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$29,000

9725 Chestnut Ridge Drive

Windermere, FL 34786

Listing updated: August 27, 2026 at 1:01 AM ET

Active

Listing courtesy of Douglas Elliman · Dianna Desboyaux · MLS #O6436860 · Active · 561-655-8600

Beds

Baths

8,000

Sq Ft

0.56

Acres

1999

Built

◆Waterfront◆Water access◆Private pool◆Fireplace◆3-car garage◆$4/sqft◆360° tour

Single Family Residence

Property type

1999

Year built

24,349 sqft

Lot size

Price / sq ft

No HOA

HOA dues

Days on market

Garage spaces

Flood zone

About this home

A rare opportunity to lease a beautifully renovated residence within Isleworth, offering exceptional space, privacy, comfort, and an elevated Central Florida lifestyle. Newly renovated and exceptionally private, this sophisticated Isleworth residence offers approximately 8,000 square feet of beautifully designed living space, combining refined luxury with the comfort and functionality of an exceptional home. Rich walnut cabinetry and custom wood detailing bring warmth and character throughout, while elegant living spaces, a fireplace, and wine cellar create an inviting setting for both everyday living and entertaining. At the heart of the home, the impressive chef’s kitchen features Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, steam oven, dual dishwashers, and a discreet hidden pantry. Two separate laundry areas add convenience for a residence of this scale. The flexible floor plan includes six bedrooms, a dedicated office, and a bonus room with a closet that may serve as an additional bedroom, guest suite, fitness room, or private retreat. Five full and two half baths are beautifully finished with a calm, contemporary aesthetic, while an elevator provides effortless access between levels. Outdoors, complete privacy and peaceful pond views create a wonderful sense of retreat. A gas-heated pool and spa, expansive outdoor living areas, and summer kitchen provide an ideal setting for relaxing, dining, and entertaining year-round. The residence also features four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors. Private showings are easily accommodated, including same-day requests.

Estimated monthly payment

Principal & interest$147

Property taxes$27

Home insurance (est.)$13

Down payment

20%

$5,800 downRate

6.5%

Term

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

Status: Active
Aug 26, 2026
Listed$29,000
Aug 26, 2026
Price increased$29,000

Facts & features

Property type: Residential Lease
Sub type: Single Family Residence
Status: Active
Days on market: 0
Subdivision: Isleworth
County: Orange
Year built: 1999
Living area: 8,000 sq ft
Price/sq ft: $4
Building area: 11,952 sq ft (Builder)
Lot size: 24,349 sq ft
Flood zone: X (12095C0385F)
Garage: 3 spaces
Pool: Private pool
Parcel #: 16-23-28-3899-00-060
MLS #: O6436860

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Interior Details

Bedrooms: 7
Full bathrooms: 5
Half bathrooms: 2
Flooring: Tile, Travertine, Wood
Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
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
Laundry: Laundry Room
Stories / Levels: Three Or More
Direction faces: West
Fireplace: Yes

Heating & Cooling

Heating: Central
Cooling: Central Air, Zoned

Parking

Garage spaces: 3
Attached garage: Yes
Parking features: Driveway, Garage Faces Side

HOA & Financial

Total monthly fees: $0/mo
Total annual fees: $0
HOA name: Dan O'Connell
Min lease term: 8-12 Months

Exterior & Construction

Exterior features: Fire Pit, Outdoor Kitchen
Pool: Private pool
Waterfront: Yes
Water access: Yes
Water view: Yes
Road surface: Asphalt

Utilities

Sewer: Septic Tank
Water source: Public
Utilities: Electricity Connected, Water Connected

Community

Pets allowed: Yes

Schools

ElementaryAWindermere ElemGreatSchools ↗

MiddleCChain of Lakes MiddleGreatSchools ↗

High SchoolAOlympia HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

Room	Level	Dimensions
Family Room	First	21x21
Kitchen	First	20x16
Dining Room	First	20x15
Living Room	First	20x13
Primary Bedroom	First

Listing Details

Listing date: 2026-08-26
On market date: 2026-08-26
Original list price: $29,000
Occupant type: Vacant
MLS area: 34786 - Windermere
Listing AOR: Orlando Regional
Status changed: 2026-08-26

Flood risk

Minimal riskFEMA Zone XPanel 12095C0385F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

Property sale history

Public records

9725 CHESTNUT RIDGE DR, Windermere 34786

Dec 2024$3,100,000

8,000 sq ft · Built 1999 · 0.5896 acres

Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.

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IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of August 27, 2026 at 1:01 AM ET. 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.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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