For sale

Price cut: $100K (9/4)

$699,000

20 Chimney Hill Road, Middletown, CT 06457

4beds

4,271sqft

$4,843/mo

Get pre-qualified

Single Family Residence

Built in 1962

0.98 Acres Lot

$-- Zestimate^®

$164/sqft

$-- HOA

What's special

En-suite bathTwo-car attached garageAmple closet spaceBright open floor planBeautifully landscaped lot

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.

31 days
968
11

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 4
Bathrooms: 3
Full bathrooms: 2
1/2 bathrooms: 1

Primary bedroom

Level: Upper

Bedroom

Level: Upper

Bedroom

Level: Upper

Bedroom

Level: Upper

Dining room

Level: Main

Living room

Level: Main

Heating

Hot Water, Oil

Cooling

None

Appliances

Included: Gas Cooktop, Electric Water Heater, Water Heater

Features

Basement: None
Attic: Pull Down Stairs
Number of fireplaces: 1

Interior area

Total structure area: 4,271
Total interior livable area: 4,271 sqft
Finished area above ground: 4,271

Property

Parking

Total spaces: 2
Parking features: Attached
Attached garage spaces: 2

Lot

Size: 0.98 Acres
Features: Cul-De-Sac

Details

Parcel number: 1013828
Zoning: R-15

Construction

Type & style

Home type: SingleFamily
Architectural style: Colonial
Property subtype: Single Family Residence

Materials

Vinyl Siding
Foundation: Concrete Perimeter
Roof: Asphalt

Condition

New construction: No
Year built: 1962

Utilities & green energy

Sewer: Public Sewer
Water: Public

Community & HOA

Community

Subdivision: Highland

HOA

Has HOA: No

Location

Region: Middletown

Financial & listing details

Price per square foot: $164/sqft
Tax assessed value: $389,540
Annual tax amount: $15,893
Date on market: 8/8/2026

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
9/4/2026	Price change	$699,000-12.5%$164/sqft
Source: Smart MLS #24197740 Report a problem
8/8/2026	Listed for sale	$799,000+111.1%$187/sqft
Source: Smart MLS #24197740 Report a problem
5/6/2019	Sold	$378,500-1.7%$89/sqft
Source: Smart MLS #170128809 Report a problem
2/12/2019	Price change	$385,000-3.7%$90/sqft
Source: William Raveis Real Estate #170128809 Report a problem
11/13/2018	Price change	$399,850-4.8%$94/sqft
Source: William Raveis Real Estate #170128809 Report a problem
9/27/2018	Listed for sale	$419,900+56.7%$98/sqft
Source: William Raveis Real Estate #170128809 Report a problem
12/2/1996	Sold	$268,000$63/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$15,634 +9.1%	$401,910 +3.2%
2024	$14,335 +4.8%	$389,540
2023	$13,673 +7.8%	$389,540 +35.1%
2022	$12,684	$288,280
2021	$12,684 -0.5%	$288,280
2020	$12,742 -0.5%	$288,280
2019	$12,800 +2.3%	$288,280 +0.7%
2018	$12,513 +12.2%	$286,350 +8.8%
2017	$11,155 +7.1%	$263,090
2015	$10,418 -1%	$263,090
2014	$10,524 -2.9%	$263,090 -17.9%
2013	$10,834 +3.4%	$320,520
2012	$10,481 +3.5%	$320,520
2011	$10,128 -0.9%	$320,520
2010	$10,225 +4.6%	$320,520
2009	$9,776 +19.6%	$320,520
2008	$8,173 -12.7%	$320,520 +30.8%
2007	$9,364 +1.3%	$245,120
2006	$9,241 +5.6%	$245,120
2005	$8,751 +6.3%	$245,120
2004	$8,236 +2.4%	$245,120
2003	$8,040 +35%	$245,120 +13.6%
1995	$5,956	$215,800