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.
For sale
Price cut: $800K (4/15)
$6,150,000
9725 Chestnut Ridge Dr, Windermere, FL 34786
7beds
8,000sqft
Est.:
Single Family Residence
Built in 1999
0.56 Acres Lot
$-- Zestimate®
$769/sqft
$1,043/mo HOA
What's special
Newly renovatedFull privacySix bedroomsDedicated officeSummer kitchenTaj mahal quartzite countertopsWine cellar
- 105 days |
- 1,285 |
- 52 |
Zillow last checked:
Listing updated:
Listing Provided by:
Dianna Desboyaux 407-920-4601,
DOUGLAS ELLIMAN 561-655-8600,
Adriana Morris 407-920-4600,
DOUGLAS ELLIMAN
Source: Stellar MLS,MLS#: O6370294
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Tour with a local agent
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: ENERGY STAR Qualified 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: $769/sqft
- Tax assessed value: $2,495,801
- Annual tax amount: $29,046
- Date on market: 1/2/2026
- Cumulative days on market: 105 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
| Date | Event | Price |
|---|---|---|
| 4/15/2026 | Price change | $6,150,000-11.5%$769/sqft |
Source:  Stellar MLS #O6370294 Report a problem | ||
| 1/2/2026 | Listed for sale | $6,950,000+75.1%$869/sqft |
Source: Stellar MLS #O6370294 Report a problem | ||
| 8/9/2024 | Listing removed | -- |
Source: Stellar MLS #O6192766 Report a problem | ||
| 6/28/2024 | Price change | $3,969,000-0.7%$496/sqft |
Source: Stellar MLS #O6192766 Report a problem | ||
| 5/1/2024 | Price change | $3,995,000-7.8%$499/sqft |
Source: Stellar MLS #O6192766 Report a problem | ||
| 4/5/2024 | Listed for sale | $4,335,000+8.5%$542/sqft |
Source: Stellar MLS #O6192766 Report a problem | ||
| 1/11/2024 | Listing removed | -- |
Source: Stellar MLS #O6128678 Report a problem | ||
| 10/10/2023 | Price change | $3,995,000-6%$499/sqft |
Source: Stellar MLS #O6128678 Report a problem | ||
| 7/25/2023 | Listed for sale | $4,249,000-1.2%$531/sqft |
Source: Stellar MLS #O6128678 Report a problem | ||
| 7/18/2023 | Listing removed | -- |
Source: Stellar MLS #S5085670 Report a problem | ||
| 5/30/2023 | Listed for sale | $4,299,000$537/sqft |
Source: Stellar MLS #S5085670 Report a problem | ||
| 5/16/2023 | Listing removed | -- |
Source: Stellar MLS #O6098611 Report a problem | ||
| 5/3/2023 | Price change | $4,299,000-2.3%$537/sqft |
Source: Stellar MLS #O6098611 Report a problem | ||
| 3/27/2023 | Listed for sale | $4,399,000+282.5%$550/sqft |
Source: Stellar MLS #O6098611 Report a problem | ||
| 11/9/1999 | Sold | $1,150,000+318.2%$144/sqft |
Source: Public Record Report a problem | ||
| 10/2/1998 | Sold | $275,000$34/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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
$42,596/mo
Principal & interest
$30637
Property taxes
$10916
HOA Fees
$1043
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Climate risks
Neighborhood: 34786
Nearby schools
GreatSchools rating
- 10/10Windermere Elementary SchoolGrades: PK-5Distance: 1.7 mi
- 3/10Chain Of Lakes Middle SchoolGrades: 6-8Distance: 1.1 mi
- 5/10Olympia High SchoolGrades: 9-12Distance: 1 mi
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.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Windermere
- 34786
- 9725 Chestnut Ridge Dr
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