Built with love and offered for the first time ever, 26 Oak Hill Road is a rare opportunity to own a home filled with character and unique workmanship. Lovingly hand built by a local craftsman for his own family in 1964, this 3-bedroom, 2-bath Cape is tucked away in a highly desirable nature-filled Greenfield neighborhood. A picturesque stone wall leads the way to a welcoming stone patio and screened porch perfect for morning coffee or quiet evenings. Inside, hardwood floors, exposed beams, custom cabinetry, handcrafted touches, Dutch doors and a wood-burning fireplace create warmth and timeless charm. The flexible floor plan includes a first-floor bedroom, full bath, and an additional room ideal for an office, den, hobby room, or guest space. Upstairs showcases 2 bedrooms and another full bathroom. From relaxing on the rear deck to gathering by the fire, this a home that becomes the backdrop for life’s most meaningful moments. Come see why you’ll feel at home the moment you arrive!
Welcome to this sweet Cape with country charm in Greenfield's desirable Four Corners neighborhood! Lovingly maintained and thoughtfully updated by the same owners for 44 years, this home is ready for its next chapter. The open floor plan features a recently remodeled kitchen with breakfast bar, flowing seamlessly into the dining area and out to the deck overlooking a peaceful in-town backyard. Enjoy the beautifully landscaped yard complete with a shed, water feature, and the perfect spot for a hammock to relax and unwind. The dining room opens to a warm and inviting living room with fireplace, built-in shelving, and a picture window offering lovely backyard views. A first-floor bedroom sits across from a spacious remodeled bath with a walk-in shower. Upstairs you'll find two additional bedrooms, a home office, and a large walk-in closet. Situated on a corner lot in one of Greenfield's favorite neighborhoods, convenient to Four Corners School, Greenfield High School, I-91, and Route 2.
Hiding behind mature apple trees and surrounded by beautiful gardens, this impeccably maintained ranch is a rare treasure. Built by a master craftsman for his son in 1948 and lovingly cared for through two generations, this home blends timeless character with thoughtful updates and a warm, welcoming feel throughout. An inviting foyer leads to a spacious living room with fireplace and dining area, while the updated kitchen features butcher block counters and is open to a dining area. Hardwood floors, custom built-ins, period hardware, and raised-panel doors showcase the home's enduring craftsmanship. A full walk-up attic offers exceptional storage, while an efficient wood pellet furnace adds comfort. Relax in the charming three-season breezeway overlooking beautifully landscaped gardens bursting with color from spring through fall. Set on .78 acres in the Meadows of Greenfield, the property includes blueberry, raspberry, and elderberry bushes, along with four varieties of apple trees.
Tucked away on the outskirts of Greenfield, this home offers the perfect balance of country feel & everyday convenience. With a manageable floor plan and easy-to-maintain lot, it's an excellent option for first-time buyers, those looking to simplify, or anyone seeking a more practical lifestyle. The main level features a spacious eat-in kitchen, comfortable living room, two bedrooms, and a full bath, while warm wood accents and natural light add character throughout. Need a little extra space? The walkout lower level offers an extra room ideal for hobbies, a home office, workout space, or guests. Outside, mature trees provide a peaceful setting with room to garden, relax, or enjoy the outdoors without the upkeep of a larger property. Conveniently located just minutes from downtown Greenfield, Bernardston, I-91, and Route 2, you'll enjoy easy access to shopping, dining, and commuting while still feeling tucked away from it all! OPEN HOUSE Saturday June 20th 3:00-5:00 PM!
Welcome to 40 Newell Pond Road! This charming ranch is nestled on a quiet dead-end street in one of North Greenfield’s most desirable neighborhoods. Solidly built and well maintained, this single-level home sits on just under a half acre and offers a comfortable floor plan with a spacious living room featuring a cozy fireplace, knotty pine accent wall, and two large picture windows. The eat-in kitchen includes original solid wood cabinets and access to a large deck overlooking the private patio and level backyard. Features include cedar siding, replacement windows, beautiful oak floors, natural woodwork, a newer septic system, and an updated electric panel in 2023. The finished basement provides additional living space with a family room, built-in storage bench, cedar closet, laundry area, and two versatile rooms ideal for a home office, playroom, or hobbies. The level yard is bordered by woods for added privacy. Move right in or bring your own ideas and make this home your own !
Unique oasis in the Middle of Greenfield! Well cared for 1992 Cape on lovely Hastings Street offers 4 bedrooms, 2 full baths and the warmth of hardwood floors throughout the kitchen, dining area, living room and a bedroom/office. Step out back on the deck to your private park - a beautiful ledge outcropping with woods behind seems like you are far removed from a city residential neighborhood! Full poured concrete foundation, part of which is 2 car garage, and the rest laundry, utilities and hobby or exercise area. Easy maintenance vinyl siding, 10 year old roof, HB Smith forced hot water heat. Schedule your showing soon....and your moving truck!
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, run-in shed, gardens, trails, private beach, dock, picnic area, fire pit and pond. With General Commercial zoning less than a mile from I-91/Route 2, the property offers flexible potential for farming, horses, recreation, or business use. This property is a one of a kind with ultimate privacy minutes away from town centers and other amenities. The Green River is a premier fishing resource with wonderful boating opportunities.
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 baths, a separate walk-in shower room, plus first floor-laundry. Additional amenities include a 4-season heated sunroom, a beautiful large barn, 3 garages, attractive landscaping, all complemented by a circular driveway and stonewalls. The home offers fabulous multi-generational potential and endless options for the gardener, small farmer or hobbyist. The abutting lot is available for sale, see MLS#73528825. Minutes to Downtown Greenfield, I-91 and Rt 2. First showings at the Open House, Sunday June 7th from Noon-2:00pm. Stop by, say hello, and check it out!
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 living room. The spacious 3 season room has a fireplace and two sliders out to the patio and spacious backyard. There are two bedrooms on the second floor, including a spacious ensuite bedroom. A home office with a separate entrance is located between the units. The second unit is located above the 2-car garage with interior & exterior access from a second-level wood deck. The second unit/accessory dwelling unit has an open floor plan with a wood-paneled vaulted ceiling, one bedroom complemented by a tray ceiling,1.5 baths, a gas stove, laundry hook-ups, & a kitchen with a breakfast bar.
This bright and quiet second-floor end unit at Myers Farm has a really comfortable, easy feel from the moment you walk in. Being an end unit, it gets great natural light throughout the day and offers a bit more privacy than most.The space features hardwood floors, an updated kitchen with quartz countertops and newer appliances, and nicely refreshed bathrooms, so it’s truly move-in ready.One of the standout features is the extra bonus room—currently set up as a second bedroom, but it could just as easily work as a home office, den, or additional living space depending on what you need.You’ll also have the convenience of a one-car garage along with a separate storage room for the extras.Overall, it’s a well-kept, flexible space in a quiet setting—easy living in a great community.
Welcome to this beautifully maintained, fully furnished 836 sq ft condominium offering comfort, convenience, and style. This inviting second-floor unit features two spacious bedrooms and a well-appointed full bathroom. The thoughtfully designed kitchen includes a gas stove, dishwasher, microwave, and refrigerator—perfect for everyday living or entertaining. Enjoy hardwood and tile flooring throughout, adding warmth and durability to the space. A sliding glass door opens to deck, ideal for relaxing or enjoying fresh air. Additional highlights include interior access to a basement with secure, caged storage, as well as exterior access for added convenience. The building also offers coin-operated washer and dryer facilities. Located just minutes from downtown Greenfield, you’ll have easy access to shops, dining, and local amenities. This move-in-ready condo is a fantastic opportunity for comfortable, low-maintenance living.
Meticulously upgraded & improved over the years this 2 bdrm/2ba Country-Side condominium is truly move-in ready. The attractive kitchen remodel features painted maple cabinets, stainless steel appliances, granite counter tops, a breakfast bar & Marmoleum flooring. The open floor plan includes an adjoining dining area & spacious living room. French doors lead into 2 bonus rooms that provide options for a family room, office space, craft room or studio. The primary suite provides ample closet space & private full bath. Off the kitchen is a walk-in pantry that provides storage & laundry facilities. In recent years the HVAC system was replaced with an efficient central ducted heat pump system that keeps the home comfortable year round. An included garage offers storage space. Country Side is a desirable place to call home that offers a pool/club house and enjoys easy access to Greenfield Country Club including Terrazza Restaurant. Open Houses: 6/16 Tues 5-7pm & 6/21 Sun 12-2pm.
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.
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 two-family property with the addition of a second egress, offering future possibilities for the next owner. Situated in a prime location with easy access to major routes, this home is ideal for commuters or anyone looking to be close to area amenities while still enjoying the charm of Greenfield. Whether you’re looking for a spacious single-family home or exploring options for multi-generational living or investment potential, this property offers a great opportunity to make it your own. Bring your vision and unlock the possibilities!
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 open space cluster development. Zoning offers a pathway for creative reconfiguration—concentrating development while preserving expansive, natural communal areas that could eventually pave the way for modern co-housing or shared amenity communities, all set against a backdrop of timeless rural charm.

Greenfield is located in Massachusetts. Greenfield, Massachusetts has a population of 17,661. Greenfield is less family-centric than the surrounding county with 23.36% of the households containing married families with children. The county average for households married with children is 23.54%.
The median household income in Greenfield, Massachusetts is $52,211. The median household income for the surrounding county is $64,949 compared to the national median of $69,021. The median age of people living in Greenfield is 44.5 years.
The average high temperature in July is 81 degrees, with an average low temperature in January of 11.3 degrees. The average rainfall is approximately 49.7 inches per year, with 57 inches of snow per year.