Berkshire County MA Homes for Sale

/53
$695,000
- 4 Beds
- 4 Baths
- 3,455 Sq Ft
64 Hewins St, Sheffield, MA 01257

A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 296-3500

64 Hewins St, Sheffield, MA 01257
/58
$1,595,000
- 6 Beds
- 3.5 Baths
- 3,905 Sq Ft
21 Stockbridge Rd, West Stockbridge, MA 01266

Tucked away on a private 2.35-acre knoll, this beautifully updated residence offers a rare blend of antique charm and modern ease in one of the Berkshires' most sought-after villages. With six generously sized bedrooms, a chef's kitchen designed for entertaining, and multiple inviting living spaces with fireplaces, the home is ideal for gatherings or quiet retreats alike. A stunning contemporary

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 675-5317

21 Stockbridge Rd, West Stockbridge, MA 01266
/40
$499,000
- 6 Beds
- 2.5 Baths
- 3,184 Sq Ft
119 S Main St, Sheffield, MA 01257

A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 481-1637

119 S Main St, Sheffield, MA 01257
/40
$1,795,000
- 4 Beds
- 3 Baths
- 5,469 Sq Ft
17 East St, Lenox, MA 01240

Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

Selina Lamb

BIRCH PROPERTIES

(413) 300-6860

17 East St, Lenox, MA 01240
/4
$49,500
- Land
- 4.04 Acres
- $12,253 per Acre
0 S Washington State Rd Unit 243702, Washington, MA 01223

Ready to build your Berkshire dream home? This parcel is waiting for you! Comprised of 4.04 wooded acres, this property offers a great value for a private building site for a first time builder or seasoned land buyer.

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 798-8137

0 S Washington State Rd Unit 243702, Washington, MA 01223
/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/5
$32,900
- Land
- 0.81 Acre
- $40,517 per Acre
Lot #50 Barker Rd, Pittsfield, MA 01201

This building lot boasts convenient access to essential utilities including water & sewer, available along the road. This parcel provides a seamless foundation for construction and future living. The lot is nestled within a residential neighborhood while being just a stone's throw away from amenities and recreational hotspots. With it's R6 zoning designation, the property presents versatile

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 798-8250

Lot #50 Barker Rd, Pittsfield, MA 01201
/6
$52,900
- Land
- 0.88 Acre
- $60,338 per Acre
L 105,106 Barker Rd, Pittsfield, MA 01201

Discover the perfect canvas for your future home with this 0.88-acre parcel of land with a R-12 Zoning. Boasting an ideal location close to shopping centers, employment opportunities, theaters, and a myriad of Berkshire attractions. This centrally located property offers unparalleled convenience and accessibility. Whether you're seeking to build now or in the future, this versatile parcel

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 722-5700

L 105,106 Barker Rd, Pittsfield, MA 01201
/5
$32,900
- Land
- 0.49 Acre
- $67,144 per Acre
Lot #112 Cadwell Rd, Pittsfield, MA 01201

This building lot boasts convenient access to essential utilities including water, sewer, and natural gas lines, available along the road. This parcel provides a seamless foundation for construction and future living. The lot is nestled within a residential neighborhood while being just a stone's throw away from amenities and recreational hotspots. With it's R6 zoning designation, the property

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 722-5737

Lot #112 Cadwell Rd, Pittsfield, MA 01201
/9
$49,900
- Land
- 2.43 Acres
- $20,535 per Acre
20 Notch Rd, North Adams, MA 01247

Nestled in the North Berkshire Hills this partially cleared 2.43 acre building lot is ready for what you've envisioned. Located not far from the Mt Greylock entrance and close to all things North Berkshire. This parcel offers town water, completed septic design, wetlands delineation, and full site plan with RU-1 Zoning. Land is still a great Investment! Build now, or build later, You decide!

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 343-4851

20 Notch Rd, North Adams, MA 01247
/12
$1,200,000
- 4 Beds
- 3.5 Baths
- 3,409 Sq Ft
140 Westbrook Terrace, Pittsfield, MA 01201

Introducing a stunning and spacious ''to be built'' single-story home designed with expandable second floor for comfortable and upscale living. Boasting over 3,400 square feet of well-appointed living space, which includes the finished lower level, this residence offers four bedrooms, three and a half bathrooms, and an array of quality finishes that elevate the living experience. As you enter

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 848-7696

140 Westbrook Terrace, Pittsfield, MA 01201
/7
$109,900
- 2 Beds
- 1 Bath
- 672 Sq Ft
27 Gwenn Ln, West Stockbridge, MA 01266

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 323-3952

27 Gwenn Ln, West Stockbridge, MA 01266
/7
$63,500
- Land
- 2.42 Acres
- $26,240 per Acre
1 Old Orebed Rd, New Ashford, MA 01237

Price improvement, seller's are MOTIVATED!!!Stunning 2.42-Acre Lot with Breathtaking Mountain Views! Prime location just minutes from the popular Jiminy Peak Ski Resort, Mt. Greylock. The property provides an excellent opportunity to build your dream home or vacation retreat, surrounded by nature's beauty and outdoor adventure. Enjoy access to skiing, hiking, lakes and more, while being

Keytoria Jenkins

THE KINDERHOOK GROUP - PITTSFIELD

(866) 436-0912

1 Old Orebed Rd, New Ashford, MA 01237
/36
$575,000
- 4 Beds
- 2 Baths
- 2,256 Sq Ft
4 Wabasso St, Pittsfield, MA 01201

Enjoy lake living year-round at this spacious 4-bedroom, 2-bath home with deeded lake rights to beautiful Pontoosuc Lake! Take in sweeping water views from the kitchen, dining room, and primary bedroom, or step out onto one of two decks to soak in the scenery. A new deck was built in 2022, and the primary suite boasts its own private balcony overlooking the lake. The fully fenced backyard is

Gary Fuls Jr

RE/MAX Transitions

(413) 339-3462

4 Wabasso St, Pittsfield, MA 01201
/25
$209,900
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
60 North St Unit 15, Dalton, MA 01226

JUST Listed. Welcome to this beautifully updated condo in Dalton’s Center Pond complex. This inviting & cheerful unit is perfect for year-round living, or a peaceful Berkshire getaway. Enjoy comfort & style with a spacious & bright living room - open concept dining area. The kitchen boasts loads of cabinets, newer appliances, new lighting & counter tops. The home is fresh throughout ~ newly

Nadine Hiser

KRG - Key Realty Group

(413) 722-5175

60 North St Unit 15, Dalton, MA 01226
/57
$3,450,000
- 6 Beds
- 5.5 Baths
- 4,681 Sq Ft
1333 Norfolk Rd, Southfield, MA 01259

Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with

Selina Lamb

BIRCH PROPERTIES

(413) 327-9228

1333 Norfolk Rd, Southfield, MA 01259
/60
$249,900 Open Sun 2PM - 4PM
- 6 Beds
- 2 Baths
- 2,592 Sq Ft
47 Hawthorne Ave, Pittsfield, MA 01201

Charming two-family duplex offering the perfect blend of move-in-ready comfort and renovation potential, just around the corner from Clapp Park. Each unit features 3 bedrooms, 1 bathroom, and a divided basement. One side is lovingly maintained with an inviting enclosed porch and warm interior details, while the other side offers original wood floors, trim, and doors--ready for your updates and

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 613-4730

47 Hawthorne Ave, Pittsfield, MA 01201
/39
$289,900
- 2 Beds
- 1 Bath
- 1,591 Sq Ft
63 Baker St, Lanesboro, MA 01237

JUST LISTED! Welcome to a gem in one of Lanesboro’s desirable hidden pockets! This adorable 2-bedroom cape is nestled on a dead-end street offering both tranquility & convenience—just minutes from Lanesboro Golf, local attractions, & the public beach at Pontoosuc Lake. Step inside through a cozy front porch & as you meander, discover a spacious living room featuring a picture window & stylish

Nadine Hiser

KRG - Key Realty Group

(844) 912-1978

63 Baker St, Lanesboro, MA 01237
/53
$2,649,000
- 6 Beds
- 6.5 Baths
- 4,289 Sq Ft
250 West St, Lenox, MA 01240

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

Selina Lamb

BIRCH PROPERTIES

(413) 423-1264

250 West St, Lenox, MA 01240
/19
$329,900
- 3 Beds
- 1.5 Baths
- 1,561 Sq Ft
106 Sampson Pkwy, Pittsfield, MA 01201

Discover the potential in this charming ranch-style home located in the desirable Parkways neighborhood. Offering three generously sized bedrooms and one and a half baths, this home features a classic layout with solid bones and room to make it your own. Original wood floors run throughout much of the home, adding warmth and character. One of the interesting features the unique dining area with a

Kellie Perrault

NOCHER REALTY

(413) 392-2886

106 Sampson Pkwy, Pittsfield, MA 01201
/5
$129,900
- 3 Beds
- 2 Baths
- 1,000 Sq Ft
11 Jennifer Ln, West Stockbridge, MA 01266

Spacious 1998 Titan double-wide with 3 bedrooms, 2 baths, cathedral ceilings, and an open living area. Features a cozy fireplace and efficient pellet stove. The primary suite includes a private bath and ample closet space. Bright kitchen and dining area with plenty of storage. Great layout for comfortable living in a peaceful setting.

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 414-5197

11 Jennifer Ln, West Stockbridge, MA 01266
/57
$575,000
- 4 Beds
- 2.5 Baths
- 2,406 Sq Ft
2 Melrose St, Adams, MA 01220

Step into a piece of Adams history with the beautifully preserved Simmons Cottage, on the market for the first time in generations. Built in 1901, this elegant Victorian residence offers a rare in-town opportunity, blending architectural charm with modern comfort.Set on a .24 acre lot, just a short stroll to the vibrant center of Adams, with its restaurants, shops, and small town charm, this 9

Diane Thorson

WILLIAM PITT SOTHEBY'S - GT BARRINGTON

(413) 666-1747

2 Melrose St, Adams, MA 01220
/28
$625,000
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
303 Lakeshore Dr, Sandisfield, MA 01255

Experience the ultimate in lakeside living with this stunning 4-bedroom, 2-bath home in the coveted Otis Wood Lands community. This property offers a perfect blend of comfort and entertainment, featuring spacious sun-filled rooms and a sprawling deck ideal for relaxation and gatherings. Enjoy the convenience of a fully furnished home, complete with game room favorites like pool and air hockey

Gary Fuls Jr

RE/MAX TRANSITIONS

(413) 884-5511

303 Lakeshore Dr, Sandisfield, MA 01255
/17
$179,000
- 2 Beds
- 1 Bath
- 816 Sq Ft
49 Access Rd Unit 3b, Windsor, MA 01270

This charming rustic seasonal lake cottage, rebuilt in 2011 with structural enhancements, replacement windows, and a large side deck, is a cozy retreat nestled on 1.24 wooded acres by Windsor Pond. The interiors are adorned with knotty pine, giving it a warm and inviting feel harkening to an era past. With two comfy bedrooms, a wood stove to keep you warm on chilly nights, a spacious screened

Lisa Carroll

Delap Real Estate LLC

(413) 741-2269

49 Access Rd Unit 3b, Windsor, MA 01270
/15
$279,900
- 3 Beds
- 1 Bath
- 1,356 Sq Ft
20 Barlow Ave, North Adams, MA 01247

Everything is brand new--inside and out! This beautifully renovated home is the closest you'll get to new construction! Featuring 3 bedrooms, 1 full bath, and an open-concept layout, it offers modern finishes, new flooring, recessed lighting, and a sleek white kitchen with granite countertops.Appliances will be included, and the home has been redone top to bottom with new siding, roof, windows,

Peter West

BISHOP WEST REAL ESTATE

(413) 675-5580

20 Barlow Ave, North Adams, MA 01247
/27
$249,900
- 4 Beds
- 1 Bath
- 1,364 Sq Ft
30 Belvidere Ave, Pittsfield, MA 01201

Welcome to this inviting four-bedroom, one-bath Colonial, nestled on a peaceful dead-end street that offers both charm and privacy. This home features beautiful hardwood floors throughout, adding warmth and character to every room.The eat in kitchen has granite countertops, stainless steel appliances, and ample cabinetry--perfect for anyone who enjoys cooking or entertaining. Step out front and

Kellie Perrault

NOCHER REALTY

(413) 741-1594

30 Belvidere Ave, Pittsfield, MA 01201
/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.

Gary Fuls Jr

RE/MAX TRANSITIONS

(413) 884-5511

0 Mohawk Lake Rd, Stockbridge, MA 01262
/5
$79,900
- Land
- 1.08 Acres
- $73,981 per Acre
Lot 144 Eastbrook Ln, Pittsfield, MA 01201

Nestled on a quiet street among upscale homes, this 1.08-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 414-5864

Lot 144 Eastbrook Ln, Pittsfield, MA 01201
/4
$79,900
- Land
- 1.23 Acres
- $64,959 per Acre
Lot 140 Westbrook Terrace, Pittsfield, MA 01201

Nestled on a quiet street among upscale homes, this 1.23-acre lot offers a prime setting to build your custom residence. Underground utilities are available at the road for a seamless start. Enjoy the privacy and natural beauty of the Berkshires with easy access to downtown Pittsfield, Tanglewood, hiking trails, and more. Protective covenants preserve the integrity and lasting value of this

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 288-3713

Lot 140 Westbrook Terrace, Pittsfield, MA 01201
/18
$285,000 Open Sun 1PM - 3PM
- 3 Beds
- 1.5 Baths
- 1,568 Sq Ft
25 Taft St, North Adams, MA 01247

Experience maintenance-free living in this stunning 3-bedroom, 1.5-bath townhouse, meticulously renovated to blend contemporary design with practicality. The open floor plan showcases exposed brick and stunning wood laminate flooring, complemented by energy-efficient stainless-steel appliances that enhance everyday living. Enjoy the convenience of flat, easy parking with a covered carport and

Gary Fuls Jr

RE/MAX Transitions

(413) 937-7308

25 Taft St, North Adams, MA 01247
/30
$265,000
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
26 Davis St, Pittsfield, MA 01201

Be sure to check out this newly renovated cute house in 1/2 an acre in Pittsfield! Centered near everything - it's so private you'd think you lived out in the woods!New Roof, Windows, Kitchen, bathroom, new flooring, new decks front and back!This home also features a large detached garage. According to the building commissioner, as it's a pre-existing building, it can be easily converted to an

Kolleen Schmitt

BISHOP WEST REAL ESTATE

(413) 288-4516

26 Davis St, Pittsfield, MA 01201
/24
$321,900
- 3 Beds
- 1.5 Baths
- 1,600 Sq Ft
171 Harryel St, Pittsfield, MA 01201

Welcome to 171 Harryel St in Pittsfield, MA! This well-maintained 3-bedroom, 1-bath home offers a spacious living area, hardwood floors, and a bright eat-in kitchen. Basement boasts a finished room perfect for entertainingly. Enjoy the private backyard--great for outdoor activities or relaxing. Located on a quiet street with convenient access to parks, shops, and downtown amenities. A great

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 331-7090

171 Harryel St, Pittsfield, MA 01201
/33
$785,000
- 3 Beds
- 2.5 Baths
- 2,853 Sq Ft
85 Sugar House Rd, Otis, MA 01253

Spotless Contemporary Retreat in the Berkshires - 85 Sugar House Rd, Otis, MAWelcome to this mint-condition, fully furnished 3-bedroom, 2.5-bath contemporary tucked on a quiet country road in Otis, adjacent to the Farmington River Wildlife Management Area. Whether you're seeking a year-round home or a turnkey retreat, this light-filled Berkshires escape offers comfort, style, and a seamless

Selina Lamb

BIRCH PROPERTIES

(413) 300-5948

85 Sugar House Rd, Otis, MA 01253
/32
$489,000
- 3 Beds
- 3 Baths
- 1,849 Sq Ft
11 Bangor St, Lanesborough, MA 01237

Welcome to your dream home! This beautifully constructed 3-bedroom, 3-bathroom residence offers modern living with deeded right of way to serene Pontoosuc Lake. Built in 2023, the home blends style, comfort, and functionality across two spacious levels.The upper level boasts 1,344 sq. ft. of thoughtfully designed living space, featuring an open-concept kitchen with granite countertops, stainless

Kellie Perrault

NOCHER REALTY

(877) 330-5991

11 Bangor St, Lanesborough, MA 01237
/32
$169,000
- 5 Beds
- 3 Baths
- 2,250 Sq Ft
136 Church St Unit 142, Cheshire, MA 01225

Situated in the heart of the quaint town of Cheshire, this 3 family offers potential for the new owner as an investment or owner occupied. First floor has 2 bedrooms, primary is large, living room and kitchen are also spacious and kitchen offers pantry w/ potential laundry hook ups. Upstairs back unit is 2 bedroom, Upstairs front unit is 1 bedrooms & currently vacant. Long term tenants &

Nadine Hiser

KRG - Key Realty Group

(413) 475-9494

136 Church St Unit 142, Cheshire, MA 01225
/28
$515,000
- 2 Beds
- 1 Bath
- 960 Sq Ft
36 Castle Ln, Great Barrington, MA 01230

Charming Renovated Cottage on The Hill - Great Barrington, MADiscover this beautifully renovated Four Square-style cottage in the heart of Great Barrington's coveted ''The Hill'' neighborhood--a rare pied-a-terre offering classic charm with modern upgrades. This delightful 2-bedroom home is nestled in the Southern Berkshires, just moments from downtown, Lake Mansfield, and preserved natural

Selina Lamb

BIRCH PROPERTIES

(413) 414-5590

36 Castle Ln, Great Barrington, MA 01230
/26
$159,000
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
108 Church St, Cheshire, MA 01225

Welcome to the quaint town of Cheshire, this 2-unit rental is situated in center of town convenient to coffee shop, town hall, post office, Ashuwillticook Rail Trail, local activities & more. Lower level unit is vacant - easy to show. Some charming details remain in the 2nd floor unit - tin ceiling in living room, spacious eat in kitchen. New septic system installed 2025, certificate of

Nadine Hiser

KRG - Key Realty Group

(413) 481-1596

108 Church St, Cheshire, MA 01225
/25
$949,000
- 3 Beds
- 2 Baths
- 1,811 Sq Ft
1 River Run Unit 1, Williamstown, MA 01267

Loft-Inspired Townhouse in the Heart of Williamstown, MA - Gateway to the BerkshiresExperience refined, loft-style living in this beautifully designed 3-bedroom, 2-bathroom condominium townhouse, ideally located just steps from Williamstown's charming New England village center. Nestled in the scenic Berkshires, this sophisticated residence offers modern elegance, open-concept design, and

Selina Lamb

BIRCH PROPERTIES

(413) 613-4813

1 River Run Unit 1, Williamstown, MA 01267
/26
$184,900
- 2 Beds
- 1.5 Baths
- 852 Sq Ft
106 E Shore Rd, Becket, MA 01223

Looking for the perfect seasonal or year round home? Look no further. 2 bed 1.5 bath cttqage includes beach, boating and fishing rights with low HOA fee. On this seren setting sits a home with large windows, abundant storage, shelving and closets. First floor laundry, 3 season porch and additional storage in pull down attic.Oversized 1 car garage with work bench and additional loft storage,

Dorothy Maiwald

NON-MEMBER / RECIPROCAL

(413) 359-6468

106 E Shore Rd, Becket, MA 01223

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.