Chester, MA Real Estate & Homes For Sale

17 homes

NEW - 2 MIN AGO
0.56 ACRES
$250,000
3 Beds
1 Bath
1,481 sqft
128 Prospect St,
Chester, MA 01011
Joy Salvini, RE/MAX Compass
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OPEN SUN, 11-12:30PM
0.36 ACRES
$229,900
3 Beds
1.5 Baths
1,968 sqft
254 Route 20,
Chester, MA 01011
Dennis LeClair, Coldwell Banker Realty - Western MA
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OPEN SUN, 12-2PM
9.7 ACRES
$495,000
3 Beds
2 Baths
1,851 sqft
47 Lyon Hill Rd,
Chester, MA 01011
Debra A. Petrovsky, Donovan Real Estate
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$290,000
3 Beds
1.5 Baths
1,384 sqft
27 Maple Ave,
Chester, MA 01011
Kathleen A. Engwer, RE/MAX Compass, Lee MA
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0.84 ACRES
$39,000
Studio
2 Taft Rd,
Chester, MA 01011
Todd Kazunas, Gallagher Real Estate
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28 ACRES
$129,000
Mica Mill Rd,
Chester, MA 01011
Jaquaine Coe, The LGCY Group LLC
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5.2 ACRES
$129,900
Studio
1 Bath
560 sqft
93 Crane Rd,
Chester, MA 01011
Daniel James Piasecki, Coldwell Banker Community REALTORS®
10 ACRES
$40,000
50 Smith Rd,
Chester, MA 01011
Nicolle Serafino, Keller Williams Realty
0.44 ACRES
$210,000
2 Beds
1 Bath
1,652 sqft
23 Maple St,
Chester, MA 01011
Keira Hildack, Keller Williams Realty
0.25 ACRES
$80,000
2 Beds
1.5 Baths
1,328 sqft
166 Route 20,
Chester, MA 01011
Thomas Despard, Nexthome Elite Realty
2.03 ACRES
$45,000
Lot 1 Holcomb Rd,
Chester, MA 01011
James Adams, Hilltown Real Estate by Adams Realty
2.06 ACRES
$45,000
2 Holcomb Rd,
Chester, MA 01011
James Adams, Hilltown Real Estate by Adams Realty
2.12 ACRES
$60,000
3 Holcomb Rd,
Chester, MA 01011
James Adams, Hilltown Real Estate by Adams Realty
3.47 ACRES
$50,000
91 Lynes Rd,
Chester, MA 01011
Cheryl Malandrinos, HB Real Estate, LLC
3.54 ACRES
$40,000
95 Lynes Rd,
Chester, MA 01011
Cheryl Malandrinos, HB Real Estate, LLC
6.83 ACRES
$135,000
4 Beds
2 Baths
2,151 sqft
1 Crane Rd,
Chester, MA 01011
Melissa L. Blondek, Gallagher Real Estate
0.7 ACRES
$365,000
5 Beds
3 Baths
2,832 sqft
56 Middlefield Rd,
Chester, MA 01011
Cynthia Gonzalez, Executive Real Estate, Inc.
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Real Estate & Homes For Sale Near Chester, MA

We found 24 more homes matching your filters just outside Chester

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2.94 ACRES
$49,999
Skyline Trl,
Middlefield, MA 01243
Dave White, OwnerEntry.com
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2.9 ACRES
$420,000
3 Beds
2.5 Baths
2,068 sqft
147 Chipman Rd,
Chester, MA 01011
Taylor Hildack, KELLER WILLIAMS REALTY
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2.9 ACRES
$420,000
3 Beds
2.5 Baths
2,068 sqft
147 Chipman Rd,
Chester, MA 01011
Taylor Hildack, Keller Williams Realty
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4.79 ACRES
$77,000
Town Hill Rd,
Middlefield, MA 01243
Karen Schneyer, CENTURY 21 NORTHEAST
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4.24 ACRES
$475,000
4 Beds
3 Baths
3,104 sqft
172 Skyline Trl,
Middlefield, MA 01243
Lisa Berry, Simply Sell Realty
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1.45 ACRES
$335,000
4 Beds
2 Baths
3,450 sqft
108 Chipman Rd,
Middlefield, MA 01243
James Adams, Hilltown Real Estate by Adams Realty
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82.13 ACRES
$400,000
Lot A/B Goss Ave,
Huntington, MA 01050
James Adams, Hilltown Real Estate by Adams Realty
FOR SALE BY OWNER
0.25 ACRES
$273,500
4 Beds
2.5 Baths
3,216 sqft
3 E Main St,
Huntington, MA 01050
12.16 ACRES
$470,000
3 Beds
2 Baths
2,055 sqft
347 Kinnebrook Rd,
Worthington, MA 01098
Linda Webster, Coldwell Banker Community REALTORS®
0.88 ACRES
$299,900
4 Beds
1 Bath
2,254 sqft
17 Blandford Hill Rd,
Huntington, MA 01050
Evamarie Best, Wolcott Realty
3D VIEW
7 ACRES
$495,000
4 Beds
2.5 Baths
2,920 sqft
2R Old Chester Rd,
Blandford, MA 01008
Mary Mangini, Kempf-Vanderburgh Realty Consultants, Inc.
3D VIEW
2.35 ACRES
$675,000
3 Beds
3.5 Baths
3,230 sqft
91 William Holmes Rd,
Becket, MA 01223
Thom Garvey, WILLIAM PITT SOTHEBY'S - LENOX
2 ACRES
$150,000
3 Beds
1 Bath
968 sqft
19 Goss Hill Rd,
Huntington, MA 01050
Adam Lajeunesse, Real Broker MA, LLC
0.42 ACRES
$335,000
4 Beds
3 Baths
3,652 sqft
27 Russell Rd,
Huntington, MA 01050
James Adams, Hilltown Real Estate by Adams Realty
35 ACRES
$350,000
18 Pond Brook Rd,
Huntington, MA 01050
Team Witalisz, Witalisz & Associates, Inc.
0.62 ACRES
$264,900
2 Beds
2 Baths
1,758 sqft
162 Skyline Trl,
Middlefield, MA 01243
The Aimee Kelly Crew, eXp Realty LLC
5.64 ACRES
$69,500
Quarry Rd,
Becket, MA 01223
Steven J. Weisz, WILLIAM PITT SOTHEBY'S - GT BARRINGTON
7.69 ACRES
$150,000
31 Goss Hill Rd,
Huntington, MA 01050
Victoria Minella-Sena, Berkshire Hathaway HomeServices Realty Professionals
3D VIEW
0.35 ACRES
$235,000
6 Beds
1.5 Baths
3,456 sqft
9 Russell Rd,
Huntington, MA 01050
The Aimee Kelly Crew, eXp Realty LLC
4.32 ACRES
$45,000
Lot 33.03 William Holmes Rd,
Becket, MA 01223
Dave White, OwnerEntry.com
2.15 ACRES
$19,000
William Holmes Rd,
Becket, MA 01223
Derek Greene, The Greene Realty Group
26.52 ACRES
$129,500
LOT Beulah Land Rd #B,
Blandford, MA 01008
Herbert Butzke, Engel & Volkers Wellesley
3D VIEW
8.2 ACRES
$625,000
4 Beds
2 Baths
2,743 sqft
125 Chester Rd,
Blandford, MA 01008
Lori Kroh, Century 21 AllPoints Realty
155 ACRES
$649,900
Johnny Cake Hill Rd,
Middlefield, MA 01243
Douglas Collins, Lamacchia Realty, Inc. - Dalton

Chester, MA Real Estate Trends

Learn about the Chester, MA housing market through trends and averages.

Affordability
Home Value
What Locals Say

Affordability of Living in Chester, MA

The median home value is $305,456

Month	Median home value
October 2025	$296k
November 2025	$296k
December 2025	$296k
January 2026	$296k
February 2026	$297k
March 2026	$299k
April 2026	$300k
May 2026	$301k
June 2026	$302k
July 2026	$303k
August 2026	$304k
September 2026	$305k

View as a graph

Trends and affordability stats are provided by third party data sources.

Average Home Value in Chester, MA, by Home Size

Currently, there are 2 new listings in Chester, MA and 17 homes for sale.

Home Size	Home Value*
2 bedrooms (2 homes)	$271,643
3 bedrooms (4 homes)	$346,566
4 bedrooms (1 home)	$339,452

*Home value over the past month

What Locals Say about Chester

Jlstathatesso
Resident
7y ago
"There’s plenty of space for dogs to run around without much worry from traffic, but bears and coyotes pose quite the threat."
2
Flag
Mary L. C.
Resident
8y ago
"We have maple fest in the spring with hayrides and also Chester on Track. There are also penny socials and a newer elementary school."
0
Flag

Browse Chester, MA homes by type

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Chester, MA Real Estate & Homes For Sale

17 homes