Sold
Last Sold Price
4 beds11,079 sqft$643/sqft
9718 Chestnut Ridge Dr, Windermere, FL 34786
Single FamilyProperty Type
2.36 acresLot Size
2002Year Built
$643/sq ftPrice per sq ft
$863/moHOA Fees
7 carsParking Spaces

Description

New Photos & Video Added! Poised on more than two acres along the shores of Lake Bessie, this extraordinary custom estate offers a prime lakefront location in the desired Isleworth Golf & Country Club. The expansive residence boasts countless custom finishes, dynamic interiors and stunning architectural styling set against a breathtaking backdrop of sparkling lake views. Beyond the circular motor court with porte cochere, an arched and beveled solid oak entry door reveals a stunning entry foyer featuring...New Photos & Video Added! Poised on more than two acres along the shores of Lake Bessie, this extraordinary custom estate offers a prime lakefront location in the desired Isleworth Golf & Country Club. The expansive residence boasts countless custom finishes, dynamic interiors and stunning architectural styling set against a breathtaking backdrop of sparkling lake views. Beyond the circular motor court with porte cochere, an arched and beveled solid oak entry door reveals a stunning entry foyer featuring a frameless glass bay window, curved floating staircase and a stunning gallery dotted with stone columns beneath a series of beautifully crafted groin vault ceilings. Sprawling travertine floors lead to the home’s main gathering area comprised of the gourmet kitchen and dining area overlooking the sunken living room. Carved wooden cabinetry and smooth granite countertops in the kitchen complement the expansive island and luxury appliances including a large, stainless-steel Wolf range. Adjacent to the spacious dining area and nearby gallery of built-in china displays, the living room features built-in media cabinets and is crowned with exposed wooden beams. The estate boasts a gift wrapping room, three en-suite bedrooms in the main home as well as a guest apartment with a kitchenette, living room, bedroom and bath. The owner’s suite offers picturesque lake views and a stunning bathroom complete with polished travertine floors, dual vanities, a center island, a walk-in steam shower, separate spa tub and beverage refrigerator. In the expansive master closet, built-ins, a special cedar closet and a dedicated laundry room with drying station offer added convenience in this exceptional suite. Two generously sized en-suite bedrooms are located on the upper level and offer spacious baths, private closets, a laundry room and a versatile bonus room adjoining both areas that can be used as an office, study room, playroom and more. Ideal for entertaining family and friends, the estate also boasts a home theater with NuVo home audio system and Apple TV connection as well as a recreation room with a built-in bar and fabulous views of the lake. The private elevator conveniently ascends to each of the home’s three levels, including the lower level featuring multiple storage areas, an exercise room and a massive garage designed for up to seven vehicles. Featuring a separate entrance, the well-appointed custom office is outfitted with a formal reception area, conference room, bathroom and a formal office overlooking the lake. At the heart of the estate, the enclosed custom pool area brings Florida lakeside living to life with multiple lounging areas, a waterslide feature, custom firepit and built-in grill for the ultimate in outdoor entertaining. Find a lakeside paradise in the expansive grounds featuring a putting green, second firepit, breathtaking scenery and direct lake access via the private dock. At sunset, enjoy the enchanting allure of nearby theme park fireworks across the sprawling waters of Lake Bessie.
  • Listed by: Monica Lochmandy 407.230.6888 mlochmandy@isleworth.com Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
  • Listed by: Dana Rohe 407.256.5098 drohe@isleworth.com Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
Listing closed: 10/15/2021 12:00 AM • Source: MFRMLS, MLS#: O5955986

Recent comparable sales

Median sold price

$6,175,000

Avg days on market

161

Sale-to-list ratio

88.6%

Windermere, FL

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Location

Listing Courtesy of ISLEWORTH REALTY LLC, Monica Lochmandy; ISLEWORTH REALTY LLC, Dana Rohe

Sold By RE/MAX PRIME PROPERTIES, Ronald Ziolkowski

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$42,624 per month

30 year fixed, 6.55% Interest

Principal and Interest

$36,190

Property Taxes

$5,571

HOA Dues

$863

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Property Information for 9718 Chestnut Ridge Drive

Property Details
  • Taxes: $66,849 / year
  • MLS Type: Residential / Single Family Residence
  • Architectural Style: Custom, Mediterranean
  • Subdivision Name: ISLEWORTH
  • Township: 23
  • Garage Spaces: 7
  • View: Water
  • Waterfront: Yes
  • Water View: Lake
Building Information
  • Stories: 3
  • Year Built: 2002
  • Lot Size: 2.36 AC / 102,890 SF
Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 20277.0
  • Building Area Units: Square Feet
  • Community Features: Community Boat Ramp, Private Boat Ramp, Water Access, Waterfront, Association Recreation - Owned, Buyer Approval Required, Fitness Center, Gated, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Playground, Pool, Special Community Restrictions, Tennis Court(s)
  • Direction Faces: Northeast
  • Directions: I-4 to Conroy Windermere Road West to Isleworth subdivision. Take first Right on Latrobe Drive upon entering the community. Turn Right on Chestnut Ridge Drive and estate is on the Left.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Olympia High
  • Other Equipment: Generator, Intercom
  • Mls Major Change Type: Sold
  • Major Change Type: Closed
  • Listing Service: Full Service
  • Road Frontage Type: Street Dead-End, Street Paved, Private Road
  • Senior Community: No
  • Subdivision Num: 3906
  • Unit Number: No
  • Street Number: 9718
  • Street Name: CHESTNUT RIDGE
  • Street Suffix: DRIVE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized, Portico, Tandem
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
  • Association Fee Requirement: Required
  • Association Name: Diane Sparrow
  • Association Phone: 407-909-2091
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Per orange County breed restrictions, number limits and leash laws.
  • Tax Block: 00
  • Tax Book Number: 33/135
  • Tax Legal Description: See attachment
  • Tax Lot: 17
  • Tax Year: 2020
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: In County, Near Golf Course, Oversized Lot, Street Dead-End
  • Lot Size Dimensions: 348 x 453 x 138 x 150 x 615
  • Parcel Number: 162328390600010
  • Total Acreage: 2 to less than 5
  • Water Access: Lake
  • Water Access: Yes
  • Water Body Name: LAKE BESSIE
  • Water Extras: Boat Ramp - Private, Lift - Covered, Skiing Allowed
  • Water Extras: Yes
  • Water: Boat Ramp - Private, Lift - Covered, Skiing Allowed
  • Zoning: P-D
  • Living Area: 11079
  • Lot Dimensions: 348 x 453 x 138 x 150 x 615
Property and Assessments
  • Year Built Numeric: 2002
  • 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, Gated, Optional Additional Fees, Playground, Security
  • Building Elevator: Yes
  • Flood Zone Code: X / AE
  • Flood Zone Date: 09-25-2009
  • Homestead: Yes
  • New Construction: No
  • Property Attached: No
  • Property Condition: Completed
  • Public Survey Range: 28
  • Public Survey Section: 16
  • Dock Description: Dock - Composite, Dock - Covered, Dock w/Electric, Dock w/Water Supply
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Public, Street Lights, Underground Utilities, Water Connected
  • Water Source: Canal/Lake For Irrigation, Public
Interior and Exterior Features
Exterior Features
  • Builder Name: Akers Custom Homes & Architect Terry Irwin
  • Construction Materials: Block, Stucco
  • Exterior Features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Rain Gutters, Sliding Doors, Storage
  • Foundation Details: Slab
  • Levels: Three Or More
  • Patio And Porch Features: Rear Porch, Screened
  • Pool Features: Heated, Lighting, Outside Bath Access, Salt Water, Screen Enclosure, Tile
  • Pool Private: Yes
  • Pool: Private, Community
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community, Security System Owned, Smoke Detector(s)
  • Spa Features: Heated
  • Spa: Yes
  • Vegetation: Fruit Trees, Mature Landscaping, Oak Trees, Trees/Landscaped
  • Waterfront Features: Waterfront, Lake Front
  • Waterfront Feet Total: 157
  • Number Of Stories: 3
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 5
  • Additional Rooms: Bonus Room, Den/Library/Office, Family Room, Inside Utility, Interior In-Law Suite, Media Room, Storage Rooms
  • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Exhaust Fan, Freezer, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Water Softener
  • Cooling: Central Air, Zoned
  • Fireplace Features: Gas, Other Room
  • Fireplace: Yes
  • Flooring: Carpet, Travertine, Hardwood
  • Heating: Central, Electric, Zoned
  • Interior Features: Built-in Features, Ceiling Fan(s), Central Vacuum, Coffered Ceiling(s), Crown Molding, Dry Bar, Eating Space In Kitchen, Elevator, High Ceilings, In Wall Pest System, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Open Floorplan, Pest Guard System, Solid Wood Cabinets, Stone Counters, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
  • Laundry Features: Inside, In Garage, Laundry Room, Upper Level
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 11.0
  • Water View: Yes
  • Window Features: Blinds, Drapes, Insulated Windows, Rods, Shades, Shutters, Window Treatments
  • Bathrooms Half: 3
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 9718 Chestnut Ridge Drive

DateEvent & SourcePriceAppreciation
Oct 15, 2021

Sold (Public Record)

Public Record #1475047229

$7,120,000
Oct 15, 2021

Sold

MFRMLS #O5955986

$7,120,000
Sep 7, 2021

Pending

MFRMLS #O5955986

DateEvent & SourcePrice
10/15/2021

Sold (Public Record)

Public Record #1475047229

$7,120,000
10/15/2021

Sold

MFRMLS #O5955986

$7,120,000
09/07/2021

Pending

MFRMLS #O5955986

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

Public Records for 9718 Chestnut Ridge Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$113,959 ($9,497 / month)
Home Facts
Beds4Total Finished SqFt11,079 SqFtAbove Grade Finished SqFt11,079 SqFtStories3Lot Size102,890 SqFtStyleSingle Family ResidenceYear Built2002Year Renovated2010ZoningP-DCountyORANGEAPN16-23-28-3906-00-010Fireplace TypeHas Fireplace

Schools near 9718 Chestnut Ridge Drive

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 5
Charter - K to 8
Public - 6 to 8
Charter - 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

Cornerstone Charter Academy High School
Charter9 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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 9718 Chestnut Ridge Drive, Windermere, FL 34786
$7,120,000
4
11,079
102,890
$4,330,000
5
5,557
24,255
$2,350,000
3
3,494
21,787
$1,290,000
5
7
6,028
80,865
$3,500,000
5
5,164
28,154
$100
5
5.5
5,323
25,008

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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, Dana Rohe

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: 02/26/2024 10:42 PM