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Homes for sale in Massachusetts - Page 1 of 28

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$8,500,000 849.7 acres
398 PLUMB Rd, Becket, Massachusetts 01223 - Hampden County

849.7 acres Becket, MA

The extraordinary Palmer Brook Lake property surrounds a totally private 125 acre lake with no development on the shore other than a 1400sf log cabin built as a clubhouse for members-only Berkshire Fishing Club. Nearly one mile of town maintained road frontage, with docks, dam and hiking trails. Limitless possibilities as an estate parcel, shared development, or to grow as a commercial enterprise.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$2,750,000 84 acres 6 Beds | 6 Baths | 5885 sqft
22 New Marlboro Rd, Monterey, Massachusetts 01245 - Berkshire County

84 acres Monterey, MA

BROOKMEAD FARM. On a quiet, scenic road within walking distance of the Monterey General Store and Lake Garfield Town Beach, this rambling 18th century farmhouse with six bedrooms on 84 acres has open views of its own extensive property. The original house has been painstakingly renovated from stem to stern, preserving its antique charm with important updates.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,700,000 20.57 acres 6 Beds | 5 Baths | 4580 sqft
1 Mahkeenac Rd, Stockbridge, Massachusetts 01262 - Berkshire County

20.57 acres Stockbridge, MA

STOCKBRIDGE BOWL PRIVATE BEACHWOOD BEACH MEMBERSHIP with this extraordinary contemporary Shingle-Style residence on 20 acres. The design concept of four cabins connected by stone and glass passageways allows for private and public spaces for friends and family, with lofty gathering rooms, a master with 2 bathrooms, multiple en-suite guest bedrooms, a bunk room, and a huge screened porch.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,495,000 72 acres 6 Beds | 7 Baths | 6600 sqft
14-16 NORFOLK Rd, New Marlborough, Massachusetts 01259 - Berkshire County

72 acres New Marlborough, MA

A beautifully maintained Georgian home on 72 exceptionally private acres. 6,600 square feet, large room and high ceilings. Six bedrooms, 6.5 baths and a caretaker/in-law apartment. Gunite pool, spacious in-ground hot tub, lush gardens, mature forest, hiking trails, river with waterfall, and wifi. Perfect for a quiet weekend for 2 or an event for 200. Near the Connecticut border, providing easy access to Litchfield, as well as Berkshire, County attractions. This property has everything and is very attractively priced.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,395,000 16.49 acres 4 Beds | 3 Baths | 4000 sqft
304 HICKEY HILL Rd, Sheffield, Massachusetts 01257 - Berkshire County

16.49 acres Sheffield, MA

Historic farmhouse originally part of Merryfield Farm in Sheffield. Built in the 1790's, it was meticulously renovated in 2012 with the help of a talented architect, renowned builder and exacting owner. Structural improvements include a new foundation, septic tank, well, roof, 5 zone heating and central air conditioning, new hot water tank, plumbing and electrical systems.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,250,000 15 acres 4 Beds | 4 Baths | 3258 sqft
170 Christian Hill Rd, Great Barrington, Massachusetts 01230 - Berkshire County

15 acres Great Barrington, MA

​A long driveway leads to this private 4000+ sf, 4 bedroom, 4 bath home on ​15 acres with a​ huge​ ​​​sunny l​awn, ​20-tree orchard, pastures and woodland trail. ​Both the ​large ​living room and kitchen great room open to a ​south-facing ​stone terrace​, and a unique screened porch is in a restored corn silo. ​The lower level holds media and recreation rooms​, a workshop and root cellar.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$995,000 4 acres 4 Beds | 5 Baths | 3100 sqft
4 WILLARD HILL Rd, Stockbridge, Massachusetts 01262 - Berkshire County

4 acres Stockbridge, MA

1834 BRICK GREEK REVIVAL ON HISTORIC WILLARD HILL RD, regally sited on 4 lovely acres, with a 19th century red carriage barn. Recently renovated, including the newer kitchen, master suite with a dressing room and marble bath, and an artist's studio or home office. French doors in the dining room open to the sylvan backyard, and the stone terrace by the Japanese maple has full sun all day.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$827,000 5.34 acres 4 Beds | 3 Baths | 2286 sqft
22 Tyringham Rd, Monterey, Massachusetts 01245 - Berkshire County

5.34 acres Monterey, MA

A lovely like-new home sighted up a long drive with westerly light and views. Just a short walk to the town beach at Lake Garfield, or stroll to sweet Monterey village center with a general store, library, meeting house and town hall. With four bedrooms and three full baths, there's plenty of room for friends and family. The living room has a towering wood-burning fireplace and the more recent truly sumptuous kitchen that would delight any cook, includes a dining area. The living room, den (could be a formal dining room), and first floor master suite all open to a large deck overlooking the big sunny lawn for gardens and play. Two-car attached garage and plenty of storage. This offering includes a second building lot. Move-in ready to inst
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$775,000 2.3 acres 4 Beds | 3 Baths | 3511 sqft
73 JUG END Rd, Egremont, Massachusetts 01258 - Berkshire County

2.3 acres Egremont, MA

1798 RENOVATED HOME. A very early Federal house, totally renovated inside and out, and featured in magazines. The original main section circles around the stairwell - a generous living room with a wood-burning fireplace and a gallery to hang an art collection. Large master and plenty of guest space. The rear wing is now a sunny great room - an open kitchen, dining with a TV area. Lovely grounds.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$645,000 4.99 acres 5 Beds | 4 Baths | 3500 sqft
399 NEW MARLBORO HILL Rd, New Marlborough, Massachusetts 01230 - Berkshire County

4.99 acres New Marlborough, MA

A SOLAR ASSISTED contemporary home with rustic details, huge windows, modern kitchen, and lots of room with multiple gathering and sleeping spaces, and home office. Very private setting and southerly exposure for the photovoltaic energy panels and winter solar gain. A lap pool for summer fun, along with an orchard, meadow and woodland, located off a beautiful gravel road not far from the Old Inn.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$585,000 9.14 acres
19 & 20 WHEATLEY Dr, Stockbridge, Massachusetts 01262 - Berkshire County

9.14 acres Stockbridge, MA

MAJOR PRICE REDUCTION - WATERFRONT: An opportunity to build a dream home on very private property with 460 ft of waterfront and panoramic views of Lily Pond, a renown unspoiled body of water that was cherished by the Gilded Age crowd. Located in Stockbridge within walking distance of Tanglewood and nearby Lenox center, and the town beach at Stockbridge Bowl. PRIME LOCATION AND VERY PRIVATE.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$439,750 2.76 acres 3 Beds | 2 Baths | 2191 sqft
141 Main Rd, Monterey, Massachusetts 01245 - Berkshire County

2.76 acres Monterey, MA

Drive past a lighted tennis court to the private setting of this Stevens Lake Association expanded Cape, protected by adjacent Beartown State Forest. The open-plan kitchen, dining and living room has a wood-burning fireplace, and the beautiful three-season room with a cathedral ceiling and lots of glass is warmed by a wood stove in winter use. There's a first floor master suite and two large guest rooms on the second floor. A full basement offers room for expansion and the oversized garage not only stores vehicles, but would make a terrific studio. Keep a kayak, canoe or sailboat at the lake or stroll the beautiful trail over the dam. Near Great Barrington with the benefit of low Monterey taxes and access to the town beach at Lake Garfield
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$425,000 5.1 acres 3 Beds | 4 Baths | 1702 sqft
77 New Marlborough Rd, Monterey, Massachusetts 01245 - Berkshire County

5.1 acres Monterey, MA

A truly unique rustic-chic handcrafted lodge, privately sited up a long drive and perched on a westerly-facing hill. The living room has a big stone fireplace and French doors to a stone patio, and the kitchen has a commercial stove. All three bedrooms are en-suite, and the master has a very cool third-story studio. The grounds offer a grape arbor, woods, pasture, views and a toolshed. Included in the offering are rights to a co-owned (six families) Har-tru tennis court near Lake Garfield. Within strolling distance to the Monterey General Store, and Monterey has the best town beach in the Berkshires.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$398,500 40.93 acres
207 BEARTOWN MOUNTAIN Rd, Monterey, Massachusetts 01245 - Berkshire County

40.93 acres Monterey, MA

SITE WORK COMPLETE AND NEWLY CLEARED, ready for a home. Beautiful long drive, a three car garage, deep drilled well, and a four bedroom septic already installed. TOTAL privacy on a coveted Monterey road, abutting 11,000 acre Beartown State Forest. Functioning half bathroom in the garage building for use while building a house, hunting, or turn the garage into living space. Subdividable.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$345,000 9.69 acres
HICKEY HILL Rd, Sheffield, Massachusetts 01257 - Berkshire County

9.69 acres Sheffield, MA

Sunny acreage of pasture and woodland, with a building site carved out on the edge of the pasture and nestled into the woodlands with views over Sheffield, including the church steeple, the Taconic Hills and the sunset. Loads of sun for gardening and farming, woodlands for hiking and foraging, and a stream gorge that cascades down the border of the property. Great spot to build a dream home.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$175,000 12.41 acres
OLD BEARTOWN MOUNTAIN Rd, Monterey, Massachusetts 01245 - Berkshire County

12.41 acres Monterey, MA

Just off of Blue Hill Road, and at the end of a dead-end gravel road by Beartown State Forest. One may hike up a trail to Benedict Pond for a swim and the AT for limitless hiking, then up to The Ledges for a three-state view. Protected on three sides by state forest and land trust. A very rare and private building parcel, in a convenient location. Low Monterey Taxes.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$155,000 7.65 acres
0 Barnum St, Sheffield, Massachusetts 01257 - Berkshire County

7.65 acres Sheffield, MA

Beautiful parcel of land on bucolic Barnum Street in the historic Ashley Falls area of Sheffield, abutting Nature Conservancy land behind and across the street. The land offers some glacial outcroppings along with a portion of and views over a secluded field at the back of the property. The driveway is roughed in and ready to use. Possible westerly views.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,950,000 2 acres 4 Beds | 4 Baths | 2 ½ Baths | 5256 sqft
117 Pattee Rd, Falmouth, Massachusetts 02536 - Barnstable County

Waterfront Home Surrounded by Public Horse Trails

Its quite rare to find a property offering such serene privacy, yet is located so close to everything. This contractor owned home has been designed and built as such, and holds many surprise unseen extras. Four bedrooms, four baths, with a fifth bath rough plumbed should you wish to finish the basement, this smart home features high ceilings and luxury finishes. Exterior walls and ceilings have double foil faced styrofoam insulation board OVER standard insulation making this home quite tight from weather. Whole house sound, three car garage, whole house generator, 5 HVAC systems, antique stained glass pieces throughout, VAC system, walk up attic. There is also a seperate workshop, plumbed and heated, with two floors of workspace, a rear ram
David Schwamb Benchmark Cape Realty
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$13,800,000 6.56 acres
16 Bayside North, Edgartown, Massachusetts 02539 - Dukes County

6.56 acres Edgartown, MA

Arguably the most rare and significant offering on Katama Bay with 6.5 acres creating an expansive waterfront compound with over 380 feet of frontage. A boardwalk over marsh allows for a scenic trespass to the shoreline to the private dock. The home site on the bay will provide spectacular water views to the south while encompassing the natural meadow to the west and the topography is varied with rolling hills and open grassland. This new enclave in Katama known as Bayside was created to embody and preserve the natural character of the old Vineyard. With over 20 acres of protected open space of native meadow and forest land, the result is an unparalleled setting and the assurance of owner privacy. Ready for building permit. Additional parce
$13,250,000 7.95 acres 5 Beds | 8 Baths | 3065 sqft
221 John Cottle Road, West Tisbury, Massachusetts 02575 - Dukes County

7.95 acres West Tisbury, MA

Paul's Point, one of the most treasured shorelines on Martha's Vineyard, known for its sandy shores, emerald waters and remarkable privacy, is home to this ocean front property. Perfectly manicured yet whimsical grounds sprawl over 8 acres with beetlebung groves, stonewalls and gently rolling meadow leading to nearly 200' of shoreline. The magic continues into the woodland over an artfully crafted footbridge through tall trees and over a rustling creek. Sitting high over the trees, the main residence offers captivating views and is an appealing design that includes 5 bedrooms on three levels of living and semi attached guest quarters. Stone steps weave through ample gardens to the vintage guest house and to the open expanse stretching to th
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$12,950,000 4.4 acres
18 Bayside South, Edgartown, Massachusetts 02539 - Dukes County

4.4 acres Edgartown, MA

BAYSIDE ~ A select offering of 4.4 acres with over 320' of sandy beach and a private deep water dock on Katama Bay. The gentle rise of the topography presents commanding views of the water and the home site provides the opportunity to build a 10 bedroom compound and accessory structures. This new enclave in Katama was created to embody and preserve the natural character of the old Vineyard. With over 20 acres of protected open space of native meadow and forest land, the result is an unparalleled setting and the assurance of owner privacy. Additional parcels also available - please inquire
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$10,995,000 2.92 acres 7 Beds | 14 Baths | 6161 sqft
520 Shore Road, Chatham, Massachusetts 02633 - Barnstable County

2.92 acres Chatham, MA

Sand Bars, a spectacular waterfront estate, perched upon the coveted stretch of Shore Road is one of the most magnificent properties in Chatham. With 2.9 acres of privacy, it is the largest waterfront parcel on Shore Road offering stunning elevated views of Chatham Harbor, the Atlantic and panoramic vistas of Chatham's unrivaled shoreline. The layout comprises both traditional and contemporary design with a flowing layout and private living quarters that accommodates entertaining or compound living. The nine bedroom septic currently holds 7 bedrooms including a first floor master suite, 2 offices, a formal dining room, and great room with chef's kitchen. Notable highlights include, a seaside gunite pool with waterfall, spacious outdoor pat
$10,500,000 3.5 acres 6 Beds | 9 Baths | 2488 sqft
22 Quitsa Lane, Chilmark, Massachusetts 02535 - Dukes County

3.5 acres Chilmark, MA

Cliff Cottage enjoys one of the most picturesque settings and water-views on Martha's Vineyard. Originally built in 1850 and painstakingly remodeled by the current owner's, along with one of the Islands finest builders to reflect today's life style and amenities. The recently constructed detached studio with over 1,400 sq' offers 2 additional bedrooms with water-views along with an office and a garage. An association stairway leads to your private sandy beach on the south shore, additionally, there is deeded access to Menemsha Pond a short walk away.
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$7,600,000 61.31 acres 8 Beds | 10 Baths | 13000 sqft
Hillsdale Rd, Egremont, Massachusetts 01258 - Berkshire County

61.31 acres Egremont, MA

A residential or private retreat compound for any discreet buyer. Built on a pleasant ridge with multi-directional views of 50 miles plus. Most convenient access to NYC, Boston and airports/train stations. Two structures with elevators, four fireplaces, two wood burning stoves. Radiant heating on all ground floors. Enviroshake roofing, hardiplank siding along with vast flower gardens and pool!
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$6,995,000 2.08 acres 12 Beds | 15 Baths | 6725 sqft
554 Wianno Avenue, Osterville, Massachusetts 02655 - Barnstable County

2.08 acres Osterville, MA

Located at the end of Wianno Avenue just down the way from the fabled Wianno Club, this incomparable site is 2.08 acres with panoramic views, almost 300 feet of sandy beach, stone revetments, and 2 stone jetties on Nantucket Sound. The house is a classic 1880s summer cottage'' with classic millwork, high ceilings, 12 bedrooms, 7 and a half baths, 3 fireplaces, covered porches, a 3 car detached garage, and a tennis court. A new Title V 12-bed septic system has been installed allowing for the house as is or a new house and guest house. A site of this size is rarely available and offers the opportunity to create a family compound for generations.
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$6,995,000 3.48 acres 4 Beds | 6 Baths | 6633 sqft
4 Bare Cove Lane, Hingham, Massachusetts 02043 - Plymouth County

3.48 acres Hingham, MA

SPECTACULAR, custom residence set on 3.48 ACRES in World's End on Hingham Harbor. Embrace beautiful sunsets, private dock, 137+ feet of water frontage, in-ground pool, putting green, and professionally landscaped grounds. PRIVATE and picturesque with a long, gated drive, this 4-level home features 12 rooms, 3+ ensuite bedrooms, 5 full and 1 half baths, walls of windows, gorgeous hardwoods, well-equiped kitchen, sunroom, multiple decks, and widow's walk. Entertain with ease inside and out. Walkout lower level includes kitchenette, family room with surround sound and fireplace, exercise room, office, laundry room and full bath. Office and full bath above attached 2-car garage. Beach rights to Seal Cove Beach Association. One of the most uniqu
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$6,900,000 33 acres 8 Beds | 10 Baths | 10971 sqft
2 Glendale Middle Rd, Stockbridge, Massachusetts 01262 - Berkshire County

33 acres Stockbridge, MA

SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool,
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$6,750,000 6.63 acres 5 Beds | 7 Baths | 2597 sqft
74 Sears Point Road, Chatham, Massachusetts 02633 - Barnstable County

6.63 acres Chatham, MA

This exceptional waterfront property offers arresting panoramas of Stage Harbor and beyond. Situated in one of Chatham's most private enclaves, the property is comprised of two adjoining lots totaling 6.6 acres and 350 feet of water frontage. A long winding driveway and charming barn enhance the property's magical approach. Currently there is an existing five bedroom, three and half bath classic Cape Cod style residence built in 1959 spanning 2,500 s.f. sited on the property. This unbeatable setting offers exceptional potential to built a dramatic dream estate or to reinvent the old. Existing Polhemus Savery DaSilva architectural plans are available. Discover more about this spectacular property upon request.
$5,900,000 8 acres 5 Beds | 9 Baths | 4000 sqft
11 Azalea Lane, Chilmark, Massachusetts 02535 - Dukes County

8 acres Chilmark, MA

With 425 ft of private ocean beach, this offering deserves its reputation as the ''ultimate beach house.'' The 5-bedroom home has been completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. The beach stairs provide access to a wide swath of sand that many consider the most beautiful stretch of beach on Martha's Vineyard. To fully appreciate this extraordinary setting, view the images in the ''photo gallery'' and watch this drone video: https://vimeo.com/175588276
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$5,395,000 3.4 acres 7 Beds | 9 Baths | 3358 sqft
82 Turkeyland Cove Road, Edgartown, Massachusetts 02539 - Dukes County

3.4 acres Edgartown, MA

Rare Find In Katama: Waterfront Compound With Pond, Dock And Private Beach Access. Located at the end of a private winding drive and set on over three bucolic acres, this spectacular waterfront property is comprised of a Main House plus Guest House -- with a total of seven bedrooms -- making it an ideal family compound or rental property. Both shingle-style contemporary homes feature open-designed living spaces with vaulted ceilings, an abundance of glass and expansive decks to maximize indoor and outdoor living. Surrounded by a natural landscape of shady mature oaks, pines and maples, and a lush lawn that leads to the water's edge, this property faces west across the Edgartown Great Pond, providing afternoons basked in warm golden light th