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Hampden, MA Homes

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  • /42

    $290,000 Open Thu 5PM - 7PM

    • 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
  • /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 RE/MAX Connections

    300 Middlefield Rd, Chester, MA 01011
    • /5

      Not Listed For Sale

      0 Abbott Hill Rd, Chester, MA 01011

      0 Abbott Hill Rd, 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
  • /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
    • /12

      Not Listed For Sale

      0 Ingell Rd, Chester, MA 01011

      0 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
  • /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
    • /18

      Est $263,439 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,509 Sq Ft

      110 Old State Hwy, Chester, MA 01011

      110 Old State Hwy, Chester, MA 01011
  • /20

    $38,497

    • Land
    • 5.00 Acres
    • $7,699 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
  • /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
    • /10

      Est $134,457 Not Listed For Sale

      • 6 Beds
      • 2 Baths
      • 2,400 Sq Ft

      664 Route 20, Chester, MA 01011

      664 Route 20, Chester, MA 01011
  • /6

    $34,000

    • Land
    • 3.24 Acres
    • $10,494 per Acre

    0 Round Hill Rd Unit 73399828, Chester, MA 01011

    A 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
  • /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
    • /26

      Est $538,706 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,407 Sq Ft

      263 Bromley Rd, Huntington, MA 01050

      263 Bromley Rd, Huntington, MA 01050
  • /42

    $519,900

    • 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
  • /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
    • /41

      Est $354,308 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft

      26 Taft Rd, Chester, MA 01011

      26 Taft Rd, 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
  • /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
    • /17

      Est $204,114 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 708 Sq Ft

      627 Skyline Trail, Chester, MA 01011

      627 Skyline Trail, Chester, MA 01011
  • /42

    $489,500

    • 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
  • /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
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,844 Sq Ft

      499 Skyline Trail, Chester, MA 01011

      499 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
  • /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
    • /20

      Est $193,756 Not Listed For Sale

      • 4 Beds

      115 Lyon Hill Rd, Chester, MA 01011

      115 Lyon Hill Rd, 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
  • /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
    • /3

      Est $143,347 Not Listed For Sale

      • 2 Beds

      72 Maynard Hill Rd, Chester, MA 01011

      72 Maynard Hill Rd, Chester, MA 01011
  • /11

    $47,000

    • 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
  • /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
    • /36

      Est $538,651 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,352 Sq Ft

      674 Skyline Trail, Chester, MA 01011

      674 Skyline Trail, Chester, MA 01011
  • /5

    $850,000

    • 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
  • /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
    • /41

      Est $241,013 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,136 Sq Ft

      15 Maple St, Chester, MA 01011

      15 Maple St, 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
  • /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
    • /24

      Est $268,555 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft

      175 Route 20, Chester, MA 01011

      175 Route 20, Chester, MA 01011
  • /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

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chester, MA

Housing Trends

Median Sale Price
$288,700
Median Single Family Sale Price
$288,700
Average Price Per Sq Ft
$194
Number of Homes for Sale
0
Last 12 months Home Sales
8
Months of Supply
0.00
Median List Price
$309,900
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-64%
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