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Middlefield, MA Houses for Sale

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  • /42

    $264,900

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

    162 Skyline Trail, Middlefield, MA 01243

    Step back in time without sacrificing modern comfort in this charming antique home, originally built in 1783. Thoughtfully updated to preserve its historic character, this home features exposed timber frame construction, wide-open living spaces, and timeless architectural details throughout. The inviting eat-in kitchen offers a farmhouse sink, vaulted ceiling, gas fireplace, open shelving,

    Aimee Kelly eXp Realty LLC

    162 Skyline Trail, Middlefield, MA 01243
  • /40

    $415,000

    • 3 Beds
    • 3 Baths
    • 1,403 Sq Ft

    143 E River Rd, Huntington, MA 01050

    Welcome to this contemporary home that features 3 bedrooms, 3 bathrooms, and sits on a sprawling 9.8-acre lot. The property offers stunning Westfield River and mountain views, a wrap-around deck, an above-ground pool, and a mostly finished walkout basement- this space offers an in-law apartment, use your imagination to personalize to your needs. This could be your own private retreat at the base

    Danielle Lafond Berkshire Hathaway HomeServices Realty Professionals

    143 E River Rd, Huntington, MA 01050
  • /42

    $450,000

    Open Sat 11AM - 12:30PM $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    147 Chipman Rd, Chester, MA 01011

    Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! Enter through the welcoming foyer to the main level that features a spacious living room & dining area w/ propane stove & sliders to a sunny deck, a kitchen with pantry closet, half bath w/ laundry, a

    Taylor Hildack Keller Williams Realty

    147 Chipman Rd, Chester, MA 01011
  • /58

    $450,000

    $10K PRICE INCREASE
    • 4 Beds
    • 1.5 Baths
    • 1,608 Sq Ft

    95 Town Hill Rd, Middlefield, MA 01243

    Set on 16 private acres, this four-bedroom, one-and-a-half-bath home has been lovingly updated while preserving its rustic warmth and character. Soulful wood floors, cozy living spaces, and a versatile attic retreat give this home an authenticity you simply cannot manufacture.A two-story wood stove heated barn bursting with natural light makes for an ideal studio or creative workspace. Step

    Dana Fuchs WILLIAM RAVEIS - BERKSHIRE

    95 Town Hill Rd, Middlefield, MA 01243

Why Live in Middlefield

Middlefield, MA, is a small town of nearly 400 residents in the northern hardwood forests of the Appalachian Mountains, about 40 miles from Springfield in Hampshire County. Known for its remote and rural setting, the town is surrounded by rivers, brooks, and hiking trails. Skyline Drive, the main road, hosts the local library, church, and fire station. Middlefield, incorporated in 1783, was once a hub for the woolen industry, but the forests have since reclaimed much of the land. The town's fringes feature state forests and wildlife management areas, popular among hunters and anglers. Glendale Falls, a scenic waterfall along Glendale Brook, is a notable attraction. Middlefield State Forest and Peru State Forest offer hiking trails through rolling hills and dense hardwood canopies.

Housing in Middlefield includes historic Colonials from the 1700s, log cabins from the 1980s, and custom-built homes on large lots. The real estate market is limited, with few properties listed at any given time. Community life centers around the Middlefield Senior Center and the Blossom Center, which host events like book clubs, meditation classes, bingo nights, and potlucks. The annual Middlefield Fair, held every August, features traditional country entertainment. While local amenities are sparse, Chester, 5 miles south, offers a small grocery store and a restaurant. For more extensive shopping, residents travel to Lee, 15 miles away, which has a major grocery store and the Lee Premium Outlets. The closest emergency room is 18 miles away in Pittsfield, and Bradley International Airport is just over 40 miles from the town.

Single Family Home Price Trends

Median Home Price
$320,000
Median 3-Bedroom Home Price
$360,000
Median 4-Bedroom Home Price
$450,000
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