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Greenfield, MA Houses for Sale

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  • /39

    $545,000

    Open Sun 12PM - 2PM
    • 5 Beds
    • 2.5 Baths
    • 2,612 Sq Ft

    198 Leyden Rd, Greenfield, MA 01301

    Once a dairy farm, this timeless Victorian, is available for the first time in 84 years. Located along Leyden Road, offering 2.71 bucolic acres for privacy, making this truly a rare find. Custom built-in’s and period lead glass windows add to the charm of the home. The open layout merges dining and living spaces with a galley kitchen for easy entertaining. Features include 5 bedrooms, 2 full

    Agent Photo

    Cathy Roberts

    Cohn & Company

    (413) 823-2492

    198 Leyden Rd, Greenfield, MA 01301
  • /32

    $840,000

    • 4 Beds
    • 2 Baths
    • 2,197 Sq Ft

    22 Conway Dr, Greenfield, MA 01301

    This 13.3±-acre Greenfield property offers end-of-road privacy with a charming 1920s Craftsman bungalow, four bedrooms, two baths, 1,500± feet of Green River frontage, and approximately eight acres of tillable farmland. Improvements include a post and beam barn with 22' x 36' workshop, 2 chicken coops, horse stalls and 12' x 33' solarium, plus a stand alone hoop heated greenhouse, pavilion,

    Keith Ross LandVest, Inc.

    22 Conway Dr, Greenfield, MA 01301
  • /42

    $599,900

    Open Sat 11AM - 1PM
    • 4 Beds
    • 4.5 Baths
    • 3,737 Sq Ft

    167 S Shelburne Rd, Greenfield, MA 01301

    Watch the narrated video. This home is a legal two-family with the look and feel of a cape-style single-family with an accessory dwelling unit. The main house has a spacious kitchen with a large island with a custom wood top and granite counters. Off the ktichen, there is a room for formal dining or whatever suits your needs. There is also a first-floor bedroom with an adjacent bathroom and a

    Michael Seward Michael Seward Real Estate

    167 S Shelburne Rd, Greenfield, MA 01301
  • /13

    $795,000

    $154K PRICE DROP
    • 10 Beds
    • 9.5 Baths
    • 4,120 Sq Ft

    151 Smead Hill Rd, Greenfield, MA 01301

    Discover the hidden potential of 151 Smead Hill—a historic property in Greenfield’s Rural Residential zone that once served as a sought-after wedding venue and now awaits a visionary entrepreneur ready to craft a multi-use enterprise. With flexible, adaptable spaces ideal for a boutique bed and breakfast, innovative event venue, or seasonal retreat, this property benefits from zoning that permits

    Zaisha Robert SR Commercial Realty

    151 Smead Hill Rd, Greenfield, MA 01301
  • /42

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,625 Sq Ft

    85 Verde Dr, Greenfield, MA 01301

    Distinguished custom Turn Key ranch in a premier newer neighborhood. Set on a generous corner lot, this exceptional home comes completely furnished and features an open-concept living and dining area with vaulted ceilings with rich Brazilian Walnut and tile flooring throughout. The gourmet kitchen offers quartz countertops, Viking appliances, and custom cabinetry perfect for everyday living and

    Doug Fontaine Maniatty Real Estate

    85 Verde Dr, Greenfield, MA 01301
  • /41

    $419,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1.5 Baths
    • 2,332 Sq Ft

    283 Chapman St, Greenfield, MA 01301

    Welcome home to your one-acre oasis in beautiful Greenfield! Just minutes from downtown, this wonderfully maintained 3-bed, 1.5-bath Cape blends modern updates with timeless historic character. A bright and inviting sunroom overlooks the expansive grounds, where mature gardens, fruit trees, and a large three-room hewn-timber barn create endless possibilities for gardening, hobbies, or future use.

    Erin Maclean Keller Williams Realty

    283 Chapman St, Greenfield, MA 01301
  • /21

    $225,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,668 Sq Ft

    427-429 Deerfield St, Greenfield, MA 01301

    Opportunity awaits at this spacious property conveniently located on Deerfield Street in Greenfield! Currently marketed as a single-family home, this versatile property offers 4 bedrooms and 2 full bathrooms with tall ceilings that create an open, airy feel throughout the living spaces. The layout provides flexibility for a variety of living arrangements and could potentially be utilized as a

    Alayna Zellmann Ruggeri Real Estate

    427-429 Deerfield St, Greenfield, MA 01301
  • /35

    $385,000

    • 3 Beds
    • 1 Bath
    • 1,688 Sq Ft

    351 Davis St, Greenfield, MA 01301

    Available for the first time in over 40 years, this impeccable Dutch Colonial blends timeless character paired with the right modern updates to create a warm & inviting home. Lovingly maintained & ready for the next chapter. Beautiful moldings and gorgeous hardwood floors set the stage. The front door opens to a lovely foyer leading through French doors to the spacious living room or straight

    Susanne Newman Duston Leddy Real Estate

    351 Davis St, Greenfield, MA 01301
  • /2

    $289,900

    • 3 Beds
    • 2 Baths
    • 2,350 Sq Ft

    13 River St, Greenfield, MA 01301

    This cozy great house has a great location near Downtown Greenfield , close to shops ,restaurants, Supermarkets , drugstore ,school easy access to the highway make this cozy Dreamhouse yours.

    Jorge Zea Jorge Andres Zea

    13 River St, Greenfield, MA 01301

Why Live in Greenfield

Greenfield, Massachusetts, is a small city in the rural northern reaches of the Pioneer Valley, home to fewer than 20,000 residents. Known for its affordability, Greenfield offers a variety of housing styles, including early 20th-century National style homes, bungalows, Queen Annes, ranch-style homes, colonials, and Cape Cods. The city’s Main Street is a hub of activity with its tree-lined streets, red brick buildings, and modern touches like the new library and the redevelopment of the old Wilson’s Department Store into a mixed-use complex. Local businesses, galleries, and event spaces contribute to a vibrant cultural district, while strip malls and big-box stores are located along state Routes 2 and 2a. Recreational opportunities abound with the Connecticut River providing boating, fishing, and biking trails, and the nearby Berkshires offering skiing within 20 miles. The historic Poet’s Seat Tower offers panoramic views of the area, and the Green River and Deerfield River are popular spots for swimming and trout fishing. Greenfield hosts numerous community events, including the annual Bee Fest and the Franklin County Fair. The city is well-connected via Interstate 91 and state routes, with bus routes linking it to nearby colleges and hubs. The private Stoneleigh-Burnham School is highly rated. Greenfield Community College offers tuition-free associate degrees through state programs. Potential homebuyers should be aware of the risk of flooding in areas near the rivers.

Single Family Home Prices in Greenfield, MA

Single Family Home Price Trends

Median Home Price
$353,300
Median 3-Bedroom Home Price
$335,000
Median 4-Bedroom Home Price
$393,000
Median 5-Bedroom Home Price
$545,000
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