4 Bedroom Homes for Sale in Chester, CT

5 Homes for Sale

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Open House

Photo 3 of Single family home for sale at 275 W Main St, Chester, CT 06412 | MLS# 24211368 | Listing updated on 2026-10-07

Photo 1 of Single family home for sale at 275 W Main St, Chester, CT 06412 | MLS# 24211368 | Listing updated on 2026-10-07

Photo 2 of Single family home for sale at 275 W Main St, Chester, CT 06412 | MLS# 24211368 | Listing updated on 2026-10-07

$779,999

count-img 2

4Bds

4Ba

2,706sqft

Single family home for sale

275 W Main St, Chester, CT 06412

Great Estates, Ct

Photo 3 of Single family home for sale at 47 E Kings Hwy, Chester, CT 06412 | MLS# 24206419 | Listing updated on 2026-09-28

Photo 1 of Single family home for sale at 47 E Kings Hwy, Chester, CT 06412 | MLS# 24206419 | Listing updated on 2026-09-28

Photo 2 of Single family home for sale at 47 E Kings Hwy, Chester, CT 06412 | MLS# 24206419 | Listing updated on 2026-09-28

$1,900,000

4Bds

4Ba

3,957sqft

Single family home for sale

47 E Kings Hwy, Chester, CT 06412

Chiarito Real Estate Llc

Photo 3 of Multi family home for sale at 84 86 Spring St, Chester, CT 06412 | MLS# 24207359 | Listing updated on 2026-09-20

Photo 1 of Multi family home for sale at 84 86 Spring St, Chester, CT 06412 | MLS# 24207359 | Listing updated on 2026-09-20

Photo 2 of Multi family home for sale at 84 86 Spring St, Chester, CT 06412 | MLS# 24207359 | Listing updated on 2026-09-20

$579,900

count-img 4

4Bds

3Ba

3,506sqft

Multi family home for sale

84 86 Spring St, Chester, CT 06412

Carbutti & Co., Realtors

Photo 3 of Single family home for sale at 13 High Fld Ln, Chester, CT 06412 | MLS# 24198973 | Listing updated on 2026-10-01

Photo 1 of Single family home for sale at 13 High Fld Ln, Chester, CT 06412 | MLS# 24198973 | Listing updated on 2026-10-01

Photo 2 of Single family home for sale at 13 High Fld Ln, Chester, CT 06412 | MLS# 24198973 | Listing updated on 2026-10-01

$764,900

count-img 1

4Bds

3Ba

2,662sqft

Single family home for sale

13 High Fld Ln, Chester, CT 06412

William Pitt Sotheby'S Int'L

Photo 3 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28

Photo 1 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28

Photo 2 of Single family home for sale at 288 Middlesex Ave, Chester, CT 06412 | MLS# 24201816 | Listing updated on 2026-09-28

$2,995,000

4Bds

6Ba

4,926sqft

Single family home for sale

288 Middlesex Ave, Chester, CT 06412

Coldwell Banker Realty

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No. of Homes

Prices

Homes for Sale New Haven

2,849

$3,500

Homes for Sale Hartford

2,425

$242,500

Homes for Sale Stamford

376

$337,000

Homes for Sale Waterbury

365

$220,000

Homes for Sale Norwalk

249

$360,000

Homes for Sale Newtown

106

$625,000

Homes for Sale Greenwich

102

$515,000

Homes for Sale Cheshire Town

$590,000

Homes for Sale Glastonbury Center

$600,000

Houses for Sale in Chester Under $100K

Houses for Sale in Chester Under $150K

Houses for Sale in Chester Under $200K

Houses for Sale in Chester Under $250K

Houses for Sale in Chester Under $300K

Houses for Sale in Chester Under $350K

Houses for Sale in Chester Under $400K

Houses for Sale in Chester Under $450K

Houses for Sale in Chester Under $500K

Houses for Sale in Chester Under $600K

Houses for Sale in Chester Under $700K

Houses for Sale in Chester Under $800K

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Based on information provided to and compiled by the SMART MLS, Inc. through Oct 9, 2026, 2:30 PM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.