge Drive is a 7-bed, 7-bath, 8,000 sqft single family home built in 1999.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of DOUGLAS ELLIMAN, Dianna Desboyaux

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 01/02/2026 07:11 AM