For sale

$599,999

Est. $4,748/mo —

•

4,271

sq ft

20 Chimney Hill Rd, Middletown, CT 06457

About this home

Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

Single-familyProperty Type

1962Year Built

0.98 acresLot Size

$140Price/Sq.Ft.

2 car garageParking

Listed by Joe Koontz • eXp Realty

Contact: Agent Attribution Contact: (203) 702-3883 | Office Attribution Contact: (866) 828-3951

Source:Smart MLS #24197740

Payment calculator

$4,748 per month

Principal and interest$3,234

Property taxes

$1,324

HOA dues

Home insurance

$190

Utilities

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See this home in person

This home is unavailable to tour on this day.

Next available date: Sunday, November 8

Open houses

No upcoming open houses.

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201 Francis St, New Britain, CT 06053
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53 Grieb Trl, Wallingford, CT 06492
4,791 sq ft lot • Built 1955
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941 Hopewell Rd, South Glastonbury, CT 06073
0.66 acre lot • 2 garage spots • Built 1975
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0.28 acre lot • 2 parking spots • Built 1917

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Around this home

Schools

K - 12
Preschool & daycare

Snow School

Public PreK-5 • Assigned • 0.8mi

4/10

Beman Middle School

Public 7-8 • Assigned • 0.7mi

4/10

Middletown High School

Public 9-12 • Assigned • 2.6mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

20 Chimney Hill Rd · $599,999

Strong offer

$600K and above

75% chance or better to win

Why $600K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 43 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Nine total rooms
One fireplace
Has attic with pull-down stairs

Bedrooms
Four bedrooms

Bathrooms
Two full bathrooms
One half bathroom

Kitchen
Gas cooktop

Heating & cooling
Hot water heating
Oil-fired heat

Sale and tax history for 20 Chimney Hill Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24197740

Nov 2, 2026

Price Changed

$599,999

$140/sq ft

Oct 4, 2026

Price Changed

$649,000

$152/sq ft

Sep 4, 2026

Price Changed

$699,000

$164/sq ft

Aug 7, 2026

Listed

$799,000

$187/sq ft

Smart MLS #170128809

May 6, 2019

Sold

$378,500

$89/sq ft

Mar 19, 2019

Contingent

—

Feb 12, 2019

Price Changed

$385,000

$90/sq ft

Nov 13, 2018

Price Changed

$399,850

$94/sq ft

Sep 27, 2018

Listed

$419,900

$98/sq ft

Here is the classic New England beauty you’ve been waiting to see! Tucked into a quiet cul de sac, this is a rarely available convenient location. You will enjoy 4+ bedrooms close to Wesleyan University and the center of town . This home is spacious and comfortable in every way you can imagine. There is truly room here to spread out, relax and entertain. And it has an enormous walk up attic that runs the full width of the house. Amazing opportunity for storage or expansion. Natural wood beams welcome all to enjoy warm, inviting family meals in the big country kitchen. Professional grade appliances offer easy cooking with a gleaming Viking Hood, Thermador 6+ burner gas cook center with griddle. Double Jenn-Air Wall Ovens and Refrigerator and more. Amazing coffered ceilings add the kind of architectural detail in both Dining Room and Living Room that enhance any design. The huge family room provides something for everyone with custom library wall built-ins, double wide brick fireplace wall and endless opportunities for relaxed living.Great bonus room with separate entrance and office on 2nd floor offers flexible living space. And your pet is welcome to play on the wide front lawn protected with a Canine Fence invisible fence system. Enjoy convenient access to all the dining, entertainment and educational facilities that Middletown has to offer. This is your chance to own a great New England home on a desirable de sac.

Public Records

Dec 2, 1996

Sold

$268,000

$63/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$12,684

$59,990 + $228,290

$288,280

2021

$12,684 (−0.5%)

$59,990 + $228,290

$288,280

2020

$12,742 (−0.5%)

$59,990 + $228,290

$288,280

2019

$12,800 (+2.3%)

$59,990 + $228,290

$288,280

2018

$12,513 (+12.2%)

$59,990 + $226,360

$286,350

2017

$11,155 (+2.9%)

$71,130 + $191,960

$263,090

2016

$10,839 (+4.0%)

$71,130 + $191,960

$263,090

2015

$10,418 (−1.0%)

$71,130 + $191,960

$263,090

2014

$10,524 (−2.9%)

$71,130 + $191,960

$263,090

2011

$10,834

$80,500 + $240,020

$320,520

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.98 Acres

Year renovated

—

Finished Sq. Ft.

4,271

Unfinished Sq. Ft.

—

Total Sq. Ft.

4,271

Year built

1962

Style

Single Family Residential

County

Middlesex County

APN

1013828

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 99° expected this year, 16 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

3/10 Air Factor

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

Provided by First Street

Historical weather

Middletown, CT • 06457

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

85/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Middletown. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.1 hrs

5.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 20 Chimney Hill Rd

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

Nearby homes have recently sold between $349,900 and $759,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $350K to $759K.

SOLD AUG 4, 2026
$485,000 Last sold price
4 beds3.5 baths3,622 sq ft
46 Bretton Rd, Middletown, CT 06457
$6/sq ft
smaller lot
62 years older
SOLD SEP 30, 2026
$759,000 Last sold price
3 beds2.5 baths3,283 sq ft
236 Maple Shade Rd, Middletown, CT 06457
$91/sq ft
larger lot
39 years newer
SOLD DEC 17, 2025
$462,300 Last sold price
4 beds3 baths2,054 sq ft
10 Lorelei Cir, Middletown, CT 06457
$85/sq ft
smaller lot
24 years newer
SOLD AUG 3, 2026
$650,000 Last sold price
3 beds3.5 baths3,644 sq ft
37 Cranberry Ln, Middletown, CT 06457
$38/sq ft
smaller lot
38 years newer
SOLD SEP 15, 2026
$535,000 Last sold price
5 beds2.5 baths3,017 sq ft
98 S Front St, Middletown, CT 06457
$37/sq ft
smaller lot
25 years newer
SOLD SEP 25, 2026
$349,900 Last sold price
4 beds2 baths1,664 sq ft
125 Stevens Ln, Middletown, CT 06457
$70/sq ft
smaller lot
9 years older

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

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