Berkshire County MA Homes for Sale

/35
$495,000
- 3 Beds
- 2.5 Baths
- 3,217 Sq Ft
2105 S Undermountain Rd, Sheffield, MA 01257

If you've been looking for a grand fixer-upper, this might be the property for you! Situated on the MA/CT line (house & 4.79 acres in MA, with 3.1 acres in CT bordering Sage's Ravine), the 1790's home has been partially updated and awaits the inspiration & vision of it's next owners. The first floor offers a large living room, parlor, dining room, semi-updated kitchen & modern full bath, large

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 393-2038

2105 S Undermountain Rd, Sheffield, MA 01257
/56
$1,150,000
- 4 Beds
- 4.5 Baths
- 2,753 Sq Ft
213 Egremont Plain Rd, Great Barrington, MA 01230

This 1700's-era former inn has been recently renovated from top to bottom, preserving its historic New England charm & seamlessly blending all the modern amenities for a comfortable country cottage lifestyle. The home offers 4 bedrooms and 4 baths over 3 generous levels of living areas. The ground level first floor features a cozy & inviting great room with decorative antique fireplace and new

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 475-9305

213 Egremont Plain Rd, Great Barrington, MA 01230
/33
$625,000
- 1 Bed
- 1 Bath
- 930 Sq Ft
210 Mt Washington Rd, Egremont, MA 01230

Set on 5.8 acres high on the side of Mt. Frey (back of Catamount), a timber and glass octagon on a concrete pedestal, ''The Pod'' is an iconic 1960's design by Guy Bartoli. Surrounded by thousands of acres of protected land, trails on the property connect to the South Taconic trail. Two streams -- one just behind the house -- run through the property. Expansive views to the east reach to the

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 481-1771

210 Mt Washington Rd, Egremont, MA 01230
/58
$1,495,000
- 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
/53
$645,000
- 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
/50
$845,000
- 4 Beds
- 3.5 Baths
- 2,955 Sq Ft
9 Castle Hill Rd, Stockbridge, MA 01262

Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated,

Selina Lamb

BIRCH PROPERTIES

(413) 269-8632

9 Castle Hill Rd, Stockbridge, MA 01262
/57
$3,250,000
- 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
/42
$264,900
- 2 Beds
- 1 Bath
- 1,591 Sq Ft
63 Baker St, Lanesboro, MA 01237

Spacious Cape, nearly 1600 sq. ft of living space includes expanded oak cabinet kitchen featuring charming built-in accents, with slider to deck; blending both indoor & outdoor entertaining; perfect to share with friends, neighbors & relatives. Spacious living room with toasty gas stove & stylish bar area for cozy gatherings, boasts picture window overlooking deck & semi private back yard, with

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
/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) 216-4201

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
$149,000
- 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
/34
$259,000
- 3 Beds
- 1 Bath
- 1,356 Sq Ft
20 Barlow Ave, North Adams, MA 01247

Everything is brand new from top to bottom--making this home the next best thing to new construction! Offering 3 bedrooms and 1 full bath, the open-concept design showcases modern finishes, new flooring, recessed lighting, and a stylish white kitchen with granite counters. Brand new stainless steel appliances are already installed for a turnkey experience. Major upgrades include new siding, roof,

Peter West

BISHOP WEST REAL ESTATE

(413) 675-5580

20 Barlow Ave, North Adams, MA 01247
/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
$275,000
- 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
/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
/32
$149,900
- 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
/29
$495,000
- 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
/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
$179,000
- 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
/8
$49,000
- Land
- 1.30 Acres
- $37,692 per Acre
205 Pecks Rd, Pittsfield, MA 01201

1.3 acre parcel zoned IL (Industrial-Light) - Well-suited for contractors needing outdoor storage or investors. Ideal for parking construction vehicles, equipment, or storage trailers. This parcel could also be good for generating passive income with storage container rentals, renting to contractors, or parking RVs/boats during the off-season. The parcel allows for temporary structures. It also

Syrah Bradley

BISHOP WEST REAL ESTATE

(413) 338-8371

205 Pecks Rd, Pittsfield, MA 01201
/6
$159,000
- Land
- 1.10 Acres
- $144,545 per Acre
1460 Cold Spring Rd, Williamstown, MA 01267

Discover the perfect canvas for your dream home on this meticulously cleared and surveyed 1+ acre lot in the picturesque Williamstown. Enjoy seasonal views of the majestic Mt. Greylock and the stunning Taconic Range, providing a serene backdrop for your future residence. With RR3 zoning, this property offers versatile options, allowing for the construction of a single or two-family dwelling, tiny

Gary Fuls Jr

RE/MAX Transitions

(413) 216-2401

1460 Cold Spring Rd, Williamstown, MA 01267
/5
$998,000
- Land
- 9 Acres
- $109,670 per Acre
19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

Selina Lamb

BIRCH PROPERTIES

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
/10
$165,000
- 6 Beds
- 3 Baths
- 1,646 Sq Ft
10 Miner St, North Adams, MA 01247

Two Family home, with one unit vacant and the other rented, providing immediate cash flow. Just minutes from downtown, MCLA, and local shopping, the location offers unbeatable convenience.The first-floor unit features two bedrooms, one bath, and an enclosed porch--perfect for morning coffee or added storage. The spacious second unit spans two levels with four bedrooms and two full baths, ideal

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 298-6352

10 Miner St, North Adams, MA 01247
/15
$110,000
- Land
- 4.62 Acres
- $23,810 per Acre
0 Dalton Division Rd, Pittsfield, MA 01201

Well located parcels with 4.2 acres of development land zoned RG with an attached .4 acre lot zoned R12. Sale includes all engineering work to date, including wetlands delineation, site plans, etc... All utilities available including water, sewer & natural gas. Possibilities include 19-20 Garden Style Apartments, 5 or 7 lot subdivision or a 3 lot ANR subdivision. Property abuts large apartment

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 366-3881

0 Dalton Division Rd, Pittsfield, MA 01201
/16
$470,000
- 8 Beds
- 6 Baths
- 8,543 Sq Ft
153 First St, Pittsfield, MA 01201

Looking to add a well-performing asset that provides you with income from day one? This six-family investment property offers investors immediate cash flow and upside potential... sitting at a 11 cap rate, this property offers a strong return on investment with room to grow based on some under market rents! This property offers a range of studio to 3-bedroom units and Off street parking.

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 728-1773

153 First St, Pittsfield, MA 01201
/3
$39,900
- Land
- 0.40 Acre
- $99,750 per Acre
90 Jones Ave, Pittsfield, MA 01201

Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

Erin Vincent

BISHOP WEST REAL ESTATE

(413) 798-8317

90 Jones Ave, Pittsfield, MA 01201
/4
$39,900
- Land
- 0.30 Acre
- $133,000 per Acre
103 Stearns Ave, Pittsfield, MA 01201

Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

Erin Vincent

BISHOP WEST REAL ESTATE

(413) 393-2149

103 Stearns Ave, Pittsfield, MA 01201
/3
$39,900
- Land
- 0.29 Acre
- $139,021 per Acre
0 Jones Ave, Pittsfield, MA 01201

Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

Erin Vincent

BISHOP WEST REAL ESTATE

(413) 798-5574

0 Jones Ave, Pittsfield, MA 01201
/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
/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
$29,900
- Land
- 2.43 Acres
- $12,305 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 your vision. Conveniently located near the Mount Greylock entrance and just minutes from all that North Berkshire has to offer, this parcel comes with town water, a completed septic design, wetlands delineation, and a full site plan within RU-1 zoning. Offered at a substantial discount due to certain

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 343-4851

20 Notch Rd, North Adams, MA 01247

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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.