20

Middlefield, MA Homes for Sale

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  • 116 Skyline Trail, Middlefield, MA 01243
    116 Skyline Trail, Middlefield, MA 01243
    116 Skyline Trail, Middlefield, MA 01243
    /37

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    116 Skyline Trail, Middlefield, MA 01243

    ***BERKSHIRE AREA Rustic Log Cabin nestled in the woods of Middlefield, MA. offering plenty of privacy and room to roam. 13.74 +/- acres with many trails for hiking, snow sports of all sorts, or just enjoying nature at its best. INVESTERS TAKE NOTE:: AIR BNB potential. Close to many cultural amenities, Jacobs Pillow Dance, Otis Reservoir, Otis Ridge Ski, Butternut, Stockbridge, Northampton,

    Evamarie Best Wolcott Realty

    116 Skyline Trail, Middlefield, MA 01243
  • 120 E River Rd, Middlefield, MA 01243
    120 E River Rd, Middlefield, MA 01243
    120 E River Rd, Middlefield, MA 01243
    /40

    $329,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    120 E River Rd, Middlefield, MA 01243

    Highest & best offer deadline Sunday 5/18 @ 3pm. Nestled in the picturesque town of Middlefield, this charming 2 bedroom Ranch style home is the perfect escape from the hustle and bustle of city life. Situated alongside the serene middle branch of the Westfield River, tranquility abounds in this peaceful setting. Step inside to find a cozy living room with a working fireplace, perfect for curling

    Dennis LeClair RE/MAX Compass

    120 E River Rd, Middlefield, MA 01243
  • 100 Town Hill Rd, Middlefield, MA 01243
    100 Town Hill Rd, Middlefield, MA 01243
    100 Town Hill Rd, Middlefield, MA 01243
    /6

    $378,500 Pending

    • 3 Beds
    • 1 Bath
    • 15,386 Sq Ft

    100 Town Hill Rd, Middlefield, MA 01243

    If you're dreaming of a true New England lifestyle in the country, look no more! This turn-key one level ranch style home has been meticulously maintained by the original owners over the years. The 7-acre property on TWO parcels includes a huge 30' x 20' well maintained separate garage with 12' ceiling height, 16' barn doors, a workroom and lean-to. All with its own oil heating system and

    Reciprocal Reciprocal Berkshire Reciprocal

    100 Town Hill Rd, Middlefield, MA 01243
  • 159 Skyline Trail, Middlefield, MA 01243
    159 Skyline Trail, Middlefield, MA 01243
    159 Skyline Trail, Middlefield, MA 01243
    /42

    $421,000 Sold Apr 28, 2025

    • 2,044 Sq Ft
    • $206/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1890

    159 Skyline Trail, Middlefield, MA 01243

    A VIEW SO GOOD YOU WILL NEVER WANT TO LEAVE! Perched in the peaceful Hilltowns, this timeless 1890 Colonial blends historic charm with modern updates. Bathed in natural light, it offers breathtaking sunset views from the back of the home. Thoughtful upgrades include a converted garage-turned-home gym with new heating, insulation, windows, flooring & garage door. The home has also been enhanced

    Aimee Kelly eXp Realty

    159 Skyline Trail, Middlefield, MA 01243
  • 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
  • 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 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243
    0 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243
    0 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243
    /12

    $649,900

    • Land
    • 155 Acres
    • $4,193 per Acre

    0 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243

    This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old

    Doug Collins Lamacchia Realty, Inc.

    0 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243
  • 0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243
    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243
    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243
    /12

    $649,900

    • Land
    • 155 Acres
    • $4,193 per Acre

    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243

    This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old

    Doug Collins LAMACCHIA REALTY, INC

    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243
  • 0 Skyline Trail Lot 24, Middlefield, MA 01243
    0 Skyline Trail Lot 24, Middlefield, MA 01243
    /2

    $45,000

    • Land
    • 10 Acres
    • $4,429 per Acre

    0 Skyline Trail Lot 24, Middlefield, MA 01243

    Over 10 acres of country land available for a private homestead, farming operation, or future development. Here is your unique opportunity to own a piece of New England's scenic beauty nestled in the Berkshires. Whether you're looking for a private retreat, a farm, or investment property, the region provides a mix of rolling hills, forests, and open meadows. Bring your vision for this land!

    Phim Mar Byrnes Real Estate Group LLC

    0 Skyline Trail Lot 24, Middlefield, MA 01243
  • Lot 0 E River Rd, Middlefield, MA 01243
    Lot 0 E River Rd, Middlefield, MA 01243
    Lot 0 E River Rd, Middlefield, MA 01243
    /8

    $79,900 Pending

    • Land
    • 4.80 Acres
    • $16,646 per Acre

    Lot 0 E River Rd, Middlefield, MA 01243

    Highest & best offer deadline Sunday 5/18 @ 3pm. Nestled alongside the gently flowing middle branch of the Westfield River in Middlefield MA. Discover unparalleled tranquility on this exceptional parcel of land. Imagine waking to the sounds of nature and enjoying breathtaking scenic views every day. This cleared and easily accessible parcel boasts significant 465' street frontage & river

    Dennis LeClair RE/MAX Compass

    Lot 0 E River Rd, Middlefield, MA 01243
  • 113 Skyline Trail, Middlefield, MA 01243
    113 Skyline Trail, Middlefield, MA 01243
    113 Skyline Trail, Middlefield, MA 01243
    /5

    $259,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,935 Sq Ft

    113 Skyline Trail, Middlefield, MA 01243

    Large home on almost 10 acres with an additional 4+ acre lot. Plenty of privacy and room. 12x14 deck off the dining room. Large heated garage with extra high ceilings for the auto enthusiast or collector. Pool is 2 years old, Roof was replaced in 2015. The house has oil heat and a pellet stove the detached garage has propane heat.

    Reciprocal Reciprocal Berkshire Reciprocal

    113 Skyline Trail, Middlefield, MA 01243
  • 71 W Hill Rd, Middlefield, MA 01243
    71 W Hill Rd, Middlefield, MA 01243
    71 W Hill Rd, Middlefield, MA 01243
    /30

    $219,900 Pending

    • 3 Beds
    • 1.5 Baths
    • 2,324 Sq Ft

    71 W Hill Rd, Middlefield, MA 01243

    Reciprocal Reciprocal Berkshire Reciprocal

    71 W Hill Rd, Middlefield, MA 01243
  • lot 94.2 Skyline Trail, Middlefield, MA 01243
    lot 94.2 Skyline Trail, Middlefield, MA 01243
    lot 94.2 Skyline Trail, Middlefield, MA 01243
    /6

    $30,000 Sold Jun 09, 2025

    • Land
    • 5.00 Acres
    • $6,000 per Acre
    • 45 Days On Market

    lot 94.2 Skyline Trail, Middlefield, MA 01243

    A great price for this wooded lot which is walking distance to Middlefield center. The land is relatively flat. An old cabin is on the property but may need to come down. Middlefield has so much to offer. Come take a look. You will love the property.

    James Adams Hilltown Real Estate by Adams Realty

    lot 94.2 Skyline Trail, Middlefield, MA 01243
  • Lot16 Chester Rd, Middlefield, MA 01011
    Lot16 Chester Rd, Middlefield, MA 01011
    Lot16 Chester Rd, Middlefield, MA 01011
    /9

    $29,900 Sold Jun 06, 2025

    • Land
    • 5 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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /5

    $34,000 Sold Jan 31, 2025

    • Land
    • 2.50 Acres
    • $13,600 per Acre
    • 126 Days On Market

    Unlisted Address

    Great Parcel of land on a country road in Middlefield with low taxes. Some of this parcel was cleared a few years back but has now grown back in. Will be easy to clear again. Farms on both the back and front sides of this land. New perc test have been done at 11 MPI and 9.3 MPI. Very good rates. There is a small sign and white ribbon in the tree. Please feel free to drive by.

    Ginger Conner RED HORSE REAL ESTATE, LLC

    Unlisted Address
  • 131 River Rd, Middlefield, MA 01050
    131 River Rd, Middlefield, MA 01050
    131 River Rd, Middlefield, MA 01050
    /43

    $262,000 Sold Nov 21, 2024

    • 1,560 Sq Ft
    • $168/SF
    • 123 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1963

    131 River Rd, Middlefield, MA 01050

    Discover your perfect retreat with this fully updated & furnished contemporary home set on serene East River Rd. Nestled between conservation land & the tranquil river,the property offers a unique combination of seclusion & accessibility. Enjoy outdoor entertaining on the newly constructed platform- perfect for dining to soothing river sounds. Mornings start with coffee on the kitchen

    Kim Bergland RED HORSE REAL ESTATE, LLC

    131 River Rd, Middlefield, MA 01050
  • 172 Skyline Trail, Middlefield, MA 01243
    172 Skyline Trail, Middlefield, MA 01243
    172 Skyline Trail, Middlefield, MA 01243
    /51

    $402,000 Sold Oct 29, 2024

    • 3,104 Sq Ft
    • $130/SF
    • 23 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1787

    172 Skyline Trail, Middlefield, MA 01243

    This beautiful property sits on 3.64 acres and consists of a cape with in-law apartment and its classified as a two-family. The main home features living room/den, large bedroom with skylights, spacious kitchen with laundry, 2 full bathrooms and large primary bedroom currently being used as an office. Upstairs you will find 2 additional bedrooms with skylights. The apartment offers an open space

    Maria Liccardi LAMACCHIA REALTY, INC

    172 Skyline Trail, Middlefield, MA 01243
  • 0 Arthur Pease Rd, Middlefield, MA 01243
    0 Arthur Pease Rd, Middlefield, MA 01243
    0 Arthur Pease Rd, Middlefield, MA 01243
    /8

    $30,000 Sold Sep 18, 2024

    • Land
    • 2.58 Acres
    • $11,628 per Acre
    • 171 Days On Market

    0 Arthur Pease Rd, Middlefield, MA 01243

    Get away from the busy city life and build your dream home on this beautiful private, 2.58 acre lot partially cleared. Perfect for nature lovers and privacy seekers. Enjoy the crisp clean air of county living but still be close to area attractions: Chester Theatre, Jacobs Pillow, Glendale Falls, Blueberry picking and Apple picking. Buyer to preform due diligence on the property and it's usage.

    Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

    0 Arthur Pease Rd, Middlefield, MA 01243
  • 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
  • 4 Bryan Rd, Middlefield, MA 01243
    4 Bryan Rd, Middlefield, MA 01243
    4 Bryan Rd, Middlefield, MA 01243
    /29

    $129,600 Pending

    • 2 Beds
    • 1 Bath
    • 1,152 Sq Ft

    4 Bryan Rd, Middlefield, MA 01243

    HUD Home, LBP. Lovely two, possibly three bedroom home in a country setting. Many updates in this home. Harwood floors and room for a finished basement. Property is situated on 1 acre of land. HUD Home. Sold "As IS" by electronic bid only. Prop avail 01-27-17. Bids due by 02-05-17 11:59PM Central Time then daily until sold. FHA Case #251-382259. Insured w Escrow Repairs TBD. Eligible for FHA

    Reciprocal Reciprocal Berkshire Reciprocal

    4 Bryan Rd, Middlefield, MA 01243
Massachusetts Hampshire County Middlefield

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