Berkshire County MA Homes for Sale with AC

/32
$779,000
- 3 Beds
- 2 Baths
- 1,771 Sq Ft
165 Maple Ave Unit D, Great Barrington, MA 01230

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless

Tony Segalla WILLIAM RAVEIS - BERKSHIRE

165 Maple Ave Unit D, Great Barrington, MA 01230
/40
$384,000
- 3 Beds
- 1.5 Baths
- 1,677 Sq Ft
20 Moscow Rd, West Stockbridge, MA 01266

Short walk to quaint downtown West Stockbridge featuring local coffee shop, variety store, restaurants and shops. Just a few minutes to local theatres, music venues, Tanglewood, historic Stockbridge, and the Mass Pike. Beautiful open yard great for summer entertaining including cookouts, yard games or just relaxing and reading a book! Cozy fireplace for those beautiful snowy New England nights.

Mark Harris SIGNATURE ASSOCIATES

20 Moscow Rd, West Stockbridge, MA 01266
/60
$4,950,000
- 7 Beds
- 8.5 Baths
- 7,073 Sq Ft
1 Pinecroft Dr, Lenox, MA 01240

Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two primary en suite bedrooms with cedar closets. Lower level: gym,

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1 Pinecroft Dr, Lenox, MA 01240
/30
$319,900
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
37 Corey Rd Unit 14, Hancock, MA 01237

Enjoy the ultimate convenience of living at a ski resort, with easy access to slopes, hiking trails, mountain biking, dining, and other resort amenities right at your doorstep. Wood burning fireplace will keep you warm on those cold winter nights. Embrace the year-round mountain lifestyle in this exceptional 3-bedroom, 2-full-bath home, ideally situated for both adventure and relaxation. Nestled

Kevin Moderski JIMINY REALTY

37 Corey Rd Unit 14, Hancock, MA 01237
/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
/48
$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
/32
$659,999
- 3 Beds
- 3 Baths
- 1,968 Sq Ft
9102 Mountainside Dr, Hancock, MA 01237

Step into this beautifully updated 3-bedroom, 3-bathroom retreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and

Kevin Moderski JIMINY REALTY

9102 Mountainside Dr, Hancock, MA 01237
/22
$264,900
- 4 Beds
- 2 Baths
- 2,132 Sq Ft
50 John St, Pittsfield, MA 01201

This fully rented two-family home was renovated in the last two years! Improvements include roof, windows, flooring, painting, and more! The home offers an enclosed front porch to access both units, and a side porch for each apartment independently. Each unit features living room, dining room, kitchen, 2 bedrooms and 1 bath. There is separate heat, hot water and electric: Unit 52 has natural gas

Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

50 John St, Pittsfield, MA 01201
/53
$3,750,000
- 4 Beds
- 3.5 Baths
- 3,225 Sq Ft
40 E Alford Rd, West Stockbridge, MA 01266

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

40 E Alford Rd, West Stockbridge, MA 01266
/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
/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
/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
/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
/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
/14
$143,000
- 1 Bed
- 1 Bath
- 500 Sq Ft
37 Corey Rd Unit 623, Hancock, MA 01237

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no

Kevin Moderski JIMINY REALTY

37 Corey Rd Unit 623, Hancock, MA 01237
/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
/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
/17
$199,000
- 1 Bed
- 1 Bath
- 304 Sq Ft
447 Notch Rd, North Adams, MA 01247

This thoughtfully designed tiny home features super-insulated construction for year-round comfort, exceptional energy efficiency, and a low carbon footprint. Large windows fill the space with natural light while maximizing its smart cozy layout. Set on a lovely lot along scenic Notch Road, the property offers privacy, natural beauty, and room to enjoy the outdoors. Just minutes from downtown

Patricia Andrew STONE HOUSE PROPERTIES, LLC

447 Notch Rd, North Adams, MA 01247
/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
/44
$3,900,000
- 10 Beds
- 5.5 Baths
- 11,200 Sq Ft
535 Main Rd, Monterey, MA 01245

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard

Steven Weisz William Pitt Sothebys Intn'l

535 Main Rd, Monterey, MA 01245
/16
$130,000
- 1 Bed
- 1 Bath
- 330 Sq Ft
19 N Church St Unit 12, North Adams, MA 01247

Come see a part of the distinguished flat iron building in the historic Eagle St area of North Adams! Comes fully furnished, and a fully functioning Airbnb. Separate bedroom and sitting area. Tastefully decorated! Perfect to add to your portfolio or live in! 330 sqft, perfect for a nice getaway to experience Mass MoCA, shopping, restaurants, and all downtown North Adams has to offer!

Susan Colvin MONARCH REALTY, INC.

19 N Church St Unit 12, North Adams, MA 01247
/60
$1,250,000
- 3 Beds
- 2.5 Baths
- 2,204 Sq Ft
905 West Rd, Great Barrington, MA 01230

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

905 West Rd, Great Barrington, MA 01230
/12
$215,000
- 4 Beds
- 1 Bath
- 1,310 Sq Ft
2 Valley St, Adams, MA 01220

Step into this vintage gem that beautifully preserves its original charm while showcasing thoughtful modern updates throughout. You'll appreciate the brand-new siding that enhances curb appeal, updated windows that offer improved energy efficiency, and stylish new flooring that ties each room together. Whether you're drawn to the character of yesteryear or the convenience of today’s upgrades,

Laura Poulin-Harkins Century 21 XSELL REALTY

2 Valley St, Adams, MA 01220
/52
$1,900,000
- 4 Beds
- 3 Baths
- 2,976 Sq Ft
1269 Clayton Mill River Rd, New Marlborough, MA 01259

Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of

Lisa Hoe THE KINDERHOOK GROUP

1269 Clayton Mill River Rd, New Marlborough, MA 01259
/29
$649,000
- 4 Beds
- 2 Baths
- 3,000 Sq Ft
783 Main St, Great Barrington, MA 01230

Renovated, well-maintained, multi-use building perfect for a live-work situation in prime location! All 4 floors offer opportunity for offices, a studio, storage, retail showroom and more! Highlights include: a large parking lot, handicap accessible ramp, 2 half baths & finished 3rd floor attic. Finished basement w/ vault & video security system. The current retail space is bright & sunny with a

Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

783 Main St, Great Barrington, MA 01230
/47
$585,000
- 2 Beds
- 2.5 Baths
- 1,935 Sq Ft
19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry

Cortney Dupont COHEN & WHITE ASSOCIATES

19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
/77
$4,500,000
- 5 Beds
- 5.5 Baths
- 4,027 Sq Ft
19 Roberts Rd, Sandisfield, MA 01255

Introducing  FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand between your home, overlooking your private

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

19 Roberts Rd, Sandisfield, MA 01255

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