Middlefield Homes for Sale

Welcome to Middlefield, Massachusetts – a hidden gem nestled in the heart of Hampshire County. This quaint town boasts a rich history and a tight-knit community, making it an ideal place for those seeking a peaceful retreat from the hustle and bustle of city life. Surrounded by the breathtaking beauty of the Berkshire foothills, Middlefield is a nature lover's paradise, offering ample opportunities for hiking, fishing, and exploring the great outdoors.

The charm of Middlefield is highlighted by its picturesque landscapes and serene atmosphere, which provide a perfect backdrop for your dream home. The real estate market here features a variety of homes for sale, catering to diverse tastes and budgets. Whether you're looking for a cozy cottage, a spacious family home, or a rustic retreat, Middlefield has something to offer everyone. Many properties come with expansive yards, allowing you to enjoy the tranquility of nature right at your doorstep.

The community is known for its friendly residents and local events, fostering a sense of belonging that is hard to find elsewhere. With its excellent schools, low crime rates, and access to outdoor recreational activities, Middlefield is not just a place to live; it's a place to thrive.

If you're ready to explore the opportunities that await you in Middlefield, browse our listings of homes for sale today. Discover the perfect blend of rural charm and modern convenience in this enchanting town, where your dream home is just a heartbeat away.

Newest Middlefield Homes for Sale

$420,000

3 Beds ⋅ 3 Baths ⋅ 73592616 MLS

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 first-floor office, & a primary bedroom w/ ensuite bath featuring a jetted tub & shower. The lower level provides flexible living w/ a 2nd office, bonus room, 2 bedrooms with forest-facing windows, a shared recreation area, kitchenette, full bath & a built-in sauna! An exterior door opens to the private trail along Glendale Brook, leading to a natural dipping pool. Additional features include an oversized 2 car garage, a whole-house humidifier, propane space heater in the basement, a newly replaced furnace, inverter for solar system, & ChargePoint EV charger. OPEN HOUSE: Saturday, 10/24 @ 11-12:30PM!

147 Chipman Road, Middlefield

Listing courtesy of Listing Agent: Taylor Hildack from Listing Office: Keller Williams Realty.

$335,000

4 Beds ⋅ 2 Baths ⋅ 73581299 MLS

Historic Country Home + Hobby Farm with majestic views of the hills and local pastures. This beautiful historic country home has been brought back to life over the last three years, with more than $100,000 invested in major improvements. Full of character—including beautiful wide plank flooring sourced from the surrounding woods—the expensive work has been done, leaving the next owner an opportunity to add their own cosmetic touches and build additional equity. Featuring two sperate living spaces this could be the ultimate multi-generational family home. The property has an outstanding, two-level insulated barn with a newer electrical service. Fencing and a stream for a water source if you plan on animals for your farm. Established blueberries, pear trees & apple trees. The farm is close to Glendale falls, the skyline trail and the Berkshires. Home is going to need further maintenance and some repairs but the low price reflects that.

108 Chipman Rd, Middlefield

Listing courtesy of Listing Agent: James Adams from Listing Office: Hilltown Real Estate by Adams Realty.

$1,550,000

3 Beds ⋅ 3 Baths ⋅ 73577291 MLS

Set on approximately 62 acres spanning both sides of Cone Road, Middle Branch Overlook Estate is a private country retreat with sweeping southeast-facing views across the Middle Branch of the Westfield River valley. Comprised of three abutting parcels and bordered by protected land to the north and south, the property features open fields, woodland, a year-round brook, ponds, fruit trees, gardens, and an extensive trail network. The three-bedroom timber-frame residence is positioned on a high point overlooking a gently sloping hayfield. Built with native wood and subsequently expanded, the home features warm pine interiors, open kitchen, dining and living areas, a first-floor primary suite with private covered deck, flexible upper-level spaces, and a spacious lower-level recreation room. Two additional rooms within the residence offer flexibility for offices, studios, or other uses, with another finished room above the garage providing additional space for work, hobbies, or future expansion. Outdoor amenities include open and covered decks, an electrified gazebo, gas fire pit, and heated pool. A total of 56 solar panels are located on the roofs of the house and garage. Three garages, including a three-story garage with finished upper level, plus a workshop, storage buildings, paver driveway, and propane generator provide exceptional utility. Offering privacy, expansive views, protected surroundings, and substantial road frontage, the acreage and frontage may offer potential for five to seven additional building lots, subject to approvals and buyer due diligence. The majority of the acreage is currently classified under Massachusetts Chapter 61B.

69 Cone Road, Middlefield

Listing courtesy of Listing Agent: Keith Ross from Listing Office: LandVest, Inc..

$264,900

2 Beds ⋅ 2 Baths ⋅ 73545087 MLS

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, abundant natural light, and a cozy sitting area. The living room showcases exposed hand-hewn beams, built-in bookshelves, and a classic wood-burning fireplace. Major improvements include drywall throughout following the removal of plaster and lath, all-new modern electrical wiring replacing knob-and-tube, a 5-bedroom septic system (2005), and an updated roof. First-floor laundry. Bedrooms w high ceilings/ oversized closets. Deck overlooking backyard w new storage shed, stone walls, and garden area. Own a piece of local history with the peace of mind that comes from substantial modern upgrades.

162 Skyline Trail, Middlefield

Listing courtesy of Listing Agent: The Aimee Kelly Crew from Listing Office: eXp Realty LLC.

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Middlefield Homes for Sale

Newest Middlefield Homes for Sale

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