For sale

$825,000

Est. $5,593/mo —

•

2,820

sq ft

26 Chittenden Hill Rd, Westbrook, CT 06498

About this home

TWO HOUSES ON 5.68 ACRES! THE SECOND RESIDENCE CAN BE RENTED! A rare opportunity to own a distinctive country estate with two full residences on 5.68 private acres. A charming circa-1710 center-chimney colonial. Offering four bedrooms, 2 full baths, approximately 2900 square feet, and three fireplaces. Rich with traditional character, the home features an updated kitchen, newer steam boiler, new cedar roof, updated full baths, and mini-split system with 10 head units. An expansive patio overlooks beautiful gardens and meadows, creating an exceptional setting for entertaining. The separate two-bedroom residence offers comfortable living space plus adjoining meeting rooms and a library with a deck overlooking the meadows-ideal for extended family, guests, a studio, home office or other flexible uses. The grounds include a barn, gardeners shed, henhouse, 2 rabbit hutches and garage. Adjoining open space and conservation land, this remarkable property offers an uncommon combination of privacy, versatility, history and the character of a true country estate.

Single-familyProperty Type

1710Year Built

4.5 acresLot Size

$293Price/Sq.Ft.

1 garage spacesParking

Listed by Camille Ackermann • Berkshire Hathaway NE Prop.

Contact: Agent Attribution Contact: (203) 640-1083 | Office Attribution Contact: (203) 245-3100

Source:Smart MLS #24203412

Payment calculator

$5,593 per month

Principal and interest$4,447

Property taxes

$885

HOA dues

Home insurance

$261

Utilities

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Next available date: Sunday, November 8

Open houses

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Nearby open houses (10)

OPEN SUN, 10AM TO 12PM
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182 Green Hill Rd, Madison, CT 06443
0.46 acre lot • 2 garage spots • Built 1951
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3 beds2.5 baths3,076 sq ft
4 Jans Way, Guilford, CT 06437
1.87 acre lot • 2 garage spots • Built 2024
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$895,000
3 beds2 baths3,032 sq ft
24 Indian Dr, Clinton, CT 06413
0.27 acre lot • 2 garage spots • Built 1968
OPEN SUN, 12PM TO 2PM
$549,900
4 beds2.5 baths1,982 sq ft
245 Chestnut Hill Rd, Killingworth, CT 06419
2 acre lot • 2 garage spots • Built 1982
OPEN SUN, 12PM TO 1:30PM
$499,900
3 beds3 baths1,944 sq ft
25 Samantha Ln, Madison, CT 06443
0.36 acre lot • 2 garage spots • Built 2000
OPEN SUN, 12PM TO 2PM
$1,175,000
4 beds3.5 baths3,637 sq ft
321 Boston St, Guilford, CT 06437
0.51 acre lot • 2 garage spots • Built 1761
OPEN SUN, 1PM TO 3PM
$525,000
3 beds2 baths1,822 sq ft
6 Gilbert Hill Rd, Chester, CT 06412
0.69 acre lot • 6 parking spots • Built 1992
OPEN SUN, 1PM TO 3PM
$429,000
2 beds1 bath960 sq ft
28 Bluff Ave, Clinton, CT 06413
0.23 acre lot • 6 parking spots • Built 1959
OPEN SUN, 1PM TO 3PM
$625,000
3 beds1 bath2,033 sq ft
22 High Ridge Rd, Guilford, CT 06437
0.7 acre lot • 4 parking spots • Built 1936
OPEN SUN, 1PM TO 4PM
$775,000
3 beds2.5 baths3,002 sq ft
7 Hickory Hill Dr, Chester, CT 06412
1.27 acre lot • 2 garage spots • Built 1984

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Around this home

Schools

K - 12
Preschool & daycare

Daisy Ingraham School

Public PreK-5 • Assigned • 4.6mi

8/10

Westbrook Middle School

Public 6-8 • Assigned • 3.5mi

10/10

Westbrook High School

Public 9-12 • Assigned • 3.3mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

26 Chittenden Hill Rd · $825,000

DAYS ON MARKET

The average home goes pending in 43 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

LIST PRICE

Median list price in this area is $471,942. (43% lower than this home)

PRICE DROP

18% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
In-law apartment in a detached guest house
Three fireplaces
Partial basement with concrete floor, sump pump and walk-out access
Attic with floored walk-up

Bedrooms
Four bedrooms

Bathrooms
Two full bathrooms

Kitchen
Gas range
Microwave
Refrigerator
Dishwasher

Laundry & utility
Washer and dryer included
Laundry located in the basement / lower level

Heating & cooling
Heat pump
Steam heat
Wall units
Zoned heating
Electric hot water

Sale and tax history for 26 Chittenden Hill Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24203412

Oct 20, 2026

Price Changed

$825,000

$293/sq ft

Oct 1, 2026

Relisted

—

Sep 27, 2026

Contingent

—

Sep 21, 2026

Price Changed

$875,000

$310/sq ft

Sep 4, 2026

Listed

$949,000

$337/sq ft

Smart MLS #N10132236

Oct 27, 2016

Sold

$525,000

$186/sq ft

Jul 11, 2016

Listing Removed

—

Jun 21, 2016

Listed

$539,000

$191/sq ft

Completely unique gentleman’s farm privately set on 5.68 acres adjoining significant open-space and conservation land. The property consists of a lovely circa 1710 center chimney Colonial, a two bedroom guest house with adjoining meeting rooms, large post and beam barn, gardeners building, hen house and a four bay garage with workshop. The property is adorned with English style gardens, lawn, stone walls, an open meadow and towering hardwoods.

Year

Property tax

Land + Additions

Assessment*

2023

$9,743 (+2.7%)

$134,390 + $322,580

$456,970

2022

$9,487 (−1.3%)

$134,390 + $322,580

$456,970

2021

$9,608

$85,040 + $299,290

$384,330

2020

$9,608 (+1.3%)

$85,040 + $299,290

$384,330

2019

$9,481 (+1.2%)

$85,040 + $299,290

$384,330

2018

$9,366 (+2.2%)

$85,040 + $299,290

$384,330

2017

$9,167 (−8.6%)

$85,040 + $291,130

$376,170

2016

$10,029 (+6.2%)

$75,610 + $357,780

$433,390

2014

$9,444 (+3.9%)

$75,610 + $357,780

$433,390

2011

$9,093

$75,610 + $357,780

$433,390

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

4.5 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Other

County

Middlesex County

APN

1038639

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Climate risks

1/10 Flood Factor

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

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 93° expected this year, 17 days in 30 years

6/10 Wind Factor

77% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Westbrook, CT • 06498

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

Redfin Estimate for 26 Chittenden Hill Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $542,500 and $761,200.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $543K to $761K.

SOLD MAY 29, 2026
$700,000 Last sold price
3 beds2 baths2,948 sq ft
24 Tower Hill Rd, Clinton, CT 06413
$56/sq ft
larger lot
280 years newer
SOLD SEP 16, 2026
$761,200 Last sold price
4 beds2.5 baths2,986 sq ft
12 Lafata Ln, Killingworth, CT 06419
$38/sq ft
smaller lot
288 years newer
SOLD SEP 24, 2026
$655,000 Last sold price
4 beds3 baths2,761 sq ft
11a/11b Pond Circle Rd, Westbrook, CT 06498
$56/sq ft
smaller lot
251 years newer
SOLD SEP 11, 2026
$675,000 Last sold price
4 beds2.5 baths2,700 sq ft
6 Elsie Ln, Clinton, CT 06413
$43/sq ft
smaller lot
289 years newer
SOLD JUL 8, 2026
$625,000 Last sold price
5 beds3.5 baths2,892 sq ft
49 Kelseytown Rd, Clinton, CT 06413
$77/sq ft
smaller lot
265 years newer
SOLD JAN 8, 2026
$542,500 Last sold price
4 beds3.5 baths2,842 sq ft
180 Malabar Dr, Westbrook, CT 06498
$102/sq ft
smaller lot
259 years newer

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Early Access listings

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Details provided by Smart MLS and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Interested in buying?

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 26 Chittenden Hill Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 26 Chittenden Hill Rd

Early Access listings

Nearby similar homes

New listings for sale in 06498

More real estate resources