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Middlefield, MA Homes

Section Image
  • 120 E River Rd, Middlefield, MA 01243
    120 E River Rd, Middlefield, MA 01243
    120 E River Rd, Middlefield, MA 01243
    /40

    $329,000

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

    120 E River Rd, Middlefield, MA 01243

    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 up with a good book on those cold New England

    Dennis LeClair RE/MAX Compass

    120 E River 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
    • 32 Chester Rd, Middlefield, MA 01243
      32 Chester Rd, Middlefield, MA 01243
      32 Chester Rd, Middlefield, MA 01243
      /23

      Est $235,511 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,672 Sq Ft

      32 Chester Rd, Middlefield, MA 01243

      32 Chester Rd, Middlefield, MA 01243
  • 122 E River Rd, Middlefield, MA 01243
    122 E River Rd, Middlefield, MA 01243
    122 E River Rd, Middlefield, MA 01243
    /8

    $79,900

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

    122 E River Rd, Middlefield, MA 01243

    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 exposure, offering potential for subdivision and creating

    Dennis LeClair RE/MAX Compass

    122 E River Rd, 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

    143 Chipman Rd, Chester, MA 01011
    • 162 Skyline Trail, Middlefield, MA 01243
      162 Skyline Trail, Middlefield, MA 01243
      162 Skyline Trail, Middlefield, MA 01243
      /47

      Est $267,309 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,758 Sq Ft

      162 Skyline Trail, Middlefield, MA 01243

      162 Skyline Trail, 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

    $35,000

    • Land
    • 5.00 Acres
    • $7,000 per Acre

    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
  • 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
    • 171 Arthur Pease Rd, Middlefield, MA 01243
      171 Arthur Pease Rd, Middlefield, MA 01243
      171 Arthur Pease Rd, Middlefield, MA 01243
      /13

      Not Listed For Sale

      171 Arthur Pease Rd, Middlefield, MA 01243

      171 Arthur Pease Rd, Middlefield, MA 01243
  • 116 Skyline Trail, Middlefield, MA 01243
    116 Skyline Trail, Middlefield, MA 01243
    116 Skyline Trail, Middlefield, MA 01243
    /25

    $435,000

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

    116 Skyline Trail, Middlefield, MA 01243

    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. 3 bedrooms 2 bathrooms. Spiral staircase to second level loft bedroom overlooking lower level, bathroom with shower stall to 3rd bedroom. Main level Kitchen, dining area, Livingroom open

    Evamarie Best Wolcott Realty

    116 Skyline Trail, Middlefield, MA 01243
  • 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
    • Lot97 Town Hill Rd, Middlefield, MA 01243
      Lot97 Town Hill Rd, Middlefield, MA 01243
      Lot97 Town Hill Rd, Middlefield, MA 01243
      /9

      Not Listed For Sale

      Lot97 Town Hill Rd, Middlefield, MA 01243

      Lot97 Town Hill Rd, Middlefield, MA 01243
  • Lot 52 Skyline Trail, Middlefield, MA 01243
    Lot 52 Skyline Trail, Middlefield, MA 01243
    /2

    $35,900

    • Land
    • 4.01 Acres
    • $8,953 per Acre

    Lot 52 Skyline Trail, Middlefield, MA 01243

    OWNER FINANCING AVAILABLE! This 4.01-acre wooded lot in Middlefield, MA, offers a private andscenic retreat in the heart of the Berkshires with an adjoining lot available as well. With nearby access toGlendale Falls, scenic hiking trails, and the Westfield River, it’s a perfect spot for outdoor enthusiasts.Enjoy the charm of small-town living while being just a short drive from Northampton and

    Derek Greene The Greene Realty Group

    Lot 52 Skyline Trail, Middlefield, MA 01243
  • 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
    • 113 Chipman Rd, Middlefield, MA 01011
      113 Chipman Rd, Middlefield, MA 01011
      113 Chipman Rd, Middlefield, MA 01011
      /56

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft

      113 Chipman Rd, Middlefield, MA 01011

      113 Chipman Rd, Middlefield, MA 01011
  • Lot 51 Skyline Trail, Middlefield, MA 01243
    Lot 51 Skyline Trail, Middlefield, MA 01243
    /2

    $35,900

    • Land
    • 4.01 Acres
    • $8,953 per Acre

    Lot 51 Skyline Trail, Middlefield, MA 01243

    Enjoy nearby outdoor adventures at Glendale Falls, scenic hiking trails, and fishing in the Westfield River, all while embracing the charm of small-town living. Just a short drive to Northampton and Pittsfield, you’ll have access to shopping, dining, and cultural attractions while still enjoying a quiet retreat. Whether you're looking to build your dream home or make a smart investment, this

    Derek Greene The Greene Realty Group

    Lot 51 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
    • 108 Chipman Rd, Chester, MA 01011
      108 Chipman Rd, Chester, MA 01011
      108 Chipman Rd, Chester, MA 01011
      /41

      Not Listed For Sale

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

      108 Chipman Rd, Chester, MA 01011

      108 Chipman Rd, Chester, MA 01011
  • lot 2 Skyline Trail, Middlefield, MA 01243
    lot 2 Skyline Trail, Middlefield, MA 01243
    /2

    $36,000

    • Land
    • 3.81 Acres
    • $9,449 per Acre

    lot 2 Skyline Trail, Middlefield, MA 01243

    Great homesite with 3.8 acres. On the corner of Lynes road, which is closed,

    James Adams Hilltown Real Estate by Adams Realty

    lot 2 Skyline Trail, 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
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 0 Skyline Trail Lot 24, Middlefield, MA 01243
    0 Skyline Trail Lot 24, Middlefield, MA 01243
    /2

    $55,000

    • Land
    • 10 Acres
    • $5,413 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
  • 104 W Hill Rd, Hinsdale, MA 01235
    104 W Hill Rd, Hinsdale, MA 01235
    104 W Hill Rd, Hinsdale, MA 01235
    /32

    $322,600 Sold Jun 28, 2024

    • 1,100 Sq Ft
    • $293/SF
    • 29 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1981

    104 W Hill Rd, Hinsdale, MA 01235

    Wildlife Sanctuary: This 3-bedroom 2 bath home sits in the middle of the Orenda Wildlife sanctuary with 9.5 acres of land. 7+ acres in Chapter 61 B -Recreation. Very peacefully. Main level has 1 bedroom and full bath. upstairs has 2 bedrooms and a 1/2 bath between with a small deck on the upper level the watch the wildlife. Plenty of room for gardening. Wonderful flowering bushes. Full house

    Ginger Conner RED HORSE REAL ESTATE, LLC

    104 W Hill Rd, Hinsdale, MA 01235
    • 576 E River Rd, Huntington, MA 01050
      576 E River Rd, Huntington, MA 01050
      576 E River Rd, Huntington, MA 01050
      /9

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft

      576 E River Rd, Huntington, MA 01050

      576 E River Rd, Huntington, MA 01050
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /9

    $34,001 Pending

    • Land
    • 5 Acres
    • $6,379 per Acre

    Unlisted Address

    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

    Unlisted Address
  • 153 Skyline Trail, Middlefield, MA 01243
    153 Skyline Trail, Middlefield, MA 01243
    153 Skyline Trail, Middlefield, MA 01243
    /143

    $302,000 Sold Jun 10, 2024

    • 945 Sq Ft
    • $320/SF
    • 8 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    153 Skyline Trail, Middlefield, MA 01243

    Welcome to Sunset Ridge. A unique and magicalhomesteaders paradise where many possibilities await. Come relax on the spacious deck as you observe the many birds & butterflies that blissfully flutter about on the approx. 4.73 open acreage and all it has to offer. Blueberry bushes, young apple orchards, strawberry patch, vegetable & flower gardens adorn the land. This warm & inviting 1900's home

    Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

    153 Skyline Trail, Middlefield, MA 01243
    • 107 Chipman Rd, Middlefield, MA 01243
      107 Chipman Rd, Middlefield, MA 01243
      107 Chipman Rd, Middlefield, MA 01243
      /14

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,400 Sq Ft

      107 Chipman Rd, Middlefield, MA 01243

      107 Chipman 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
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /16

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 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
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /21

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
  • 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
    • 8 Clark Wright Rd, Middlefield, MA 01243
      8 Clark Wright Rd, Middlefield, MA 01243
      8 Clark Wright Rd, Middlefield, MA 01243
      /22

      Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,925 Sq Ft

      8 Clark Wright Rd, Middlefield, MA 01243

      8 Clark Wright Rd, Middlefield, MA 01243
  • 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
    • 0 W Hill Rd, Middlefield, MA 01243
      0 W Hill Rd, Middlefield, MA 01243
      0 W Hill Rd, Middlefield, MA 01243
      /19

      Not Listed For Sale

      0 W Hill Rd, Middlefield, MA 01243

      0 W Hill Rd, Middlefield, MA 01243
    • 142 W Hill Rd, Middlefield, MA 01235
      142 W Hill Rd, Middlefield, MA 01235
      142 W Hill Rd, Middlefield, MA 01235
      /28

      Not Listed For Sale

      • 3 Beds
      • 2 Baths

      142 W Hill Rd, Middlefield, MA 01235

      142 W Hill Rd, Middlefield, MA 01235
    • 140 Arthur Pease Rd, Chester, MA 01011
      140 Arthur Pease Rd, Chester, MA 01011
      140 Arthur Pease Rd, Chester, MA 01011
      /43

      Est $469,410 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,496 Sq Ft

      140 Arthur Pease Rd, Chester, MA 01011

      140 Arthur Pease Rd, Chester, MA 01011
    • 142 Chipman Rd, Chester, MA 01011
      142 Chipman Rd, Chester, MA 01011
      142 Chipman Rd, Chester, MA 01011
      /42

      Est $230,546 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 792 Sq Ft

      142 Chipman Rd, Chester, MA 01011

      142 Chipman Rd, Chester, MA 01011
    • 138 Skyline Trail, Middlefield, MA 01243
      138 Skyline Trail, Middlefield, MA 01243
      138 Skyline Trail, Middlefield, MA 01243
      /21

      Est $384,134 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,372 Sq Ft

      138 Skyline Trail, Middlefield, MA 01243

      138 Skyline Trail, Middlefield, MA 01243
    • 9 Bell Rd, Middlefield, MA 01243
      9 Bell Rd, Middlefield, MA 01243
      9 Bell Rd, Middlefield, MA 01243
      /18

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,162 Sq Ft

      9 Bell Rd, Middlefield, MA 01243

      9 Bell Rd, Middlefield, MA 01243

Showing Results 1 - 40, Page 1 of 12

Massachusetts Middlefield

Real Estate & Homes

Home Trends in Middlefield, MA

On average, homes in Middlefield, MA sell after 62 days on the market compared to the national average of 47 days. The average sale price for homes in Middlefield, MA over the last 12 months is $331,766, up 16% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$312,300
Median Single Family Price
$371,800
Average Price Per Sq Ft
$240
Number of Homes for Sale
2
Last 12 months Home Sales
6
Months of Supply
4.00
Median List Price
$349,000
Median Discount From 1st List Price
7%
Median Home Sale Price YoY Change
10%
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