9731 Chestnut Ridge Dr

Windermere, FL 34786

$3,400,000
Price
4
Beds
4,877 Sq. Ft.
$697 / Sq. Ft.
4,877
Sq. Ft.
$697
per Sq. Ft.
a front view of a house with a yard
a swimming pool with outdoor seating yard and yard
a view of a house with a swimming pool and a yard
a front view of a house with garden
a front view of a house with garden
a living room with furniture and a large window
a living room with furniture and a chandelier
a view of a dining room with furniture window and outside view
a dining room with furniture a chandelier and window
a kitchen with stainless steel appliances granite countertop a stove refrigerator and cabinets
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a view of a dining room with furniture window and outside view
a view of a dining room with furniture window and outside view
a dining room with furniture a chandelier and window
a kitchen with stainless steel appliances granite countertop a sink a stove and a wooden floors
a living room with furniture and a wooden floor
a living room with furniture and large windows
a living room with furniture and a flat screen tv
a bedroom with a bed and a flat screen television
a view of a room with a window and deck
a bedroom with a bed and a flat screen tv
a living room with furniture and a window
a bathroom with a tub shower sink and mirror
a bath tub sitting next to a window
a bathroom with a tub sink shower and mirror
a living room with furniture a window and bookshelf
a bedroom with a bed and a large window
a bedroom with a large bed and a large window
a bathroom with a granite countertop sink a toilet a mirror and shower
a bedroom with a bed chandelier and window
a bedroom with a bed and a chandelier
a bathroom with a sink toilet and shower
a bedroom with furniture and a window
a living room with furniture and a window
a bedroom with a bed and wooden floor
a hallway with front door windows and stairs
a kitchen with stainless steel appliances granite countertop a stove and a sink
a view of a livingroom with workspace
a kitchen with a sink and cabinets
an aerial view of a house with a garden
a view of a yard in front of house
an aerial view of a houses with outdoor space and lake view
a view of a house with backyard sitting area and garden
a view of a house with backyard and sitting area
a view of lake from a balcony
a view of a house with backyard sitting area and garden
a view of a garden with large trees
a view of a house with a swimming pool
a swimming pool with outdoor seating and yard
an aerial view of a house with swimming pool

Description

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a...Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.
  1. Listed by Monica Lochmandy • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-230-6888 C: (407)-230-6888 mlochmandy@isleworth.com
  2. Listed by Michelle Corbin • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-491-2690 C: (407)-491-2690 michelle.corbin@isleworth.com

Property Details for 9731 Chestnut Ridge Drive

Subdivision Name
ISLEWORTH
Township
23
Garage Spaces
2
View
Pool
Waterfront
No
LISTING UPDATED: 08/17/2025 06:50 AM

Property Details for 9731 Chestnut Ridge Drive

StatusActive
MLS #O6336655
Days on Market139
Taxes$19,867 / year
HOA Fees$12,516 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1986
Lot Size0.54 AC / 23,624 SF
CountyOrange County

Location

Listing Courtesy of ISLEWORTH REALTY LLC, Monica Lochmandy; ISLEWORTH REALTY LLC, Michelle Corbin
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Building Information for 9731 Chestnut Ridge Drive

Stories2Year Built1986Building Size-Lot Size0.54 AC / 23,624 SF

Payment Calculator

$19,499 per month

30 year fixed, 6.28% Interest

Principal and Interest

$16,801

Property Taxes

$1,656

HOA Dues

$1,043

The Payment Calculator is for illustrative purposes only.

Property Information for 9731 Chestnut Ridge Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 6151.0
  • Building Area Units: Square Feet
  • Community Features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - No Guard, Golf Carts OK, Golf, Playground
  • Direction Faces: Northeast
  • Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Turn right on Latrobe, turn right on Chestnut Ridge Drive. Estate will be on the Right.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Olympia High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 9731
  • Street Name: CHESTNUT RIDGE
  • Street Suffix: DRIVE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Golf Cart Garage
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
  • Association Fee Requirement: Required
  • Association Name: Dan O'Connell
  • Association Phone: 407-909-2071
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
  • Tax Block: 3899
  • Tax Book Number: 16-118
  • Tax Legal Description: ISLEWORTH 16/118 LOT 7
  • Tax Lot: 7
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Additional Water Information: The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
  • Lot Features: Landscaped, Near Golf Course
  • Parcel Number: 162328389900070
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE BUTLER CHAIN OF LAKES
  • Water Extras: No
  • Zoning: P-D
  • Living Area: 4877
Property and Assessments
  • Year Built Numeric: 1986
  • Amenities Additional Fees: Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
  • Association Amenities: Cable TV, Playground, Security
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0385F
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 16
  • Dock YN: No
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Street Lights, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: Balcony, Irrigation System, Outdoor Grill, Rain Gutters
  • Foundation Details: Block, Slab
  • Levels: Two
  • Pool Features: Heated, In Ground, Lighting, Self Cleaning
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community, Security Lights, Security System, Smoke Detector(s)
  • Spa Features: Heated, In Ground
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 4
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Trash Compactor, Washer, Water Filtration System, Water Purifier, Water Softener
  • Cooling: Central Air, Zoned
  • Fireplace: No
  • Flooring: Marble, Travertine
  • Heating: Central, Electric, Natural Gas
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 10.0
  • Water View: No
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Breed Restrictions

Property History for 9731 Chestnut Ridge Drive

DateEvent & SourcePriceAppreciation
Aug 16, 2025

Listed (Active)

MFRMLS #O6336655

$3,400,000—
Feb 10, 2021

Sold (Public Record)

Public Record #690703047

$1,170,000

-0.6% / yr

Nov 8, 2016

Expired

MFRMLS #O5415241

$1,590,000—
Jan 19, 2016

Listed (Active)

MFRMLS #O5415241

$1,590,000—
Feb 12, 2010

Sold (Public Record)

Public Record #283320483

$1,250,000—
Feb 12, 2010

Sold

MFRMLS #O4864044

$1,250,000—
Feb 2, 2010

Pending

MFRMLS #O4864044

—
Apr 24, 2009

Listed (Active)

MFRMLS #O4864044

$2,999,000—
DateEvent & SourcePrice
08/16/2025

Listed (Active)

MFRMLS #O6336655

$3,400,000
02/10/2021

Sold (Public Record)

Public Record #690703047

$1,170,000

-0.6% / yr

11/08/2016

Expired

MFRMLS #O5415241

$1,590,000
01/19/2016

Listed (Active)

MFRMLS #O5415241

$1,590,000
02/12/2010

Sold (Public Record)

Public Record #283320483

$1,250,000
02/12/2010

Sold

MFRMLS #O4864044

$1,250,000
02/02/2010

Pending

MFRMLS #O4864044

—
04/24/2009

Listed (Active)

MFRMLS #O4864044

$2,999,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 9731 Chestnut Ridge Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$19,867 ($1,656 / month)
Home Facts
Beds4Total Finished SqFt4,877 SqFtAbove Grade Finished SqFt4,877 SqFtStories2Lot Size23,624 SqFtStyleSingle Family ResidenceYear Built1986Year Renovated1990ZoningP-DCountyORANGEAPN16-23-28-3899-00-070

Schools near 9731 Chestnut Ridge Drive

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Chain Of Lakes Middle School
Public - 6 to 8
Olympia High School
Public - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Chain Of Lakes Middle School
Public6 to 8

Olympia High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 9731 Chestnut Ridge Drive, Windermere, FL 34786

9731 Chestnut Ridge Drive is a single family home for sale in Windermere, FL 34786. This property was listed for sale on August 16, 2025 by ISLEWORTH REALTY LLC, it's currently listed at $3,400,000. It has been on the market for a total of 139 days and was last sold on February 10, 2021. This listing's school district is Orange County Public Schools. Nearby schools include Windermere Elementary School, Cornerstone Academy Charter and Chain Of Lakes Middle School. 9731 Chestnut Ridge Drive is a 4-bed, 4-bath, 4,877 sqft single family home built in 1986.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of ISLEWORTH REALTY LLC, Monica Lochmandy; ISLEWORTH REALTY LLC, Michelle Corbin

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 08/17/2025 06:50 AM