253 Chestnut Hill Rd, Killingworth, CT 06419

Off market sep 2020 for $360K

$632,525

Est. refi paymentEst. refi $2,470/mo

•

2,180

sq ft

253 Chestnut Hill Rd, Killingworth, CT 06419

About this home

Charming, well cared for home, move-in ready! Light floods through the family room bay window. Large living area. Eat-in kitchen. Sunny, bright bedrooms. Wide board pine flooring throughout. Enjoy the spacious screen porch with ceiling fan, open to a sun porch. Additional space in lower level for playroom, den, workshop. This home backs up to woods, with dramatic rock outcroppings. A large deck, built into the hill behind the house, overlooks the property. A side yard gives room for play. The 2+ acres, with the home sited above the road, provide a wonderful sense of privacy. Interior spaces open to the beauty of the natural surrounds. Convenient location! 4 miles to the center of Madison and shore. Hammonasset and Chatfield Hollow State Parks within reach. Easy access to commuting routes. Enjoy your ride home along scenic Chestnut Hill Road.

Single-familyProperty Type

1973Year Built

2.1 acresLot Size

$290Est. Price/Sq.Ft.

2 car garageParking

Listed by Laurie Trulock • Compass Connecticut, LLC

Bought with Roger Beale • Coldwell Banker Realty

Source:Smart MLS #170319723

Redfin Estimate

$632,525

$273K since sold in September 2020$4,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.7% lower than the average sale price ($751K) of 6 comparable homes.

SOLD AUG 26, 2026
$819,000
A
4 beds2.5 baths2,260 sq ft
49 Hammonassett Meadows Rd, Madison, CT 06443
SOLD OCT 1, 2026
$1,100,000
B
4 beds2.5 baths2,493 sq ft
177 Warpas Rd, Madison, CT 06443
SOLD AUG 20, 2026
$769,000
C
4 beds2.5 baths2,647 sq ft
89 Summer Hill Rd, Madison, CT 06443
SOLD MAY 29, 2026
$620,000
D
4 beds2.5 baths2,590 sq ft
271 Chestnut Hill Rd, Killingworth, CT 06419
SOLD SEP 2, 2026
$460,000
E
4 beds2.5 baths2,024 sq ft
53 Summer Hill Rd, Madison, CT 06443
SOLD JUL 2, 2026
$735,000
F
4 beds2.5 baths2,657 sq ft
40 Harkness Dr, Madison, CT 06443

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Earn from this home

Sell

$340,133

Est. take-home

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Refinance

Est. cash available

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Rent

$3,353/mo

Redfin rental estimate

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Market trends in 06419, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.9%

1.3% MoM

Median sale price

$775K

$38K MoM

Avg. days on market

44d

10 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 16 HRS AGO
$106,000
1 bed1 bath720 sq ft
16 Country Club Trl, Killingworth, CT 06419
OPEN SUN, 1PM TO 3PM
$619,900
3 beds2 baths2,480 sq ft
433 Route 148, Killingworth, CT 06419
REDFIN OPEN SAT, 1PM TO 3PM
$529,000
3 beds3 baths2,059 sq ft
240 Route 148, Killingworth, CT 06419
$223,900
2 beds1.5 baths990 sq ft
11 Bridlepath Trl, Killingworth, CT 06419
See all

Provided by Redfin

Sale history for 253 Chestnut Hill Rd

Date

Event

Price

Smart MLS #170319723

Sep 14, 2020

Sold

$360,000

$165/sq ft

Jul 27, 2020

Contingent

—

Jul 24, 2020

Listed

$350,000

$161/sq ft

Smart MLS #N10078098

Mar 7, 2016

Sold

$287,000

$132/sq ft

Jan 21, 2016

Listing Removed

—

Sep 9, 2015

Listed

$289,000

$133/sq ft

HOME WARRANTY INCLUDED if under contract by the end of the month. Excellent price for a great home in the woods! Trees, stunning rock outcroppings, koi pond, brook across the street--yet convenient to everything! Spacious rooms, great flow, Central Air, many updates and wide board floors throughout. Screen Porch, Sundeck with sweeping views of Nature. Get away from it all, but be near everything--between downtown Madison and the heart of Killingworth --all at a PHENOMENAL price! Immediate occupancy. Come take a look!

Smart MLS #N10056143

Sep 1, 2015

Listing Removed

—

Jun 18, 2015

Listed

$312,000

$143/sq ft

Smart MLS #M9135691

Jun 25, 2013

Listing Removed

—

Jul 12, 2012

Listed

$325,000

$149/sq ft

Smart MLS #M9125049

Oct 20, 2011

Listing Removed

—

Oct 20, 2010

Listed

$350,000

$161/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$5,983 (+1.1%)

$66,500 + $188,440

$254,940

2022

$5,920 (+3.0%)

$66,500 + $188,440

$254,940

2021

$5,748

$75,950 + $139,170

$215,120

2020

$5,748 (−2.7%)

$75,950 + $139,170

$215,120

2018

$5,909

$75,950 + $139,170

$215,120

2017

$5,909 (−9.6%)

$75,950 + $139,170

$215,120

2016

$6,534 (+5.5%)

$110,860 + $141,510

$252,370

2014

$6,191

$110,860 + $141,510

$252,370

2011

$6,191

$110,860 + $141,510

$252,370

Tax history for 253 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,983 (+1.1%)

$66,500 + $188,440

$254,940

2022

$5,920 (+3.0%)

$66,500 + $188,440

$254,940

2021

$5,748

$75,950 + $139,170

$215,120

2020

$5,748 (−2.7%)

$75,950 + $139,170

$215,120

2018

$5,909

$75,950 + $139,170

$215,120

2017

$5,909 (−9.6%)

$75,950 + $139,170

$215,120

2016

$6,534 (+5.5%)

$110,860 + $141,510

$252,370

2014

$6,191

$110,860 + $141,510

$252,370

2011

$6,191

$110,860 + $141,510

$252,370

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

2.1 Acres

Year renovated

1995

Sq. Ft.

2,180

Year built

1973

Style

Single Family Residential

County

Middlesex County

APN

997674

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 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 Info: Main Level
In-Law Apartment: No
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Oven/Range, Microwave, Refrigerator, Washer, Dryer

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Room Count: 9
Basement Description: Partially Finished, Interior Access, Garage Access, Storage
Has Attic
Attic Description: Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Deck, Porch, Porch-Screened, Shed

Lot Information
Lot Description: Lightly Wooded, Sloping Lot

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

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2180
Driveway Type: Paved

Financial

Assessments Information
Assessed Value: $215,120

Utilities

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

Location

School Information
High School: Haddam-Killingworth
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Directions: Route 79 or Route 80 to Chestnut Hill Road
County: Middlesex

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,180
Stories: 2.0
Lot Size: 2.1 acres
Style: Single Family Residential
Year Built: 1973
Year Renovated: 1995
County: Middlesex County
APN: 997674

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Killingworth Elementary School

Public PreK-3 • Assigned • 3.6mi

8/10

Haddam-Killingworth Middle School

Public 6-8 • Assigned • 4.3mi

7/10

Haddam-Killingworth High School

Public 9-12 • Assigned • 9.6mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

In this area, properties receive around 9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$601,000 – $728,000

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New listings for sale in 06419

NEW 16 HRS AGO

$106,000

1 bed1 bath720 sq ft

16 Country Club Trl, Killingworth, CT 06419

OPEN SUN, 1PM TO 3PM

$619,900

3 beds2 baths2,480 sq ft

433 Route 148, Killingworth, CT 06419

REDFIN OPEN SAT, 1PM TO 3PM3D WALKTHROUGH

$529,000

3 beds3 baths2,059 sq ft

240 Route 148, Killingworth, CT 06419

$223,900

2 beds1.5 baths990 sq ft

11 Bridlepath Trl, Killingworth, CT 06419

Home values near 253 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
281 Chestnut Hill Road, Killingworth, CT 4 Beds \| 2.5 Baths \| 2274 Sq. Ft.	$803,791
271 Chestnut Hill Road, Killingworth, CT 4 Beds \| 2.5 Baths \| 2590 Sq. Ft.	$737,878

Address	Redfin Estimate
263 Chestnut Hill Road, Killingworth, CT 3 Beds \| 2.5 Baths \| 2646 Sq. Ft.	$730,134
277 Chestnut Hill Road, Killingworth, CT 4 Beds \| 2.5 Baths \| 2648 Sq. Ft.	$777,632

Address	Redfin Estimate
267 Chestnut Hill Road, Killingworth, CT 4 Beds \| 2.5 Baths \| 2734 Sq. Ft.	$683,694
258 Chestnut Hill Road, Killingworth, CT 3 Beds \| 2 Baths \| 1600 Sq. Ft.	$492,808

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 06419, CT

Sale history for 253 Chestnut Hill Rd

Tax history for 253 Chestnut Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06419

Home values near 253 Chestnut Hill Rd

More real estate resources