81 Main Street Chester, CT $ 550,000
81 Main Street
$ 550,000
Recently Listed
Share Save

81 Main Street

Chester, CT, 06412
$ 550,000
Bedrooms2 Baths2.0 Sq 1,128

Monthly Estimate*

$ 3,386

81 Main Street, Chester, CT 06412 - Image 1
81 Main Street, Chester, CT 06412 - Image 2
81 Main Street, Chester, CT 06412 - Image 3
81 Main Street, Chester, CT 06412 - Image 4
81 Main Street, Chester, CT 06412 - Image 5
81 Main Street, Chester, CT 06412 - Image 6
81 Main Street, Chester, CT 06412 - Image 7
81 Main Street, Chester, CT 06412 - Image 8
81 Main Street, Chester, CT 06412 - Image 9
81 Main Street, Chester, CT 06412 - Image 10
81 Main Street, Chester, CT 06412 - Image 11
81 Main Street, Chester, CT 06412 - Image 12
81 Main Street, Chester, CT 06412 - Image 13
81 Main Street, Chester, CT 06412 - Image 14
81 Main Street, Chester, CT 06412 - Image 15
81 Main Street, Chester, CT 06412 - Image 16
81 Main Street, Chester, CT 06412 - Image 17
81 Main Street, Chester, CT 06412 - Image 18
81 Main Street, Chester, CT 06412 - Image 19
81 Main Street, Chester, CT 06412 - Image 20
81 Main Street, Chester, CT 06412 - Image 21
81 Main Street, Chester, CT 06412 - Image 22
81 Main Street, Chester, CT 06412 - Image 23
81 Main Street, Chester, CT 06412 - Image 24
81 Main Street, Chester, CT 06412 - Image 25
81 Main Street, Chester, CT 06412 - Image 26
81 Main Street, Chester, CT 06412 - Image 27
81 Main Street, Chester, CT 06412 - Image 28
81 Main Street, Chester, CT 06412 - Image 29
81 Main Street, Chester, CT 06412 - Image 30
81 Main Street, Chester, CT 06412 - Image 31
81 Main Street, Chester, CT 06412 - Image 32
81 Main Street, Chester, CT 06412 - Image 33
81 Main Street, Chester, CT 06412 - Image 34
81 Main Street, Chester, CT 06412 - Image 35
81 Main Street, Chester, CT 06412 - Image 36
81 Main Street, Chester, CT 06412 - Image 37
81 Main Street, Chester, CT 06412 - Image 38
81 Main Street, Chester, CT 06412 - Image 39

Single Family Home for sale in Chester, CT

for $550,000 with 2 bedrooms and 2 full baths. This 1,128 square foot home was built in 1950 on a lot size of 0.15.

Discover the perfect blend of mid-century character and modern efficiency in the heart of Chester Village. This impeccably maintained home offers a vibrant "walk-to-everything" lifestyle, just steps from award-winning dining, boutiques, and the theater. Officially a 2-bedroom home per town records, the layout offers incredible flexibility. The main level features a stunning den currently utilized as a primary suite. This light-filled space features a private, fully renovated ensuite full bath and a handsome armoire for storage, offering a sophisticated retreat for those seeking first-floor living. Note: This serves as the primary bath for the main level, enhancing the "suite" feel of the space. Upstairs, you will find two additional well-appointed rooms and a second fully renovated full bath, providing ample space for guests or a home office. The home's infrastructure has been flawlessly upgraded, featuring a new 50-year roof, on-demand propane heat/hot water, and an electric heat pump for heating and cooling (A/C on the first floor). The updated eat-in kitchen is a chef's delight, while the professional landscaping and beautiful stone patio create a private oasis for outdoor entertaining. Rarely does a home combine such high-end mechanical peace of mind with the undeniable charm of a downtown location. Turn-key and ready for its next chapter-experience the best of Chester right outside your front door.

See more

Single Family Active

Price

$ 550,000

Bedrooms

2

Full Bath

2

Property Type

Single Family

Taxes

$ 5,503

Style

Lot Size

0.15

Year Built

1950

Town/City

Chester

MLS | Web ID

24172804

Features
General
Zoning C
Neighborhood N/A
County Middlesex
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.15
Directions GPS friendly.
High School Per Board of Ed
City Chester
Elementary School Per Board of Ed
Sq Ft Total 1128
DOM 0
Year Built 1950
Style Cape Cod
Year Built Source Public Records
Energy Features Storm Doors Thermopane Windows
See more
Interior
Cooling System Heat Pump Window Unit
Total Rooms 5
Basement Description Crawl Space
See more
Exterior
Water Source Public Water Connected
Lot Description Treed Level Lot Professionally Landscaped
See more
* Excluded Features
List By
Susan Woods

Listing Agent

William Pitt Sotheby's Int'l

Broker

swoods@wpsir.com

Email

Affordability Calculator

$3,845
Per Month
88%
12%
0%
Monthly Principal & Interest
$3,386
Monthly Property Taxes
$459
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
5/8/2026$550,000 Listed Price

Map


See all

81 Main Street, Chester, CT, 06412 is a Single Family Home for sale at $550,000 with 1,128 sqft and a lot size of 0.15. 81 Main Street has 2 bedrooms, 2.0 baths, and was built in 1950. The property's zip code is 06412 which is in Chester, CT