9725 Chestnut Ridge Dr Windermere, FL 34786
Lake Tibet NeighborhoodEstimated payment $36,273/month
Highlights
- 113 Feet of Pond Waterfront
- Golf Course Community
- Heated Indoor Pool
- Windermere Elementary School Rated A
- Fitness Center
- Media Room
About This Home
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.
Listing Agent
DOUGLAS ELLIMAN Brokerage Phone: 305-695-6070 License #3311098 Listed on: 01/02/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $29,046
Year Built
- Built in 1999
Lot Details
- 24,349 Sq Ft Lot
- 113 Feet of Pond Waterfront
- West Facing Home
- Mature Landscaping
- Landscaped with Trees
- Property is zoned P-D
HOA Fees
- $1,043 Monthly HOA Fees
Parking
- 3 Car Attached Garage
- Side Facing Garage
- Driveway
Property Views
- Pond
- Garden
- Pool
Home Design
- Slab Foundation
- Tile Roof
- Block Exterior
- Stucco
Interior Spaces
- 8,000 Sq Ft Home
- 2-Story Property
- Open Floorplan
- Wet Bar
- Built-In Features
- Bar Fridge
- High Ceiling
- Ceiling Fan
- Skylights
- Gas Fireplace
- ENERGY STAR Qualified Windows
- Family Room Off Kitchen
- Living Room with Fireplace
- Media Room
- Den
- Fire and Smoke Detector
Kitchen
- Breakfast Bar
- Built-In Oven
- Range with Range Hood
- Recirculated Exhaust Fan
- Microwave
- Freezer
- Ice Maker
- Dishwasher
- Wolf Appliances
- Stone Countertops
- Disposal
Flooring
- Wood
- Tile
- Travertine
Bedrooms and Bathrooms
- 7 Bedrooms
- Primary Bedroom on Main
- Fireplace in Primary Bedroom
- Split Bedroom Floorplan
- Walk-In Closet
- In-Law or Guest Suite
- Soaking Tub
Laundry
- Laundry Room
- Dryer
- Washer
Pool
- Heated Indoor Pool
- Screened Pool
- Heated Lap Pool
- Heated In Ground Pool
- Heated Spa
- In Ground Spa
- Fence Around Pool
- Outside Bathroom Access
- Pool Tile
Outdoor Features
- Access To Pond
- Access To Chain Of Lakes
- Enclosed Patio or Porch
- Outdoor Kitchen
- Fire Pit
Location
- Property is near golf course
Schools
- Windermere Elementary School
- Chain Of Lakes Middle School
- Olympia High School
Utilities
- Zoned Heating and Cooling
- Thermostat
- Septic Tank
Listing and Financial Details
- Visit Down Payment Resource Website
- Tax Lot 6
- Assessor Parcel Number 16-23-28-3899-00-060
Community Details
Overview
- Association fees include 24-Hour Guard, pool, ground maintenance, management, security
- Dan O'connell Association, Phone Number (407) 909-2071
- Isleworth Subdivision
- On-Site Maintenance
- The community has rules related to allowable golf cart usage in the community, no truck, recreational vehicles, or motorcycle parking
Amenities
- Restaurant
- Sauna
- Clubhouse
- Community Storage Space
- Elevator
Recreation
- Golf Course Community
- Tennis Courts
- Pickleball Courts
- Racquetball
- Recreation Facilities
- Community Playground
- Fitness Center
- Community Pool
- Community Spa
- Park
Security
- Security Guard
- Gated Community
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $42,817 | $2,555,390 | $725,000 | $1,830,390 |
| 2025 | $42,817 | $2,588,050 | $725,000 | $1,863,050 |
| 2024 | $27,092 | $2,502,090 | $725,000 | $1,777,090 |
| 2023 | $27,092 | $1,740,289 | $0 | $0 |
| 2022 | $26,331 | $1,689,601 | $0 | $0 |
| 2021 | $26,031 | $1,640,389 | $475,000 | $1,165,389 |
| 2020 | $24,860 | $1,619,460 | $0 | $0 |
| 2019 | $25,701 | $1,583,050 | $0 | $0 |
| 2018 | $25,526 | $1,553,533 | $0 | $0 |
| 2017 | $25,262 | $1,605,397 | $475,000 | $1,130,397 |
| 2016 | $25,243 | $1,574,569 | $475,000 | $1,099,569 |
| 2015 | $25,691 | $1,540,282 | $475,000 | $1,065,282 |
| 2014 | $25,929 | $1,468,180 | $425,000 | $1,043,180 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/26/2026 08/26/26 | For Rent | $29,000 | 0.0% | -- |
| 08/22/2026 08/22/26 | Price Changed | $5,975,000 | -0.4% | $747 / Sq Ft |
| 05/02/2026 05/02/26 | Price Changed | $6,000,000 | -2.4% | $750 / Sq Ft |
| 04/15/2026 04/15/26 | Price Changed | $6,150,000 | -11.5% | $769 / Sq Ft |
| 01/02/2026 01/02/26 | For Sale | $6,950,000 | -- | $869 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $3,100,000 | None Listed On Document | |
| Warranty Deed | $1,150,000 | -- | |
| Warranty Deed | $275,000 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $2,170,000 | New Conventional | |
| Previous Owner | $1,500,000 | New Conventional | |
| Previous Owner | $1,000,000 | Adjustable Rate Mortgage/ARM |
Source: Stellar MLS
MLS Number: O6370294
APN: 16-2328-3899-00-060
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
- 5073 Latrobe Dr
- 1009 Down Reserve Ct
- 5074 Isleworth Country Club Dr
- 4812 Alexandra Garden Ct
- 5070 Down Point Ln
- 5145 Latrobe Dr
- 4819 Alexandra Garden Ct
- 5151 Latrobe Dr
- 4906 Aviva Garden Ct
- 436 E 7th Ave
- 5199 Latrobe Dr
- 9433 Palm Tree Dr
- 930 East Blvd
- 9319 Woodbreeze Blvd
- 9144 Isleworth Gardens Dr
- 715 Magnolia St
- 4301 Down Point Ln
- 9316 Gladys Garden Ct
- 9237 Sabal Palm Cir
- 9323 Gladys Garden Ct
- 9508 Pine Terrace Ct
- 6119 Payne Stewart Dr
- 8644 Sandberry Blvd
- 5554 Palm Lake Cir
- 5150 Vistamere Ct
- 7560 Blue Quail Ln
- 5927 Caymus Loop
- 8516 Cedar Cove Ct
- 6260 Morning Mist Ln
- 8021 Sandberry Blvd
- 5212 Abelia Dr
- 5212 Abelia Dr
- 2521 Roat Dr
- 8334 Crosswicks Dr
- 7460 Park Springs Cir
- 7830 Saint Andrews Cir
- 7830 St Andrews Cir
- 4500 S Hiawassee Rd
- 1243 Dingens Ave
- 7600 Debeaubien Dr
Ask me questions while you tour the home.