9725 Chestnut Ridge Dr, photo 1
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Overview

7 bd7 ba8,000 sqft3 car garageSingle Family
TypeSingle Family
HOA$3,129/qtr
Built1999
Lot24,349 sqft
Living area8,000 sqft
Price / sqft$747
Garage3 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Built-in FeaturesCeiling Fans(s)ElevatorHigh CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main Floor

9725 Chestnut Ridge Dr is a 1999-built home in Isleworth, Windermere. Inside you'll find 7 bedrooms, 7 bathrooms, and 8,000 square feet of living space. Listed at $5,975,000 (about $747/sqft), 285 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $3,129 quarterly.

From the listing

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.

The essentials

Built
1999
Price / sqft
$747
On market
285 days
Annual tax
$29,046
HOA
$3,129/qtr
Flood zone
X · Low risk
Lot
24,349 sqft
Type
Single Family Residence

At a glance

Single family
Built 1999
Waterfront
Pond
Private pool
Heated
3 car garage
Driveway
0.56 acres
Lot size

Payment

Est. monthly payment
$37,613/mo
Down payment (20%)
$1,195,000
Property taxes
$2,421/mo
HOA
$3,129/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1999
Lot
24,349 sqft
Cooling
Central Air, Zoned
Heating
Central
Parking
Driveway, Garage Faces Side
Pool
Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
Waterfront
Pond
Days on Market
285
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
Fire Pit
Outdoor Kitchen
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)
Bar Fridge
Built-in Oven
Dishwasher
Disposal
Dryer
Exhaust Fan
Freezer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Washer
Elementary
Windermere Elem
Middle
Chain of Lakes Middle
High
Olympia High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2024)
$29,046
Parcel #
16-23-28-3899-00-060

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Isleworth
County
Orange
MLS Area
34786 - Windermere
Lot Size
24,349 sqft
LandscapedNear Golf CoursePaved
HOA
$3,129/qtr
Dan O'Connell

Price history

Date
Event
Price
8/22/2026
Price change
Source: Stellar MLS #O6370294
$5,975,000-0.4%
$747/sqft
-
Price change
Source: Stellar MLS #O6370294
$6,000,000-13.7%
$750/sqft
1/2/2026
Listed for sale
Source: Stellar MLS #O6370294
$6,950,000
$869/sqft

Neighborhood

9725 Chestnut Ridge Dr
Windermere, FL, 34786 · 34786 - Windermere

Market insights

Offer Insights

Choose an offer strength

List price: $5,975,000
$5.88M – $5.97M
98.4% – 100% of listTops out right at the list price
80% of listList price
152 of the last 302 home closings in 34786 landed at this number or higher (50%). The median one sat 31 days before it went under contract, and this one is on day 285 after a $975,000 cut.

Sample: 302 closed home sales in 34786 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$37,613/mo
Principal & interest$31,162
Property taxes$2,421
Insurance$2,988
HOA$1,043
Down payment20% · $1,195,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$5,975,000

$747 per sq ft

Beds and baths

7 beds, 7 baths

Size

8,000 sq ft

Time on market

285 days

Year built

1999

Monthly payment

About $37,613/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $29,046 annual tax bill, insurance, and the $3,129/qtr HOA fee.

HOA fee

$3,129/qtr

Managed by Dan O'Connell.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byDOUGLAS ELLIMANListing agent: Dianna DesboyauxListing data from Stellar MLS, MLS# O6370294.

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