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Massachusetts Homesteads for Sale

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  • /32

    $3,000,000

    • 3 Beds
    • 1 Bath
    • 1,512 Sq Ft

    335 Old Fall River Rd, Dartmouth, MA 02747

    EVER DREAM OF OWNING YOUR OWN WINERY & VINEYARD? Let's make it happen! Running Brook Winery in Dartmouth MA would be the perfect place where you work and live on the same property. Create your new homestead in the existing home that has been gutted, plans are available if you'd like to use them. Enjoy running your own business and watching the joy you bring to the community as well as those who

    Agent Photo

    Sharon Simmons

    Sharon Simmons Real Estate

    335 Old Fall River Rd, Dartmouth, MA 02747
  • /83

    $3,998,000

    $997K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 5,002 Sq Ft

    764 E Hill Rd, New Marlborough, MA 01230

    East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property:

    Agent Photo

    Chapin Fish

    WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    764 E Hill Rd, New Marlborough, MA 01230
  • /7

    $719,000

    • Land
    • 3.52 Acres
    • $204,261 per Acre

    147 Washington Street Lot 2, Sherborn, MA 01770

    A rare offering at a great price! Beautiful 3.5 acre wooded lot with house set approximately 270 feet back from the road. Fully approved 8 bedroom septic design in hand, this is an amazing opportunity to build a gracious home with plenty of space and capacity for two additional ADUs as part of a family compound or for great rental income. Whether you are looking for a country escape, a functional

    Agent Photo

    Maryann Clancy

    Berkshire Hathaway HomeServices Commonwealth Real Estate

    147 Washington Street Lot 2, Sherborn, MA 01770
  • /33

    $299,000

    $21K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    3186 Main St, Becket, MA 01223

    Tucked against hundreds of acres of protected forest, this beautifully preserved late 1700s Berkshire homestead offers a rare blend of historic New England character, thoughtful modern upgrades, and direct access to the outdoors. Rich in period detail, the home showcases authentic craftsmanship, including hand-hewn beams, wooden pegs, and square nails, timeless elements seldom found beyond true

    Agent Photo

    Nick Geranios

    WILLIAM PITT SOTHEBY'S - LENOX

    3186 Main St, Becket, MA 01223
  • /41

    $975,000

    Open Sat 12PM - 1:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,795 Sq Ft

    555 Main St, West Newbury, MA 01985

    This circa-1840 Colonial offers a rare opportunity to own a piece of West Newbury's past. Set on 8 scenic acres, it was once part of a local potato farm. With over 2,700 square feet of thoughtfully renovated living space, the home features 4 bedrooms, 2.5 baths, and wide pine floors, blending antique charm with modern convenience. Outside, enjoy your own private retreat complete with an inground

    Cheryl Grant RE/MAX Bentley's

    555 Main St, West Newbury, MA 01985
  • /31

    $1,299,000

    $200K PRICE DROP
    • 7 Beds
    • 3 Baths
    • 3,831 Sq Ft

    368 Essex Ave, Gloucester, MA 01930

    Investors, developers, and homesteading enthusiasts — take note! Rare opportunity to acquire a 3.7-acre parcel in highly desirable West Gloucester. Includes a spacious three-family home on 2.44 acres plus an additional 1.26-acre lot, sold together. The existing property offers immediate income potential with three units — ideal for multi-generational living or rental income. Beyond investment

    Antonia Tullercash Churchill Properties

    368 Essex Ave, Gloucester, MA 01930
  • /15

    $120,000

    $10K PRICE DROP
    • Land
    • 10.08 Acres
    • $11,905 per Acre

    199 Goss Hill Rd, Montgomery, MA 01050

    Beautiful 10-acre building lot offering a rare blend of open meadow, wooded privacy, and peaceful country setting in the foothills of the Berkshires and Pioneer Valley hilltowns. Surrounded on two sides by 1,300+ acres of Mass Fish & Game conservation land and the Hiram H. Fox Wildlife Management Area, the property features level, open-sky acreage ideal for horses, a small farm, barn, workshop,

    Holly Young Delap Real Estate LLC

    199 Goss Hill Rd, Montgomery, MA 01050
  • /42

    $699,999

    • 5 Beds
    • 1 Bath
    • 3,064 Sq Ft

    482 Holyoke St, Ludlow, MA 01056

    Welcome home to this timeless 5 bedroom Victorian Farmhouse sitting on over 5 acres. Conveniently located less than 3 miles from the MA Turnpike and Interstate 291 and close to local businesses. Whether you are an investor looking for land on a corner lot with plenty of public and private frontage, or looking for a homestead to launch your agricultural dreams, the opportunities are limitless.

    Giana Aragon Gallagher Real Estate

    482 Holyoke St, Ludlow, MA 01056
  • /17

    $599,900

    • 3 Beds
    • 2 Baths
    • 2,486 Sq Ft

    15 Allen Coit Rd, Huntington, MA 01050

    Presenting for the first time, a modern and efficient single-family residence constructed in 2002, This property offers a substantial private estate, encompassing 8.59 acres of land . The home features a main floor master bedroom with bath and 2 more bedrooms on upper level. Further enhancing the property's appeal is a heated two-car garage, providing secure parking and additional storage

    Gerry Roy Royal Real Estate Service

    15 Allen Coit Rd, Huntington, MA 01050
  • /42

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,427 Sq Ft

    227 East St, Granby, MA 01033

    Experience luxury and privacy in this stunning executive ranch set on 13.3 acres, an ideal blend of refined living and modern homestead potential. With 3,427sq ft, this home offers a grand foyer, dedicated office, and an expansive living room with walk-out to a back patio. The chef’s kitchen features a large island, pantry, and dining area. The layout includes two bedrooms and a full bath with

    Karolina Podolska Naples Realty Group

    227 East St, Granby, MA 01033
  • /42

    $719,900

    • 3 Beds
    • 1.5 Baths
    • 1,618 Sq Ft

    151 Summer St, Rehoboth, MA 02769

    Welcome to 151 Summer Street, Rehoboth—a private 2.5-acre retreat where country charm meets modern comfort. Nestled among mature trees, this unique property offers the perfect blend of peaceful living and functional outdoor space.Inside, you'll find a thoughtfully designed kitchen with peninsula seating and an open flow to the living room, creating an inviting space for everyday living and

    Marlene Sequeira The Mello Group, Inc.

    151 Summer St, Rehoboth, MA 02769
  • /5

    $495,000

    • Land
    • 19 Acres
    • $26,053 per Acre

    0 Mohawk Lake Rd, Stockbridge, MA 01262

    Wonderful opportunity to own 19 acres in Stockbridge for your dream home! The parcel features acres of deciduous trees with an abundance of peacefulness and tranquility. Gentle upward slope from the street then levels off. Providing several options for building. Freestanding fireplace/chimney remains from a former homestead. Norman Rockwell Museum, Chesterwood and Berkshire Botanical Gardens down

    Debra Petrovsky DONOVAN REAL ESTATE

    0 Mohawk Lake Rd, Stockbridge, MA 01262
  • /11

    $450,000

    $275K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,766 Sq Ft

    1386 Pleasant St, Athol, MA 01331

    MOTIVATED SELLERS.. A rare offering awaits at 1386 Pleasant Street, Athol where a legacy of history, was established in 1750. This unique 41.1 acre property formerly known as Nye Tree Farm (37.85 acres in Chapter 61B Recreation protection) is located in one of Athol’s prestigious neighborhoods. The property offers endless potential for those seeking privacy, recreation, or agricultural use. The

    Lee Chauvette LAER Realty Partners

    1386 Pleasant St, Athol, MA 01331
  • /38

    $1,395,000

    • 8 Beds
    • 2.5 Baths
    • 4,228 Sq Ft

    14 Poplar St, Danvers, MA 01923

    Rare opportunity to own a landmark 1848 Georgian brick estate set on nearly one acre of land with dual access from both Poplar Street and Winthrop Street. Rich in historic character and original architectural details, the spacious main residence features 5 bedrooms, 2 bathrooms, 3 fireplaces, generous sun-filled living spaces, and a walk-up unfinished attic offering additional expansion

    Francesca Little Little & Co., REALTORS®

    14 Poplar St, Danvers, MA 01923
  • /23

    $145,000

    • Land
    • 22.33 Acres
    • $6,494 per Acre

    138 Ragged Hill Rd, West Brookfield, MA 01585

    Looking for your own personal retreat, homestead or farm... this is just what you need in your life! This property is one of a kind! 22.33 scenic acres on a quiet country road! This property features 816.49 ft of frontage and enough frontage and acreage for 3 ANR lots. A beautiful, clean freshwater Lamberton Brook spans through the back of the property. Peaceful and one of a kind. The Lot was

    Nicole Palmerino Keller Williams Boston MetroWest

    138 Ragged Hill Rd, West Brookfield, MA 01585
  • /22

    $159,900

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    1155 Main Rd, Savoy, MA 01256

    Opportunity is knocking--and it brought 5 acres with it. Set on a generous parcel, this 3-bedroom, 1-bath home offers the kind of space and privacy that's getting harder to find. A solid structure provides the perfect starting point for your vision, whether you're looking to renovate, invest, or create your dream homestead. The 2-car garage adds convenience and storage, while the expansive land

    Sara Bresett NOCHER REALTY

    1155 Main Rd, Savoy, MA 01256
  • /31

    $588,000

    Open Sun 1PM - 2:30PM $27K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,393 Sq Ft

    10 Avila Rd, Billerica, MA 01821

    Set on an expansive, oversized lot, this exceptional property offers a rare combination of space, flexibility, and lifestyle. From the moment you enter, you’ll be welcomed by soaring cathedral ceilings that create a bright, open, and airy living environment filled with natural light. The home’s thoughtfully designed layout provides comfortable everyday living along with great potential for

    Rebecca Huang William Raveis R.E. & Home Services

    10 Avila Rd, Billerica, MA 01821
  • /9

    $49,900

    $9K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,244 Sq Ft

    477 Mohawk Trail, Drury, MA 01343

    Nestled along the scenic Mohawk Trail in Drury, MA, this 3.5-acre parcel offers a unique opportunity to build your dream home or getaway retreat in the heart of the Berkshires. While the existing structure is likely a teardown, the land itself boasts natural beauty, privacy, & convenient road frontage. Just minutes from Savoy Mountain State Forest, Mohawk Trail State Forest, and the Western

    Laiken Rapisarda Lamacchia Realty, Inc. - Dalton

    477 Mohawk Trail, Drury, MA 01343
  • /6

    $390,000

    $35K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,584 Sq Ft

    427 West Rd, Clarksburg, MA 01247

    Nestled in the scenic beauty of Clarksburg, this charming thirty acre farmhouse property offers endless potential and peaceful country living, Surrounded by rolling landscapes and natural beauty. The property includes a former barn on site that will have to be removed and a quaint chicken coop adds to the rustic charm and country feel, perfect for hobby farming or enjoying a simpilar lifestyle.

    Michelle Picard NOCHER REALTY

    427 West Rd, Clarksburg, MA 01247
  • /26

    $139,900

    • 4 Beds
    • 1 Bath
    • 1,271 Sq Ft

    36 Chase Ave, North Adams, MA 01247

    Step back in time and bring your vision to life! Built in the late 1800s, this classic Colonial matches the historic, industrial-chic soul of North Adams. It is entirely livable and functional today, but it's ready for a passionate new owner to polish its vintage edges and write its next chapter. Features 4 bedrooms, 1 bathroom, and a rock-solid foundation. It boasts a timeless, original slate

    Jason Nocher NOCHER REALTY

    36 Chase Ave, North Adams, MA 01247
  • /27

    $2,695,000

    $130K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,386 Sq Ft

    187 Lagoon Pond Rd, Vineyard Haven, MA 02568

    For the very first time, the historic Ben Luce Homestead (circa 1850) is being offered on the open market. This charming farmhouse blends rich Island history with timeless appeal.Once home to Benjamin Norton Luce (1840–1912) — Civil War veteran, blacksmith, and town constable — the property sits on 1.5 acres of pastoral land and offers 5 bedrooms, 2 full baths, solar panels, barn, and a newly

    Erin Leighton Compass

    187 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /42

    $599,000

    $150K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,527 Sq Ft

    4 Blackhall Ct, Marion, MA 02738

    OPEN HOUSE SAT 5/23 12:00-1:00. Charming 3-bedroom, 2 bath home with many recent updates situated on a beautiful and natural landscaped yard located within Hammett’s Cove Village with its own coveted Association dock. Hammett’s Cove Village is a collection of 13 freestanding homes in a private Association ($810/yearly fee) that includes the management of the road and a private pier/dock. 4

    Christopher Demakis Demakis Family Real Estate, Inc.

    4 Blackhall Ct, Marion, MA 02738
  • /11

    $150,000

    • Land
    • 5.22 Acres
    • $28,736 per Acre

    Lot 0 N Sturbridge Rd, Charlton, MA 01507

    5.22 acre lot in Charlton. A wooded drive opens to a beautiful meadow. Level with rough driveway already in place and location cleared. Lot offers advantage of being set back from the road with existing trees for privacy and shade. Come walk this property and picture your own homestead

    Pete Rotondo OWN IT

    Lot 0 N Sturbridge Rd, Charlton, MA 01507
  • /30

    $1,400,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,912 Sq Ft

    22 Homestead Rd, Lynnfield, MA 01940

    Nestled in one of Lynnfield’s most coveted neighborhoods, 22 Homestead Rd is a 4bd 2.5b Colonial thoughtfully reimagined in 2022, taken to the studs and rebuilt with no expense spared. After pulling in your garage, step into your mudroom before enter the main level. Here you’ll find an epicurean kitchen with Miele appliances, quartz counters, and oversized island. The front-to-back living room

    Molly Walker Coldwell Banker Realty - Scituate

    22 Homestead Rd, Lynnfield, MA 01940
  • /6

    $48,000

    $5K PRICE DROP
    • Land
    • 4.88 Acres
    • $9,836 per Acre

    lt3 West Rd, New Braintree, MA 01531

    Want to get away from it all then check out this lot not far from New Braintree Center. Handy to Barre, West Brookfield and commuting to Worcester. Close to routes 32, 67, 122 for commuting but enjoy the peace of the country roads coming home. Many farms near by. Some wetlands on the property would possibly limit its uses but there is still plenty of room for a small homestead. Come view the

    Sue Como Buy Rite Home

    lt3 West Rd, New Braintree, MA 01531
  • /42

    $739,900

    • 5 Beds
    • 4 Baths
    • 3,810 Sq Ft

    299 Sterling Rd, Princeton, MA 01541

    Discover this hidden treasure in this extraordinary Antique homestead set on 2.47 acres of natural beauty and privacy. Surrounded on all sides by protected DCR land and built in 1760~this original post-and-beam Buck Homestead blends timeless character with the rare serenity of its setting. A welcoming, oversized farmer’s porch wraps around three-quarters of the home with decking, offering

    Diane DeCiccio Acres Away Realty, Inc.

    299 Sterling Rd, Princeton, MA 01541
  • /10

    $125,000

    • Land
    • 2.12 Acres
    • $58,962 per Acre

    0 N Bear River Rd Unit 73485981, Ashfield, MA 01330

    Beautiful parcel on scenic Bear River Road in Ashfield offering a wonderful opportunity to build in the heart of the Hilltowns. The property includes an old apple barn full of rustic charm, along with a completed septic design and architectural plans for an approximately 1,000 sq ft home. The proposed siting thoughtfully takes advantage of the natural landscape and provides a strong starting

    Jocelyn O'Shea REMAX Connections - Greenfield

    0 N Bear River Rd Unit 73485981, Ashfield, MA 01330
  • /12

    $650,000

    • Land
    • 20.25 Acres
    • $32,099 per Acre

    0 Center Rd, Dudley, MA 01571

    A rare and unique opportunity awaits to make a buyer’s dreams come true! This 20.25 acre parcel offers a multitude of possibilities. Fall in love with the picturesque view of Woodstock Valley, create a gentleman’s farm ideal for horses and cows, complete with your own pasture and watering hole. Build your legacy with a family homestead for parents and siblings. Builders, make your mark in the

    Lee Joseph Coldwell Banker Realty - Worcester

    0 Center Rd, Dudley, MA 01571
  • /8

    $265,000

    $30K PRICE DROP
    • Land
    • 5.51 Acres
    • $48,094 per Acre

    82 Dodge Hill Rd, Sutton, MA 01590

    Prime 5.5-acre lot in historic Sutton that was once part of the Dudley family Homestead. Septic design is Town approved...town water at street. Conveniently located to Route 146, MA Pike & the Blackstone Shoppes. One of the best school systems in the State. See the attached plot to build your dream home. The lot is the wooded area in the pictures and attached aerial video.

    Richard Stockhaus Lakefront Living Realty, LLC

    82 Dodge Hill Rd, Sutton, MA 01590
  • /11

    $215,000

    $50K PRICE DROP
    • Land
    • 3.59 Acres
    • $59,889 per Acre

    767 Stony Hill Rd, Wilbraham, MA 01095

    Build Your Dream Home on 3.59 Acres — With the Option to Purchase the Front Home & Studio! Situated just off desirable Stony Hill Road, this 3.59-acre lot offers a unique opportunity for new construction in a sought-after Wilbraham location. The parcel sits behind the front lot, where a charming bungalow and finished studio space are also available for purchase (see 763 Stony Hill Road),

    Casey Miner ERA M Connie Laplante Real Estate

    767 Stony Hill Rd, Wilbraham, MA 01095
  • /40

    $649,000

    • 4 Beds
    • 2.5 Baths
    • 2,458 Sq Ft

    27 Davis St, Rutland, MA 01543

    This one feels like home! Serene and set back from the world, this expansive 4-bedroom Cape offers the kind of seclusion that does not come along every day. For those dreaming of a homestead, the pieces are here. Welcome home through the Farmer's Porch to ample living space perfect for hosting, hardwood floors, and an updated kitchen with stainless steel appliances. The spacious main level

    Sheila Brady-Savard ERA Key Realty Services - Worcester

    27 Davis St, Rutland, MA 01543
  • /45

    $589,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    1 Jody Ln, Forestdale, MA 02644

    Opportunity awaits in the heart of Forestdale! This 3+ bedroom, 2 full bath home is situated on a generous fully fenced in .59-acre lot just minutes from Joint Base Cape Cod, offering incredible value for buyers looking to build equity. The backyard provides plenty of space for pets, gardening, and outdoor entertaining, while the existing chicken coop adds a charming homestead touch.Inside,

    Amanda Defazio William Raveis Real Estate & Home Services

    1 Jody Ln, Forestdale, MA 02644
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