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Recently Sold Homes in 01011

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  • /42

    $315,000 Sold Sep 15, 2025

    • 1,458 Sq Ft
    • $216/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1947

    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
  • /11

    $40,000 Sold Sep 11, 2025

    • Land
    • 6.75 Acres
    • $5,926 per Acre
    • 166 Days On Market

    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
  • /37

    $480,000 Sold Sep 08, 2025

    • 2,560 Sq Ft
    • $188/SF
    • 45 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1999

    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 ten 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 huge 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
  • /42

    $489,500 Sold Sep 05, 2025

    • 2,012 Sq Ft
    • $243/SF
    • 98 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    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
  • /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
  • /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
  • /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
  • /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
  • /9

    $29,900 Sold Jun 06, 2025

    • Land
    • 5.33 Acres
    • $5,610 per Acre
    • 24 Days On Market

    Lot16 Chester Rd, Middlefield, MA 01011

    Good sized lot - over five acres - on Chester Road in the town of Middlefield. Located just off Skyline Trail this wooded lot is a great place to build a house and start something new.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot16 Chester Rd, Middlefield, 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
  • /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
  • /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
  • /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

    $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
  • /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
  • /22

    $100,000 Sold Dec 30, 2024

    • 990 Sq Ft
    • $101/SF
    • 169 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1850

    1088 Chester Rd, Becket, MA 01223

    Move in READY. Everything is working Wonderful little cape sitting across the road from Walker brook. Great Fishing or taking a dip. 2or 3 bedrooms 1 bath newer appliances, new chimney linerGreat patio porch. Many updates throughout the house. Roof is about 15 years old. The home has a natural spring, and the owner is offering $10,000 credit for a new septic system at closingThe Town of Becket

    Ginger Conner RED HORSE REAL ESTATE, LLC

    1088 Chester Rd, Becket, MA 01223
  • /25

    $30,000 Sold Dec 23, 2024

    • Land
    • 5.73 Acres
    • $5,236 per Acre
    • 237 Days On Market

    Unlisted Address

    Nestled within the breathtaking Berkshires, a pristine piece of land spanning 5.73 acres awaits your vision of tranquility and adventure. Welcome to the Indian Lake Association, where nature's splendor meets unparalleled recreational opportunities.This Association offers private beaches, roads, and tennis courts. Whether you envision a full-time residence or a summer retreat, this property offers

    Kimberly Kuplast LAER REALTY PARTNERS

    Unlisted Address
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /7

    $42,500 Sold Nov 12, 2024

    • Land
    • 7.21 Acres
    • $5,895 per Acre
    • 198 Days On Market

    Unlisted Address

    Nicely wooded 7 plus acre lot located at the end of Skyline Ridge Road. Possible views to the northeast. Older perc, private road - dues $700.00 per year. Survey, covenants and perc test can be viewed in documents.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Unlisted Address
  • /13

    $59,000 Sold Oct 15, 2024

    • 1,884 Sq Ft
    • $31/SF
    • 79 Days On Market
    • 6 Beds
    • 2.5 Baths
    • Built 1880

    850 Chester Rd, Becket, MA 01223

    This is a great opportunity to own a unique property with frontage on Highway 20. A perfect location for a store front, artist studio or a great retreat. It is on 4.9 acres of land and a beautiful brook that combines forest and aquatic environments. Spectacular natural views bordering the State Forest and protected lands. Becket is characterized by open forest land and known internationally as

    Jose Larios LAMACCHIA REALTY, INC

    850 Chester Rd, Becket, MA 01223
  • /7

    $42,000 Sold Oct 11, 2024

    • Land
    • 19.37 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
  • /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
  • /4

    $55,000 Sold Oct 04, 2024

    • Land
    • 7.53 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
  • /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
  • /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
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