Berkshire County MA Homes for Sale with Basement

/28
$329,000
- 4 Beds
- 3 Baths
- 2,276 Sq Ft
44 Main St, West Stockbridge, MA 01266

Discover the charm of downtown living in this Colonial home located in the heart of West Stockbridge. This home features four bedrooms, two full baths, kitchen, living room, dining room and a deck overlooking the river. In addition to the main living area the property also includes an in-law or studio apartment with it's own kitchen and bathroom. With a nice flat yard for outdoor activities,

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

44 Main St, West Stockbridge, MA 01266
/43
$3,850,000
- 4 Beds
- 3.5 Baths
- 4,000 Sq Ft
21A Interlaken Rd, Stockbridge, MA 01262

Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

21A Interlaken Rd, Stockbridge, MA 01262
/56
$1,490,000
- 4 Beds
- 4.5 Baths
- 3,991 Sq Ft
9 October Hill Dr, Lenox, MA 01240

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

Paula McLean PAULA MCLEAN REALTORS INC.

9 October Hill Dr, Lenox, MA 01240
/50
$360,000
- 3 Beds
- 2 Baths
- 1,916 Sq Ft
135 Allengate Ave, Pittsfield, MA 01201

This classic brick Cape-style home blends comfort, convenience, and charm. Come sit in living room and curl up in front of the fireplace on chilly days, or settle in the south facing sunroom overlooking the deep, fenced back yard The floor plan flows easily from one room to the next, connected by the inviting dining room. Two bedrooms and a full bath are on the first floor with the primary suite

Anne Meczywor ROBERTS & ASSOC. REALTY, INC

135 Allengate Ave, Pittsfield, MA 01201
/50
$499,000
- 3 Beds
- 3 Baths
- 3,228 Sq Ft
16 Opeechee St, Lanesborough, MA 01237

Welcome to this spacious and light-filled home just moments from scenic Pontoosuc Lake! Enjoy breathtaking sunrises and sunsets from your open-concept upper level, featuring soaring ceilings and expansive windows that fill the space with natural light. The beautifully updated kitchen offers ample room for dining and entertaining, complete with a breakfast bar and generous seating options--all

Laiken Rapisarda LAMACCHIA REALTY, INC

16 Opeechee St, Lanesborough, MA 01237
/43
$495,000
- 3 Beds
- 1.5 Baths
- 1,686 Sq Ft
155 Laurel St, Lee, MA 01238

This thoughtfully updated home blends warmth, comfort, and history. An amazing front porch welcomes you before you even step inside, and the short walk to downtown or quick drive to the lake offers an easy, connected Berkshire lifestyle. Inside, bright and inviting rooms and beautiful wood floors create a natural sense of warmth, while the layout makes everyday living feel effortless. Flexible

Katie Soules WILLIAM RAVEIS REAL ESTATE

155 Laurel St, Lee, MA 01238
/35
$288,900
- 2 Beds
- 2 Baths
- 1,352 Sq Ft
55 Newton Ave, Pittsfield, MA 01201

Welcome to this warm and inviting home just minutes from Pontoosuc Lake offering a comfortable layout, charming details, and a generous outdoor space. The main level features a spacious living room filled with natural light, vaulted ceilings, and an open concept into the dining area, and a beautifully updated kitchen. Conveniently, there is also a first-floor bathroom and laundry. Upstairs boasts

Jessica Rizzo LAMACCHIA REALTY, INC

55 Newton Ave, Pittsfield, MA 01201
/22
$280,000
- 6 Beds
- 2 Baths
- 2,214 Sq Ft
3 Pleasant St, Pittsfield, MA 01201

Two Family Flat fully rented in the Morningside Neighborhood! Each unit has three bedrooms and one bathroom. Updated kitchens and hardwood floors. Heat and hot water included. Washer and dryer hookups in the basement. Fully fenced in yard on a corner lot. Well maintained and ready for its new owner!

Derek Strzepa NOCHER REALTY

3 Pleasant St, Pittsfield, MA 01201
/42
$1,399,900
- 12 Beds
- 7 Baths
- 7,956 Sq Ft
45 Forest St, Lee, MA 01238

This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and

Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

45 Forest St, Lee, MA 01238
/54
$630,000
- 4 Beds
- 3 Baths
- 4,930 Sq Ft
342/344 New Ashford (Route 7) Rd, New Ashford, MA 01237

A Berkshire landmark ready for its next chapter. Once home to the beloved BONDHU and Mill on the Floss restaurants, this multi-use property offers endless opportunity -- from a charming single-family residence to a live/work haven, a boutique inn, or a luxury destination dining experience reborn. The second-floor living quarters feature four bedrooms, including a primary suite, plus an open

Stephanie Rapisarda WILLIAM PITT SOTHEBY'S - GT BARRINGTON

342/344 New Ashford (Route 7) Rd, New Ashford, MA 01237
/42
$559,000
- 3 Beds
- 2 Baths
- 1,842 Sq Ft
16 Swamp Rd, West Stockbridge, MA 01266

The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the

Vashti Poor WILLIAM RAVEIS - BERKSHIRE

16 Swamp Rd, West Stockbridge, MA 01266
/16
$235,000
- 2 Beds
- 1 Bath
- 912 Sq Ft
13 Water St, Adams, MA 01220

Just starting out or downsizing. This 2 bedroom 6 room ranch is just what you need. Located at the foot of Mt.Greylock and the Greylock Glen. Oversized, level, corner lot, with sheds, gardens, stunning mountain views and is completely reinforced strong sturdy fencing. Parking not an issue with a driveway on each side of the house plus an attached garage. Step inside to a warm cozy home. The

Barbara DeMers NOCHER REALTY

13 Water St, Adams, MA 01220
/50
$269,900
- 4 Beds
- 2 Baths
- 2,208 Sq Ft
31 Apremont St, Adams, MA 01220

Welcome to 31-33 Apremont Street in the lovely town of Adams MA. This two family duplex is an excellent opportunity for investors and owner occupied alike. The 33 side offers a bright sun filled living room and eat in kitchen on the first floor with 2 bedrooms and a full bath on the 2nd floor. The 31 side is very similar in make up with a spacious living room and eat in kitchen on the first floor

Doug Collins LAMACCHIA REALTY, INC

31 Apremont St, Adams, MA 01220
/4
$474,900
- 4 Beds
- 2 Baths
- 1,964 Sq Ft
41 Pearl St Unit 1-2, Great Barrington, MA 01230

Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, containing that classic period charm.Step inside to discover a welcoming floor plan with ample natural light, hardwood floors, and

David Carlson FAIRGROUND REAL ESTATE, INC

41 Pearl St Unit 1-2, Great Barrington, MA 01230
/70
$2,250,000
- 4 Beds
- 6 Baths
- 4,846 Sq Ft
302 Egremont Plain Rd, Great Barrington, MA 01230

A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with the Green River just beyond.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

302 Egremont Plain Rd, Great Barrington, MA 01230
/35
$434,900
- 2 Beds
- 1 Bath
- 1,182 Sq Ft
245 Long Pond Rd, Great Barrington, MA 01230

Tucked away on a quiet country road just minutes from downtown Great Barrington, this charming single-level ranch offers the perfect Berkshire retreat. Set on two private acres, the home is surrounded by mature trees and natural beauty- with nearby access to trails. Step inside to a bright interior featuring a spacious living room anchored by a beautiful stone fireplace. The kitchen offers crisp

Jessica Rizzo Lamacchia Realty, Inc.

245 Long Pond Rd, Great Barrington, MA 01230
/32
$1,395,000
- 5 Beds
- 4 Baths
- 4,200 Sq Ft
6 Thrushwood Ln, Great Barrington, MA 01230

MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

6 Thrushwood Ln, Great Barrington, MA 01230
/53
$3,750,000
- 5 Beds
- 7.5 Baths
- 6,022 Sq Ft
2650 Swamp Rd, Richmond, MA 01254

April Hill, an exquisite 1850 Greek Revival masterpiece. This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate

Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

2650 Swamp Rd, Richmond, MA 01254
/12
$485,000
- 1 Bed
- 1 Bath
- 1,344 Sq Ft
2 Devon Rd, Lee, MA 01238

Bring your contractors and your imagination to this unique fixer-upper, an old carriage barn with an attached apartment. The spacious barn features original beams with large open areas. The lush grounds are complemented by charming rock walls and rustic outbuildings. With a convenient location close to all the Berkshire attractions, this property is ideal for transformation into a one-of-a-kind

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

2 Devon Rd, Lee, MA 01238
/28
$360,000
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
194 Canaan Southfield Rd, Southfield, MA 01259

Enjoy peaceful country living in this 3-bedroom, 2-bath home set on 8.6 scenic acres along the Umpachene River and surrounded by abundant wildlife. The property offers endless potential for gardening, recreation, or creating your private retreat. Solar panels are included and will be paid off at closing, providing long-term energy savings. Conveniently located near the Southfield Store, The Old

Freddy Friedman BIRCH PROPERTIES

194 Canaan Southfield Rd, Southfield, MA 01259
/42
$2,500,000
- 4 Beds
- 5 Baths
- 6,100 Sq Ft
60 Old Cheshire Rd, Lanesborough, MA 01237

BREATHTAKING 360 DEGREE VIEWS Rarely does such a magical property come along with so much to offer. A well built and spacious home with Pickle Ball, Tennis, Swimming Pool, Gazebo, Lake frontage, Lush Green Lawn, Pastures, A Three Car Garage, Outbuildings, VIEWS FROM EVERY ROOM. Kitchen has Sub-Zero refrigerator, Wolf cooktop, large center island and a wall of windows overlook the gorgeous gardens

Mauren White-Kirkby Berkshire Hathaway Home Services Barnbrook Realty

60 Old Cheshire Rd, Lanesborough, MA 01237
/28
$650,000
- 2 Beds
- 2 Baths
- 1,098 Sq Ft
46 Housatonic St Unit 2B, Lenox, MA 01240

Beautiful two bedroom, two bath condo perfectly situated in the center of Lenox, Massachusetts-the cultural heart of the Berkshires. Enjoy high Ceilings, beautiful wood floors, large windows, and abundant natural light throughout. The spacious layout features a gas fireplace, granite countertops, and a gas stove in the modern kitchen. The inviting living room opens to a private balcony, perfect

Patricia Andrew STONE HOUSE PROPERTIES, LLC

46 Housatonic St Unit 2B, Lenox, MA 01240
/32
$549,000
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
7 Park St, Stockbridge, MA 01262

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The

Samantha Homeyer BIRCH PROPERTIES

7 Park St, Stockbridge, MA 01262
/46
$375,000
- 3 Beds
- 1 Bath
- 1,413 Sq Ft
2801 State Rd, Richmond, MA 01254

You'll feel right at home in this charming Richmond farmhouse, just minutes from West Stockbridge center and close to everything the Berkshires has to offer. Set on two beautiful, private acres in the historic Richmond Furnace district, this three-bedroom house blends New England charm with modern amenities, including energy-efficient solar panels, newer appliances, and Buderus boiler. The main

Stephen Daoust STONE HOUSE PROPERTIES, LLC

2801 State Rd, Richmond, MA 01254
/35
$275,000
- 7 Beds
- 3 Baths
- 2,664 Sq Ft
86 W Main St, North Adams, MA 01247

Turnkey 3-family in the heart of North Adams! Features two 3-bedroom, 1-bath units and a renovated basement studio. 2nd floor unit is vacant with potential rent $1,400–$1,600/month. 3rd floor unit tenant moving out; after updates can rent $1,600/month. Basement studio rented $1,000/month. All units separately metered; tenants pay all utilities except water. Large unfinished attic (~1,200 sq ft)

Monette Valliere Keller Williams Elite

86 W Main St, North Adams, MA 01247
/50
$7,975,000
- 8 Beds
- 6.5 Baths
- 9,364 Sq Ft
399 Under Mountain Rd, Lenox, MA 01240

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

399 Under Mountain Rd, Lenox, MA 01240
/55
$4,300,000
- 7 Beds
- 8 Baths
- 5,885 Sq Ft
8 Webster Rd, Tyringham, MA 01264

Brooke Astor's COBBLE HOUSEWhere Land, Light, and Legacy ConvergeTYRINGHAM VALLEY BERKSHIRE COUNTY MASSACHUSETTS$4,300,0005,885 square feet7 bedrooms8.5 bathrooms27.9 private acres1909 Harrie T. Lindeberg design2,321 +/- feet road frontageThe Valley That Time ForgotThe drive through Tyringham Valley never fails to quiet the soul. Past stone walls that have marked these fields for centuries,

John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

8 Webster Rd, Tyringham, MA 01264
/31
$349,900
- 4 Beds
- 3 Baths
- 2,320 Sq Ft
74 Washington Ave, North Adams, MA 01247

Completely renovated 4-bedroom home in North Adams, near MCLA. Newly renovated kitchen and bathrooms with new cabinets, quartz countertops, and all new appliances. New flooring throughout. The first floor offers the kitchen, a full bathroom, an office, a large open living room/dining area, and an entry with beautiful staircase to second floor. The second floor features three bedrooms, a second

Allison Pacelli PACELLI ZEPKA

74 Washington Ave, North Adams, MA 01247
/68
$1,350,000
- 5 Beds
- 4.5 Baths
- 4,948 Sq Ft
65 Crofut St, Pittsfield, MA 01201

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5

Conor Meehan STONE HOUSE PROPERTIES, LLC

65 Crofut St, Pittsfield, MA 01201
/28
$495,000
- 4 Beds
- 2 Baths
- 1,531 Sq Ft
95 Water Farm Rd, Sheffield, MA 01257

New roof, siding, and house fully painted. Newer heating system. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanics. This home is truly move-in ready. The stonework patio

Suzann Ward HOUSATONIC REAL ESTATE

95 Water Farm Rd, Sheffield, MA 01257
/36
$229,900
- 3 Beds
- 2 Baths
- 1,454 Sq Ft
156 Elizabeth St, Pittsfield, MA 01201

Charming 2-Family Flat - Great Investment or Owner-Occupied Opportunity!Don't miss this 2-family flat offering classic charm and modern convenience. Each spacious unit features hardwood floors The second-floor unit boasts an enclosed porch--perfect for relaxing or additional living space. Separate utilities, off street parking and shed add to the property. This property has potential to be used

Robin Moore 413 REAL ESTATE

156 Elizabeth St, Pittsfield, MA 01201
/73
$889,900
- 5 Beds
- 3.5 Baths
- 3,370 Sq Ft
5 Crofut St, Pittsfield, MA 01201

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

5 Crofut St, Pittsfield, MA 01201
/64
$1,199,800
- 9 Beds
- 4.5 Baths
- 5,319 Sq Ft
5 Crofut St, Pittsfield, MA 01201

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, Upstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

5 Crofut St, Pittsfield, MA 01201
/42
$489,000
- 3 Beds
- 3 Baths
- 1,716 Sq Ft
190 Willow St, Lee, MA 01238

: Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare

Kim Bergland RED HORSE REAL ESTATE, LLC

190 Willow St, Lee, MA 01238
/43
$1,290,000
- 5 Beds
- 4.5 Baths
- 2,900 Sq Ft
228 East St, Great Barrington, MA 01230

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort.Property Highlights5 Bedrooms | 4 Full Baths + 1 Half Bath**Complex rebuild from the ground up** - preserved nod to the town's heritage with a

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

228 East St, Great Barrington, MA 01230
/55
$3,500,000
- 5 Beds
- 6.5 Baths
- 6,088 Sq Ft
110 Alford Rd, Great Barrington, MA 01230

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside,

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

110 Alford Rd, Great Barrington, MA 01230
/80
$995,000
- 5 Beds
- 4.5 Baths
- 4,102 Sq Ft
1030 Simonds Rd, Williamstown, MA 01267

Escape to your own private retreat in Williamstown, 'The Village Beautiful.' This spacious 5-bedroom, 4.5-bath home sits on 7.5 private acres and offers over 4,000 sq. ft. of living space throughout three levels, plus a finished basement with full bath and sauna. This home blends classic and modern features: exposed wood beam ceilings and a new, private primary suite with soaking tub. The home

Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB

1030 Simonds Rd, Williamstown, MA 01267
/33
$464,000
- 5 Beds
- 2 Baths
- 3,062 Sq Ft
103 Holmes Rd, Hinsdale, MA 01235

The Woolen House stands as a rare piece of prestigious Hinsdale history. Once the home of the Woolen Mill superintendent, it has been fully reimagined for modern living. The craftsmanship is unmistakable: original woodwork, 16 inch brick construction, and a sense of permanence rarely found today. Inside, five bedrooms, two full bathrooms, a spacious laundry, and a versatile first floor room offer

Harmony Edwards KELLER WILLIAMS REALTY

103 Holmes Rd, Hinsdale, MA 01235
/39
$759,000
- 3 Beds
- 2.5 Baths
- 2,381 Sq Ft
103 Alpine Trail, Pittsfield, MA 01201

Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open

Cortney Dupont COHEN & WHITE ASSOCIATES

103 Alpine Trail, Pittsfield, MA 01201
/70
$849,000
- 3 Beds
- 3 Baths
- 3,204 Sq Ft
211 Cottage St, Housatonic, MA 01236

Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

211 Cottage St, Housatonic, MA 01236

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