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Homes for sale in Berkshire County Massachusetts - Page 1 of 23

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$2,995,000 16.53 acres 7 Beds | 5 Baths | 1 ½ Bath | 5500 sqft
50 Mount Hunger Estates --, Monterey, MA 01245 - Berkshire County

16.53 acres Monterey, MA

THREE STATE SOUTH WESTERLY VIEW over Lake Garfield to the Catskill range all the way on the other side of the Hudson River. Built on a mountaintop in 2005 down a long gated drive, this seven-bedroom, five-bath, 5700sf Contemporary home in Monterey, MA enjoys ultimate privacy on over 16 acres. Enter a two-story great room and be immediately knocked out by the view, possibly the best from any home in the southern Berkshires. The generous first floor master suite has an office library, and there are two more bedrooms on the main floor. Guests have their own floor with four bedrooms, two baths, and a second kitchen and family room, all with the same panoramic vistas. Four fireplaces, two-car attached garage, and separate two car garage for coun
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$2,750,000 84 acres 6 Beds | 6 Baths | 1 ½ Bath | 5885 sqft
22 New Marlboro Rd, Monterey, MA 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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$1,925,000 14.69 acres 5 Beds | 3 Baths | 4400 sqft
101 Green River Rd, Alford, MA 01230 - Berkshire County

14.69 acres Alford, MA

This artist and gardener's homestead in Alford comprises an 1840s renovated farmhouse, studio and barn, all on 14 very private acres much of it fenced around, with an automatic entry gate at the driveway entrance. The farmhouse has 4,400 square feet of living space on three floors, with five bedrooms and three baths, as well as an attached large art studio or family room, conservatory greenhouse, library, and more. Scandinavian wood stoves warm the house if wanted, inviting covered porches bring everyone outside, and the finished lofted attic space has limitless possibilities. All have the appeal and authenticity of an old house mixed with a modernist-style sensibility, as the bathrooms and kitchen have been completely renovated and the flo
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,495,000 72 acres 6 Beds | 7 Baths | 1 ½ Bath | 6600 sqft
14-16 NORFOLK Rd, New Marlborough, MA 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, MA 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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$1,350,000 13.76 acres 5 Beds | 5 Baths | 1 ½ Bath | 4788 sqft
170 GOULD Rd, Monterey, MA 01245 - Berkshire County

13.76 acres Monterey, MA

Casual and elegant country home secluded on 13.76 acres with a romantic approach through rolling pastures past one of the two spring-fed swimming ponds. Views out every window of gardens and flowering trees, from the open-plan great room and first-floor master suite, to the sunny porch and deck. Graciously host guests throughout, and in new guest quarters above an attached garage. DSL internet.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$1,250,000 15 acres 4 Beds | 4 Baths | 1 ½ Bath | 3258 sqft
170 Christian Hill Rd, Great Barrington, MA 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 | 2 ½ Baths | 3100 sqft
4 WILLARD HILL Rd, Stockbridge, MA 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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$795,000 5.34 acres 4 Beds | 3 Baths | 2286 sqft
22 Tyringham Rd, Monterey, MA 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, MA 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 | 1 ½ Bath | 3500 sqft
399 NEW MARLBORO HILL Rd, New Marlborough, MA 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, MA 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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$448,000 5.03 acres 3 Beds | 4 Baths | 3150 sqft
276 South Undermountain Rd, Sheffield, MA 01257 - Berkshire County

5.03 acres Sheffield, MA

Gilded Age converted carriage house to a three bedroom, four bath home, with waterfront lots across the street on Berkshire Lake. The huge great room has a big stone fireplace, views to the lake, and is open to the kitchen. Two of the three bedrooms are two-room suites, and all are ensuite. The ground floor has limitless possibilities, original wooden stable walls, and a wood stove. Recent renovations include a Buderus boiler, all new electric, and full insulation. Cell service, cable TV and Internet, and fresh mountain spring drinking water.
TIM LOVETT BERKSHIRE PROPERTY AGENTS
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$439,750 2.76 acres 3 Beds | 2 Baths | 2191 sqft
141 Main Rd, Monterey, MA 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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$398,500 40.93 acres
207 BEARTOWN MOUNTAIN Rd, Monterey, MA 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, MA 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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$155,000 7.65 acres
0 Barnum St, Sheffield, MA 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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$150,000 12.41 acres
OLD BEARTOWN MOUNTAIN Rd, Monterey, MA 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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$69,900 30 acres
Savoy, MA 01256 - Berkshire County

30 Acres - Ready to build!

30 acres of beautiful woods in The Berkshires. Private homesite with substantial amount of land to hike, hunt, snowmobile, atv, etc. Frontage on main route through Savoy. Minutes to Plainfield pond, Windsor Pond, and Savoy State Forest. Recent perc test and survey. Now only 69,900! Financing available. Call today!
Jake Belanger Mountain Stream Land
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$59,900 5 acres
Dalton, MA 01226 - Berkshire County

5 Acres w/ Sewer - Nearby Appalachian Trail Land!

Beautiful homesite in The Berkshires. 5 acres with town sewer! Steps to Appalachian Trail land to the west, Protected lands across the street! Gravel driveway installed to a level building site. 10 minutes to Pittsfield. Only $59,900! Financing available. Call/text/email today!
Jake Belanger Mountain Stream Land
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$6,900,000 33 acres 8 Beds | 10 Baths | 2 ½ Baths | 10971 sqft
2 Glendale Middle Rd, Stockbridge, MA 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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$4,750,000 4.6 acres 8 Beds | 8 Baths | 2 ½ Baths | 8500 sqft
106 & 114 Cliffwood St, Lenox, MA 01240 - Berkshire County

4.6 acres Lenox, MA

Unsurpassed 19th Century Queen Anne Style Berkshire Lenox ''Cottage'' restored and reinvented for today's most discriminating family wishing for an understatedly elegant, 'cool' and comfortable Twenty-First Century lifestyle. See attached document for all details. Shown by advance appointment only.
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$4,600,000 11.11 acres
82 Interlaken Rd, Stockbridge, MA 01262 - Berkshire County

11.11 acres Stockbridge, MA

Rare opportunity: 11 Acres on the beautiful Stockbridge Bowl. Nearly 400 ft of pristine lake frontage across the big part of the Bowl. Amazing mountain and water views in every season. Build one private home or a family compound. Three home sites with existing structure for possible rare opportunity to have your dream home within 71 feet of the lake. Minutes to Tanglewood, Kripalu, Canyon Ranch.
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$4,500,000 3.69 acres
109 Stockbridge Rd, Great Barrington, MA 01230 - Berkshire County

3.69 acres Great Barrington, MA

Great exposure in high-traffic location on Route 7. B2 zoning for a variety of businesses. 26,012 square foot building currently a successful turn-key 24-lane bowling alley with indoor miniature golf, bar and lounge area, pro shop, snack bar, and arcade area. 3.69 acres, 275 feet of frontage with plenty of parking for over 100 vehicles. MA DOT average daily traffic total for Stockbridge Road was 15,000.
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$4,250,000 12.76 acres 10 Beds | 10 Baths | 2 ½ Baths | 6934 sqft
151 Walker St, Lenox, MA 01240 - Berkshire County

12.76 acres Lenox, MA

Thistlewood - A classic Berkshire Cottage that has been meticulously restored & updated for a modern lifestyle. Designed by noted Boston architects Rotch & Tilden, the main house offers classic proportions and elegant details throughout. The grounds wrap the house with stately gardens, pool & poolhouse.
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$4,250,000 153.9 acres 4 Beds | 4 Baths | 4228 sqft
720 West Rd, Richmond, MA 01254 - Berkshire County

153.9 acres Richmond, MA

Set on 154 secluded acres, this Adirondack style home features the finest in craftsmanship & design. Open floor plan, high vaulted ceilings, balconies & large windows throughout bring the magical outdoor surroundings indoors. Large level backyard w/ gunite pool, many pvt trails & streams right outside your door - ideal for horse riding, hiking, xc skiing & snow shoeing. Truly a yr round paradise.
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$3,995,000 0.69 acres 11 Beds | 10798 sqft
51 Walker St, Lenox, MA 01240 - Berkshire County

0.69 acres Lenox, MA

Gilded Age ''Cottage'' Mansion built for Handel Proctor of Proctor & Gamble. Residence currently an upscale 11 room B&B with full restaurant, bar, Terrance lounge --all is PRISTINE condition. Grossing over $1M annually. Property has a newly built Owner/Manager 3 bedroom home -- elegant presentation in downtown Lenox -- All F,F&E, licenses and client details included in purchase price.
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$3,950,000 250 acres
Long Pond Rd, Great Barrington, MA 01230 - Berkshire County

250 acres Great Barrington, MA

This scenic 56 acre lake and nature sanctuary can be all yours! 250 acres of pristine water and woods. Round Pond is a private lake only 5 miles from downtown Great Barrington! The park-like setting includes a pure, spring-fed lake, hardwood forest, lovely plantings, nature trails, and sandy beach. Spectacular lake and mountain views! It just doesn't get any better than this.
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$3,950,000 3.17 acres 6 Beds | 8 Baths | 3 ½ Baths | 10333 sqft
89 Cliffwood St, Lenox, MA 01240 - Berkshire County

3.17 acres Lenox, MA

SUPREMELY WELCOMING...One of Lenox's last 19th century Berkshire''cottages'' that has been meticulously restored and updated.
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$3,650,000 106 acres 7 Beds | 9 Baths | 2 ½ Baths | 10629 sqft
390&399 Under Mountain Rd, Lenox, MA 01240 - Berkshire County

106 acres Lenox, MA

''High Wick Farm,'' a magnificent, superbly located 106-Acre estate--a once-in-a-lifetime opportunity. At its centerpiece is a baronial Tudor mansion with impressive yet comfortable light-filled rooms, exquisite architectural details, 7 bedrooms, 11 fireplaces, indoor & outdoor swimming pools. The mansion is set on 11 acres across from a 95-acre parcel, providing gorgeous open views of fields & mountains to the south. Abutting future Berkshire Natural Resources conservation land, this parcel contains an indoor riding ring, stables (50 stalls, a 2BR/1BA groom's quarters), several residences (5BR,2BA) (3BR,2BA), on a building envelope limited to 10 acres. Minutes to Tanglewood and Lenox village, Shakespeare & Co., restaurants, and shops. See