$29,000
 $156 est/mo Sourced by Back At You

9725 Chestnut Ridge Dr,WINDERMERE, FL 34786

WINDERMERE, FL 34786

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Description

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.

Details

MLS #O6436860
Listing TypeFor Lease
StyleHouse
Sub-TypeFor-lease
StatusActive
Year1999
Days On Site10
Listing Provided ByDOUGLAS ELLIMAN | Dianna Desboyaux

Features

Bed(s)7
Bath(s) 7 Total
SQ Feet8,000
Garage3
PoolYes
Story(s)2
Acreage0.56
Golf CourseYes
Water FrontYes
Property ViewGarden, Pool, Water

Area Information

StateFL
CountyOrange
CityWINDERMERE
Zip Code34786
Area34786 Windermere
Community NameISLEWORTH
School DistrictOlympia High
Elementary SchoolWindermere Elem
High SchoolOlympia High
Listing VS Median (in ISLEWORTH)
Price:
$29,000
low | high
Med:
$3,749,500
100% of Average
sqft:
8,000
low | high
Med:
4,507
93.66875% of Average
$ / sqft:
$4
low | high
Med:
$834
100% of Average
On site:
10
low | high
Med:
355.5
2.8129395218% of Average
Sourced by Back At You

Market Activity 34786

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 Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 5, 2026 at 10:42:35 PM PDT 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. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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Learn More About This Property

StateFL
CountyOrange
CityWINDERMERE
Zip Code34786
Area34786 Windermere
Community NameISLEWORTH
School DistrictOlympia High
Elementary SchoolWindermere Elem
High SchoolOlympia High
Listing VS Median (in ISLEWORTH)
Price:
$29,000
low | high
Med:
$3,749,500
100% of Average
sqft:
8,000
low | high
Med:
4,507
93.66875% of Average
$ / sqft:
$4
low | high
Med:
$834
100% of Average
On site:
10
low | high
Med:
355.5
2.8129395218% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $21K - $36K
sqft: 6,000 - 10,000
Nearby Listings Property ImageNearby Listings Details
9725 CHESTNUT RIDGE DR Property Photo 1
$5,975,000
9725 Chestnut Ridge Dr
Windermere, FL 34786
Listing Updated: August 27, 2026 at 12:08:55 AM PDT
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