Google street view image for 5 Chestnut Hill Rd, Killingworth, CT 06419

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Sold

$1,427,350

Est. refi paymentEst. refi $5,621/mo

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sq ft

5 Chestnut Hill Rd, Killingworth, CT 06419

About this home

Gracious country estate. Meticulously restored antique farmhouse combined with dramatic additions. Three bedroom guesthouse, post and beam barn, heated pool andmagnificent plantings. Minutes to beaches.Price is firm.

3.47 acresLot Size

3 car garageParking

Source:Public Records

Redfin Estimate

$1,427,350

$427K since sold in June 2006$13K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17% higher than the average sale price ($1.22M) of 6 comparable homes.

SOLD OCT 22, 2026
$1,350,000
A
3 beds2.5 baths2,767 sq ft
1308 Durham Rd, Madison, CT 06443
SOLD SEP 1, 2026
$1,250,000
B
4 beds3 baths3,816 sq ft
128 Concord Dr, Madison, CT 06443
SOLD OCT 13, 2026
$1,350,000
C
4 beds4.5 baths4,421 sq ft
77 Hickory Ln, Madison, CT 06443
SOLD JUL 23, 2026
$1,070,000
D
4 beds3.5 baths4,015 sq ft
351 Bartlett Dr, Madison, CT 06443
SOLD JUN 25, 2026
$1,100,000
E
4 beds3.5 baths4,242 sq ft
82 Concord Dr, Madison, CT 06443
SOLD JUL 23, 2026
$1,200,000
F
4 beds3.5 baths4,250 sq ft
86 Nursery Ln, Madison, CT 06443

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Earn from this home

Sell

$1,343,335

Est. take-home

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Refinance

Est. cash available

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Market trends in 06419, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.9%

1.1% MoM

Median sale price

$794K

$19K MoM

Avg. days on market

47d

3 days MoM

Recently sold homes

0 MoM

New listings for sale

$415,000
3 beds1 bath983 sq ft
7 Kelseytown Rd, Killingworth, CT 06419
$549,900
4 beds2.5 baths1,982 sq ft
245 Chestnut Hill Rd, Killingworth, CT 06419
$699,000
2 beds2 baths1,386 sq ft
511 Route 81, Killingworth, CT 06419
See all

Provided by Redfin

Sale history for 5 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$14,725 (+1.1%)

$93,240 + $534,170

$627,410

2022

$14,568 (−12.1%)

$93,240 + $534,170

$627,410

2021

$16,582

$105,840 + $514,760

$620,600

2020

$16,582 (−2.7%)

$105,840 + $514,760

$620,600

2018

$17,041

$105,600 + $514,760

$620,360

2017

$17,041 (+4.8%)

$105,600 + $514,760

$620,360

2016

$16,268 (+5.5%)

$163,980 + $464,370

$628,350

2014

$15,413

$163,980 + $464,370

$628,350

2011

$15,413

$163,980 + $464,370

$628,350

Tax history for 5 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$14,725 (+1.1%)

$93,240 + $534,170

$627,410

2022

$14,568 (−12.1%)

$93,240 + $534,170

$627,410

2021

$16,582

$105,840 + $514,760

$620,600

2020

$16,582 (−2.7%)

$105,840 + $514,760

$620,600

2018

$17,041

$105,600 + $514,760

$620,360

2017

$17,041 (+4.8%)

$105,600 + $514,760

$620,360

2016

$16,268 (+5.5%)

$163,980 + $464,370

$628,350

2014

$15,413

$163,980 + $464,370

$628,350

2011

$15,413

$163,980 + $464,370

$628,350

*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

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Stories

—

Lot width

—

Lot depth

—

Lot size

3.47 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Middlesex County

APN

996974

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Around this home

Schools

K - 12
Preschool & daycare

Killingworth Elementary School

Public PreK-3 • Assigned • 2.2mi

7/10

Haddam-Killingworth Middle School

Public 6-8 • Assigned • 2.7mi

6/10

Haddam-Killingworth High School

Public 9-12 • Assigned • 7.6mi

10/10

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

5/10 Heat Factor

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

6/10 Wind Factor

67% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Killingworth, CT • 06419

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

$1.36M – $1.64M

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Nearby similar homes

$1,295,000

4 beds4 baths5,979 sq ft

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Chef's kitchen • Separate music room • Finished lower level

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4 beds1.5 baths1,890 sq ft

201 Emanuel Church Rd, Killingworth, CT 06419

Front bay window • New deck • Updated windows

$795,000

4 beds2.5 baths2,572 sq ft

3 Little Hollow Rd, Madison, CT 06443

Wide plank flooring • New light fixtures • New roof

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3 beds1 bath1,077 sq ft

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New cedar siding • Roof replaced • 1.03 acre lot

$834,900

4 beds2.5 baths3,016 sq ft

26 Overlook Farms Rd, Killingworth, CT 06419

Private acres • Walk-out basement • Mature trees

$999,000

5 beds5.5 baths3,832 sq ft

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4 acre compound • Guest house • In home gym

New listings for sale in 06419

$415,000

3 beds1 bath983 sq ft

7 Kelseytown Rd, Killingworth, CT 06419

2.1-acre lot • Level backyard • Full basement

$549,900

4 beds2.5 baths1,982 sq ft

245 Chestnut Hill Rd, Killingworth, CT 06419

Updated kitchen • Vinyl siding • Replacement windows

$699,000

2 beds2 baths1,386 sq ft

511 Route 81, Killingworth, CT 06419

35 acre property • Cranberry bog • Hay fields

Home values near 5 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
25 North Chestnut Hill Rd, Killingworth, CT 2 Beds \| 2.5 Baths \| 1857 Sq. Ft.	$638,452
3 North Chestnut Hill Rd, Killingworth, CT 3 Beds \| 1.5 Baths \| 1310 Sq. Ft.	$413,436
36 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 3 Baths \| 2378 Sq. Ft.	$701,051
10 Chestnut Hill Rd, Killingworth, CT 3 Beds \| 1.5 Baths \| 1584 Sq. Ft.	$538,627
35 Chestnut Hill Rd, Killingworth, CT 3 Beds \| 2 Baths \| 1740 Sq. Ft.	$561,462
499 Route 80, Killingworth, CT 4 Beds \| 2 Baths \| 2234 Sq. Ft.	$616,326
540 Route 80, Killingworth, CT 5 Beds \| 3 Baths \| 2313 Sq. Ft.	$646,111

Address	Redfin Estimate
10 North Chestnut Hill Rd, Killingworth, CT 5 Beds \| 4.5 Baths \| 4250 Sq. Ft.	$908,743
2 North Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2 Baths \| 4420 Sq. Ft.	$626,492
30 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 1 Baths \| 1756 Sq. Ft.	—
25 Chestnut Hill Rd, Killingworth, CT 3 Beds \| 3 Baths \| 2496 Sq. Ft.	$992,039
39 North Chestnut Hill Rd, Killingworth, CT 4 Beds \| 1.5 Baths \| 2160 Sq. Ft.	$828,859
501 Route 80, Killingworth, CT 3 Beds \| 2 Baths \| 1142 Sq. Ft.	$321,569
530 Route 80, Killingworth, CT 2 Beds \| 1 Baths \| 624 Sq. Ft.	$348,257

Address	Redfin Estimate
5 North Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2 Baths \| 1880 Sq. Ft.	$520,663
26 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2.5 Baths \| 1984 Sq. Ft.	$650,327
22 Chestnut Hill Rd, Killingworth, CT 5 Beds \| 3 Baths \| 2706 Sq. Ft.	$655,243
44 Chestnut Hill Rd, Killingworth, CT 2 Beds \| 1 Baths \| 1207 Sq. Ft.	$628,954
6 Owl Hollow Ln, Killingworth, CT 4 Beds \| 4 Baths \| 5784 Sq. Ft.	$1,474,724
497 Route 80, Killingworth, CT 3 Beds \| 1.5 Baths \| 1550 Sq. Ft.	$496,504
2 Owl Hollow Ln, Killingworth, CT 4 Beds \| 3.5 Baths \| 3378 Sq. Ft.	$699,384

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5 Chestnut Hill Rd, Killingworth, CT 06419

About this home

Redfin Estimate

Earn from this home

Market trends in 06419, CT

Sale history for 5 Chestnut Hill Rd

Tax history for 5 Chestnut Hill Rd

Public record

Property details

Public facts

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06419

Home values near 5 Chestnut Hill Rd

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