35

Massachusetts Homesteads for Sale

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  • /42

    $399,000

    • 3 Beds
    • 1 Bath
    • 2,472 Sq Ft

    66 Wellington Rd, Ashby, MA 01431

    Enjoy direct access to the abutting 105 acres of state-owned land with hiking trails and also 123’ of waterfront on Watatic Pond, the iconic Wellington Homestead that was established in 1759, offering unparalleled privacy and tranquility. This antique gem showcases timeless craftsmanship, with original details throughout. Step inside and be captivated by the charm of yesteryear, featuring

    Agent Photo

    Cory Gracie

    LAER Realty Partners

    (351) 247-4610

    66 Wellington Rd, Ashby, MA 01431
  • /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

    (508) 952-9791

    335 Old Fall River Rd, Dartmouth, MA 02747
  • /75

    $1,745,000

    • 3 Beds
    • 3 Baths
    • 2,110 Sq Ft

    188 Rock Harbor Rd, Orleans, MA 02653

    Exquisitely Renovated 1830 Greek Revival estate on 1+ acre... Step into timeless elegance blending historical charm with modern updates. Known as the historic Jabez Sparrow Homestead and set on a level and meticulously maintained 1.04-acre lot in a prime near beach location.Inside, the home features a desirable first-floor primary suite with spacious, brand new, modern full bathroom. Two

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    (508) 719-6484

    188 Rock Harbor Rd, Orleans, MA 02653
  • /41

    $810,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    345 Ireland St, West Chesterfield, MA 01084

    This is the place where dreams come true! A large 3 bed/2.5 bath modern home, classic 2 stall barn with hayloft and insulated, heated 30x50 garage/barn w/ 16' ceilings on nearly 70 acres. Just 30 mins from Northampton this idyllic setting features bucolic views, open green fields and woods with stone walls and winding trails that lead to Jackson’s Brook. A contemporary home with warm traditional

    Agent Photo

    Lisa Carroll

    Delap Real Estate LLC

    (413) 366-3784

    345 Ireland St, West Chesterfield, MA 01084
  • /14

    $1,395,000

    • Land
    • 7 Acres
    • $190,314 per Acre

    65 Farm Road Lot 6, Sherborn, MA 01770

    A rare offering! Spectacular country estate lot set well back from the road on 7.33 acres. Situated in a prestigious location abutting hundreds of acres of conservation. Choose to build one magnificent home with up to an 8 bedroom septic design which will provide plenty of space and capacity for an additional ADU as part of a family compound, or create a beautiful retreat with every amenity

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    Maryann Clancy

    Berkshire Hathaway HomeServices Commonwealth Real Estate

    (508) 882-6299

    65 Farm Road Lot 6, Sherborn, MA 01770
  • /61

    $1,280,000

    • 3 Beds
    • 3 Baths
    • 2,002 Sq Ft

    276 Great Barrington Rd, West Stockbridge, MA 01236

    Price Improvement! Motivated Seller!This 52-acre homestead blends early American heritage with modern sustainability and self-sufficiency. Originally built in 1802, this stunning property offers privacy, fertile farmland, and breathtaking mountain views-including Monument Mountain/Flag Rock. Mature fruit orchard with over 15 trees, 30-tree sugar bush with a sugarhouse for maple syrup

    Agent Photo

    Keytoria Jenkins

    THE KINDERHOOK GROUP - PITTSFIELD

    (413) 675-5502

    276 Great Barrington Rd, West Stockbridge, MA 01236
  • /6

    $650,000

    • Land
    • 19 Acres
    • $34,211 per Acre

    0 Mohawk Lake Rd, Stockbridge, MA 01262

    Discover a rare opportunity to own a piece of history in Stockbridge, available for the first time in over 120 years. This stunning land offers a private setting perfect for building your dream home, while being just moments away from the renowned Norman Rockwell Museum, Chesterwood, the enchanting Berkshire Botanical Gardens, and the charming downtown Stockbridge, all within a 3-mile radius.

    Agent Photo

    Gary Fuls Jr

    RE/MAX TRANSITIONS

    (413) 884-5511

    0 Mohawk Lake Rd, Stockbridge, MA 01262
  • /41

    $695,000

    • 1 Bed
    • 1 Bath
    • 1,169 Sq Ft

    30 Bailey Rd, West Townsend, MA 01474

    Discover this charming Shingle-style retreat on 7.7 acres with an adorable Cottage featuring an enclosed porch, top-of- the-line Viessmann heating system, central vacuum and generator hook-up. The back deck overlooks your own private pond. Leased Sunova solar panels enhance energy efficiency. A standout feature is the 4,000 sq. foot, five-car, two-story heated garage—complete with a Viesmann

    Agent Photo

    Cory Gracie

    LAER Realty Partners

    (978) 958-9209

    30 Bailey Rd, West Townsend, MA 01474
  • /42

    $925,000

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    74 Nautical Way, Plymouth, MA 02360

    Spectacular homestead, sited and framed by stunning stonework and appointed landscape in one of the town's most desirable neighborhoods. This wonderfully cared for and immaculate home offers 4 bedrooms, 2.5 baths and a 2 car garage. Perfection shines with the welcoming front porch overlooking the manicured lawn lined with fruit trees, gardens and irrigation. The front foyer allows you access to

    Laurie Bailey-Gates Coldwell Banker Realty - Cotuit

    74 Nautical Way, Plymouth, MA 02360
  • /42

    $734,900

    • 4 Beds
    • 2 Baths
    • 2,188 Sq Ft

    6 Magnolia Ave, Billerica, MA 01821

    Huge Price Improvement! Nicely Maintained Split-entry set on a HUGE, LEVEL LOT in FANTASTIC neighborhood PERFECTLY CLOSE to BRAND NEW public schools, shopping, restaurants, & commuter routes. Perfect opportunity for POTENTIAL ADU! Inside, main level LARGE eat-in kitchen (all appliances stay!), Sun-filled living room, & full bath with laundry (Washer and Dryer to stay!) w/relaxing spa tub &

    Sharon Narbonne LAER Realty Partners

    6 Magnolia Ave, Billerica, MA 01821
  • /42

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,010 Sq Ft

    162 Plympton St, Middleboro, MA 02346

    Undeniably one of Middleboro's finest properties, a former parcel of the Eddy Homestead just 2.3 miles from Rt44 yet seemingly your own zip code of paradise as you enter a gated 1000ft long winding driveway to your own 5.91 acres of mature landscaping including dozens of producing maple trees, a river-side private retreat to process the syrup or relax, 2 stall barn with power and 4-season water.

    Craig Gillis Keller Williams Elite

    162 Plympton St, Middleboro, MA 02346
  • /36

    $1,175,000 Open Sun 2PM - 3PM

    • 4 Beds
    • 2 Baths
    • 2,280 Sq Ft

    1056 Curve St, Carlisle, MA 01741

    The Swanson Homestead - a rare and wonderful 6 acre property nestled in the Carlisle countryside. The property includes a move-in-ready 1930's 4 bedroom, 2 bath Farmhouse Colonial with refinished hardwood floors, fresh interior paint, plumbing updates, & repointed chimneys. Inside you'll find a sun-filled country kitchen with a butler's pantry, a front to back living room with a fireplace, a

    Amy Rutkowski A. Rutkowski Realty, Inc.

    1056 Curve St, Carlisle, MA 01741
  • /42

    $1,500,000

    • 4 Beds
    • 4 Baths
    • 5,101 Sq Ft

    499 Main St, Boxford, MA 01921

    Beautiful Harry Lee Cole homestead boasting a seamless blend of history & today’s must haves on a breathtaking, one of a kind 9-acre property featuring a tranquil pond offering recreation and an unrivaled connection to nature. Masterfully renovated, this home showcases wide pine floors, hand-hewn beams & exquisite millwork. The gourmet kitchen centers around an original hearth, blending old-world

    North Shore Real Estate Home Group Realty One Group Nest

    499 Main St, Boxford, MA 01921
  • /39

    $950,000

    • 4 Beds
    • 2 Baths
    • 2,346 Sq Ft

    310 S River Rd, Charlemont, MA 01339

    Exceptionally well kept family homestead being offered for the first time in almost 60 years with an amazing mix of open meadow and forestlands. Your land stretches to Hawley and Berkshire East Mountain Resort! the home has been restored and updated over the years including electrical, plumbing/heating, structural and cosmetic . The expansive road frontage offers more options as to the

    Jeffrey Loholdt WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    310 S River Rd, Charlemont, MA 01339
  • /36

    $1,150,000

    • 3 Beds
    • 3 Baths
    • 2,377 Sq Ft

    102 Portanimicut Rd, Orleans, MA 02653

    Near the end of quintessential Portanimicut Road, in Orleans, is this unique house. Inside is the original antique homestead, an updated addition and a studio bedroom over the garage to complete the package. The antique side was built in 1880's and could become a summer art studio or guest quarters. The main updated house has a living room, dining room, galley kitchen, and a bedroom with a

    Sarah Gammons - Ciampa Berkshire Hathaway HomeServices Robert Paul Properties

    102 Portanimicut Rd, Orleans, MA 02653
  • /23

    $699,900

    • 4 Beds
    • 1.5 Baths
    • 2,948 Sq Ft

    3258 Main St, Becket, MA 01223

    Available for the first time in decades, this exceptional property offers peace, privacy, and endless opportunities to explore nature! Set on 77 acres with brooks and meandering trails, it's a true retreat for those seeking both solitude and adventure.The home features a spacious, sunlit first-floor layout with an eat-in kitchen, dining room, living room with pellet stove, heated porch/bonus

    Nancy Bush Brooks SIGNATURE ASSOCIATES

    3258 Main St, Becket, MA 01223
  • /42

    $399,900 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 2 Baths
    • 2,598 Sq Ft

    244 Ontario Ave, Holyoke, MA 01040

    You’ll fall in love with this Move-in ready ranch offering nearly 2,600 sq. ft. in one of Holyoke’s most desirable neighborhoods. This 3-bed, 2-bath home features hardwood floors, a bright living room with sliders to a massive 25x27 front deck, and a dining area that flows into the kitchen with granite countertops, ceramic tile flooring, stainless steel appliances, gas stove, and upgraded

    Carlos Ramos Executive Real Estate, Inc.

    244 Ontario Ave, Holyoke, MA 01040
  • /19

    $559,000

    • 3 Beds
    • 1.5 Baths
    • 1,363 Sq Ft

    5 Craig St, Carver, MA 02330

    Welcome to 5 Craig Street in Carver, a peaceful country retreat set on 1.17 private acres.This 3-bedroom, 1.5-bath home blends comfort and charm with newly refinished hardwood floors, a cozy gas fireplace, and central air. The main level features a serene primary bedroom, two additional bedrooms, and a full bath. Downstairs, enjoy a finished space ideal for a home gym or family room, complete

    Mike & Maria Real Estate Waterfront Realty Group

    5 Craig St, Carver, MA 02330
  • /42

    $95,900

    • Land
    • 10 Acres
    • $10,095 per Acre

    00 Amherst Rd, Pelham, MA 01002

    Discover Your Woodland Sanctuary in Pelham, MA. Nestled amidst gentle hills and forested tranquility in the charming town of Pelham, Massachusetts, this enchanting parcel offers a rare opportunity to create your dream escape. Whether you're envisioning a custom-built retreat, a sustainable homestead, or simply a peaceful getaway, this serene thicket is your canvas. This is a hunter's paradise!

    Derek Greene The Greene Realty Group

    00 Amherst Rd, Pelham, MA 01002
  • /32

    $624,000 Open Sun 1PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft

    28 Dix St Unit 3, Dorchester, MA 02122

    Stylish Top-Floor Condo with City Views & Modern Finishes. This meticulously maintained iron grey clapboard home offers a bright, open-concept 3rd floor unit with vaulted ceilings, city views, and a cozy gas fireplace. The updated white kitchen features a large island, marble countertops, and premium KitchenAid appliances, flowing into a spacious dining area that opens to a large private

    James Silva At Home Real Estate Group, Inc

    28 Dix St Unit 3, Dorchester, MA 02122
  • /41

    $515,000

    • 4 Beds
    • 1.5 Baths
    • 1,546 Sq Ft

    323 New Boston Rd, Sturbridge, MA 01566

    Are You Looking for Your Own Private Homestead? Charming 4-Bed Cape on 3.38 Acres Welcome to this classic New England Cape nestled on a beautiful 3.38-acre lot in Desirable Area! Offering the perfect blend of privacy and convenience, this well-maintained home features Large Kitchen, 4 Generous Bedrooms and 1 Full Bath, Large Living Room ideal for growing families, or those seeking flexible living

    Lori Berry The Neighborhood Realty Group

    323 New Boston Rd, Sturbridge, MA 01566
  • /41

    $519,900

    • 3 Beds
    • 2 Baths
    • 2,008 Sq Ft

    164 Alexander Rd, Bernardston, MA 01337

    Nestled on nearly 8 peaceful acres, this 2013 custom-built ranch home offers space, comfort, and the perfect backdrop for your next chapter. Designed with an open layout, the main living area welcomes you with vaulted ceilings & warm, wood flooring that flows seamlessly from the living room into the dining area & kitchen. Hickory cabinets, a center island, and plenty of counter space make the

    Donald Mailloux Coldwell Banker Community REALTORS®

    164 Alexander Rd, Bernardston, MA 01337
  • /39

    $629,900

    • 4 Beds
    • 2.5 Baths
    • 1,982 Sq Ft

    36 Pioneer Cir, Attleboro, MA 02703

    Welcome to this warm & welcoming 4-bdrm, 2.5-bath Split Colonial nestled in the desirable Homestead Estates neighborhood. You'll love the comfortable layout featuring a spacious eat-in kitchen w/center island, pull out drawers, granite counters & SS appliances & a slider leading to a 3-season room—perfect for morning coffee or relaxing evenings. Sunlight pours through bay windows into the formal

    Kathy Thomson Berkshire Hathaway HomeServices Evolution Properties

    36 Pioneer Cir, Attleboro, MA 02703
  • /9

    $59,000

    • 4 Beds
    • 1.5 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

    477 Mohawk Trail, Drury, MA 01343
  • /24

    $195,000

    • Land
    • 12 Acres
    • $16,638 per Acre

    0 Patrill Hollow Rd Unit 73389714, Hardwick, MA 01031

    First time to the market: 11.72 Acres and 1290 feet of road frontage offer many opportunities on Patrill Hollow Road. Ideal for anyone looking to live on the countryside. Mixed use, Residential / Agricultural, would make an excellent homestead with small farming operation and perhaps an in-law or multi generational compound for family. Potential for 6 total housing lots. With correct engineering,

    David Geraway Properties Central Realty

    0 Patrill Hollow Rd Unit 73389714, Hardwick, MA 01031
  • /9

    $79,900

    • Land
    • 8 Acres
    • $10,513 per Acre

    0 Covell Unit 73387967, Tolland, MA 01034

    7.6 Acres with Barn – Peaceful Retreat with Open Fields & Woods. Tucked at the end of a quiet path, this 7.6-acre property offers a rare mix of open meadows, wooded trails, and total privacy. Whether you're dreaming of a future home, weekend escape, or small homestead, this land is full of potential.An old barn adds rustic charm and functional space—perfect for storage, projects, or restoration.

    Melody Sotolongo Coldwell Banker Realty - Western MA

    0 Covell Unit 73387967, Tolland, MA 01034
  • /38

    $2,900,000

    • 5 Beds
    • 2 Baths
    • 3,344 Sq Ft

    136 Main Rd, Westhampton, MA 01027

    Historic Westhampton Treasure! In 1781 Eliza Norton built the Norton Tavern at the top of the hill in Westhampton. The front upstairs of the house was an open air dance hall and the original fiddler's step still remains! In 1860 Warner Bartlett bought the Tavern. He ran the farm until 1920 when Will Fiske bought the homestead and renamed it Outlook Farm and started peddling his farm products,

    Kristin Vevon The Murphys REALTORS®, Inc.

    136 Main Rd, Westhampton, MA 01027
  • /31

    $1,499,000

    • 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
  • /28

    $499,900

    • 4 Beds
    • 2 Baths
    • 2,532 Sq Ft

    727 Brattleboro Rd, Bernardston, MA 01337

    Welcome to your very own piece of history with this 1795 antique cape nestled on 15.84 picturesque acres in Bernardston, MA. This charming home includes 4 bedrooms and 2 full bathrooms, offering plenty of space for family and guests. Imagine starting your day with a cup of coffee on the porch, soaking in the serene views of your expansive property. The land features several outbuildings, perfect

    Donald Mailloux Coldwell Banker Community REALTORS®

    727 Brattleboro Rd, Bernardston, MA 01337
  • /42

    $747,000

    • 2 Beds
    • 1 Bath
    • 1,154 Sq Ft

    336 King St Unit 105, Littleton, MA 01460

    LAST UNIT AVAILABLE! NEW CONSTRUCTION! Welcome to your next chapter at Hager Homestead Condominium, a thoughtfully designed 55+ cohousing condo community with 12 acres preserved for conservation, residents enjoy peaceful walking trails along a meadow and a small pond right outside their door. This 2 BR unit offers open living space enhanced by high ceilings, wood floors, quartz countertops and

    Karen Wallace Barrett Sotheby's International Realty

    336 King St Unit 105, Littleton, MA 01460
  • /6

    $600,000

    • Land
    • 9 Acres
    • $67,950 per Acre

    Lot A Homestead Ave, Holyoke, MA 01040

    Exceptional Development Opportunity on Lower Homestead Avenue - Attention Builders and Developers! Don't miss this fantastic opportunity to develop an approximate 8.83-acre parcel with preliminary subdivision approval. This property can accommodate large size frontage lots. The proposed layout features a cul-de-sac street. This property is within 1 mile of Ingleside Mall, Barnes & Nobles,

    Daisy Sanchez RE/MAX IGNITE

    Lot A Homestead Ave, Holyoke, MA 01040
  • /42

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 2,814 Sq Ft

    356 Hunt Rd, Oakham, MA 01068

    Timeless charm meets modern luxury in this quintessential New England farmhouse set on a serene 3.27-acre lot with an attached 3-stall barn. This beautifully remodeled home features 5 spacious bedrooms, including a primary suite with its own private deck, en suite bath and walk-in closet. The main level offers a flowing floor plan anchored by a large living room, dining area with a cozy wood

    Benjamin Hause Keller Williams Realty North Central

    356 Hunt Rd, Oakham, MA 01068
  • /34

    $699,000

    • 3 Beds
    • 2 Baths
    • 2,244 Sq Ft

    466 Hadley Rd, Sunderland, MA 01375

    Attention developers and farmers this property offers fantastic potential for development for up to 3 additional lots and farmland with over 12.59 acres of land, boasting approximately 520 feet of frontage on Hadley Rd and approximately 818 feet on Plumtree Rd. Enough land for a potential street or frontage lots. The spacious colonial home features 3 bedrooms, 2 baths. The restored barn is

    Jocelyn Maggi LPT Realty, LLC

    466 Hadley Rd, Sunderland, MA 01375
  • /4

    $449,000

    • Land
    • 3.04 Acres
    • $147,697 per Acre

    56 Red Wing Ln, Barnstable, MA 2630

    Back on the Market!!! Here is your truly rare opportunity to own a 3.04 acre Barnstable Village Homesite on which to build your custom Cape Cod homestead. This is a bona fide "Walk-To" location within strolling distance to the Village, as well as to the Barnstable Marina and Millway Beach. This homesite includes 354 feet of picturesque stonewall frontage on Main Street, Old King's Highway. The

    Matthew Chase Grove Property Group

    56 Red Wing Ln, Barnstable, MA 2630
  • /2

    $34,900

    • Land
    • 10 Acres
    • $3,435 per Acre

    0 Skyline Trail Lot 24, Middlefield, MA 01243

    Over 10 acres of country land available for a private homestead, farming operation, or future development. Here is your unique opportunity to own a piece of New England's scenic beauty nestled in the Berkshires. Whether you're looking for a private retreat, a farm, or investment property, the region provides a mix of rolling hills, forests, and open meadows. Bring your vision for this land!

    Phim Mar Byrnes Real Estate Group LLC

    0 Skyline Trail Lot 24, Middlefield, MA 01243
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