Homes for Sale near Monument Mountain Regional High School

/35
$525,000
- 3 Beds
- 1 Bath
- 1,075 Sq Ft
6 Locust St, Great Barrington, MA 01230

Tucked away in a walkable east-side neighborhood of Great Barrington, this custom 3-bedroom bungalow is anything but ordinary. From the moment you step inside, the care and creativity in every corner are impossible to miss--handcrafted woodwork, thoughtful built-ins, and artful finishes infuse the home with a personality all of its own.The inviting and cozy open floor plan make everyday living

Paige Paluch LANCE VERMEULEN RE, INC

6 Locust St, Great Barrington, MA 01230
/3
$95,000
- Land
- 2.92 Acres
- $32,534 per Acre
0 Hemlock Hill Rd, Great Barrington, MA 01230

PREMIERE LOCATION JUST FIVE MINUTES FROM MAIN STREET. Good percs. Building site cleared. Rough driveway in. Electricity easily accessible. An excellent investment in the ''boom town'' of the Berkshires.

Tom Lynch COMPASS MASSACHUSETTS , LLC GB

0 Hemlock Hill Rd, Great Barrington, MA 01230
/15
$649,000
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
17 Beachwood Dr, Stockbridge, MA 01262

Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves.Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents enjoy steps to a private beach,

Franz Forster FRANZ J. FORSTER R. E.

17 Beachwood Dr, Stockbridge, MA 01262
/20
$595,000
- Land
- 8.1 Acres
- $73,457 per Acre
11 Roger Rd, Great Barrington, MA 01230

A rare opportunity to own a versatile 8+ acre parcel in a prime Great Barrington location. Accessed by an established roadway, this property presents a unique canvas for a private estate, a multi-home development, or a commercial enterprise. The property features a substantial 3,000 square foot building with radiant heat. With three large garage bays, an office, and a loft, it can serve as the

Tony Segalla LANCE VERMEULEN RE, INC

11 Roger Rd, Great Barrington, MA 01230
/19
$550,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
15 W Stockbridge, Stockbridge, MA 01262

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect

C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

15 W Stockbridge, Stockbridge, MA 01262
/38
$600,000
- 2 Beds
- 4 Baths
- 1,870 Sq Ft
19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262

WHITE PINES IN STOCKBRIDGE Tasteful 2 bed 2 full and 2 half bath home offers generous great room with windows showcasing beautiful views. Wood burning fireplace graces open living/dining room with beautiful hardwood floors. Large en-suite primary has spa-like bath. Community amenities include private beach at Stockbridge Bowl, indoor pool, HarTru tennis courts and fitness center. Covered parking.

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262
/6
$500,000
- Land
- 0.66 Acre
- $757,565 per Acre
185 A State Rd, Great Barrington, MA 01230

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success,

Tony Segalla LANCE VERMEULEN RE, INC

185 A State Rd, Great Barrington, MA 01230
/6
$1,000,000
- Land
- 1.07 Acres
- $934,583 per Acre
185 State Rd, Great Barrington, MA 01230

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include two oversized curb cuts for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success,

Tony Segalla LANCE VERMEULEN RE, INC

185 State Rd, Great Barrington, MA 01230
/6
$500,000
- Land
- 0.41 Acre
- $1,219,485 per Acre
185 B State Rd, Great Barrington, MA 01230

A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success,

Tony Segalla LANCE VERMEULEN RE, INC

185 B State Rd, Great Barrington, MA 01230
/30
$435,000
- 3 Beds
- 1 Bath
- 1,025 Sq Ft
8 Stillwell St, Great Barrington, MA 01230

Enjoy one-level living in downtown Great Barrington! This charming 3-bed, 1-bath mid-century ranch is your perfect Berkshire retreat. Nestled on a quiet cul-de-sac, the home sits on a spacious 0.41-acre lot with mature trees. Features include an attached 2-car garage/workshop, large private yard, original wood floors and an updated heating system. The real gem? Unique B2 zoning allows for a home

Tony Segalla LANCE VERMEULEN RE, INC

8 Stillwell 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

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 closet. The second

Cortney Dupont COHEN & WHITE ASSOCIATES

19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
/52
$675,000
- 3 Beds
- 3 Baths
- 1,708 Sq Ft
416 Monterey Rd, Great Barrington, MA 01230

This charming ranch is in great condition, perfect for easy one-level living! This well-maintained home features numerous updates, including modern flooring, and newer mechanicals. The open floor plan offers a comfortable flow from the bright living room to the dining area and updated kitchen. Enjoy the convenience of everything on one level--no stairs! Ideal for anyone seeking a move-in-ready

Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

416 Monterey Rd, Great Barrington, MA 01230
/37
$495,000
- 3 Beds
- 2 Baths
- 1,992 Sq Ft
35 Mechanic St, Great Barrington, MA 01230

Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system, fully owned, brings energy efficiency and

Christine Martin COMPASS MASSACHUSETTS , LLC GB

35 Mechanic St, Great Barrington, MA 01230
/31
$649,000
- 3 Beds
- 1.5 Baths
- 1,600 Sq Ft
77 Grove St, Great Barrington, MA 01230

LOCATION LOCATION LOCATION! Nestled on a quiet dead-end street near the Great Barrington Food Co-op and River Walk, this beautifully maintained Victorian blends charm and convenience. Inside, you'll find many original details, including hardwood floors, classic moldings, and a welcoming wrap-around front porch. The updated kitchen features a cozy breakfast nook, and very recent improvements

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

77 Grove St, Great Barrington, MA 01230
/43
$650,000
- 3 Beds
- 2 Baths
- 1,618 Sq Ft
2 Lake Ave, Great Barrington, MA 01230

WONDERFUL CONTEMPORARY HOME '' ON THE HILL'' IN GB. CONSIDERED ONE OF GB'S MOST DESIRED AREAS. ENJOY THE CONVENIENCE OF BEING CENTRALLY LOCATED TO SHOPPING, RESTAURANTS, AND ENTERTAINMENT ARE JUST WALKING DISTANCE TO ONE OF NEW ENGLAND'S BEST DOWNTOWN AREAS.THIS OPEN CONCEPTED HOME OFFERS GREAT NATURAL LIGHT AND THE ABILITY AND OPPORTUNITY TO COMMUNE AND ENTERTAIN.THREE BEDROOMS- MAIN BEDROOM

David Carlson FAIRGROUND REAL ESTATE, INC

2 Lake Ave, Great Barrington, MA 01230
/3
$315,000
- Land
- 14.74 Acres
- $21,370 per Acre
0 E Alford Rd, West Stockbridge, MA 01266

Beautiful and pristine 14.7 acre lot, family owned since 1963. 3-4 acres are an open field; a former Christmas tree farm. Rear portion of property is largely wooded with a stream. This area of East Alford Road has many million dollar plus homes. Perfect lot to build your tranquil dream home. Lot was perc tested in 2007. 10 Minutes to the center of West Stockbridge, 15 minutes to Great

Matt DeLucia William Pitt Sotheby's International Realty

0 E Alford Rd, West Stockbridge, MA 01266
/54
$2,500,000
- 5 Beds
- 4.5 Baths
- 5,233 Sq Ft
55 Main St, Stockbridge, MA 01262

Historic Elegance Reimagined!Wellness-forward design. Artisan craftsmanship. In-town privacy.A Kitchen Rebuilt from the Ground Up: At the heart of the home, a brand-new chef's kitchen makes a bold, refined statement with honed dark gray granite countertops, crisp white shaker cabinetry, and minimalist matte black fixtures. Oversized divided-light windows flood the space with natural light, while

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

55 Main St, Stockbridge, MA 01262
/34
$1,795,000
- 4 Beds
- 4 Baths
- 3,524 Sq Ft
1 Old Tree Farm Rd, Stockbridge, MA 01262

Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.16 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

Suzann Ward Housatonic Real Estate

1 Old Tree Farm Rd, Stockbridge, MA 01262
/55
$1,490,000
- 4 Beds
- 2 Baths
- 2,200 Sq Ft
5 Glendale Rd, Stockbridge, MA 01262

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

Martha Piper THE KINDERHOOK GROUP

5 Glendale Rd, Stockbridge, MA 01262
/40
$389,000
- 3 Beds
- 2 Baths
- 1,618 Sq Ft
212 Highland St, Housatonic, MA 01236

Indulge in the picturesque ''ski season'' at this charming New England farmhouse. Immerse yourself in a comfortable space with a ski boot/mudroom entryway and a cozy wood stove for post-ski relaxation. Situated on a corner lot, this 3 bed/2 bath offers a rocking chair-front porch, private rear courtyard, 1 car garage. 1st floor features a spacious living room with wood floors, a primary bedroom,

Lori Rose STONE HOUSE PROPERTIES, LLC

212 Highland St, Housatonic, MA 01236
/56
$1,200,000
- 3 Beds
- 3.5 Baths
- 2,447 Sq Ft
6 Muddy Brook Cir, Great Barrington, MA 01230

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

6 Muddy Brook Cir, Great Barrington, MA 01230
/24
$695,000
- 2 Beds
- 2 Baths
- 1,308 Sq Ft
80 Taconic Ave Unit 3, Great Barrington, MA 01230

Welcome to Oakwood Condominium. A one car garage comes with unit. Plenty of additional parking. Lovely inground well manicured pool. Beautiful outdoor landscaping and sitting area. Private deck attached to unit for outdoor entertaining. This unit has been renovated over the years with updated kitchen with eat in nook area. All new windows and sliding doors. Gorgeous primary bathroom with radiant

Suzann Ward HOUSATONIC REAL ESTATE

80 Taconic Ave Unit 3, Great Barrington, MA 01230
/41
$635,000
- 3 Beds
- 3 Baths
- 2,476 Sq Ft
4 Main St, West Stockbridge, MA 01266

Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. Whether you're a small business owner, creative entrepreneur, or an astute homebuyer creating a unique lifestyle setup - this is your opportunity to own a space that works as hard as you do. This efficiently

Conor Meehan STONE HOUSE PROPERTIES, LLC

4 Main St, West Stockbridge, MA 01266
/62
$1,330,000
- 16 Beds
- 10 Baths
- 8,870 Sq Ft
6 Manville St, Great Barrington, MA 01230

A prime investment opportunity in the heart of downtown Great Barrington. This 10-unit residential property features a desirable mix of six spacious two-bedroom apartments and four one-bedroom units. The two-bedroom apartments are particularly appealing, all offering private balconies and fireplaces, with three of these premium units also including formal dining rooms and Jack-and-Jill style

Tony Segalla LANCE VERMEULEN RE, INC

6 Manville St, Great Barrington, MA 01230
/37
$600,000
- 6 Beds
- 5 Baths
- 3,502 Sq Ft
53 Mahaiwe St, Great Barrington, MA 01230

A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to

Tony Segalla LANCE VERMEULEN RE, INC

53 Mahaiwe St, Great Barrington, MA 01230
/31
$589,000
- 4 Beds
- 2 Baths
- 2,148 Sq Ft
70 Main St, Great Barrington, MA 01230

Charming 1790 Historic Home in the Heart of South EgremontNestled on a beautifully landscaped 0.8-acre lot in the heart of the village, this 4-bedroom, 2-bath home blends timeless charm with modern convenience. Built in 1790 it features wide plank floors, built-ins, and a fireplace with a historic Dutch oven.Enjoy local access to shops and dining, with scenic hiking at Jug End Reservation just

Judi Panzano HOUSATONIC REAL ESTATE

70 Main St, Great Barrington, MA 01230
/52
$1,675,000
- 4 Beds
- 3.5 Baths
- 3,783 Sq Ft
42 Seekonk Rd, Great Barrington, MA 01230

The Piano House was named for the ornamental Dentil wood trim at the top of the facade an 1810 Center Hall Federal Colonial, located on 4.59 acres at Alford Brook, Features a Rumford Fireplace in the Front Lounge and in the Sitting Room. Also, a Large Wood Burning Stove in the Dining Room-Family/Sunroom. In addition, an 1810, two story Barn with 1185 sq. ft. of refurbished space. Includes a

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

42 Seekonk Rd, Great Barrington, MA 01230
/19
$775,000
- 8 Beds
- 4 Baths
- 3,192 Sq Ft
35 Main St, West Stockbridge, MA 01266

Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

Matt Carlino MACCARO REAL ESTATE

35 Main St, West Stockbridge, MA 01266
/19
$929,000
- 11 Beds
- 6 Baths
- 4,863 Sq Ft
Unlisted Address

Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

Matt Carlino MACCARO REAL ESTATE

Unlisted Address
/20
$950,000
- 5 Baths
- 5,180 Sq Ft
406 Main St, Great Barrington, MA 01230

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for

Jason Saphire www.HomeZu.com

406 Main St, Great Barrington, MA 01230
/20
$1,250,000
- 2 Beds
- 2 Baths
- 1,584 Sq Ft
114 Brush Hill Rd, Great Barrington, MA 01230

New Build Contemporary. Timbercraft Homes & Rosengren Architects collaborated to create this Contemporary 1584 square foot 2 bedroom home. Clean lines and simple one level living. Energy efficient Home with beautiful oak floors, custom kitchen open to dining and living room. Primary bedroom spacious and bright with well appointed bathroom and walk-in closet. Fireplace, dual fuel heating and AC. 1

Mark Rosengren LANCE VERMEULEN RE, INC

114 Brush Hill Rd, Great Barrington, MA 01230
/36
$775,000
- 10 Beds
- 4 Baths
- 5,293 Sq Ft
458 Monterey Rd, Great Barrington, MA 01230

This rare find, located on the Great Barrington/Monterey line, offers the right buyer a unique opportunity to live, work, and play in the heart of the Berkshires. Situated on 4.32 acres, this 1958 ranch-style home has evolved over the years into a sprawling 5,200 square-foot property boasting endless potential. While it currently serves as an owner-operated wellness facility, an expansive

Cortney Dupont COHEN & WHITE ASSOCIATES

458 Monterey Rd, Great Barrington, MA 01230
/46
$625,000
- 9 Beds
- 4 Baths
- 4,152 Sq Ft
1057 Main St, Great Barrington, MA 01236

Great investment opportunity! A very rare property offered for the first time outside the family in over 90 years! This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior and updated units are just a few of the benefits of this investment. In the bustling village of

Ryan Lane GILCREST PROPERTIES

1057 Main St, Great Barrington, MA 01236
/51
$2,100,000
- 4 Beds
- 4 Baths
- 2,738 Sq Ft
8 Yale Hill Rd, Stockbridge, MA 01262

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

8 Yale Hill Rd, Stockbridge, MA 01262
/56
$1,395,000
- 4 Beds
- 2 Baths
- 2,058 Sq Ft
45 Swamp, West Stockbridge, MA 01266

1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

Paige Paluch LANCE VERMEULEN RE, INC

45 Swamp, West Stockbridge, MA 01266
/48
$2,995,000
- 4 Beds
- 4.5 Baths
- 5,300 Sq Ft
116 Brush Hill Rd, Great Barrington, MA 01230

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

Mark Rosengren LANCE VERMEULEN RE, INC

116 Brush Hill Rd, Great Barrington, MA 01230
/3
$975,000
- Land
- 131.69 Acres
- $7,404 per Acre
0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

Jim Stark L. J. STARK AND CO.

0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
/30
$655,000
- 5 Beds
- 3 Baths
- 3,035 Sq Ft
133 Front St, Great Barrington, MA 01236

Unique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal

Judi Panzano HOUSATONIC REAL ESTATE

133 Front St, Great Barrington, MA 01236
/35
$499,000
- 3 Beds
- 2.5 Baths
- 1,922 Sq Ft
220 N Plain Rd, Great Barrington, MA 01230

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could

Martin Albert COMPASS MASSACHUSETTS , LLC GB

220 N Plain Rd, Great Barrington, MA 01230
/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

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