265 Chestnut Hill Rd, Litchfield, CT 06759

Off Market Feb 2021 for $699K

$1,097,554

Est. refi paymentEst. refi $4,635/mo

•

3,277

sq ft

265 Chestnut Hill Rd, Litchfield, CT 06759

About this home

Welcome to the country! Bring your creative ideas and open mind and transform this 1930 Colonial into your dream country home. This home sits beautifully on 9 quiet acres with an in-ground propane-heated pool, play area and garden area. Detached office/home-schooling building is perfect for a home business or modify it to be a pool house. It has a full bath and two levels with gas heat and AC via a split unit. Main house has central AC and oil heat. Just a short way from the home, the road changes to dirt. This a perfect location for walking, running, bike riding and more. Miles and miles of trails are close too. Close proximity to Litchfield Green, wineries, restaurants, shopping, skiing, golf, hiking and more. Private and prep schools are also very close. 100 miles to Manhattan. It's time to call Litchfield home. Schedule your private showing today.

Single-familyProperty Type

1930Year Built

9 acresLot Size

$335Est. Price/Sq.Ft.

2 car garageParking

Listed by Chris LaCava • Coldwell Banker Realty

Bought with Marc Maclean • Houlihan Lawrence

Source:Smart MLS #170359082

Redfin Estimate

$1,097,554

$399K since sold in February 2021$35K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 47.7% higher than the average sale price ($743K) of 6 comparable homes.

SOLD OCT 15, 2025
$660,000
A
3 beds3 baths3,514 sq ft
284 Buell Rd, Litchfield, CT 06759
SOLD AUG 28, 2026
$1,150,000
B
4 beds4.5 baths4,152 sq ft
415 South St, Litchfield, CT 06759
SOLD AUG 17, 2026
$420,000
C
4 beds2 baths1,728 sq ft
66 Isaiah Smith Ln, Morris, CT 06763
SOLD JUL 10, 2026
$610,000
D
4 beds2 baths1,788 sq ft
11 Sheldon Ln, Litchfield, CT 06759
SOLD MAR 20, 2026
$770,000
E
4 beds2.5 baths2,702 sq ft
137 Old South Rd, Litchfield, CT 06759
SOLD MAY 11, 2026
$850,000
F
4 beds2.5 baths2,658 sq ft
273 Bantam Lake Rd, Morris, CT 06763

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Earn from this home

Sell

$533,470

Est. take-home

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Refinance

Est. cash available

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Market trends in 06759, CT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.1%

2.1% MoM

Median sale price

$622K

$27K MoM

Avg. days on market

51d

12 days MoM

Recently sold homes

3 MoM

New listings for sale

$695,000
3 beds2 baths2,328 sq ft
27 Sally Burr Rd, Litchfield, CT 06759
$449,000
4 beds2 baths1,790 sq ft
85 E Litchfield Rd, Litchfield, CT 06759
$2,395,000
4 beds3.5 baths4,346 sq ft
171 South St, Litchfield, CT 06759
See all

Provided by Redfin

Sale history for 265 Chestnut Hill Rd

Date

Event

Price

Smart MLS #170359082

Feb 26, 2021

Sold

$699,000

$213/sq ft

Dec 19, 2020

Contingent

—

Dec 15, 2020

Listed

$699,000

$213/sq ft

Smart MLS #L10209540

Dec 21, 2017

Listing Removed

—

Apr 7, 2017

Listed

$575,000

$175/sq ft

Smart MLS #L123106

Aug 10, 2007

Listed

$995,000

$304/sq ft

Smart MLS #98270081

Feb 7, 2007

Listing Removed

—

Feb 13, 2006

Listed

$1,199,000

$366/sq ft

Smart MLS #L116536

Jan 7, 2007

Listing Removed

—

Feb 10, 2006

Listed

$1,199,000

$366/sq ft

Public Records

Jun 17, 2005

Sold

$1,060,000

$323/sq ft

Smart MLS #L113889

Jun 15, 2005

Listed

$995,000

$304/sq ft

Public Records

Apr 9, 2002

Sold

$657,000

$200/sq ft

Smart MLS #L102326

Dec 1, 2001

Listed

$695,000

$212/sq ft

Public Records

Nov 2, 1999

Sold

$438,000

$134/sq ft

Smart MLS #98036286

Aug 15, 1999

Listing Removed

—

Feb 23, 1999

Listed

$435,000

$133/sq ft

Public Records

Dec 22, 1997

Sold

$600,000

$183/sq ft

Public Records

Jun 25, 1990

Sold

$420,000

$128/sq ft

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Year

Property tax

Land + Additions

Assessment*

2022

$15,689 (+13.1%)

$152,540 + $432,860

$585,400

2021

$13,873 (−0.4%)

$152,540 + $350,120

$502,660

2020

$13,924 (−1.8%)

$152,540 + $350,120

$502,660

2019

$14,175 (−11.5%)

$152,540 + $350,120

$502,660

2018

$16,014 (+0.4%)

$241,190 + $336,920

$578,110

2017

$15,956 (+3.4%)

$241,190 + $336,920

$578,110

2016

$15,436 (+6.0%)

$241,190 + $336,920

$578,110

2014

$14,568

$241,190 + $336,920

$578,110

Tax history for 265 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2022

$15,689 (+13.1%)

$152,540 + $432,860

$585,400

2021

$13,873 (−0.4%)

$152,540 + $350,120

$502,660

2020

$13,924 (−1.8%)

$152,540 + $350,120

$502,660

2019

$14,175 (−11.5%)

$152,540 + $350,120

$502,660

2018

$16,014 (+0.4%)

$241,190 + $336,920

$578,110

2017

$15,956 (+3.4%)

$241,190 + $336,920

$578,110

2016

$15,436 (+6.0%)

$241,190 + $336,920

$578,110

2014

$14,568

$241,190 + $336,920

$578,110

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

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

9 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Litchfield County

APN

819299

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 25, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 2

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 9
Laundry Room Location: Off Kitchen
Laundry Room Info: Main Level
Interior Features: Cable - Pre-wired, Security System
In-Law Apartment: Possible
In-Law Access: Detached
Fireplaces Total: 2
Cooling System: Ceiling Fans, Central Air, Split System
Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 4

Room Information
Room Count: 9
Basement Description: Partial With Walk-Out, Unfinished, Concrete Floor, Interior Access
Has Attic
Attic Description: Pull-Down Stairs, Storage Space

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Aluminum
Exterior Features: Guest House, Gutters, Patio, Shed, Stone Wall

Lot Information
Lot Description: Some Wetlands, Dry, Cleared, Lightly Wooded, Rolling, Treed

Pool Information
Swimming Pool
Pool Description: In Ground Pool, Heated, Vinyl

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: White

Property Information
Radon Mitigation Air
Property Type: Single Family For Sale
Driveway Type: Private, Circular, Dirt, Gravel

Financial

Assessments Information
Assessed Value: $502,660

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric
Heat Type: Hot Air, Zoned
Heat Fuel Type: Oil, Propane
Fuel Tank Location: In Basement

Location

School Information
Middle Jr High School: Per Board of Ed
Intermediate School: Litchfield
High School: Litchfield
Elementary School: Center

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Playground/Tot Lot, Private School(s), Stables/Riding
Directions: GPS Friendly
County: Litchfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 9 acres
Style: Other
Year Built: —
Year Renovated: —
County: Litchfield County
APN: 819299

Home facts updated by county records on May 25, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

Litchfield Center School

Public PreK-3 • Assigned • 2.4mi

Plumb Hill Middle School

Public 6-8 • Assigned • 2.7mi

Region 20 High School

Public 9-12 • Assigned • 3.1mi

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

4/10 Fire Factor

0.93% chance of being in a wildfire in next 30 years

3/10 Heat Factor

7 days above 93° expected this year, 16 days in 30 years

5/10 Wind Factor

22% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Litchfield, CT • 06759

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$1.04M – $1.26M

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Land— sq ft

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31 Wheeler Rd, Litchfield, CT 06759

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$1,250,000

3 beds1.5 baths1,257 sq ft

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New listings for sale in 06759

$695,000

3 beds2 baths2,328 sq ft

27 Sally Burr Rd, Litchfield, CT 06759

$449,000

4 beds2 baths1,790 sq ft

85 E Litchfield Rd, Litchfield, CT 06759

$2,395,000

4 beds3.5 baths4,346 sq ft

171 South St, Litchfield, CT 06759

Home values near 265 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
254 Chestnut Hill Rd, Litchfield, CT 4 Beds \| 7 Baths \| 6081 Sq. Ft.	$1,981,579
190 East Chestnut Hill Rd, Litchfield, CT 5 Beds \| 2.5 Baths \| 2588 Sq. Ft.	$687,691

Address	Redfin Estimate
220 East Chestnut Hill Rd, Litchfield, CT 4 Beds \| 2.5 Baths \| 3004 Sq. Ft.	$716,009
176 East Chestnut Hill Rd, Litchfield, CT 3 Beds \| 2 Baths \| 1866 Sq. Ft.	$547,643

Address	Redfin Estimate
243 Chestnut Hill Rd, Litchfield, CT 4 Beds \| 3.5 Baths \| 3565 Sq. Ft.	$1,251,577
160 East Chestnut Hill Rd, Litchfield, CT 4 Beds \| 3.5 Baths \| 3176 Sq. Ft.	$761,130

Property information provided by Smart MLS when last listed in 2020. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06759, CT

Sale history for 265 Chestnut Hill Rd

Tax history for 265 Chestnut Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06759

Home values near 265 Chestnut Hill Rd

More real estate resources