Massachusetts Homesteads for Sale

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  /51

  $3,998,000

  $997K PRICE DROP

  • 5 Beds
  • 5.5 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:

  

  Chapin Fish

  WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  764 E Hill Rd, New Marlborough, MA 01230
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  /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

  

  Maryann Clancy

  Berkshire Hathaway HomeServices Commonwealth Real Estate

  147 Washington Street Lot 2, Sherborn, MA 01770
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  /24

  $499,900

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,111 Sq Ft

  19 King St, Norfolk, MA 02056

  Nestled on a private, wooded horse farm, this charming 3 BR Cape offers a rare opportunity to create your dream country retreat. Set well back from the road, the property provides peace, privacy, and plenty of space for both horses and outdoor living. Equestrian amenities include paddock areas, horse stalls, and multiple sheds for storage, equipment, or feed. Whether you're an experienced horse

  

  Barbara O'Hara

  NorthStar Real Estate, LLC

  19 King St, Norfolk, MA 02056
• 

  

  

  /12

  $1,999,999

  • Land
  • 18.57 Acres
  • $107,701 per Acre

  276 Middle Rd, Boxborough, MA 01719

  Calling all builders, developers, homesteaders and farmers! Welcome to 276 Middle Road, a single family home with a barn, detached garage and more than 18 acres of open land and mature woods along with approximately 479 feet of frontage. Whether you’re considering residential development, a private homestead or agricultural use, this substantial parcel offers room to bring a thoughtful plan to

  

  Kristin Hilberg

  Keller Williams Realty Boston Northwest

  276 Middle Rd, Boxborough, MA 01719
• 

  

  

  /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

  

  Sharon Simmons

  Sharon Simmons Real Estate

  335 Old Fall River Rd, Dartmouth, MA 02747
• 

  /2

  $11,650,000

  • 3 Beds
  • 3.5 Baths
  • 4,435 Sq Ft

  9 Sesachacha Rd, Nantucket, MA 02554

  Set on nearly an acre of beautifully landscaped grounds in the heart of Quidnet Village, The Homestead, the original Norcross farmhouse, is a truly magical seaside property that captures the essence of Nantucket living.Every aspect of the home has been thoughtfully designed, with exceptional craftsmanship, refined finishes, and meticulous attention to detail throughout. Light-filled

  Bill Liddle Great Point Properties

  9 Sesachacha Rd, Nantucket, MA 02554
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  /8

  $165,000

  $100K PRICE DROP

  • Land
  • 3.59 Acres
  • $45,961 per Acre

  767 Stony Hill Rd, Wilbraham, MA 01095

  Build Your Dream Home on 3.59 Acres! Situated just off desirable Stony Hill Road, this unique parcel offers a wonderful opportunity for new construction in a sought-after Wilbraham location—just minutes from Wilbraham & Monson Academy. The lot has been perced and approved for a single-family home and accessory buildings. Featuring mature trees, open areas, and a gently sloping landscape, the

  Casey Miner ERA M Connie Laplante Real Estate

  767 Stony Hill Rd, Wilbraham, MA 01095
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  /42

  $429,000

  • 5 Beds
  • 3 Baths
  • 1,850 Sq Ft

  17 Congamond Rd, Southwick, MA 01077

  Country views. Lake life. Room to breathe. This is the kind of home that makes staying home feel like getting away. Nearly an acre gives you space to garden, homestead, entertain, or simply slow down and take in the sweeping views of the neighboring farm. Inside, every room has been beautifully renovated, creating a fresh, welcoming home made for gathering. The privately positioned primary suite

  Dawn Ezold Naples Realty Group

  17 Congamond Rd, Southwick, MA 01077
• 

  

  /38

  $749,000

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft

  66 Cottage Ln, Weymouth, MA 02188

  Cared for by the same family for 28 years, this charming Weymouth Cape tucked on a quiet cul-de-sac in the desirable Homestead area, is ready for its next chapter! Gather in the spacious kitchen with granite counters, island, and breakfast bar, then unwind by the fireplace in the living room, which features a slider to a large deck for effortless indoor-outdoor living. A formal dining room and

  Jessica Molisse William Raveis R.E. & Home Services

  66 Cottage Ln, Weymouth, MA 02188
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  /37

  $350,000

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  49 Mt Hitchcock Rd, Wales, MA 01081

  Opportunity awaits on this unique property offering over 23 acres of land, a one-bedroom, one-bath home, and plenty of possibilities! The home features lots of updates, a bonus room for additional living, office, or hobby space, a hot tub and a sauna for relaxing after a long day. Multiple outbuildings provide excellent storage and workspace options, while the expansive acreage offers room to

  The Jackson & Nale Team REMAX Connections - Belchertown

  49 Mt Hitchcock Rd, Wales, MA 01081
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  /33

  $820,000

  • 3 Beds
  • 1.5 Baths
  • 2,458 Sq Ft

  6 Old Homestead Rd, Methuen, MA 01844

  This meticulously maintained English Tudor home sits on a corner lot in the established and desirable Homestead Acres area of Methuen. The home boasts classic architectural details, custom windows, 8 total rooms, 3+ bedrooms, 1 & 1 half baths, and a large, dry, unfinished level below to customize to fit your needs! Unfinished level above the attached two car garage is perfect for storage, or

  Corinne Letourneau KSRJ - Signature Realty Group

  6 Old Homestead Rd, Methuen, MA 01844
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  /40

  $1,990,000

  $3M PRICE DROP

  • 11 Beds
  • 7 Baths
  • 5,878 Sq Ft

  775 Williamstown Rd, Lanesborough, MA 01237

  Spectacular Homestead! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 pristine acres with stunning views, mountain paths, and stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the

  Andy Kelly BERKSHIRE BUSINESS PROPERTIES

  775 Williamstown Rd, Lanesborough, MA 01237
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  /42

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 3,736 Sq Ft

  30 Arnold Place, New Bedford, MA 02740

  Built in 1896 by Willard Nye, Jr., this remarkable home stands out as one of New Bedford’s most unique properties. Nestled on a charming tree-lined street, its exterior features rough fieldstone sourced from the stone wall that once surrounded the Nye homestead. Inside, the layout flows seamlessly, perfectly suited for modern living. The sprawling fireplaced living room opens to the study or home

  Diana Henry Diana Henry Realty

  30 Arnold Place, New Bedford, MA 02740
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  /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
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  /38

  $499,900

  $50K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,960 Sq Ft

  63 Gardner Rd, Hubbardston, MA 01452

  This Beautiful Antique Hubbardston homestead is getting a major exterior refresh. Exterior Paint and Brand New Shutters are underway to elevate its timeless curb appeal. Take advantage of the recent price reduction along with the peace of mind that these major exterior updates will be completed prior to closing!! This home features modern updates including a new water system, updated heating

  Sarah Vincent Keller Williams Realty North Central

  63 Gardner Rd, Hubbardston, MA 01452
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  /41

  $739,500

  • 3 Beds
  • 1.5 Baths
  • 3,042 Sq Ft

  102 Overlook Rd, Westminster, MA 01473

  Welcome to your own private, sustainable sanctuary nestled on a serene 4.6-acre lot. This property perfectly blends modern efficiency with classic country charm, offering the ultimate setup for a buyer seeking a self-sufficient homestead lifestyle. At the heart of this eco-conscious home is a massive 18.4 kW solar panel system, paired with two backup generator batteries and a dedicated EV

  Katey Tata Keller Williams Realty North Central

  102 Overlook Rd, Westminster, MA 01473
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  /9

  $135,000

  • Land
  • 11.38 Acres
  • $11,863 per Acre

  0 Laurel Lake Rd, Royalston, MA 01331

  Discover 11.38 acres of beautiful, usable land in a peaceful country setting in Royalston. Much of the groundwork has already been completed, including a started driveway, engineered septic plans for a 4-bedroom single family home that includes a garage with a 1-bedroom adu, an approved Wetland Determination of Applicability, and a successful perc test. Also, electric is at the street too. This

  Amanda Roberts Four Columns Realty, LLC

  0 Laurel Lake Rd, Royalston, MA 01331
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  /40

  $650,000

  $70K PRICE DROP

  • 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
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  /35

  $618,000

  $15K PRICE DROP

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

  9 Waters St, Millbury, MA 01527

  Welcome to this charming, expansive cape where space, versatility, and outdoor living come together beautifully in this lovely neighborhood home close to Millbury Center! Be a part of town festivities during the seasons-enjoy sitting on your enclosed farmers porch with screens or glass and watch as the parades go by! This charming 3-4 BEDROOM home offers TWO FULL BATHS(plus one in the Pool House)

  Kimberlee Hughes eXp Realty LLC

  9 Waters St, Millbury, MA 01527
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  /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
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  /31

  $800,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,620 Sq Ft

  308 Salem Rd, Billerica, MA 01821

  A rare opportunity to own one of Billerica’s oldest significant homes! The Patten Family Homestead at 308 Salem Road dates to the early 18th century and is recognized in the Town of Billerica’s Historical Resources Inventory. Steeped in local history, this remarkable 3-bedroom, 2-bath residence offers approximately 3,620 square feet of living space on 1.27 acres, with six fireplaces and

  Linda Glennon Conway - Hanover

  308 Salem Rd, Billerica, MA 01821
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  /22

  $280,000

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  31 Fair St, Northampton, MA 01060

  A classic 4 Bed, 2 bath Farmhouse-Colonial with detached 3 bay garage on over 1/2 an acre within walking distance to downtown Northampton shops, cafes, restaurants, the fairgrounds and the picturesque ‘meadows’ along the Connecticut River. Convenient access to I-91, Hadley and Amherst. This adaptable 2 unit home was most recently used as a single family residence. The home has good bones but

  Jessica Lapinski Delap Real Estate LLC

  31 Fair St, Northampton, MA 01060
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  /18

  $475,000

  • 4 Beds
  • 3 Baths
  • 3,104 Sq Ft

  172 Skyline Trail, Middlefield, MA 01243

  Unique small-farm, homestead and income-property opportunity with established growing infrastructure! Currently operated as a no-till, no-spray farm with eight permanent 100-ft growing beds within electric fencing and room to expand. Additional garden area, field and hydroponic tomato production. Farm stand may be included. Hydroponic system and training negotiable. Character-filled home offers a

  Lisa Berry Simply Sell Realty

  172 Skyline Trail, Middlefield, MA 01243
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  /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
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  /4

  $800,000

  • Land
  • 14.1 Acres
  • $56,738 per Acre

  0 Meadowbrook Rd, Holyoke, MA 01040

  Attention Residential Developers - Rehab Centers - Child Care Operators and many more. Unique Opportunity for both Residential or Commercial Development at the former Whiting Estates. Possibility for Many and Diverse Uses Including: Residential Care or Rehabilitation Center, Child Care Facility, Family Day Care Home, Residential Subdivision, Religious Centers, etc. This 14.1 AC parcel with

  Linda Houllahan Jacob Realty, LLC

  0 Meadowbrook Rd, Holyoke, MA 01040
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  /9

  $49,900

  $9K PRICE DROP

  • 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. - Dalton

  477 Mohawk Trail, Drury, MA 01343
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  /41

  $569,900

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  130 Creamery Hill Rd, Orange, MA 01364

  OPEN HOUSE SAT. 8/8 AND SUN 8/9, 11-12:30. Steeped in New England history and surrounded by nature, this remarkable farmhouse has been lovingly cared for by the same family for generations. Set on 13.73 breathtaking acres and bordered by conservation land, the property offers unparalleled privacy with majestic Tully Mountain rising behind the home as a stunning natural backdrop. Once home to the

  Linda Lee LAER Realty Partners

  130 Creamery Hill Rd, Orange, MA 01364
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  /84

  $2,499,000

  $100K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 3,940 Sq Ft

  30 Childs Homestead Rd, Orleans, MA 2653

  Cape Cod living comes easy at 30 Childs Homestead. Built by renowned local builder Eastward Companies in 2024, this beautifully designed home is made for relaxed summers, weekends with friends and year-round enjoyment. Inside, bright, open spaces and elevated finishes feel fresh and inviting, while outside, a newly constructed private oasis awaits, with pool, patio, outdoor kitchen and bar

  Evan Dean Christie's International Real Estate Atlantic Brokerage

  30 Childs Homestead Rd, Orleans, MA 2653
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  /18

  $149,000

  • Land
  • 5.01 Acres
  • $29,741 per Acre

  0 Oxbow Rd, Charlton, MA 01507

  Tucked away on a quiet country road, this beautiful 5-acre wooded lot at 0 Oxbow Rd in Charlton offers the perfect setting for your dream home. The parcel stretches deep off the road, with a prime homesite perched atop a gentle hill—giving you a scenic vantage point and exceptional privacy. Mature trees and natural surroundings create a peaceful, secluded feel while still keeping you conveniently

  Samuel Danis eXp Realty LLC

  0 Oxbow Rd, Charlton, MA 01507
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  /39

  $1,200,000

  $300K PRICE DROP

  • 8 Beds
  • 2.5 Baths
  • 3,513 Sq Ft

  12 Nelson Place, Worcester, MA 01605

  Antique two family farmhouse on 3.49 acres of prime land, owned by the same family for six generations. Spacious layout with 15 rooms, 2 full baths, and multiple half baths across both units. Classic New England setting with a three story barn and several outbuildings, offering exceptional potential for restoration, multi generational living, or investment. Property sold as is, including a

  Jane O'Connor Coldwell Banker Realty - Worcester

  12 Nelson Place, Worcester, MA 01605
• 

  

  /26

  $1,100,000

  • 2 Beds
  • 1 Bath
  • 860 Sq Ft

  116 Hill St, Topsfield, MA 01983

  This charming Arts & Crafts cottage on 13+ acres was built in 1911 by J.D.Phillips (Salem merchant family) as chronicled in C.L.Bond's "The Houses of Topsfield". Extra-tall ceilings elevate the sense of space of the 8-room residence blending period details with an airy layout. At the heart of the cottage is an eat-in kitchen featuring large original built-in cabinets, rich butcher block

  Jonathan Minerick homecoin.com

  116 Hill St, Topsfield, MA 01983
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  /42

  $485,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,733 Sq Ft

  17 Main St, Wales, MA 01081

  Step back in time and experience the timeless charm and elegance of this exceptional 18th-century center chimney Colonial. Rich in historic character, this one-of-a-kind home showcases five fireplaces, original wide pine floorboards, hand-cut raised panel doors, custom built-ins, and the craftsmanship of a bygone era. The thoughtfully updated kitchen blends modern convenience with period

  Brenda Binczewski REMAX Connections

  17 Main St, Wales, MA 01081
• 

  

  /42

  $940,000

  • 3 Beds
  • 1 Bath
  • 1,920 Sq Ft

  295 Old Post Rd, Worthington, MA 01098

  A rare opportunity to become the next steward of a treasured Worthington homestead. Built in 1820 and lovingly maintained, this seven-room antique home rests on approximately 51.6 beautiful acres and Ward stream winding through the property. The home offers three bedrooms, one oversized full bath with laundry, a welcoming living room with fireplace, and a country kitchen warmed by a wood stove.

  Angela Cooley Keller Williams Realty

  295 Old Post Rd, Worthington, MA 01098
• 

  

  /17

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  1415 Canaan Southfield Rd, Southfield, MA 01259

  3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  1415 Canaan Southfield Rd, Southfield, MA 01259
• 

  

  /42

  $1,750,000

  • 4 Beds
  • 5 Baths
  • 5,006 Sq Ft

  3147 Sharps Lot Rd, Dighton, MA 02715

  Privately set behind a gated driveway on 10.6 acres, this custom-built contemporary estate offers over 5,000 square feet of living space and a rare combination of privacy, space, and versatility. The expansive 4-bedroom home features 2 full and 3 half baths, an open-concept floor plan, soaring cathedral ceilings, and generous living areas designed for both everyday living and entertaining. Set

  Christopher Woodard Keller Williams Coastal

  3147 Sharps Lot Rd, Dighton, MA 02715
• 

  

  /42

  $1,675,000

  • 5 Beds
  • 2.5 Baths
  • 4,728 Sq Ft

  166 Salem St, North Andover, MA 01845

  Welcome to Captain Nathaniel Berry’s Homestead, an extraordinary New England Colonial where centuries of character meet beautifully updated modern living. Set on picturesque pastoral grounds framed by classic stone walls and stately white fencing, this exceptional property offers privacy, timeless architecture, and an unforgettable setting for everyday living and entertaining. Inside, rich

  Julie Ratte Berkshire Hathaway HomeServices Verani Realty

  166 Salem St, North Andover, MA 01845
• 

  

  /10

  $80,000

  • Land
  • 3 Acres
  • $26,667 per Acre

  0 Valley Rd, Barre, MA 01005

  Not often does 3 acres in an established residential neighborhood become available in the beautiful town of Barre! Build your home or your homestead on this incredible parcel with electric and town water and sewer at the street! Plenty of frontage and a gentle upward slope make this the site you've been waiting for in a town private enough to be peaceful but close enough to be convenient.

  Sarah Schouler Lamacchia Realty, Inc.

  0 Valley Rd, Barre, MA 01005
• 

  

  /25

  $899,000

  • 5 Beds
  • 2 Baths
  • 3,381 Sq Ft

  374 High St, Pembroke, MA 02359

  Proudly presenting the Thomas Loring house c.1702, nestled on a bucolic 13-acre homestead on one of the most picturesque streets in town. This beautiful period home has fortunately retained the hand-hewn beams, fireplaces, wide pine flooring, & detailed moldings that give it warmth & character while boasting spacious rooms & versatile floorplan suited for modern living. Recently renovated

  Christian Jevne Coldwell Banker Realty - Norwell - Hanover Regional Office

  374 High St, Pembroke, MA 02359
• 

  

  /9

  $565,000

  $70K PRICE DROP

  • Land
  • 10.5 Acres
  • $53,810 per Acre

  218 American Legion Hwy, Westport, MA 02790

  Rare opportunity to own approximately 10 acres in beautiful Westport. This unique Lot offers the potential for a single-family Maybe you envision a Luxury style home or always wanted to homestead while maintaining the privacy and natural beauty that make Westport so desirable. A perc test has been completed, and Planning Board determinations regarding access and frontage are available. The

  Sheri Francis Bold Real Estate Inc.

  218 American Legion Hwy, Westport, MA 02790
• 

  

  /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

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