5-Bedroom Homes for Sale in Berkshire County MA

/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
/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
/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
/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
/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
/82
$2,550,000
- 6 Beds
- 6.5 Baths
- 7,143 Sq Ft
13 Taconic Ave, Lenox, MA 01240

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

13 Taconic Ave, 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
/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
/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
/69
$5,900,000
- 11 Beds
- 10 Baths
- 9,748 Sq Ft
25 W Sheffield Rd, Great Barrington, MA 01230

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

Lauren Molk ELYSE HARNEY REAL ESTATE

25 W Sheffield Rd, Great Barrington, MA 01230
/20
$3,995,000
- 15 Beds
- 15 Baths
- 11,945 Sq Ft
615 Laurel St, Lee, MA 01238

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

Pamela J Long EAST COAST INN BROKERS

615 Laurel St, Lee, MA 01238
/58
$4,995,000
- 7 Beds
- 8 Baths
- 13,261 Sq Ft
319 Under Mountain Rd, Lenox, MA 01240

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

319 Under Mountain Rd, Lenox, MA 01240
/64
$1,900,000
- 5 Beds
- 4.5 Baths
- 4,500 Sq Ft
355 Adsit Crosby Rd, New Marlborough, MA 01230

Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with

Cortney Dupont COHEN & WHITE ASSOCIATES

355 Adsit Crosby Rd, New Marlborough, MA 01230
/32
$1,250,000
- 5 Beds
- 5.5 Baths
- 4,645 Sq Ft
7 Perry Rd, Sandisfield, MA 01255

WHERE EVERY SEASON FEELS LIKE HOME16 acres at the end of a quiet country road where your shoulders drop the moment you arrive. This five bedroom retreat with over 4,600 square feet gets Berkshire living right: soaring great room with fireplace, granite kitchen, four-season sunroom, and that incredible finished lower level with radiant floors, full bar, and walkout to covered patio. Mudroom with

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

7 Perry Rd, Sandisfield, MA 01255
/39
$1,650,000
- 5 Beds
- 3 Baths
- 3,043 Sq Ft
593 Lakeway Dr, Pittsfield, MA 01201

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

Janet Benoit Janet L. Benoit

593 Lakeway Dr, Pittsfield, MA 01201
/44
$1,800,000
- 5 Beds
- 3.5 Baths
- 3,768 Sq Ft
307 Stanley Rd, Otis, MA 01253

Welcome to this Berkshire Waterfront Paradise! With amazing lake and sunset views this home has it all. Five bedrooms all with lake views. Your family and friends will find the total relaxation the Berkshires can offer. Whether it's a swim, paddle, fishing or a water ski on the lake it's all just steps out the door. The beautiful stone fireplace sores to compliment this open space and provides a

David St. Laurent BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS OTIS

307 Stanley Rd, Otis, MA 01253
/40
$1,240,000
- 5 Beds
- 4.5 Baths
- 3,100 Sq Ft
60 Parsley Ln, Sheffield, MA 01257

This newly constructed 5-bedroom farmhouse is priced well below the current cost to build per square foot--truly an exceptional value! Tucked away in a well-established neighborhood convenient to both the Berkshires and Litchfield Connecticut, this energy-efficient home features spray foam insulation and a ductless AC/heat pump system. The open kitchen/dining area is filled with natural light,

Vashti Poor LANCE VERMEULEN RE, INC

60 Parsley Ln, Sheffield, MA 01257
/33
$1,500,000
- 7 Beds
- 7.5 Baths
- 4,000 Sq Ft
802 State Rd, Richmond, MA 01254

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see

Diana Bisselle William Pitt Sotheby's Int'l

802 State Rd, Richmond, MA 01254
/16
$1,800,000
- 40 Beds
- 20 Baths
- 30,000 Sq Ft
15 East St, Stockbridge, MA 01262

Located in a Sngle Family zoned area on a desirablle, private parcel consisting of nine total buildings with an in-ground pool amongst other amenities. Property is available for sale, lease or equity investment by new partners. This is an amazing property on the border of Stockbridge and Lenox with close proximity to Albany / Hartford / I-91. Many opportunities for possible hotel, B&B, family

Tim Damon Mercury Real Estate

15 East St, Stockbridge, MA 01262
/81
$1,195,000
- 5 Beds
- 2.5 Baths
- 3,087 Sq Ft
18 Old Farm Ln, Pittsfield, MA 01201

Newly Constructed Farmhouse Style Home in coveted Woodmonte Estates central to all Berkshire attractions. Over the bridge into the woods escape to a magical setting amidst a woodland preserve of 2+ acres. Build a family compound of your own with 1 extra homesites to create your dreams with incredible peace and privacy yet all city conveniences. Unique living to mingle in a community with

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

18 Old Farm Ln, Pittsfield, MA 01201
/52
$1,295,000
- 5 Beds
- 3.5 Baths
- 4,000 Sq Ft
82 West Ave, Great Barrington, MA 01230

Classic turn-of-the-century Berkshire residence on the Hill. Rich w/ history & ready for new memories, this home is a rare gem in an ideal location. Lovingly maintained by the same family for over 60 yrs. Nestled on 1.6 acres, this 4,000 SF residence offers 5 BRs, 3.5 BAs & an abundance of historic charm. Original wood floors, high ceilings & period details fill the home, while the grand

Claire Pollart LANCE VERMEULEN RE, INC

82 West Ave, Great Barrington, MA 01230
/40
$1,590,000
- 11 Beds
- 12.5 Baths
- 8,134 Sq Ft
518 Main St, Great Barrington, MA 01230

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved

Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

518 Main St, Great Barrington, MA 01230
/41
$1,800,000
- 22 Beds
- 21 Baths
- 9,018 Sq Ft
885 Washington Mountain Rd, Washington, MA 01223

The Possibilities are endless! Family Compound & Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl

Joy Salvini RE/MAX Compass

885 Washington Mountain Rd, Washington, MA 01223
/41
$1,450,000 New Construction
- 5 Beds
- 3.5 Baths
- 3,978 Sq Ft
37 Old Farm Ln, Pittsfield, MA 01201

LOOK AT THIS! Did you know you may qualify for construction loans with VA, FHA, or even with less than 20% down? Your dream home is just a build away! Imagine living in a modern oasis surrounded by nature — where space, comfort, and serenity come together in perfect harmony. This TO BE BUILT home at 37 Old Farm Ln offers nearly 4,000 sqft of luxurious living with 5 bedrooms, 4.5 baths, a sunlit

Mg Group Century 21 North East

37 Old Farm Ln, Pittsfield, MA 01201
/26
$177,000
- 23 Beds
- 13 Baths
- 14,514 Sq Ft
Unlisted Address

Rare chance to own three historic homes, two iconic Queen Anne Victorians (''The Grand Dames'') and a former Baptist Parsonage, plus an additional lot in North Adams' Church Street Historic District. These 1800s-era properties feature original brick and granite masonry, hand-carved woodwork, grand staircases, fireplaces, pocket doors, and soaring ceilings. All require full renovation, offering a

Pam Tworig BISHOP WEST REAL ESTATE

Unlisted Address
/30
$67,000
- 10 Beds
- 3 Baths
- 6,076 Sq Ft
124 Church St, North Adams, MA 01247

Discover a rare opportunity to restore this architecturally significant home in the heart of downtown North Adams, nestled within the iconic Church Street Historic District. Known locally as one of The Grand Dames, two circa-1800s Queen Anne Victorians--This stately residence, while in need of full renovation, boasts extraordinary craftsmanship and historic detail throughout, including:elaborate

Pam Tworig BISHOP WEST REAL ESTATE

124 Church St, North Adams, MA 01247
/27
$53,000
- 7 Beds
- 6 Baths
- 4,244 Sq Ft
116 Church St, North Adams, MA 01247

Discover a rare opportunity to restore this architecturally significant home in the heart of downtown North Adams and nestled within the iconic Church Street Historic District. Known locally as one of The Grand Dames, two circa-1800s Queen Anne Victorians--This stately residence, while in need of full renovation, boasts extraordinary craftsmanship and historic detail throughout,

Pam Tworig BISHOP WEST REAL ESTATE

116 Church St, North Adams, MA 01247
/19
$42,000
- 6 Beds
- 3.5 Baths
- 4,194 Sq Ft
130 Church St, North Adams, MA 01247

Discover a rare opportunity to restore this historically significant home in downtown North Adams. Nestled in the iconic Church Street Historic District, this stately residence was once a Baptist Parsonage. While in need of full renovation, it boasts extraordinary craftsmanship and historic detail, including wonderful fireplaces, beautiful woodwork and very high ceilings. Ideally located in a

Pam Tworig BISHOP WEST REAL ESTATE

130 Church St, North Adams, MA 01247
/43
$367,000
- 5 Beds
- 2 Baths
- 1,716 Sq Ft
132 S Washington State Rd, Washington, MA 01223

A very special 15+ acre historic property with hidden delights. A 1930 Colonial w/ a brand new septic system & delightful Art Deco features sprinkled throughout. This home has 4 original bedrooms & a full bath upstairs, w/ a large bedroom & spacious full bath downstairs as part of a newer addition. The addition includes a deck to the back yard, a laundry room & a large basement 1 car garage. The

Lisa Peltier ROBERTS & ASSOC. REALTY, INC

132 S Washington State Rd, Washington, MA 01223
/54
$979,000
- 5 Beds
- 4.5 Baths
- 2,800 Sq Ft
850 Summer St, Lee, MA 01238

Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

Katie Williams STONE HOUSE PROPERTIES, LLC

850 Summer St, Lee, MA 01238
/56
$979,000
- 5 Beds
- 4.5 Baths
- 2,800 Sq Ft
850 Summer St Unit M14, Lee, MA 01238

Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

Katie Williams STONE HOUSE PROPERTIES, LLC

850 Summer St Unit M14, Lee, MA 01238
/7
$595,000
- 17 Beds
- 4 Baths
- 13,608 Sq Ft
20 Wesleyan St, North Adams, MA 01247

Fully operating, long term tenants, lot for parking, each apartment has its own forced hot air furnace and gas hot water tank. Many updates including new roof in 2015, basement engineered fortified, new furnaces over the years. 3 stalls of storage space. Tenants pay their own utilities. The building was repainted last summer,2024.

David White OwnerEntry.com

20 Wesleyan St, North Adams, MA 01247
/41
$179,900
- 8 Beds
- 5 Baths
- 3,324 Sq Ft
233 1st St, Pittsfield, MA 01201

MAKE YOUR HIGHEST & BEST! Ready to rehab! This legal 5 family home spans over 3,000 sqft. First floor offers 2 one-bedroom units on left and right side of the building as well as a small efficiency unit with plumbing ready for kitchen and existing full bath. Second floor offers two 3-bedroom units including the 3rd bedroom on third floor plus storage space. hardwood floors ready to be restored.

Xavier Cruz Fathom Realty

233 1st St, Pittsfield, MA 01201
/53
$695,000
- 6 Beds
- 5 Baths
- 4,572 Sq Ft
604 Sheffield Plain, Sheffield, MA 01257

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and

Tony Segalla LANCE VERMEULEN RE, INC

604 Sheffield Plain, Sheffield, MA 01257
/6
$75,000
- 12 Beds
- 5 Baths
- 4,032 Sq Ft
48 Brown St, Pittsfield, MA 01201

Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered.

Xavier Cruz Fathom Realty

48 Brown St, Pittsfield, MA 01201
/12
$175,000
- 6 Beds
- 2 Baths
- 2,128 Sq Ft
242 Wahconah St, Pittsfield, MA 01201

Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd & 48 Brown st

Xavier Cruz Fathom Realty

242 Wahconah St, Pittsfield, MA 01201
/40
$589,500
- 5 Beds
- 3 Baths
- 3,576 Sq Ft
210 Pine Cone Ln, Hinsdale, MA 01235

Lake Front Living at its Best!! Welcome to 210 Pine Cone Lane in Hinsdale. This condominium is one of the most well appointed units and has been tastefully renovated and maintained throughout the years and it shows. As you enter the home you are warmly greeted by an open concept living area that is just flooded with natural light, spectacular lake views, high ceilings, propane fireplace, a

Doug Collins Lamacchia Realty, Inc.

210 Pine Cone Ln, Hinsdale, MA 01235
/10
$98,900
- 5 Beds
- 2 Baths
- 2,460 Sq Ft
135 E Quincy St, North Adams, MA 01247

Charming 5-bed, 2-bath historic home (2,460 sq ft) built in 1900, nestled on a .09-acre lot in a vibrant North Adams neighborhood. Features durable slate roofing, vinyl siding, and a spacious unfinished basement. Oil-fired hot water heat keeps it cozy, and the frame-style architecture offers character and charm. Excellent location near schools, downtown amenities, and cultural attractions like

Derek Greene The Greene Realty Group

135 E Quincy St, North Adams, MA 01247
/24
$569,000
- 5 Beds
- 3.5 Baths
- 3,307 Sq Ft
867 Notch Rd, Cheshire, MA 01225

A charming, spacious Colonial with privacy, and lovely grounds. Breathtaking mountain views. Built in 2005 and set on 7.25 acres, this 5-bedroom, 4.5-bathroom residence offers 3,307 square feet of living space. Two primary suites, one up and one down. The open-concept kitchen flows seamlessly into a great room, perfect for entertaining. This home does need work but is priced accordingly. Make

Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

867 Notch Rd, Cheshire, MA 01225

Showing Results 1 - 40, Page 1 of 4

Massachusetts Berkshire County

How to Buy a Home How to Finance a Home How to Sell a Home

Berkshire County Types of Homes for Sale

Berkshire County Real Estate Listings

More About Living in Berkshire County

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage