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Chester, MA Homes for Sale

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  • 73 Ingell Rd, Chester, MA 01011
    73 Ingell Rd, Chester, MA 01011
    73 Ingell Rd, Chester, MA 01011
    /19

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft

    73 Ingell Rd, Chester, MA 01011

    A diamond in the rough! Located on a country road with expansive views. Rustic ranch-style farmhouse with a western flair. Notable improvements in the last 10 years roof/windows/skylight/furnace and updates to the electric. Generous open floor plan for the kitchen and living room with peaceful outside views to expansive skies. Second floor heated studio with approximately 385sf, potential to

    Debra Petrovsky Donovan Real Estate

    73 Ingell Rd, Chester, MA 01011
  • 274 Goss Hill Rd, Huntington, MA 01050
    274 Goss Hill Rd, Huntington, MA 01050
    274 Goss Hill Rd, Huntington, MA 01050
    /42

    $499,900 Open Sat 1PM - 2:30PM

    • 3 Beds
    • 3 Baths
    • 2,644 Sq Ft

    274 Goss Hill Rd, Huntington, MA 01050

    Tucked just minutes off Route 112, this well-maintained 2,644 sq ft cedar-sided Colonial is located in Chester, with full services provided by the town of Huntington. Set on 4.25 private acres abutting state land, the property offers scenic views, a peaceful pond, and charming stone walls—creating a picturesque and tranquil setting. Inside, the spacious kitchen is ideal for entertaining, with

    Darcie Gasperini Taylor Agency

    274 Goss Hill Rd, Huntington, MA 01050
  • 12 Riverfront St, Chester, MA 01011
    12 Riverfront St, Chester, MA 01011
    12 Riverfront St, Chester, MA 01011
    /36

    $339,900

    • 2 Beds
    • 1 Bath
    • 1,450 Sq Ft

    12 Riverfront St, Chester, MA 01011

    Charming riverfront home in historic Chester, close to all main attractions in Berkshire County and the college towns of Amherst and Northampton. The house has been lovingly maintained as a short-term rental since 2018, with excellent occupancy rates for visitors looking for a quiet getaway with a small town atmosphere while also central to all of Western Massachusetts. Single floor living,

    Stephen Daoust STONE HOUSE PROPERTIES, LLC

    12 Riverfront St, Chester, MA 01011
  • 613 Skyline Trail, Chester, MA 01011
    613 Skyline Trail, Chester, MA 01011
    613 Skyline Trail, Chester, MA 01011
    /42

    $489,500 Pending

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft

    613 Skyline Trail, Chester, MA 01011

    Complete privacy awaits you in this charming Cape-style home! Perfect for easy entertaining, the home features a spacious three-season lanai with a wet bar, a covered patio, a large level yard, vibrant flowering gardens, and raspberry and blueberry bushes — plus a barn for added versatility. Inside, the cozy living room with a wood stove opens seamlessly to the kitchen, which is outfitted with

    Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

    613 Skyline Trail, Chester, MA 01011
  • 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
  • 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
  • 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
  • 11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    /23

    $235,000

    • 2 Beds
    • 1 Bath
    • 1,076 Sq Ft

    11 Taft Rd, Chester, MA 01011

    This cedar sided bungalow in a peaceful setting offers an open floor plan, 5.61 acres of land, a private deck overlooking the beautiful yard w/ blueberry bushes, apple & pear trees. Kitchen w/appliances to stay. Cozy DR. Large open LR w/cathedral ceilings. First floor laundry. Full bath w/tub & shower. Potential for a half bath off the empty bedroom (it was a half bath at one time) Abbott Brook

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    11 Taft Rd, Chester, MA 01011
  • 76 Hampden St, Chester, MA 01011
    76 Hampden St, Chester, MA 01011
    76 Hampden St, Chester, MA 01011
    /27

    $260,000

    • 3 Beds
    • 1 Bath
    • 1,048 Sq Ft

    76 Hampden St, Chester, MA 01011

    Country Charm Meets Comfort and Nature-Outdoor living at its finest! Nestled on a generous double lot, this delightful country home offers an enchanting retreat just minutes from the heart of Westfield. Surrounded by mature landscaping, fruit trees, and a lush forest brimming with wildlife, it’s a nature lover’s dream come true. Step onto the enclosed side porch, relax as birds sing and deer

    Stacey Silvia Lock and Key Realty Inc.

    76 Hampden St, Chester, MA 01011
  • 0 N Chester Rd, Chester, MA 01011
    0 N Chester Rd, Chester, MA 01011
    0 N Chester Rd, Chester, MA 01011
    /20

    $19,497

    • Land
    • 5.00 Acres
    • $3,899 per Acre

    0 N Chester Rd, Chester, MA 01011

    Here's your opportunity to own an amazing 5-acre property nestled in the heart of Chester, MA, in Hampden County. Located off Chester Rd, the parcel is considered landlocked, while a paper road provides recorded access, there is currently no vehicle access, and the land is being sold as-is. A plat map is available for review. Set on a gently sloping hillside overlooking a small river, the

    Derek Greene The Greene Realty Group

    0 N Chester Rd, Chester, MA 01011
  • 0 Round Hill Rd Unit 73399828, Chester, MA 01011
    0 Round Hill Rd Unit 73399828, Chester, MA 01011
    0 Round Hill Rd Unit 73399828, Chester, MA 01011
    /6

    $28,000

    • Land
    • 3.24 Acres
    • $8,642 per Acre

    0 Round Hill Rd Unit 73399828, Chester, MA 01011

    Price drop on this great get away with over three acres. There is a recent perk test, if you want to build on the land. This property comes with a newer camper. Walking distance to the hiking trails of the expansive Chester State Forest. The road does not have electric at this time, so off grid living is the way to go. 200 feet north of Smithy Road.

    James Adams Hilltown Real Estate by Adams Realty

    0 Round Hill Rd Unit 73399828, Chester, MA 01011
  • 0 Skyline Trail, Chester, MA 01011
    0 Skyline Trail, Chester, MA 01011
    0 Skyline Trail, Chester, MA 01011
    /10

    $150,000

    • Land
    • 39 Acres
    • $3,846 per Acre

    0 Skyline Trail, Chester, MA 01011

    Embrace the beauty of nature with this incredible opportunity to own several acres of serene, wooded land! Featuring a peaceful, gently sloping terrain, a fresh, flowing stream, and abundant wildlife, this property offers endless potential. Whether you’re envisioning your dream home or simply looking for a private retreat to enjoy nature at its finest, this land has it all. Don’t miss out on the

    Brenda Cuoco Cuoco & Co. Real Estate

    0 Skyline Trail, Chester, MA 01011
  • 31 Skyline Trail, Chester, MA 01011
    31 Skyline Trail, Chester, MA 01011
    31 Skyline Trail, Chester, MA 01011
    /24

    $299,800

    • Land
    • 70 Acres
    • $4,283 per Acre

    31 Skyline Trail, Chester, MA 01011

    This 70-acre parcel in Chester & Huntington, MA offers a rare opportunity for privacy and natural beauty. There is a mix of wooded areas and a beautiful stream with a magnificent waterfall. This land is perfect for a private estate, recreational use, or development. Zoned for residential use, it provides flexibility for various projects, including potential subdivision (subject to local

    Brenda Cuoco Cuoco & Co. Real Estate

    31 Skyline Trail, Chester, MA 01011
  • lot 3 Skyline Trail, Chester, MA 01011
    lot 3 Skyline Trail, Chester, MA 01011
    lot 3 Skyline Trail, Chester, MA 01011
    /4

    $50,000

    • Land
    • 3.00 Acres
    • $16,667 per Acre

    lot 3 Skyline Trail, Chester, MA 01011

    A great 3-acre parcel on a paved road with stone walls. Lightly forested and flat. This is a relatively easy building site for your new home. Land is just north of 590 Skyline trail.

    James Adams Hilltown Real Estate by Adams Realty

    lot 3 Skyline Trail, Chester, MA 01011
  • 0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    /7

    $75,000

    • Land
    • 18 Acres
    • $4,155 per Acre

    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050

    Private 18 acre lot! 200 feet of frontage & 3000 feet back w/winding trails & a brook. From the road there is a little clearing with ATV trails to the right & an old over grown skidder trail to the left as land has not been logged since 2007. The skidder trail rises up to the top of a ridge & there is a brook in the back left corner. The ATV trails wind gently leading up to the flatter portions

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
  • lot 13 Skyline Trail, Chester, MA 01011
    lot 13 Skyline Trail, Chester, MA 01011
    lot 13 Skyline Trail, Chester, MA 01011
    /11

    $47,000 Pending

    • Land
    • 7 Acres
    • $6,963 per Acre

    lot 13 Skyline Trail, Chester, MA 01011

    Wonderful level lot with perk test in hand. This flat lot has a survey and has been flagged. A wooded property with a year-round brook. The area has newer homes and is quite convenient to shopping and Berkshire attractions. If you're ready to build, then this lot is ready to go! 200 feet north of 698 Skyline trail

    James Adams Hilltown Real Estate by Adams Realty

    lot 13 Skyline Trail, Chester, MA 01011
  • lot 61 Skyline Trail, Chester, MA 01011
    lot 61 Skyline Trail, Chester, MA 01011
    lot 61 Skyline Trail, Chester, MA 01011
    /5

    $850,000 Pending

    • Land
    • 191 Acres
    • $4,450 per Acre

    lot 61 Skyline Trail, Chester, MA 01011

    Subdivision available. A 191-acre property with open land, forest and potential views. We have a plan dividing this property into 14 homesites. These lots would be spectacular with some lots having meadow, some wooded and some with potentially beautiful views. Subdivision needs town approval. The Holcomb Road lots may not be available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 61 Skyline Trail, Chester, MA 01011
  • 124 Skyline Trail, Chester, MA 01011
    124 Skyline Trail, Chester, MA 01011
    124 Skyline Trail, Chester, MA 01011
    /43

    $749,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,871 Sq Ft

    124 Skyline Trail, Chester, MA 01011

    Discover the perfect sanctuary in the serene hills of Chester, where this breathtaking custom-built post-and-beam contemporary home awaits you. Set on an expansive 16 acres of stunning natural beauty, this residence offers an incredible blend of elegance and comfort. Step inside the 2,871 square foot haven and be captivated by the open chef's kitchen that boasts top-of-the-line appliances,

    Herb Butzke WILLIAM PITT SOTHEBY'S - LENOX

    124 Skyline Trail, Chester, MA 01011
  • 9 William St, Chester, MA 01011
    9 William St, Chester, MA 01011
    9 William St, Chester, MA 01011
    /42

    $290,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,458 Sq Ft

    9 William St, Chester, MA 01011

    Welcome to 9 William St - A gem of the valley nestled in the foothills of the Berkshires situated on a quiet dead-end street. This stunning 3-bedroom 1-bath home has been completely refreshed from top to bottom and is ready for you to move-in and start making memories! Fresh interior paint throughout has been professionally designed to welcome you into each space as Boho style meets Farmhouse

    Adam Lajeunesse Real Broker MA, LLC

    9 William St, Chester, MA 01011
  • 279 Goss Hill Rd, Huntington, MA 01050
    279 Goss Hill Rd, Huntington, MA 01050
    279 Goss Hill Rd, Huntington, MA 01050
    /24

    $494,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    279 Goss Hill Rd, Huntington, MA 01050

    Country Living at its best! Discover the perfect blend of space, comfort and opportunity with this large 4-bedroom, 2-bath home on 10 acres (consisting of two 5-acre lots). The welcoming layout includes a first floor bedroom and a convenient first floor laundry, making daily living easy and accessible. The great room boasts cathedral ceilings, creating an open and airy feel, perfect for

    Linda Webster COLDWELL BANKER COMMUNITY REALTORS

    279 Goss Hill Rd, Huntington, MA 01050
  • 110 Middlefield Rd, Chester, MA 01011
    110 Middlefield Rd, Chester, MA 01011
    110 Middlefield Rd, Chester, MA 01011
    /33

    $300,000 Sold Aug 22, 2025

    • 1,712 Sq Ft
    • $175/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    110 Middlefield Rd, Chester, MA 01011

    Welcome to this well-cared-for 1,712 sq ft home in the charming town of Chester. The first floor features an updated kitchen with granite counters, new bathroom with double sinks, open living and dining areas with easy-to-maintain bamboo flooring and an office that could serve as a first-floor bedroom. A spacious mudroom that includes laundry. The enclosed front porch provides a bright, sunny

    Darcie Gasperini Taylor Agency

    110 Middlefield Rd, Chester, MA 01011
  • 20 William St, Chester, MA 01011
    20 William St, Chester, MA 01011
    20 William St, Chester, MA 01011
    /41

    $299,900 Sold Aug 21, 2025

    • 2,570 Sq Ft
    • $117/SF
    • 5 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1880

    20 William St, Chester, MA 01011

    Beautifully updated 1880's home with 3BR/1.5BA home in downtown Chester. Nestled on a quiet dead-end street, this charming and spacious single-family home offers over 2,500 sq ft of well-maintained living space. Boasting timeless character and thoughtful updates, this home is move-in ready and perfect for comfortable everyday living. Property Highlights: 3 generously sized bedrooms, 1.5

    Tammy Weidhaas Today Real Estate, Inc.

    20 William St, Chester, MA 01011
  • 45 Middlefield Rd, Chester, MA 01011
    45 Middlefield Rd, Chester, MA 01011
    45 Middlefield Rd, Chester, MA 01011
    /39

    $233,000 Sold Aug 14, 2025

    • 3,058 Sq Ft
    • $76/SF
    • 41 Days On Market
    • 7 Beds
    • 2 Baths
    • Built 1900

    45 Middlefield Rd, Chester, MA 01011

    Large Side-by-Side Duplex – Great Investment Opportunity! This spacious duplex offers a fantastic investment or owner occupied opportunity, each unit featuring generous layouts and separate utilities and propane heat. Situated on a nice lot with a large backyard, dog kennel, and space for a garden, this property provides both comfort and versatility. Left Unit: 3 bedrooms upstairs, plus an

    Joy Salvini RE/MAX Compass

    45 Middlefield Rd, Chester, MA 01011
  • 300 Middlefield Rd, Chester, MA 01011
    300 Middlefield Rd, Chester, MA 01011
    300 Middlefield Rd, Chester, MA 01011
    /40

    $250,000 Sold Jul 18, 2025

    • 1,152 Sq Ft
    • $217/SF
    • 14 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 2004

    300 Middlefield Rd, Chester, MA 01011

    Charming 3-Bedroom Home on 2 Acres – Just Outside the City!Looking for country living with room to grow? This 3-bedroom, 1-bath home sits on a spacious 2-acre lot, offering the perfect blend of privacy and potential. Just a short drive from the city, this property is ideal for those seeking peace and quiet. New furnace – stay cozy all year long. Needs some TLC – bring your vision and make it

    Nicolle Serafino Keller Williams Realty

    300 Middlefield Rd, 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
  • 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
  • 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
  • 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
  • 10 William St, Chester, MA 01011
    10 William St, Chester, MA 01011
    10 William St, Chester, MA 01011
    /19

    $110,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,394 Sq Ft

    10 William St, Chester, MA 01011

    Come see this charming colonial-style home featuring four bedrooms and two full bathrooms, encompassing nearly 2,400 square feet of living space! Nestled on an expansive 24.8-acre lot, the property does provide some nice privacy potential. A spacious barn is also included, presenting numerous opportunities for use as a workshop or additional storage. Additionally, the property features an

    Nicholas Decaro Property Works New England

    10 William St, Chester, MA 01011
Massachusetts Hampden County Chester

Real Estate & Homes for Sale in Chester, MA

Home Trends in Chester, MA

On average, homes in Chester, MA sell after 57 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MA over the last 12 months is $300,000, up 32% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$300,000
Average Price Per Sq Ft
$198
Number of Homes for Sale
4
Last 12 months Home Sales
16
Months of Supply
3.00
Median List Price
$309,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
32%
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