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Chester, CT
City
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1 - 30 of 30 listings (30 total matches)
Newest Listings
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189 Middlesex Avenue Chester CT 06412
1 / 7
$3,300,000
IDX Logo for Smart MLS
Commercial Sale For Sale
Active
21,905
SQFT
189 Middlesex Avenue
Chester, CT 06412
 
Listing courtesy of Stephen Press of Press/Cuozzo Realtors Office Phone: (203) 288-1900 Broker Contact: (203) 288-1900
288 Middlesex Avenue Chester CT 06412
1 / 38
$2,995,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
4
BEDS
6
TOTAL BATHS
4,926
SQFT
288 Middlesex Avenue
Chester, CT 06412
 
Listing courtesy of Nancy Mesham of Coldwell Banker Realty Office Phone: (860) 434-8600 Broker Contact: (860) 227-9071
59-65 Maple Street Chester CT 06412
1 / 6
$1,995,000
IDX Logo for Smart MLS
Multi Family For Sale
Active Under Contract
7
BEDS
7
TOTAL BATHS
8,500
SQFT
59-65 Maple Street
Chester, CT 06412
 
Listing courtesy of Connor Wenchell of VC Property Group, LLC Office Phone: (860) 300-3102 Broker Contact: (860) 343-7800
47 East Kings Highway Chester CT 06412
1 / 40
$1,900,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,957
SQFT
47 East Kings Highway
Chester, CT 06412
 
Listing courtesy of Al Chiarito of Chiarito Real Estate LLC Office Phone: (860) 227-2074 Broker Contact: (860) 227-2074
10 Denlar Drive Chester CT 06412
1 / 30
$1,450,000
IDX Logo for Smart MLS
Commercial Sale
Pending
28,525
SQFT
10 Denlar Drive
Chester, CT 06412
 
Listing courtesy of Susan Malan of William Pitt Sotheby's Int'l Office Phone: (860) 767-7488 Broker Contact: (860) 767-5011
21 Main Street Chester CT 06412
1 / 37
$995,000
IDX Logo for Smart MLS
Business For Sale
Active
3,000
SQFT
21 Main Street
Chester, CT 06412
 
Listing courtesy of Maureen Evans of William Raveis Real Estate Office Phone: (860) 388-3936 Broker Contact: (860) 391-3747
21 Main Street Chester CT 06412
1 / 35
$995,000
IDX Logo for Smart MLS
Commercial Sale For Sale
Active
1
TOTAL BATH
3,000
SQFT
21 Main Street
Chester, CT 06412
 
Listing courtesy of Maureen Evans of William Raveis Real Estate Office Phone: (860) 388-3936 Broker Contact: (860) 391-3747
132 Main Street Chester CT 06412
1 / 4
$975,000
IDX Logo for Smart MLS
Commercial Sale
Pending
23,467
SQFT
132 Main Street
Chester, CT 06412
 
Listing courtesy of Janet Peckinpaugh of William Pitt Sotheby's Int'l Office Phone: (203) 245-6700 Broker Contact: (860) 985-3659
15 Hickory Hill Drive Chester CT 06412
1 / 39
$875,000
IDX Logo for Smart MLS
Single Family Residence
Pending
3
BEDS
3
TOTAL BATHS
3,233
SQFT
15 Hickory Hill Drive
Chester, CT 06412
 
Listing courtesy of Kathy Schellens of William Pitt Sotheby's Int'l Office Phone: (860) 767-7488 Broker Contact: (860) 395-4441
7 Hickory Hill Drive Chester CT 06412
Open House Sun, Nov 8, 1 PM
Please verify times due to COVID-19
1 / 39
$775,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
3,002
SQFT
7 Hickory Hill Drive
Chester, CT 06412
 
Listing courtesy of Rachel Welch of William Raveis Real Estate Office Phone: (860) 388-3936 Broker Contact: (860) 304-6896
13 High Field Lane Chester CT 06412
New Listing - a week on site
1 / 40
$749,900
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,662
SQFT
13 High Field Lane
Chester, CT 06412
 
Listing courtesy of Susan Malan of William Pitt Sotheby's Int'l Office Phone: (860) 767-7488 Broker Contact: (860) 767-5011
275 West Main Street Chester CT 06412
New Listing - 4 weeks on site
1 / 39
$715,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active Under Contract
4
BEDS
4
TOTAL BATHS
2,706
SQFT
275 West Main Street
Chester, CT 06412
 
Listing courtesy of Nancy Bullis of Coldwell Banker Realty Office Phone: (860) 434-8600 Broker Contact: (203) 856-9060
42 Straits Road Chester CT 06412
Price Change - 9 hours ago
1 / 40
$674,900
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,882
SQFT
42 Straits Road
Chester, CT 06412
 
Listing courtesy of Donna Genovese of Great Estates, CT Office Phone: (203) 200-7030 Broker Contact: (860) 280-4334
84-86 Spring Street Chester CT 06412
1 / 36
$579,900
IDX Logo for Smart MLS
Duplex For Sale
Active
4
BEDS
3
TOTAL BATHS
3,506
SQFT
84-86 Spring Street
Chester, CT 06412
 
Listing courtesy of Carrie Vass Brainerd of Carbutti & Co., Realtors Office Phone: (203) 269-4910 Broker Contact: (203) 927-8993
6 Gilbert Hill Road Chester CT 06412
Open House Sun, Nov 8, 1 PM
Please verify times due to COVID-19
1 / 40
$525,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,822
SQFT
6 Gilbert Hill Road
Chester, CT 06412
 
Listing courtesy of Carolyn Kress of Berkshire Hathaway NE Prop. Office Phone: (860) 537-6699 Broker Contact: (860) 908-4716
55 Wig Hill Road Chester CT 06412
1 / 38
$499,900
IDX Logo for Smart MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,774
SQFT
55 Wig Hill Road
Chester, CT 06412
 
Listing courtesy of Kelly Puorro of Puorro Realty Group Office Phone: (860) 558-9740 Broker Contact: (860) 575-8666
135 Middlesex Avenue Chester CT 06412
1 / 35
$475,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,188
SQFT
135 Middlesex Avenue
Chester, CT 06412
 
Listing courtesy of Lisa Genovali of Re/Max Valley Shore Office Phone: (860) 388-1228 Broker Contact: (860) 510-3293
6 School Lane Chester CT 06412
New Listing - a week on site
1 / 40
$450,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
1,179
SQFT
6 School Lane
Chester, CT 06412
 
Listing courtesy of Hilary Reid of Coldwell Banker Realty Office Phone: (860) 434-8600 Broker Contact: (860) 304-1259
6 Castle View Drive Chester CT 06412
1 / 32
$449,000
IDX Logo for Smart MLS
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,031
SQFT
6 Castle View Drive
Chester, CT 06412
 
Listing courtesy of Alan Spotlow of William Raveis Real Estate Office Phone: (203) 453-0391 Broker Contact: (203) 584-4300
40 Castle View Drive Chester CT 06412
New Listing - 4 weeks on site
1 / 25
$349,900
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,142
SQFT
40 Castle View Drive
Chester, CT 06412
 
Listing courtesy of Craig Milton of Re/Max Valley Shore Office Phone: (860) 388-1228 Broker Contact: (860) 388-4663
173 West Main Street Chester CT 06412
New Listing - 3 weeks on site
1 / 25
$289,000
IDX Logo for Smart MLS
Mobile Home For Sale
Active
2
BEDS
1
TOTAL BATH
1,392
SQFT
173 West Main Street
Chester, CT 06412
 
Listing courtesy of Erica Stone of iHeart Homes Real Estate LLC Office Phone: (203) 433-2007 Broker Contact: (203) 671-0491
92 Water Street Chester CT 06412
Price Change - a week ago
1 / 30
$252,500
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
1,217
SQFT
92 Water Street
Chester, CT 06412
 
Listing courtesy of Ryan O'Keeffe of Salzillo Realty Company Office Phone: (860) 637-1379 Broker Contact: (203) 297-0849
90 Water Street Chester CT 06412
Price Change - a week ago
1 / 24
$237,500
IDX Logo for Smart MLS
Single Family Residence For Sale
Active
1
BED
1
TOTAL BATH
1,034
SQFT
90 Water Street
Chester, CT 06412
 
Listing courtesy of Ryan O'Keeffe of Salzillo Realty Company Office Phone: (860) 637-1379 Broker Contact: (203) 297-0849
3 Inspiration Lane 1 Chester CT 06412
1 / 24
$5,500
IDX Logo for Smart MLS
Commercial Lease For Rent
Active
4,000
SQFT
3 Inspiration Lane 1
Chester, CT 06412
 
Listing courtesy of Kevin Brignole of Spaulding Realty Group, LLC Office Phone: (860) 564-8000 Broker Contact: (860) 564-8000
70 Goose Hill Road Chester CT 06412
1 / 19
$5,000
IDX Logo for Smart MLS
Single Family Residence For Rent
Active
4
BEDS
2
TOTAL BATHS
2,383
SQFT
70 Goose Hill Road
Chester, CT 06412
 
Listing courtesy of Matthew Guida of Eagle Eye Realty PLLC Office Phone: (860) 263-9102 Broker Contact: (860) 888-2732
100 West Main Street B Chester CT 06412
1 / 20
$2,300
IDX Logo for Smart MLS
Multi Family For Rent
Active
1
BED
2
TOTAL BATHS
800
SQFT
100 West Main Street B
Chester, CT 06412
 
Listing courtesy of Aschly Daggett of VC Property Group, LLC Office Phone: (860) 300-3102 Broker Contact: (860) 803-2520
19 Denlar Drive E Chester CT 06412
New Listing - 3 weeks on site
1 / 23
$2,250
IDX Logo for Smart MLS
Multi Family For Rent
Active
2
BEDS
2
TOTAL BATHS
1,206
SQFT
19 Denlar Drive E
Chester, CT 06412
 
Listing courtesy of Tom Clancy of William Pitt Sotheby's Int'l Office Phone: (203) 245-6700 Broker Contact: (203) 415-3888
6 Pleasant Street 2 Chester CT 06412
1 / 12
$1,750
IDX Logo for Smart MLS
Multi Family For Rent
Active
2
BEDS
1
TOTAL BATH
800
SQFT
6 Pleasant Street 2
Chester, CT 06412
 
Listing courtesy of Tom Clancy of William Pitt Sotheby's Int'l Office Phone: (203) 245-6700 Broker Contact: (203) 415-3888
184 Middlesex Avenue Chester CT 06412
1 / 9
$1,500
IDX Logo for Smart MLS
Multi Family For Rent
Active
1
TOTAL BATH
4,060
SQFT
184 Middlesex Avenue
Chester, CT 06412
 
Listing courtesy of Connor Wenchell of VC Property Group, LLC Office Phone: (860) 300-3102 Broker Contact: (860) 343-7800
1 Maple Street Chester CT 06412
1 / 17
$550
IDX Logo for Smart MLS
Commercial Lease For Rent
Active
4,757
SQFT
1 Maple Street
Chester, CT 06412
 
Listing courtesy of Kelly Puorro of Puorro Realty Group Office Phone: (860) 558-9740 Broker Contact: (860) 575-8666
1 - 30 of 30 listings (30 total matches)


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-11-08 01:18 AM UTC.


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