Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$550,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,128 Sq. Ft.
  • Updated 2 days ago
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 81 Main St

General

  • Price: $550,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24172804
  • Updated: 5/11/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 5
  • Interior Features: Open Floor Plan
  • Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2
  • Primary Bedroom: Primary Bedroom - Full Bath, Hardwood Floor, 14.3 x 10.3, Main
  • Bedroom 1: Bedroom - Vaulted Ceiling, Built-Ins, Ceiling Fan, Hardwood Floor, 10.6 x 13, Upper

Other Rooms

  • Living Room: Living Room - Combination Liv/Din Rm, Dining Area, Hardwood Floor, 13.7 x 11.11, Main
  • Kitchen: Kitchen - Remodeled, Built-In Hutch, Quartz Counters, Eating Space, Hardwood Floor, 15.4 x 14, Main
  • Dining Room: Dining Room - Combination Liv/Din Rm, Hardwood Floor, 10 x 11, Main
  • Office: Office - Vaulted Ceiling, Ceiling Fan, Hardwood Floor, 10 x 13, Upper
  • Laundry: Main Level

Exterior

  • Exterior Features: Gutters, Garden Area, Patio
  • Color: Sage

Location

  • County: Middlesex
  • Driving Directions: GPS friendly.

School Information

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

Heating & Cooling

  • Cooling Type: Heat Pump, Window Unit
  • Heating Type: Heat Pump, Radiator, Electric, Propane
  • Heating Fuel: Electric, Propane
  • Water Heater: Domestic, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Crawl Space
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,128
  • Above Ground: 1,128 Sq. Ft.
  • Year Built: 1950

Lot Features

  • Lot Size (Acres): 0.15
  • Zoning: C
  • Lot Description: Treed, Level Lot, Professionally Landscaped

Green Features

  • Energy Features: Storm Doors, Thermopane Windows

Financial Considerations

  • Annual Sewer Fee: $750
  • Assessment Amount: $203,210
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 940179

Listed by William Pitt Sotheby's Int'l, Susan Woods

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 81 Main St —

  • Susan Woods

    William Pitt Sotheby's Int'l

Agent Contact: (203) 215-8676 Office Contact: (203) 245-6700

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 81 Main St

School Districts:Regional High School District 04, Chester School District
NameGradesDistance
Chester Elementary School, Chester, CT
23 Ridge Road, Chester, CT 06412
K-61.1 mi
John Winthrop Middle School
1 Winthrop Road, Deep River, CT 06417
7-83.1 mi
Valley Regional High School
256 Kelsey Hill Road, Deep River, CT 06417
9-122.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 81 Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/11/2026
Listed
$550,000
111.54%
MLS
7/18/2013
Sold
$260,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 81 Main St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,503
11%
$203,210
—
2023
$4,968
12%
$203,210
36%
2023
$4,450
1%
$149,840
—
2022
$4,420
—
$149,840
—
2021
$4,420
3%
$149,840
—
2020
$4,288
-1%
$149,840
—
2019
$4,314
-1%
$149,840
-7%
2018
$4,365
3%
$161,020
—
2017
$4,244
3%
$161,020
—
2016
$4,117
1%
$161,020
—
2015
$4,077
2%
$161,020
—
2014
$3,997
-2%
$161,020
-13%
2011
$4,082
—
$185,970
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 81 Main St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by William Pitt Sotheby's Int'l, Susan Woods

Similar Properties near 81 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

135 Middlesex Ave, Chester, CT 06412 - Photo 1
$525,000
Open House

135 Middlesex Ave  Chester, CT 06412

  • Single Family
  • Active
  • Updated 12 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,188
    Sq. Ft.
Listed by Re/Max Valley Shore
7 Mitchel Terrace, Essex, CT 06442 - Photo 1
$597,900
Open House

7 Mitchel Terrace  Essex, CT 06442

  • Single Family
  • Active
  • Updated 12 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,880
    Sq. Ft.
Listed by Re/Max Valley Shore
42 Parker Hill Rd, Killingworth, CT 06419 - Photo 1
$518,000

42 Parker Hill Rd  Killingworth, CT 06419

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,842
    Sq. Ft.
Listed by Shelly Cumpstone (860) 434-8600
110 Town Woods Rd, Lyme, CT 06371 - Photo 1
$569,900

110 Town Woods Rd  Lyme, CT 06371

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 2,238
    Sq. Ft.
Listed by Wayne Realty

Just Listed near 81 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

[Address not provided], Deep River, CT 06417 - Photo 1 Just Listed
$595,000

[Address not provided]  Deep River, CT 06417

  • Commercial
  • Active
Listed by Berkshire Hathaway NE Prop.
15 Pent Rd, Deep River, CT 06417 - Photo 1 Just Listed
$924,000
Open House

15 Pent Rd  Deep River, CT 06417

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,774
    Sq. Ft.
Listed by Ki Property Group
45 Falls River Dr, Essex, CT 06442 - Photo 1 Just Listed
$1,250,000

45 Falls River Dr  Essex, CT 06442

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,467
    Sq. Ft.
Listed by William Raveis Real Estate
81 Meeting House Rd, Haddam, CT 06438 - Photo 1 Just Listed
$699,900

81 Meeting House Rd  Haddam, CT 06438

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 4,841
    Sq. Ft.
Listed by Santana Realty Group LLC

Price Reduced near 81 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

112 Main St, Essex, CT 06409 - Photo 1 Price Reduced
-$24,900 (-3.11%)
$775,000
Open House

112 Main St  Essex, CT 06409

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,407
    Sq. Ft.
Listed by Century 21 Classic Homes
154 Falls Rd, East Haddam, CT 06469 - Photo 1 Price Reduced
-$10,000 (-1.67%)
$589,999

154 Falls Rd  East Haddam, CT 06469

  • Single Family
  • Active
  • Updated 12 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,000
    Sq. Ft.
Listed by Century 21 AllPoints Realty
5 Cook Terrace, Westbrook, CT 06498 - Photo 1 Price Reduced
-$9,000 (-6%)
$141,000

5 Cook Terrace  Westbrook, CT 06498

  • Mobile Home
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 672
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
44 Linden Ave N, Westbrook, CT 06498 - Photo 1 Price Reduced
-$5,000 (-3.57%)
$134,900

44 Linden Ave N  Westbrook, CT 06498

  • Mobile Home
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 672
    Sq. Ft.
Listed by Social & Co Realty

Recent Sales near 81 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

131 Middlesex Ave, Chester, CT 06412 - Photo 1 Sold
$530,000

131 Middlesex Ave  Chester, CT 06412

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,664
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by Reyher Real Estate
36 Kings Hwy, Chester, CT 06412 - Photo 1 Sold
$469,900

36 Kings Hwy  Chester, CT 06412

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 1,516
    Sq. Ft.
Listed by Re/Max Valley Shore
Sold by Redfin Corporation
21 River Ln, Deep River, CT 06417 - Photo 1 Sold
$495,000

21 River Ln  Deep River, CT 06417

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,018
    Sq. Ft.
Listed by Team Jermainne Real Estate Services, LLC
Sold by Re/Max Valley Shore
87 Rattling Valley Rd, Deep River, CT 06417 - Photo 1 Sold
$525,000

87 Rattling Valley Rd  Deep River, CT 06417

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,639
    Sq. Ft.
Listed by William Pitt Sotheby's International Realty
Sold by Berkshire Hathaway NE Prop.

81 Main Street, Chester, CT 06412 (MLS# 24172804) is a Single Family property with 2 bedrooms and 2 full bathrooms. 81 Main Street is currently listed for $550,000 and was received on May 11, 2026. Want to learn more about 81 Main Street? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

Tour this property