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Connecticut · Real Estate

Homes for Sale in
Chester, CT

There are currently 6 homes for sale in Chester, Connecticut with an average list price of $1,267,038.

Chester is a small Connecticut River Valley town of about 3,900 that punches well above its weight in culture and character. Part of the loosely defined "Connecticut River Valley arts corridor," it's home to upscale galleries, destination restaurants, and a walkable village center. The Goodspeed Opera House is a short ferry ride across the river in East Haddam. Small, charming, and genuinely distinctive.

For Sale

6

active listings

Avg. Sale Price

$705K

$214K–$3.1M

Avg. Size Sold

2,162 sf

last 12 mo

vs. Ask Price

+1.3%

avg. paid vs. ask

Stats based on 40 closings in the last 12 months

Showing 6 of 6 listings in Chester

136 Goose Hill Road, Chester, CT
Coming Soon
$995,000
4 bd · 3.00 ba · 3,343 sqft
136 Goose Hill Road
Chester, CT 06412
RE/MAX One SmartMLS
3 KIRTLAND Avenue, Chester, CT
Active
$282,225
2 bd · 2.00 ba · 1,344 sqft
3 KIRTLAND Avenue
Chester, CT 06412
Realhome Services & Solutions SmartMLS
81 Main Street, Chester, CT
Active
$550,000
2 bd · 2.00 ba · 1,128 sqft
81 Main Street
Chester, CT 06412
William Pitt Sotheby's Int'l SmartMLS
59-65 Maple Street, Chester, CT
Active
$2,100,000
11 bd · 12.00 ba · 8,500 sqft  ·  5 Family+
59-65 Maple Street
Chester, CT 06412
VC Property Group, LLC SmartMLS
135 Middlesex Avenue, Chester, CT
Active
$525,000
3 bd · 2.00 ba · 1,188 sqft
135 Middlesex Avenue
Chester, CT 06412
Re/Max Valley Shore SmartMLS
288 Middlesex Avenue, Chester, CT
Active
$3,150,000
4 bd · 6.00 ba · 4,926 sqft
288 Middlesex Avenue
Chester, CT 06412
Coldwell Banker Realty SmartMLS

Buying a Home in Chester, CT

Current Market Snapshot

Entry Price
$282K
lowest listed
Avg. Price
$1.3M
list price
Top of Market
$3.2M
highest listed
Listings by Bedroom Count
2 beds
2
3 beds
1
4 beds
2
11 beds
1
Property Types Available
Single Family · 5 Multi-Family For Sale · 1

The Chester real estate market currently has 6 active listings with an average list price of $1,267,038 and a price range from $282,225 to $3,150,000. Single Family homes make up the largest share of available inventory. Most listings are 2-bedroom homes. The average home size is 3,405 sq ft. All listings are sourced directly from SmartMLS and updated every 15 minutes.

Frequently Asked Questions

How many homes are for sale in Chester, CT right now?
As of May 2026, there are 6 active listings in Chester, CT. All listings are updated every 15 minutes directly from SmartMLS.
What is the average home price in Chester, CT?
The average list price in Chester is $1,267,038. Homes currently range from $282,225 to $3,150,000.
What size homes are most common in Chester, CT?
The most common listing in Chester is a 2-bedroom home (2 listings). Other common sizes include 4-bedroom (2) and 3-bedroom (1). The average home size is 3,405 sq ft.
What types of homes are available in Chester, CT?
Current listings in Chester include: Single Family (5), Multi-Family For Sale (1).
Is Chester, CT a good place to buy a home?
Chester is a small Connecticut River Valley town of about 3,900 that punches well above its weight in culture and character. Part of the loosely defined "Connecticut River Valley arts corridor," it's home to upscale galleries, destination restaurants, and a walkable village center. The Goodspeed Opera House is a short ferry ride across the river in East Haddam. Small, charming, and genuinely distinctive.
Does RYZE Realty Group serve Chester, CT?
Yes — RYZE Realty Group is a Connecticut real estate team serving buyers and sellers across Middlesex County and the greater Connecticut market, including Chester. Contact us for a free consultation.

Nearby Towns

Middletown, CT 54 listings
Clinton, CT 33 listings
Old Saybrook, CT 33 listings
Essex, CT 33 listings
East Haddam, CT 31 listings
East Hampton, CT 25 listings

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