258 Chestnut Hill Rd, Killingworth, CT 06419

Off Market Jun 2018 for $180K

$493,227

Est. refi paymentEst. refi $1,401/mo

•

1,600

sq ft

258 Chestnut Hill Rd, Killingworth, CT 06419

About this home

"The river runs past it" - magical setting along the Hammonasset River. Towering hemlocks surround this mid-century modern ranch with large glass sliders in every room except kitchen and one BR. "Peaceful" is what best describes this woodland setting. Sit on the deck or grab a fishing pole and catch a couple of trout for dinner - either way this is truly restful, restorative. House is in need of updating (being sold "as is") - deck has been power washed, looks terrific, gutters and roof have been cleaned, looks good. The well has good pressure - ran for hours while the deck and gutters were being power washed. Kitchen and baths need remodeling, windows and sliders are in good shape, hardwood floors are in good shape. Interior needs painting. Chestnut Hill Road is a beautiful country road. This location is right over the border with Madison, minutes from shopping and beaches. The area has Chatfield Hollow and Cockaponsett State Park as well as Hammonassett Beach Park nearby - beautifully maintained recreational facilities - don't wait too long; this might just be the one place you have always dreamed of.

Single-familyProperty Type

1965Year Built

2 acresLot Size

$308Est. Price/Sq.Ft.

2 car garageParking

Listed by Rena Powell • Coldwell Banker Realty

Bought with Rena Powell • Coldwell Banker Realty

Source:Smart MLS #170080631

Redfin Estimate

$493,227

$313K since sold in June 2018$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.3% lower than the average sale price ($643K) of 6 comparable homes.

SOLD AUG 7, 2026
$539,000
A
3 beds1.5 baths1,666 sq ft
21 Pierce Ln, Madison, CT 06443
SOLD JUN 30, 2026
$640,000
B
4 beds2.5 baths1,894 sq ft
9 Monroe Ln, Madison, CT 06443
SOLD AUG 26, 2026
$819,000
C
4 beds2.5 baths2,260 sq ft
49 Hammonassett Meadows Rd, Madison, CT 06443
SOLD APR 9, 2026
$725,000
D
3 beds2.5 baths1,589 sq ft
21 Little Hollow Rd, Madison, CT 06443
SOLD AUG 19, 2026
$540,000
E
3 beds2 baths2,630 sq ft
252 Cow Hill Rd, Clinton, CT 06413
SOLD JUN 25, 2026
$597,104
F
3 beds2.5 baths2,022 sq ft
1353 Durham Rd, Madison, CT 06443

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Earn from this home

Sell

$342,831

Est. take-home

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Refinance

Est. cash available

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Rent

$2,768/mo

Redfin rental estimate

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Market trends in 06419, CT

Last updated August 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

COMING SOON
$750,000
3 beds3.5 baths2,354 sq ft
628 Route 148 Rte, Killingworth, CT 06419
$98,500
2 beds1 bath672 sq ft
12 Country Club Trl, Killingworth, CT 06419
$599,000
5 beds2 baths2,090 sq ft
100 N Tower Hill Rd, Killingworth, CT 06419
See all

Provided by Redfin

Sale history for 258 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,533 (+1.1%)

$73,500 + $119,630

$193,130

2022

$4,484 (−1.1%)

$73,500 + $119,630

$193,130

2021

$4,534

$84,000 + $85,670

$169,670

2020

$4,534 (−2.7%)

$84,000 + $85,670

$169,670

2018

$4,661 (+2.8%)

$84,000 + $85,670

$169,670

2017

$4,535 (+0.1%)

$84,000 + $81,100

$165,100

2016

$4,530 (+5.5%)

$122,500 + $52,490

$174,990

2014

$4,293

$122,500 + $52,490

$174,990

2011

$4,293

$122,500 + $52,490

$174,990

Tax history for 258 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,533 (+1.1%)

$73,500 + $119,630

$193,130

2022

$4,484 (−1.1%)

$73,500 + $119,630

$193,130

2021

$4,534

$84,000 + $85,670

$169,670

2020

$4,534 (−2.7%)

$84,000 + $85,670

$169,670

2018

$4,661 (+2.8%)

$84,000 + $85,670

$169,670

2017

$4,535 (+0.1%)

$84,000 + $81,100

$165,100

2016

$4,530 (+5.5%)

$122,500 + $52,490

$174,990

2014

$4,293

$122,500 + $52,490

$174,990

2011

$4,293

$122,500 + $52,490

$174,990

*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

2 Acres

Year renovated

1991

Sq. Ft.

1,606

Year built

1965

Style

Single Family Residential

County

Middlesex County

APN

997186

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

Interior Information
Total Rooms: 6
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener
Security System, Thermostat(s)
Fireplaces Total: 1
Appliances Included: Electric Cooktop, Oven/Range, Refrigerator, Dishwasher

Bathroom Information
# of Baths (Full): 2

Bedroom Information
Beds Total: 3

Room Information
Room Count: 6
Basement Description: Crawl Space
Has Attic
Attic Description: Access Via Hatch

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vertical Siding, Cement Block
Exterior Features: Deck, Gutters

Lot Information
Lot Description: Some Wetlands, Water View

Building Information
Foundation Type: Concrete
Construction Description: Frame, Concrete
Color: red

Property Information
Waterfront Description: Direct Waterfront, River
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1606
Driveway Type: Private, Asphalt

Financial

Assessments Information
Assessed Value: $165,100

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric
Heat Type: Hot Air, Wood/Coal Stove
Heat Fuel Type: Oil, Wood
Fuel Tank Location: In Basement

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Directions: off Rt 79 right on Chestnut Hill, stay on Chestnut Hill over small bridge, first house on the right (red ranch)
Direct Waterfront
County: Middlesex

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,606
Stories: 1.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1965
Year Renovated: 1991
County: Middlesex County
APN: 997186

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

Killingworth Elementary School

Public PreK-3 • Assigned • 3.7mi

8/10

Haddam-Killingworth Middle School

Public 6-8 • Assigned • 4.4mi

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

Climate risks

10/10 Flood Factor

Estimated 80%+ chance 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

6/10 Heat Factor

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

6/10 Wind Factor

71% chance of strong winds in next 30 years

5/10 Air Factor

5 unhealthy days expected this year, 8 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

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

$469,000 – $568,000

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Nearby similar homes

NEW CONSTRUCTION

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New listings for sale in 06419

COMING SOON

$750,000

3 beds3.5 baths2,354 sq ft

628 Route 148 Rte, Killingworth, CT 06419

$98,500

2 beds1 bath672 sq ft

12 Country Club Trl, Killingworth, CT 06419

$599,000

5 beds2 baths2,090 sq ft

100 N Tower Hill Rd, Killingworth, CT 06419

Home values near 258 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
40 Chestnut Hill Rd, Madison, CT 3 Beds \| 3 Baths \| 2435 Sq. Ft.	$857,806
267 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2.5 Baths \| 2734 Sq. Ft.	$678,505

Address	Redfin Estimate
281 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2.5 Baths \| 2274 Sq. Ft.	$779,889
271 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2.5 Baths \| 2590 Sq. Ft.	$723,939

Address	Redfin Estimate
263 Chestnut Hill Rd, Killingworth, CT 3 Beds \| 2.5 Baths \| 2646 Sq. Ft.	$723,536
277 Chestnut Hill Rd, Killingworth, CT 4 Beds \| 2.5 Baths \| 2648 Sq. Ft.	$774,170

Property information provided by Smart MLS when last listed in 2018. 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 06419, CT

Sale history for 258 Chestnut Hill Rd

Tax history for 258 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 06419

Home values near 258 Chestnut Hill Rd

More real estate resources