9730 Chestnut Ridge Dr, Windermere, FL 34786

Off Market Oct 2016 for $3.5M

$6,836,222

Est. refi paymentEst. refi $23,323/mo

•

5,164

sq ft

9730 Chestnut Ridge Dr, Windermere, FL 34786

About this home

Rare Find! NEW 5 bed/5 bath European-inspired transitional home w/ picturesque lake frontage in Isleworth. Stripped down to four walls and a slab, this custom masterpiece was re-built w/ state-of-the-art technology, open floorplan & a contemporary design without sacrificing ‘warmth’ of a home. Upon entry you are immediately greeted by wall-to-wall unobstructed views over Lake Bessie & openness that has to be seen to appreciate. Modern design includes linear tray & false ceilings, 24” porcelain floors, custom moldings, sleek cabinetry & fixtures, & chic glass-front gas fireplace. Equipped w/ home automation, enjoy the power of complete control of media, changeable LED accent lighting, shades, cameras & many other hidden features from your tablet. The home is centered around the living spaces & lake front views w/ the kitchen, formal rooms and family room all unimpeded by walls. Large kitchen boasts induction & gas stoves, 2 refrigerators, wine cooler, and bar seating. Master suite has a large walk-in closet, multiple wardrobes, a private patio looking over the lake, and a bath with dual sinks, walk-in shower and soaking tub. The outdoor living is superb with covered & uncovered areas that can be separated by electric screens & shades for privacy or opened up for entertaining or taking in views of the lake, golf course, & fireworks. The pit-master will appreciate a full outdoor kitchen with grill, sinks, refrigerators and bar seating, as everyone can enjoy the sandy beach, covered dock and sparkling pool.

Single-familyProperty Type

1995Year Built

0.65 acresLot Size

$1,324Est. Price/Sq.Ft.

2 car garageParking

Listed by Frank Del Toro • SUZI KARR REALTY

Listed by Chris Sapp • SUZI KARR REALTY

Bought with Dawn Calo • ALLISON JAMES ESTATES & HOMES

Redfin checked: a minute ago

•Source:Stellar MLS as Distributed by MLS Grid #O5439585

Redfin Estimate

$6,836,222

$3.3M since sold in October 2016$360K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 138.5% higher than the average sale price ($2.87M) of 6 comparable homes.

SOLD JUL 15, 2026
$4,350,000
A
5 beds4.5 baths5,548 sq ft
5036 Latrobe Dr, Windermere, FL 34786
SOLD JUL 31, 2026
$2,200,000
B
5 beds4.5 baths4,284 sq ft
81 Oakdale St, Windermere, FL 34786
SOLD MAR 9, 2026
$2,250,000
C
5 beds4.5 baths4,688 sq ft
409 W 2nd Ave, Windermere, FL 34786
SOLD MAY 22, 2026
$1,175,000
D
4 beds4.5 baths3,831 sq ft
3138 Seigneury Dr, Windermere, FL 34786
SOLD OCT 31, 2025
$2,750,000
E
5 beds7 baths6,219 sq ft
5067 Latrobe Dr, Windermere, FL 34786
SOLD MAR 25, 2026
$4,475,000
F
6 beds5.5 baths5,853 sq ft
6474 Deacon Cir, Windermere, FL 34786

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Earn from this home

Sell

$4,232,738

Est. take-home

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Est. cash available

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Rent

$5,006/mo

Redfin rental estimate

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Market trends in 34786, FL

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

96.1%

0.3% MoM

Median sale price

$872K

$40K MoM

Avg. days on market

37d

4 days MoM

Recently sold homes

216

11 MoM

New listings for sale

NEW 17 HRS AGO
$647,000
3 beds2.5 baths2,229 sq ft
7033 Bramlea Ln, Windermere, FL 34786
$3,400,000
4 beds3.5 baths3,872 sq ft
5379 Isleworth Country Club Dr, Windermere, FL 34786
COMING SOON
$1,395,000
5 beds4 baths4,186 sq ft
101 Lee St, Windermere, FL 34786
$759,000
4 beds3.5 baths2,886 sq ft
8104 Jailene Dr, Windermere, FL 34786
$399,000
3 beds2.5 baths1,651 sq ft
14077 Ancilla Blvd, Windermere, FL 34786
OPEN SAT, 11AM TO 2PM
$1,399,900
5 beds3 baths3,356 sq ft
2540 Hempel Cove Ct, Windermere, FL 34786
$445,000
3 beds2.5 baths1,748 sq ft
13048 Garridan Ave, Windermere, FL 34786
$1,500,000
5 beds6.5 baths5,312 sq ft
13503 Lake Cawood Dr, Windermere, FL 34786
HOT HOME
$710,999
4 beds3.5 baths2,745 sq ft
13239 Jervey St, Windermere, FL 34786
$2,500,000
5 beds4 baths4,661 sq ft
5526 Marleon Dr, Windermere, FL 34786
See all

Provided by Redfin

Sale history for 9730 Chestnut Ridge Dr

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O5439585

Oct 28, 2016

Sold

$3,500,000

$678/sq ft

Sep 8, 2016

Pending

—

May 13, 2016

Listed

$3,949,000

$765/sq ft

Stellar MLS as Distributed by MLS Grid #O5037027

Apr 26, 2013

Sold

$1,150,000

$223/sq ft

Mar 28, 2011

Listed

$1,550,000

$300/sq ft

SUNSETS AND FIREWORKS! Enjoy exquisite sunsets over beautiful Lake Bessie and watch the spectacular nightly fireworks while relaxing on your 1000+ square foot screened patio and roasting s`mores in your outdoor fireplace. This 3bedroom, 3 1/2 bath lake front pool home offers an open and airy floor plan with large picture windows to better appreciate the gorgeous lake views. Enhanced with magnificent open beams, wood & tile floors throughout, and cathedral ceilings, this is definitely a must see! Spacious, yet cozy, with 4400 square feet of comfortable one level living space, this home is the perfect blend of form and function. A lake front Master Suite is situated on one entire end of the house offering complete privacy with French doors that lead to the patio and pool. Entertaining is never easier with an outdoor kitchen, two fireplaces, and a large temperature controlled wine room. This is Isleworth living at its best!

Public Records

Apr 18, 2007

Sold

$2,900,000

$562/sq ft

Stellar MLS as Distributed by MLS Grid #O4666910

Mar 13, 2006

Listed

$657/sq ft

Public Records

Apr 1, 1999

Sold

$1,589,900

$308/sq ft

Public Records

Jun 28, 1993

Sold

$300,000

$58/sq ft

** Price available after signing in.

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2025

$76,251 (+7.0%)

$1,900,000 + $2,946,750

$4,846,750

2024

$71,280 (+11.7%)

$1,900,000 + $2,946,750

$4,846,750

2023

$63,824 (+11.0%)

$1,900,000 + $2,809,129

$4,709,129

2022

$57,511 (+16.0%)

$1,800,000 + $2,187,773

$3,987,773

2021

$49,596 (+2.8%)

$1,800,000 + $2,187,773

$3,987,773

2020

$48,236 (−6.0%)

$950,000 + $2,114,123

$3,064,123

2019

$51,303 (+0.6%)

$950,000 + $2,145,543

$3,095,543

2018

$51,007 (+0.7%)

$950,000 + $2,145,543

$3,095,543

2017

$50,654 (+134.4%)

$950,000 + $2,035,951

$2,985,951

2016

$21,608 (−30.7%)

$950,000 + $2,035,951

$2,985,951

2015

$31,187 (+8.0%)

$950,000 + $802,353

$1,752,353

2014

$28,877 (+2.5%)

2013

$28,162 (−5.2%)

2012

$29,707

Tax history for 9730 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$76,251 (+7.0%)

$1,900,000 + $2,946,750

$4,846,750

2024

$71,280 (+11.7%)

$1,900,000 + $2,946,750

$4,846,750

2023

$63,824 (+11.0%)

$1,900,000 + $2,809,129

$4,709,129

2022

$57,511 (+16.0%)

$1,800,000 + $2,187,773

$3,987,773

2021

$49,596 (+2.8%)

$1,800,000 + $2,187,773

$3,987,773

2020

$48,236 (−6.0%)

$950,000 + $2,114,123

$3,064,123

2019

$51,303 (+0.6%)

$950,000 + $2,145,543

$3,095,543

2018

$51,007 (+0.7%)

$950,000 + $2,145,543

$3,095,543

2017

$50,654 (+134.4%)

$950,000 + $2,035,951

$2,985,951

2016

$21,608 (−30.7%)

$950,000 + $2,035,951

$2,985,951

2015

$31,187 (+8.0%)

$950,000 + $802,353

$1,752,353

2014

$28,877 (+2.5%)

2013

$28,162 (−5.2%)

2012

$29,707

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

2.27 Acres

Year renovated

2015

Sq. Ft.

5,217

Year built

1995

Style

Single Family Residential

County

Orange County

APN

282316389900140

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

P-D

Planned Development District

To provide for planned residential communities, containing a variety of residential structures and diversity of building arrangements, with complementary and compatible commercial or industrial uses or both; planned commercial centers with complementary and compatible residential or industrial uses or both; planned tourist commercial centers with complementary and compatible uses which may include tourist attractions, theme parks, residential and light storage; or planned industrial parks with complementary and compatible residential or commercial uses or both; and public and quasipublic facilities developed in accordance with an approved development plan; To allow diversification of uses, structures, and open spaces in a manner compatible with existing and permitted land uses on abutting properties; To reduce improvement and energy costs through a more efficient use of land design and smaller networks of utilities and streets than is possible through application of other zoning districts and subdivision requirements; To ensure that development will occur according to limitations of use, design, density, coverage and phasing stipulated on an approved development plan; To preserve the natural amenities and environmental assets of the land by encouraging the preservation and improvement of scenic and functional open areas; To encourage an increase in the amount and use of open space areas by permitting a more economical and concentrated use of building areas than would be possible through conventional zoning districts; To provide maximum opportunity for application of innovative concepts of site planning in the creation of aesthetically pleasing living, shopping and working environments on properties of adequate size, shape and location; The P-D district is a flexible zoning district which is intended to provide an appropriate balance between the intensity of development and the ability to provide adequate capacity within the support services and facilities.

Permitted uses

Include but are not limited to:

No uses permitted by right

Property details

Parking

Parking Information
Garage Dimensions: 26x25
Parking Features: Garage Door Opener, Parking Pad
Garage Spaces: 2
Has Attached Garage
Has Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms: 5

Bathroom Information
# of Full Baths (Total): 5

Laundry Room Information
Laundry Features: Inside

Other Rooms Information
Additional Rooms: Attic,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Foyer,Inside Utility
# of Rooms: 10

Fireplace Information
Has Fireplace
Fireplace Features: Family Room, Gas

Heating & Cooling
Heating Information: Central, Zoned
Cooling Information: Central Air, Zoned

Interior Features
Interior Features: Attic, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-in Closet(s), Window Treatments
Window Features: Blinds, Thermal Windows, Window Treatments
Appliances: Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Exhaust Fan, Gas Water Heater, Microwave, Oven, Range, Refrigerator, Tankless Water Heater, Wine Refrigerator
Flooring: Carpet, Tile

Exterior

Building Information
Construction Materials: Block, Stucco
Roof: Tile

Exterior Features
Patio And Porch Features: Covered, Deck, Patio, Porch, Screened
Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters

Pool Information
Has Private Pool
Pool Features: Gunite, In Ground

Waterfront Information
On Waterfront
Waterfront Features: Lake
Water Body Name: LAKE BESSIE
Waterfront Feet Total: 134
Water Frontage Feet Lake: 134
Water View Y/N: 1
Water View Description: Lake
Water Access Y/N: 1
Water Access Description: Lake,Lake - Chain of Lakes
Water Extras Y/N: 1
Water Extras Description: Dock - Open,Dock w/Electric,Skiing Allowed

Property Information
CDD Y/N: 0
Homestead Y/N: 0
Property Type: Residential
Property Sub Type: Single Family Residence
Other Structures: Outdoor Kitchen
Zoning: P-D

Land Information
Vegetation: Mature Landscaping, Trees/Landscaped
Total Acreage: 1/2 Acre to 1 Acre

Lot Information
Lot Features: In County, Street Dead-End, Paved, Private
Lot Size Acres: 0.65

Financial

Tax Information
Tax Annual Amount: $31,188
Tax Year: 2015

Lease / Rent Details
Lease Restrictions YN: 1

Utilities

Utility Information
Water Source: Public
Sewer: Septic Tank
Utilities: Cable Available, Electricity Connected, Street Lights, Underground Utilities

Location

HOA Information
Has HOA
Association Fee Requirement: Required
Association Approval Required Y/N: 1
Monthly HOA Amount: 530.00
Association Amenities: Fitness Center, Gated, Optional Additional Fees, Playground, Security, Tennis Court(s), Vehicle Restrictions
Association Fee: $1,590
Association Fee Frequency: Quarterly
Association Fee Includes: Private Road, Recreational Facilities, Security

School Information
Elementary School: Windermere Elem
Middle Or Junior High School: Chain of Lakes Middle
High School: Olympia High

Location Information
Directions: Conroy-Windermere Rd into Windermere, Isleworth on the left, Rt on Latrobe, Rt on Chestnut Ridge. House will be on the left

Community Information
Community Features: Buyer Approval Required, Boat Ramp, Deed Restrictions, Fitness Center, Gated, Golf, Playground, Tennis Courts
Pets Allowed: Yes

Public facts

Beds: 5
Baths: 5.0
Sq. Ft.: 5,217
Stories: 1.0
Lot Size: 2.27 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: 2015
County: Orange County
APN: 282316389900140

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 1

Listing Information
Previous Status: Pending
Home Warranty YN: No

Listing Date Information
Days to Contract: 118
Status Contractual Search Date: 2016-10-28T00:00:00.000

Listing Price Information
Calculated List Price By Calculated Sq Ft: 764.72

Home Information
Living Area: 5164
Living Area Units: Square Feet
Living Area Source: Builder
Building Area Total: 6798
Building Area Units: Square Feet
Building Area Source: Builder
Foundation Details: Slab
Levels: One
Security Features: Closed Circuit Camera(s), Gated Community, Security System Owned, Smoke Detector(s)

Around this home

Schools

Windermere Elementary School

Public PreK-5 • Assigned • 1.7mi

10/10

Chain Of Lakes Middle School

Public 6-8 • Assigned • 1.1mi

3/10

Olympia High School

Public 9-12 • Assigned • 1.1mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

6 days above 108° expected this year, 18 days in 30 years

10/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Windermere, FL • 34786

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 6.7 hours in December, placing it above the U.S. average for solar exposure.

8.6 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$6.50M – $7.86M

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Nearby similar homes

$3,400,000

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5379 Isleworth Country Club Dr, Windermere, FL 34786

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3D WALKTHROUGH

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New listings for sale in 34786

NEW 17 HRS AGO

$647,000

3 beds2.5 baths2,229 sq ft

7033 Bramlea Ln, Windermere, FL 34786

$3,400,000

4 beds3.5 baths3,872 sq ft

5379 Isleworth Country Club Dr, Windermere, FL 34786

COMING SOON

$1,395,000

5 beds4 baths4,186 sq ft

101 Lee St, Windermere, FL 34786

$759,000

4 beds3.5 baths2,886 sq ft

8104 Jailene Dr, Windermere, FL 34786

$399,000

3 beds2.5 baths1,651 sq ft

14077 Ancilla Blvd, Windermere, FL 34786

OPEN SAT, 11AM TO 2PM

$1,399,900

5 beds3 baths3,356 sq ft

2540 Hempel Cove Ct, Windermere, FL 34786

$445,000

3 beds2.5 baths1,748 sq ft

13048 Garridan Ave, Windermere, FL 34786

$1,500,000

5 beds6.5 baths5,312 sq ft

13503 Lake Cawood Dr, Windermere, FL 34786

HOT HOME

$710,999

4 beds3.5 baths2,745 sq ft

13239 Jervey St, Windermere, FL 34786

Home values near 9730 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
9754 Chestnut Ridge Dr, Windermere, FL 7 Beds \| 11 Baths \| 14002 Sq. Ft.	$8,296,237
9731 Chestnut Ridge Dr, Windermere, FL 4 Beds \| 4 Baths \| 4785 Sq. Ft.	$2,650,225

Address	Redfin Estimate
9719 Chestnut Ridge Dr, Windermere, FL 3 Beds \| 3.5 Baths \| 3494 Sq. Ft.	$2,551,337
9743 Chestnut Ridge Dr, Windermere, FL 5 Beds \| 6.5 Baths \| 6328 Sq. Ft.	$3,931,919

Address	Redfin Estimate
9725 Chestnut Ridge Dr, Windermere, FL 7 Beds \| 6 Baths \| 8000 Sq. Ft.	—
9724 Chestnut Ridge Dr, Windermere, FL 5 Beds \| 6 Baths \| 5557 Sq. Ft.	$4,833,201

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2016. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 34786, FL

Sale history for 9730 Chestnut Ridge Dr

Tax history for 9730 Chestnut Ridge Dr

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 34786

Home values near 9730 Chestnut Ridge Dr

More real estate resources