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Recently Sold Chester, MA Homes

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  • 424 Route 20, Chester, MA 01011
    424 Route 20, Chester, MA 01011
    424 Route 20, Chester, MA 01011
    /42

    $440,000 Sold Apr 30, 2025

    • 2,165 Sq Ft
    • $203/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1986

    424 Route 20, Chester, MA 01011

    Step inside this inspiring Contemporary home filled w/ warm wood tones, elevated ceilings & artistic angles flooded w/ natural light! The main living areas offer open sightlines w/ no shortage of oversized windows framing the natural beauty of the Berkshire Hills. Guests are greeted in a 2-story entry leading to a half-vaulted living room open to the dining room. The heart of the home is found in

    Angela Accorsi Coldwell Banker Realty - Western MA

    424 Route 20, Chester, MA 01011
  • 143 Chipman Rd, Chester, MA 01011
    143 Chipman Rd, Chester, MA 01011
    143 Chipman Rd, Chester, MA 01011
    /25

    $288,700 Sold Mar 31, 2025

    • 1,486 Sq Ft
    • $194/SF
    • 113 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    143 Chipman Rd, Chester, MA 01011

    *Highest and Best offers due by 1PM on 1/13/25* Come see this exquisite contemporary style home featuring two bedrooms, two full bathrooms, and a generous 1,486 square feet of living area. Nestled on a 3-acre lot, the property is surrounded by trees, ensuring both privacy and serenity. Upon entering, you will be greeted by an abundance of natural light pouring in through the numerous custom-sized

    Zachary DeCaro Property Works New England

    143 Chipman Rd, Chester, MA 01011
  • 54 Route 20, Chester, MA 01011
    54 Route 20, Chester, MA 01011
    54 Route 20, Chester, MA 01011
    /29

    $242,000 Sold Mar 21, 2025

    • 1,411 Sq Ft
    • $172/SF
    • 116 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1875

    54 Route 20, Chester, MA 01011

    Located in Chester, The Gem of the Valley, is this quaint home with character and charm.This 19th century home has many updates done by the current owners. The list includes chimney work, front porch built, roof updated, new boiler, well pump and all plumbing redone. Passing Title V septic inspection September 2024. Drilled well for your water source. Storm windows installed. Walker Brook is

    Susan Deacon RE/MAX COMPASS

    54 Route 20, Chester, MA 01011
  • 166 Bromley Rd, Chester, MA 01011
    166 Bromley Rd, Chester, MA 01011
    166 Bromley Rd, Chester, MA 01011
    /42

    $445,000 Sold Mar 14, 2025

    • 2,094 Sq Ft
    • $213/SF
    • 79 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1996

    166 Bromley Rd, Chester, MA 01011

    Seller is still allowing showings and back up offers. Welcome to this expansive Ranch set on 4.3 acres of serene land. The home features wood floors throughout, with a kitchen that boasts tile flooring, granite countertops, a breakfast bar, and under-cabinet lighting. The open floor plan seamlessly connects the kitchen to the living and dining areas, both with wood floors. The spacious living

    Taylor Hildack Keller Williams Realty

    166 Bromley Rd, Chester, MA 01011
  • 396 Route 20, Chester, MA 01011
    396 Route 20, Chester, MA 01011
    396 Route 20, Chester, MA 01011
    /26

    $240,000 Sold Jan 31, 2025

    • 1,156 Sq Ft
    • $208/SF
    • 47 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1957

    396 Route 20, Chester, MA 01011

    Single story 2 bedroom ranch located in the gateway of the Berkshire range. Hardwood floors through most of the home. Large open Kitchen/Dining area with cozy vintage appeal. Main bedroom with 6 windows is bright and spacious. Easy to heat home features double pane windows, a newer heating system, new oil tank, electrical panel and new water heater, and a roof on the main house, just over a year

    Maureen Borg Delap Real Estate LLC

    396 Route 20, Chester, MA 01011
  • 56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    /42

    $270,000 Sold Jan 17, 2025

    • 2,832 Sq Ft
    • $95/SF
    • 124 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1900

    56 Middlefield Rd, Chester, MA 01011

    Well loved, well maintained 2 family home located in the heart of Chester. Each unit consists of 3 good sized beds, 1 and 1/2 baths, large living room, dining area, kitchen, and first floor laundry. Barn has parking for 2 cars, and a lofted space for storage. Large front yard and large back yard that includes parking for approximately 6 additional vehicles. If you are looking for a place away

    Craig Perras Real Broker MA, LLC

    56 Middlefield Rd, Chester, MA 01011
  • 40 Holcomb Rd, Chester, MA 01011
    40 Holcomb Rd, Chester, MA 01011
    40 Holcomb Rd, Chester, MA 01011
    /34

    $300,000 Sold Dec 16, 2024

    • 2,236 Sq Ft
    • $134/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1769

    40 Holcomb Rd, Chester, MA 01011

    Highest & Best offers due Wednesday 10.23 at 12pm. Welcome to a slice of history in Chester! This enchanting 5-acre property dates back to 1769 & offers a unique blend of rustic elegance & modern comfort. The heart of the home features a large kitchen seamlessly connected to a sun-drenched solarium. Imagine enjoying your coffee surrounded by lush greenery, or hosting gatherings w/ friends &

    Kelsey Thompson Team Lock and Key Realty Inc.

    40 Holcomb Rd, Chester, MA 01011
  • 59 Middlefield Rd, Chester, MA 01011
    59 Middlefield Rd, Chester, MA 01011
    59 Middlefield Rd, Chester, MA 01011
    /40

    $210,000 Sold Dec 13, 2024

    • 1,320 Sq Ft
    • $159/SF
    • 43 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1920

    59 Middlefield Rd, Chester, MA 01011

    Welcome home to this charming two bedroom home out in the country! This home offers an open concept first floor. The kitchen boasts plenty of cabinets and ample counter tops. The dining area is open to the living room with replacement windows which offers plenty of natural light. There are two enclosed porches, one in the front and one in the back, both perfect for enjoying morning coffee and

    Shanna DeGray Keller Williams Realty

    59 Middlefield Rd, Chester, MA 01011
  • 21 Middlefield Rd, Chester, MA 01011
    21 Middlefield Rd, Chester, MA 01011
    21 Middlefield Rd, Chester, MA 01011
    /23

    $350,000 Sold Nov 26, 2024

    • 2,100 Sq Ft
    • $167/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1910

    21 Middlefield Rd, Chester, MA 01011

    Graciously restored 1910 center hall colonial in the Gateway of the Hilltowns. The Haley house is located in the charming village of Chester very close to local shopping, restaurants and entertainment with the Chester Theatre Company right next door! The home has deep heritage in town with ties to Hamilton Emery Mill being built for its GM at the time, Thomas Haley. Recent improvements include

    Altaluxre Group WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    21 Middlefield Rd, Chester, MA 01011
  • 52 Middlefield Rd, Chester, MA 01011
    52 Middlefield Rd, Chester, MA 01011
    52 Middlefield Rd, Chester, MA 01011
    /42

    $185,000 Sold Nov 26, 2024

    • 2,280 Sq Ft
    • $81/SF
    • 178 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    52 Middlefield Rd, Chester, MA 01011

    Welcome to quaint Chester, MA. Approximately thirty minutes from Northampton and minutes to the Berkshires. This farm house located within walking distance from town sits on 1.2 acres of land perfect for relaxing, enjoying nature, and gardening. The main level of living has had many improvements including: full renovation on the lower level with newer windows, updated kitchen and bath, heating

    Kate Hogan Brick & Mortar

    52 Middlefield Rd, Chester, MA 01011
  • 147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    /55

    $380,000 Sold Nov 15, 2024

    • 2,068 Sq Ft
    • $184/SF
    • 169 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    147 Chipman Rd, Chester, MA 01011

    GLENDALE BROOK CONTEMPORARY!!! Three bedroom, 2.5 bath contemporary featuring an open floor plan, main level primary bedroom & bath and a trail leading to the wild streambed of Glendale Brook. Enter the foyer through the oversized 2 car garage. The main level incudes the living/dining room with a slider to the sunny deck, a kitchen off the the dining area with a pantry closet, half bath &

    Kim Bergland RED HORSE REAL ESTATE, LLC

    147 Chipman Rd, Chester, MA 01011
  • 0 Bay State Dr Unit 73281011, Chester, MA 01011
    0 Bay State Dr Unit 73281011, Chester, MA 01011
    /2

    $28,000 Sold Nov 13, 2024

    • Land
    • 4.74 Acres
    • $5,907 per Acre
    • 78 Days On Market

    0 Bay State Dr Unit 73281011, Chester, MA 01011

    Nearly 5 acre lot very close to town offices and post offices. SEE MAP IN MLS GALLERY. Buyers can go directly to lot and walk the lot using the map. Train tracks and active stream nearby. Owned by out-of-state entity who never lived on this lot. Public record lists land as "industrial developable land."

    Amy Heflin Keller Williams Realty

    0 Bay State Dr Unit 73281011, Chester, MA 01011
  • 0065 Round Hill Rd, Chester, MA 01011
    0065 Round Hill Rd, Chester, MA 01011
    0065 Round Hill Rd, Chester, MA 01011
    /7

    $42,000 Sold Oct 11, 2024

    • Land
    • 19 Acres
    • $2,168 per Acre
    • 16 Days On Market

    0065 Round Hill Rd, Chester, MA 01011

    19 acres of land near the top of Round Hill. Walk to the miles of hiking trails of the Chester State Forest This is an ideal site for a solar cabin. The property is close to all the Berkshire attractions. The road is not plowed by the town in the winter at this time. Electric is a distance away, so this is best for an off-grid build.

    James Adams Hilltown Real Estate by Adams Realty

    0065 Round Hill Rd, Chester, MA 01011
  • 36 Lyon Hill Rd, Chester, MA 01011
    36 Lyon Hill Rd, Chester, MA 01011
    36 Lyon Hill Rd, Chester, MA 01011
    /38

    $430,000 Sold Oct 04, 2024

    • 2,144 Sq Ft
    • $201/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 2007

    36 Lyon Hill Rd, Chester, MA 01011

    TODAY YOU'VE FOUND YOUR PERFECT HOME You'll find this completely private and move in ready contemporary Cape instantly appealing, and anything but traditional! This extensive and well-cared for home provides a blend of indoor and outdoor living at its best. Offering a versatile floor plan, you'll love the light and air feel that's enhanced by the oversized windows and vaulted ceiling. Open and

    Jill Vincent-Lapan Canon Real Estate, Inc.

    36 Lyon Hill Rd, Chester, MA 01011
  • 000 Lynes Rd, Chester, MA 01011
    000 Lynes Rd, Chester, MA 01011
    000 Lynes Rd, Chester, MA 01011
    /4

    $55,000 Sold Oct 04, 2024

    • Land
    • 8 Acres
    • $7,304 per Acre
    • 37 Days On Market

    000 Lynes Rd, Chester, MA 01011

    Stone walls line these two building lots being sold as one. Over 7.5 acres. Some land already cleared for your homesite, and we have a perk test in hand. The electric is over 200feet from property so you will need to invest to bring it to your site. This is a private lot. The road is not well maintained now but will be once you start your construction of your new home. The owners are open to

    James Adams Hilltown Real Estate by Adams Realty

    000 Lynes Rd, Chester, MA 01011
  • 006 Round Hill Rd, Chester, MA 01011
    006 Round Hill Rd, Chester, MA 01011
    006 Round Hill Rd, Chester, MA 01011
    /5

    $19,000 Sold Sep 25, 2024

    • Land
    • 3.24 Acres
    • $5,864 per Acre
    • 5 Days On Market

    006 Round Hill Rd, Chester, MA 01011

    Over 3 acres of land within walking distance to the Chester DCR Forest with miles of Hiking trails. The land has a flat area and then a slope towards the west. The road is not plowed by the town in the winter at this time. Electric is a distance away, so this is best for an off-grid build.

    James Adams Hilltown Real Estate by Adams Realty

    006 Round Hill Rd, Chester, MA 01011
  • 67 Crane Rd, Chester, MA 01011
    67 Crane Rd, Chester, MA 01011
    67 Crane Rd, Chester, MA 01011
    /21

    $46,000 Sold Sep 12, 2024

    • Land
    • 3.00 Acres
    • $15,333 per Acre
    • 8 Days On Market

    67 Crane Rd, Chester, MA 01011

    OFFERS DUE Wednesday 8/21 by 10am. This beautiful 3-acre partially cleared lot in Chester offers a perfect blend of natural beauty and tranquility. Surrounded by lovely stone walls and situated on a serene country road, this property provides an ideal setting for your dream home or a peaceful getaway. Enjoy the charm of this quaint town while being surrounded by nature's bounty. Don't miss the

    Jennifer Wilson Berkshire Hathaway HomeServices Realty Professionals

    67 Crane Rd, Chester, MA 01011
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /11

    $32,000 Sold Aug 30, 2024

    • Land
    • 6 Acres
    • $5,766 per Acre
    • 27 Days On Market

    Unlisted Address

    Beautiful Skyline Trail six-acre parcel with new percolation test. Small cut in ruff driveway with new perc test. This will be an easy parcel to start building. Skyline Trail is one of the most scenic roads in the Berkshires. Very level land & gorgeous Cattle farming to blue berry farms. Home of the Glendale Falls wild and rocky Glendale brook one of the state's highest and longest waterfalls

    Ginger Conner RED HORSE REAL ESTATE, LLC

    Unlisted Address
  • 278 Route 20, Chester, MA 01011
    278 Route 20, Chester, MA 01011
    278 Route 20, Chester, MA 01011
    /24

    $226,000 Sold Aug 21, 2024

    • 1,399 Sq Ft
    • $162/SF
    • 35 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1920

    278 Route 20, Chester, MA 01011

    Fabulous upgrades and improvements all throughout this unique colonial home. Gorgeous newer kitchen & bath. Newer roof, windows, electrical and more. First floor laundry, 2 Car attached garage and large back yard! Charm, character, quaint country built-ins and finishings will surprise you at every turn. Open kitchen and living room with sliders to a covered front porch. The main bedroom on the

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    278 Route 20, Chester, MA 01011
  • 78 Lyon Hill Rd, Chester, MA 01011
    78 Lyon Hill Rd, Chester, MA 01011
    78 Lyon Hill Rd, Chester, MA 01011
    /54

    $520,000 Sold Aug 16, 2024

    • 2,130 Sq Ft
    • $244/SF
    • 7 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1982

    78 Lyon Hill Rd, Chester, MA 01011

    A Gem In The Valley.This home is aesthetically pleasing in all ways. Breathtaking views with a truly unique design, make this expansive A Frame stand out from the others. Whether you are sitting in the vaulted ceiling living room by the fireplace, on the deck, or in the primary bedroom, you can relax & soak in the views. Since this property is move-in ready with a new septic system, boiler, metal

    Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

    78 Lyon Hill Rd, Chester, MA 01011
  • 85 Lyman Rd, Chester, MA 01011
    85 Lyman Rd, Chester, MA 01011
    85 Lyman Rd, Chester, MA 01011
    /34

    $415,000 Sold Aug 08, 2024

    • 1,440 Sq Ft
    • $288/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1978

    85 Lyman Rd, Chester, MA 01011

    Discover this stunning three-bedroom, one-bath, ranch style home perfectly situated on 2.11 acres of land. Enjoy the spectacular views from the living and front porch. This home boasts beautiful wood floors, a remodeled kitchen, impressive patio and deck area, ideal for entertaining or just to enjoy the tranquility. Its oversized, detached barn has a multitude of uses, including storage of tools,

    Heather Witalisz Siegel Witalisz & Associates, Inc.

    85 Lyman Rd, Chester, MA 01011
  • 29 William St, Chester, MA 01011
    29 William St, Chester, MA 01011
    29 William St, Chester, MA 01011
    /39

    $230,000 Sold Jul 30, 2024

    • 1,056 Sq Ft
    • $218/SF
    • 5 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1830

    29 William St, Chester, MA 01011

    Affordable and Adorable! Coming Home you will always start to feel relaxed entering a spacious Mudrm with closet and room to add seating. From there you enter into a spacious Kit. & Dining Area. partially opened to the Living Rm with wood flooring. Off the LR is a cozy Den/Family Rm w/built-in seating. It has great use of windows to enjoy the peaceful backyard. The downstairs Half Bath has a

    Dan Schachter DCS Real Estate, LLC

    29 William St, Chester, MA 01011
  • 483 Skyline Trail, Chester, MA 01011
    483 Skyline Trail, Chester, MA 01011
    /2

    $295,000 Sold Dec 12, 2024

    • 2,184 Sq Ft
    • $135/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    483 Skyline Trail, Chester, MA 01011

    Stunning country setting on 3.34 acres! Cathedral ceilings, spiral staircase, 22x24 great room with fire place, original hardwoods in 2 bedrooms, open concept country kitchen, 2 pellet stoves and back up electric baseboard heat, newer water heater +/-5 yrs, newer Metal roof +/-10yrs, generator switch, finished walk-out basement, huge deck, fire pit, established gardens, landscaping, & X-large

    Tori Denton Coldwell Banker Realty - Western MA

    483 Skyline Trail, Chester, MA 01011
Massachusetts Chester

Recently Sold Real Estate & Homes in Chester, MA

Frequently Asked Questions

What is the average home price in Chester, MA?
Homes for sale in Chester, MA have an average home price of $332,687.
What is the average time to sell a house in Chester, MA?
The houses for sale in Chester, MA spend an average of 49 days on the market.
What is the number of active homes for sale in Chester, MA?
There is 1 active home for sale in Chester, MA.
How many homes have sold over the last 12 months in Chester, MA?
6 homes have sold in Chester, MA over the last 12 months.

Home Trends in Chester, MA

On average, homes in Chester, MA sell after 49 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, MA over the last 12 months is $236,000, down 55% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$236,000
Median Single Family Sale Price
$271,000
Average Price Per Sq Ft
$191
Number of Homes for Sale
1
Last 12 months Home Sales
6
Months of Supply
2.00
Median List Price
$268,750
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
-55%
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