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81 Main Street, Chester, CT 06412

Single Family For Sale

$550,000
$488/sqft
81 Main Street, Chester, CT
Coming Soon
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2
Bedrooms
2
Bathrooms
1,128
Sq Ft
0.15
Acres
1950
Year Built

About 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.

Listed by Susan Woods (203) 215-8676 with William Pitt Sotheby's Int'l (203) 245-6700

Listing Snapshot

Price $550,000 Days on Our Site 0 days
Property Tax $5,503/yr Style Cape Cod
Year Built 1950 Total Sq Ft 1,128
Lot Size 0.15 acres HOA Fees N/A
Bedrooms 2 Full Bathrooms 2
Total Rooms 5 Half Baths 0

Key Features

Interior
  • Open Floor Plan
Appliances
  • Gas Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Gutters
  • Garden Area
  • Patio

Structure & Parking

Construction Frame
Roof Asphalt Shingle

Systems & Utilities

Heat Heat Pump, Radiator
Fuel Electric, Propane
Cooling Heat Pump, Window Unit
Hot Water Domestic, Tankless Hotwater
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $459/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
May 4, 2026 Listed $550,000

Frequently Asked Questions

How much does 81 Main Street in Chester, CT cost?
This property is listed at $550,000, which works out to $488 per square foot.
How many bedrooms does 81 Main Street have?
This home has 2 bedrooms and 2 bathrooms.
What is the square footage of 81 Main Street?
The home is 1,128 square feet, situated on 0.15 acres.
When was 81 Main Street in Chester built?
This property was built in 1950.
Is 81 Main Street, Chester, CT still available?
The current MLS status of this property is "Coming Soon". Contact RYZE Realty Group for the latest availability.
What school district is 81 Main Street, Chester in?
This home is served by the Chester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 81 Main Street, Chester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Susan Woods · (203) 215-8676

William Pitt Sotheby's Int'l · (203) 245-6700

MLS# 24172804 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated May 8, 2026 7:58 PM UTC