Berkshire, MA Homes

/77
$5,800,000
- 15 Beds
- 14.5 Baths
- 11,670 Sq Ft
764 E Hill Rd, New Marlborough, MA 01230

High on a hilltop in the Southern Berkshires stands East Hill Farm. 227 cultivated acres encompassing pristine forest, spring-fed pond, striking barn, verdant pastures, formal and vegetable gardens, pool, and tennis court. The centerpiece: a 1798 Georgian home, 5,000sf. & 5 bedrooms.Ready for private living, entertaining, horses, farming, a bespoke destination, or simply: tranquility. Includes a

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

764 E Hill Rd, New Marlborough, MA 01230
/31
$392,000 Sold Jul 23, 2025
- 8,048 Sq Ft
- $49/SF
- 13 Days On Market
- 8 Beds
- 4 Baths
- Built 1990
14 Westminster St, Pittsfield, MA 01201

Here is your opportunity to own this conveniently located, 4-family investment property in Pittsfield! Each spacious apartment consists of 2 bedrooms and 1 bathroom. The property features front and back porch/decks, a large back yard that is partially fenced, natural gas heating and plenty of off-street paved parking. Schedule a viewing today to explore this investment opportunity firsthand and

Nancy Bush Brooks SIGNATURE ASSOCIATES

14 Westminster St, Pittsfield, MA 01201

/26
Est $446,289 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,538 Sq Ft
26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

/69
$565,900
- 8 Beds
- 3 Baths
- 4,034 Sq Ft
144 Brombach St, Pittsfield, MA 01201

Beautiful, spacious 8 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated

Darcy Reid MOCKINGBIRD REAL ESTATE

144 Brombach St, Pittsfield, MA 01201
/30
$300,000 Sold Jul 23, 2025
- 1,354 Sq Ft
- $222/SF
- 22 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1957
86 Asci Dr, Pittsfield, MA 01201

Pittsfield - Location, Location, Location!Enjoy the ease of true one-level living in this charming, well-maintained home featuring a one-car attached garage and inviting living room with hardwood floors and a cozy fireplace. With two generously sized bedrooms and a full bath, this home offers comfortable space and functionality. The galley kitchen flows seamlessly into the dining area and

Colleen Zajac MONARCH REALTY, INC.

86 Asci Dr, Pittsfield, MA 01201

/17
Est $434,743 Not Listed For Sale
- 1 Bed
- 1 Bath
- 781 Sq Ft
281 Main St Unit 4, Great Barrington, MA 01230

281 Main St Unit 4, Great Barrington, MA 01230

/40
$785,000
- 3 Beds
- 3 Baths
- 2,073 Sq Ft
424 N Hemlock Ln, Williamstown, MA 01267

If your taste leans toward classic contemporary spaces and crisp design details, you won't find much to compare in Williamstown to this completely renovated condominium in the sought-after North Hemlock Brook complex. The gallery-like renovation of this dramatic 2,073 SF condominium includes three en-suite bedrooms, featuring the finest materials, fixtures, and appliances for the most discerning

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

424 N Hemlock Ln, Williamstown, MA 01267
/23
$132,000 Sold Jul 23, 2025
- 2,934 Sq Ft
- $45/SF
- 30 Days On Market
- 4 Beds
- 2 Baths
- Built 1930
23 Laurel Way, North Adams, MA 01247

Don't miss this opportunity to own a two-family home in a prime location near downtown North Adams, offering stunning mountain views and close proximity to all the cultural attractions the Northern Berkshires have to offer.This duplex features two 2-bedroom, 1-bath units with separate utilities, a detached 2-car garage, and ample off-street parking. One unit is currently occupied and in need of

Jose Larios LAMACCHIA REALTY, INC

23 Laurel Way, North Adams, MA 01247

/10
Est $350,972 Not Listed For Sale
- 1 Bed
- 1 Bath
- 567 Sq Ft
281 Main St Unit 3, Great Barrington, MA 01230

281 Main St Unit 3, Great Barrington, MA 01230

/61
$1,790,000
- 6 Beds
- 6.5 Baths
- 5,115 Sq Ft
76 Lenox Rd, West Stockbridge, MA 01266

New World meets Old in this impeccably designed and elegant French Country inspired estate nestled perfectly on the hillside, affording gorgeous westerly mountain and sunset views. Situated on 3.76 acres, the home offers ample privacy, yet it is just a stone's throw from Tanglewood and downtown Lenox and West Stockbridge. Designed for hosting extended family and friends, it offers generously

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

76 Lenox Rd, West Stockbridge, MA 01266
/37
$365,000 Sold Jul 23, 2025
- 2,912 Sq Ft
- $125/SF
- 6 Days On Market
- 5 Beds
- 6 Baths
- Built 1924
303 Springside Ave, Pittsfield, MA 01201

If your an investor or looking to owner occupy and have your tenants help pay your mortgage don't look any further. This 3 family and its 5 Garages is in excellent condition. Newer roof and windows, All separate utilities, Newer hot water heaters, laundry hook ups for all units. All tenants have been informed of probable rent increases after sale.

James Gelinas GELINAS REAL ESTATE

303 Springside Ave, Pittsfield, MA 01201

/44
Est $500,944 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,710 Sq Ft
221 Middle Rd, Clarksburg, MA 01247

221 Middle Rd, Clarksburg, MA 01247

/47
$1,750,000
- 5 Beds
- 3 Baths
- 2,808 Sq Ft
353 State Rd, Great Barrington, MA 01230

The Woodlands, A RARE OPPORTUNITY TO OWN YOUR OWN 74-ACRE PRIVATE SANCTUARY IN THE HEART OF GREAT BARRINGTON.This property abuts the Thomas & Palmer Brook preserve on three sides, is a two-minute drive to Ski Butternut and five minutes to dining and shopping in downtown Great Barrington. A picturesque pond flows into a babbling brook right outside of the large cathedral-ceiling primary suite's

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

353 State Rd, Great Barrington, MA 01230
/60
$875,000 Sold Jul 23, 2025
- 2,287 Sq Ft
- $383/SF
- 4 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2011
157 Pike Rd, Otis, MA 01253

Nestled just steps from the shores of Otis Reservoir--the largest recreational lake in Massachusetts--this stunning 4-bedroom, 3.5-bath home offers the perfect balance of refined comfort and year-round adventure. Tucked away on a beautifully wooded 1+ acre lot, enjoy your own private dock just a short stroll down a scenic forest path, where boating, swimming, and serene lakeside moments

Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

157 Pike Rd, Otis, MA 01253

/27
Est $433,337 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,352 Sq Ft
86 Earl Taylor Rd, North Adams, MA 01247

86 Earl Taylor Rd, North Adams, MA 01247

/28
$525,000
- 4 Beds
- 2 Baths
- 2,530 Sq Ft
127 Main St, Charlemont, MA 01339

Don't miss your chance to own this iconic Charlemont building in the heart of downtown. Excellent short term rental potential. 2nd floor is residential with huge windows, hardwood floors, tall ceilings, built in shelves and cabinets throughout. The 2500 sq ft apt includes: 4 bedrooms, 2 full baths, 2 large living rooms, dining room, large kitchen, dedicated laundry room, 2nd floor porch, and

Jocelyn O'Shea Coldwell Banker Community REALTORS®

127 Main St, Charlemont, MA 01339
/27
$265,000 Sold Jul 23, 2025
- 800 Sq Ft
- $331/SF
- 89 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1860
34 Church St Unit 2, Lenox, MA 01240

Discover the perfect opportunity in the heart of downtown Lenox with a Church Street view! This charming condo is an ideal choice for investors, second homeowners, or those seeking a convenient lifestyle. This unit boasts two bedrooms, two full baths, beautiful wood floors, and a cozy gas fireplace. You will immediately have access to various shops, restaurants, and Tanglewood just minutes away!

Jessica Rizzo Lamacchia Realty, Inc.

34 Church St Unit 2, Lenox, MA 01240

/27
Est $142,393 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
65 Carson Ave, Clarksburg, MA 01247

65 Carson Ave, Clarksburg, MA 01247

/73
$1,650,000
- 4 Beds
- 3 Baths
- 3,043 Sq Ft
593 Lakeway Dr, Pittsfield, MA 01201

Discover lakefront living in this stunning home, boasting nearly 100' of shoreline with the added feature of a built in swimming pool. From the moment you cross the threshold the breathtaking lake and mountain views draw you in, visible from almost every room. The inviting open concept layout seamlessly connects the kitchen, living and dining areas. The large kitchen complete with center

Janet Benoit MOCKINGBIRD REAL ESTATE

593 Lakeway Dr, Pittsfield, MA 01201
/2
$316,641 Sold Jul 23, 2025
- Land
- 43 Acres
- $7,419 per Acre
- 423 Days On Market
Lot A Reservoir Rd, Westhampton, MA 01027

Large acreage in Westhampton with several potential buildable lots. Close to Northampton and Easthampton for great restaurants and shopping. Close to 5 area colleges, abundant hiking and everything that the Pioneer Valley has to offer! In addition there other parcels in 30 western MA towns are also available from 30-1000++ acres.

Stiles & Dunn William Raveis R.E. & Home Services

Lot A Reservoir Rd, Westhampton, MA 01027

/13
Est $142,207 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
57 Carson Ave, Clarksburg, MA 01247

57 Carson Ave, Clarksburg, MA 01247

/36
$610,000
- 4 Beds
- 2.5 Baths
- 2,464 Sq Ft
304 Dalton Division Rd, Pittsfield, MA 01201

Welcome to 304 Dalton Division Road in Pittsfield! This charming property blends country living with city access, set on over 6 acres of land offering privacy, outdoor space, and beautifully landscaped grounds. It includes three sheds, one a wood shed, for ample storage. The home features a mudroom, first-floor laundry, and a kitchen with quartz countertops and sliding doors to the backyard. The

Patrick Cathro NON-MEMBER / RECIPROCAL

304 Dalton Division Rd, Pittsfield, MA 01201
/25
$610,000 Sold Jul 22, 2025
- 1,720 Sq Ft
- $355/SF
- 11 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2011
2 Evergreen Trail, Lenox, MA 01240

Enjoy the peaceful life at Lenox Woods...look out your back windows or screened porch at conservation land and the occasional deer. And inside, you'll enjoy the open living with great room and gas fireplace, kitchen with granite, first floor Primary Suite with vaulted ceiling, plus the finished 2nd floor with family room, 2 large bedrooms with full bath in between and a sweet, newly finished 4th

Mary Jo Piretti PIRETTI REAL ESTATE

2 Evergreen Trail, Lenox, MA 01240

/36
Est $512,893 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
220 General Knox Rd, Russell, MA 01071

220 General Knox Rd, Russell, MA 01071

/7
$325,000
- Land
- 9 Acres
- $36,517 per Acre
0 E Mountain Rd Unit 24226231, Adams, MA 01220

Development Opportunity! 3 approved building lots sold togetherAll 3 perc tested and surveyed - keep them separate or consolidateOver 300' on year round trout stream!Half meadow with stunning Mt. Greylock views - Half woods with old stonewalls and sugar maple trees3 driveways installed as well as split rail fencingPerfect for the person looking to build a small farm, main

Jake Belanger

0 E Mountain Rd Unit 24226231, Adams, MA 01220
/18
$420,000 Sold Jul 22, 2025
- 2,100 Sq Ft
- $200/SF
- 13 Days On Market
- 4 Beds
- 2 Baths
- Built 1978
632 N State Rd, Cheshire, MA 01225

Welcome to your dream home in the heart of Cheshire! This stunning 4 bedroom 2 bath raised ranch has been completely renovated with modern touches and high quality finishes throughout. Step inside to discover brand-new-life proof vinyl and porcelain vinyl flooring that combines style and durability in every room. The kitchen is a chefs delight, featuring all-new cabinets, gleaming quartz

James Gelinas GELINAS REAL ESTATE

632 N State Rd, Cheshire, MA 01225

/36
Est $477,509 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,285 Sq Ft
11 Beulah Land Rd, Blandford, MA 01008

11 Beulah Land Rd, Blandford, MA 01008

/8
$2,150,000
- 4 Beds
- 2 Baths
- 1,200 Sq Ft
199 West St, South Egremont, MA 01258

Rare Opportunity: 185 Acres of Natural Beauty in the Southern BerkshiresWe are offering one of the largest remaining privately owned parcels of natural acreage in the Southern Berkshires 185 private acres atop a mountain in Mount Washington, Massachusetts.Surrounded by protected forestland, this extraordinary property features over 10,000 feet of road frontage in a 3-acre zoning

David Singer

199 West St, South Egremont, MA 01258
/37
$800,000 Sold Jul 22, 2025
- 2,085 Sq Ft
- $384/SF
- 8 Days On Market
- 4 Beds
- 3 Baths
- Built 1944
6 Valley View Rd, Williamsburg, MA 01096

Highest and Best by 6/4, 5 pm. Nestled on a serene, one-acre lot, along a dead end street, this spacious Cape-style home offers the perfect blend of comfort, nature and convenience. Step inside to discover a flowing floor plan that effortlessly connects each thoughtfully designed space. Wake to the soothing sounds of the river, enjoy morning coffee on a stone patio, and indulge in direct water

Liz Helliwell 5 College REALTORS® Northampton

6 Valley View Rd, Williamsburg, MA 01096

/40
Est $395,000 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
136 N Washington State Rd, Washington, MA 01223

136 N Washington State Rd, Washington, MA 01223

/14
$85,000
- Land
- 4.79 Acres
- $17,745 per Acre
121 Stage Rd, Cummington, MA 01026

Escape the noise and reconnect with nature on this 4.79-acre wooded parcel in Hampshire County, Massachusetts. Located along scenic Stage Road with 440 feet of road frontage, this property offers a rare opportunity for building a private residence, establishing a hobby farm, or investing in land with flexible zoning potential.Set in a peaceful rural setting, the lot features mature trees

Community Lands

121 Stage Rd, Cummington, MA 01026
/9
$80,000 Sold Jul 22, 2025
- Land
- 10 Acres
- $7,992 per Acre
- 29 Days On Market
#16 Jenks Rd, Cheshire, MA 01225

Affordable, private and picturesque 10+ acres in Cheshire, with potential views galore is the perfect place to build your new home! Although tucked away in the hills, this location is in close proximity to shopping and dining and nearby to the Ashuwillticook Rail Trail and Cheshire Lake. Some light clearing has already been done!

Tracy Munger KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

#16 Jenks Rd, Cheshire, MA 01225

/20
Est $227,225 Not Listed For Sale
- 4 Beds
- 1 Bath
- 2,509 Sq Ft
1 Howes Rd, Cummington, MA 01026

1 Howes Rd, Cummington, MA 01026

/12
$59,000
- Land
- 1.00 Acre
- $59,000 per Acre
0 Westbrook Terrace, Pittsfield, MA 01201

Build your dream home in the prestigious gated enclave of Woodmonte Estates, located in the heart of Berkshire County, Massachusetts. This cleared 1-acre corner lot offers a rare opportunity to create a custom residence in one of the regions most desirable communities, surrounded by privacy, beauty, and high-end homes.With access to public utilities and underground electricity already in

Community Lands

0 Westbrook Terrace, Pittsfield, MA 01201
/24
$305,000 Sold Jul 22, 2025
- 4,000 Sq Ft
- $76/SF
- 35 Days On Market
- 7 Beds
- 4 Baths
- Built 1910
207-209 Main St, Becket, MA 01223

Bring your imagination and contractors to this magical property. This could be a family compound or income producing. 12 acres, pond, two car garage and three buildings consisting of a guest house, main house and cottage. Guest House has two bedrooms and one bathroom. Main house has three bedrooms and two bathrooms. Cottage has two bedrooms and one bathroom as well. There are endless

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

207-209 Main St, Becket, MA 01223

/18
Est $348,348 Not Listed For Sale
- 4 Beds
- 1 Bath
- 1,596 Sq Ft
51 Elm St, Shelburne Falls, MA 01370

51 Elm St, Shelburne Falls, MA 01370

/9
$379,500 Pending
- Land
- 6 Acres
- $60,720 per Acre
0 S Main St, Sheffield, MA 01257

Mountain views with Rt 7 access. Whether you are interested in a private residence to farm, raise horses, or escape the city life or if you are looking for a business opportunity with amazing Rt 7 exposure this land is the perfect opportunity. Totaling 6.25 acres of completely usable, flat, dry land. Currently the fields are hayed and have an approximate 1 acre vineyard. The 6.25 acres is

Grace Golden EQUINE HOMES REAL ESTATE, LLC

0 S Main St, Sheffield, MA 01257
/32
$300,000 Sold Jul 22, 2025
- 1,365 Sq Ft
- $220/SF
- 29 Days On Market
- 3 Beds
- 1 Bath
- Built 1955
35 Deborah Ave, Pittsfield, MA 01201

Your new home awaits! Enjoy this charming ranch style home in the heart of Southeast Pittsfield, situated between Williams Street and Elm Street. Featuring 3 bedrooms, spacious living room with fireplace, an abundance of natural lighting, and original hardwood floors throughout. The home has a new roof, central air conditioning, updated appliances, partially finished basement, & new hot water

Laiken Rapisarda LAMACCHIA REALTY, INC

35 Deborah Ave, Pittsfield, MA 01201

/31
Est $473,254 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,670 Sq Ft
166 Berkshire School Rd, Sheffield, MA 01257

166 Berkshire School Rd, Sheffield, MA 01257

/30
$537,000
- 3 Beds
- 2 Baths
- 2,300 Sq Ft
40 Ryan Rd, Washington, MA 01223

Contemporary cape with an open, single floor design combines charm and practicality on two private acres. The walk out lower level features an expansive family room with two additional bonus rooms. Heated garage, central vac, Vt Castings wood stove, underground propane, whole house generator and a screened porch to observe the private, landscaped lawn and gardens. This beautifully designed, well

Henry Hagenah OCTOBER MOUNTAIN REAL ESTATE

40 Ryan Rd, Washington, MA 01223

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