Homes for Sale near W.E.B Du Bois Regional Middle School

/40
$1,880,000
- 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
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/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
/28
$555,000
- 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
/6
$1,025,000
- Land
- 9 Acres
- $112,637 per Acre
19 and 12 Wheatleigh Dr, Stockbridge, MA 01240

RARE Lily Pond Homesite with Permits & Plans | Stockbridge, MAAccessed by a long, meandering drive alongside a babbling brook, this secluded, fully permitted homesite offers a magical approach and unmatched privacy directly on a serene pond. A graceful bridge (completion expected summer 2025) enhances the setting. The site includes architect-designed plans and a building permit for a 5-bedroom

Selina Lamb

Birch Properties

(413) 307-6639

19 and 12 Wheatleigh Dr, Stockbridge, MA 01240
/58
$1,300,000
- 3 Beds
- 3 Baths
- 2,002 Sq Ft
276 Great Barrington Rd, West Stockbridge, MA 01236

This 52-acre homestead blends early American heritage with modern sustainability and self-sufficiency. Originally built in 1802, this stunning property offers privacy, fertile farmland, and breathtaking mountain views' including Monument Mountain/Flag Rock. Mature fruit orchard with over 15 trees: apples, peaches, pears, cherries, plums.30-tree sugar bush with a sugarhouse for maple syrup

Keytoria Jenkins

THE KINDERHOOK GROUP - PITTSFIELD

(413) 675-5502

276 Great Barrington Rd, West Stockbridge, MA 01236
/5
$1,025,000
- Land
- 9 Acres
- $112,637 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
/40
$869,000
- 3 Beds
- 3 Baths
- 2,747 Sq Ft
8 Interlaken Rd, Stockbridge, MA 01262

Beautifully renovated & meticulously maintained New England Farmhouse in Stockbridge. Offering a comfortable layout, this beautiful home seamlessly blends modern updates while maintaining a classic country charm. A coveted mudroom entry leads to a gorgeous kitchen with custom cabinetry, stainless appliances, sliders to the patio, and a wood stove for ambiance. Also on the main level are a full

Lori Rose STONE HOUSE PROPERTIES, LLC

8 Interlaken Rd, Stockbridge, MA 01262
/58
$1,499,000
- 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
$995,000
- 7 Beds
- 4 Baths
- 2,998 Sq Ft
49 South St, Great Barrington, MA 01230

Immaculate home on ''The Hill'' with stunning hardwood floors and abundant natural light from its many large windows. This versatile three-level property is currently enjoyed as a stately single-family residence, but can seamlessly be divided into two separate apartments, offering a range of layout options and rental income potential. The ground floor features a bright, modern kitchen, a spacious

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

49 South St, Great Barrington, MA 01230
/49
$925,000
- 3 Beds
- 2.5 Baths
- 1,979 Sq Ft
18 Glendale Rd, West Stockbridge, MA 01266

Architect designed Mid Century home with spectacular western views from every window. Multi level living has been updated with new roof, Pella windows, entry and sliding doors, interior doors, refinished wood floors, modern primary bathroom, heat pump and mini-splits controlled remotely, a whole house generator and recently painted interior and exterior. There is a lovely two sided fireplace

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

18 Glendale Rd, West Stockbridge, MA 01266
/58
$1,795,000
- 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

21 Stockbridge Rd, West Stockbridge, MA 01266
/61
$1,950,000
- 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
/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
/57
$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
/63
$1,100,000
- 4 Beds
- 3.5 Baths
- 2,861 Sq Ft
1 Train Hill Rd, Stockbridge, MA 01262

This Stockbridge Colonial has it all....location, separate guest suite and plenty of country chic design. This historic home boasts all the charm of yesteryear with fabulous wide pine floors, state of the art country kitchen that retains it's charm, formal dining room with fireplace, gracious banister to the second floor of guest bedrooms with renovated bath all while seamlessly blending with the

Cortney Dupont COHEN & WHITE ASSOCIATES

1 Train Hill Rd, Stockbridge, MA 01262
/13
$549,000
- 3 Beds
- 2 Baths
- 2,280 Sq Ft
1 Christian Hill Rd, Great Barrington, MA 01230

Two Family Duplex within walking distance to town. Nicely updated and well maintained.

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

1 Christian Hill Rd, Great Barrington, MA 01230
/31
$539,000
- 4 Beds
- 2 Baths
- 2,112 Sq Ft
115 Bridge St, Great Barrington, MA 01230

BRIDGERTOWN Investment opportunity or live with income potential. This 2 unit in-town has a 3 bedroom 1 bath on the 1st floor apartment and a 1 bedroom 1 bath on the 2nd floor with room to expand to in the 3rd floor attic space. 1st floor apartment has 1 year lease with responsible tenants. Walk to town of Great Barrington with all it has to offer, 1/2 block to Co-op and Main St. Utilities are

Mark Rosengren LANCE VERMEULEN RE, INC

115 Bridge St, Great Barrington, MA 01230
/36
$472,000
- 3 Beds
- 2.5 Baths
- 2,232 Sq Ft
45 State Line Rd, West Stockbridge, MA 01266

Meticulously maintained colonial within walking distance to town. The main level features a family room, an open-concept kitchen and dining area, a convenient half bath, and a versatile bonus room perfect for a home office. Upstairs, the primary suite includes a jetted tub and walk-in closet, accompanied by two additional bedrooms and another full bath. A heated sunroom leads to the large

Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB

45 State Line Rd, West Stockbridge, MA 01266
/26
$825,000
- 3 Beds
- 2 Baths
- 1,771 Sq Ft
165 Maple Ave Unit D, Great Barrington, MA 01230

Beautiful condo with open plan concept, wide pine flooring and so much light. Upscale kitchen, first floor primary with bath and laundry. Three bedrooms, two full baths plus a bonus room waiting to be finished. There is also a lovely screened porch plus a rear deck for grilling. Live on one level. The walk out lower level could also be additional living space. It is beautifully landscaped within

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

165 Maple Ave Unit D, Great Barrington, MA 01230
/43
$799,000
- 3 Beds
- 2.5 Baths
- 2,007 Sq Ft
40 Russell St, Great Barrington, MA 01230

Picture-perfect in town victorian w/ many tasteful updates! This home has been lovingly cared for and updated by the owners over the years, with many recent finishing touches including a new primary bath & walk-in closet, fresh paint and landscaping. The classic layout offers well-proportioned rooms with high ceilings and great light throughout. The first floor includes two living rooms, dining

Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

40 Russell St, Great Barrington, MA 01230
/29
$415,000
- 2 Beds
- 2 Baths
- 1,485 Sq Ft
16 Forest Row, Great Barrington, MA 01230

Forest Row is a Community Land Trust neighborhood, set on 20 acres with 18 households. Unit 16 sits on the southern end of the property looking into the woods. It is the back unit of one of the quadruplexes giving it a little more privacy. Entry is a tiled mud room/hall with coat closet bringing you into the main living level with an open plan; kitchen, living and dining with glass slider to the

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

16 Forest Row, Great Barrington, MA 01230
/23
$710,000
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
111 Castle Hill Ave, Great Barrington, MA 01230

Just around the corner from lovely Lake Mansfield in Great Barrington this comfortable cape is located in a most desirable site on the 'Hill'. Surrounded by blooming shrubs and trees, this 3 bedroom, two bath home has great classic character. Living room with fireplace, separate dining room, and an unfinished walkout allow potential expansion. Perfect spot to access biking, swimming, kayaking and

Martha Piper WILLIAM PITT SOTHEBY'S - GT BARRINGTON

111 Castle Hill Ave, Great Barrington, MA 01230
/23
$825,000
- 3 Beds
- 2 Baths
- 2,620 Sq Ft
9 Iron Mine Rd, West Stockbridge, MA 01266

Located in the town of West Stockbridge just 1 1/2 miles from the village center home to an eclectic array of shops, restaurants, a very cool bookstore, No. Six Depot Roastery & Cafe and the annual West Stockbridge Zucchini Festival is this contemporary style home. With smart planting the home on 2+ acres feels totally private. Enjoy the great outdoors from the spacious deck or lawn. Inside

Deborah Mielke CORASHIRE REALTY

9 Iron Mine Rd, West Stockbridge, MA 01266
/48
$3,750,000
- 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
/26
$695,000
- 3 Beds
- 2.5 Baths
- 1,790 Sq Ft
3 Roger Rd, Great Barrington, MA 01230

Stylish Contemporary Home in a Prime Great Barrington Location! This beautifully maintained 3-bedroom, 2.5-bath Contemporary offers a lot of space and light-filled layout with high ceilings. The open-concept living area features a cathedral ceiling & gas fireplace, creating a warm and inviting atmosphere.Enjoy the convenience of a first-floor primary suite, filled with natural light from

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

3 Roger Rd, Great Barrington, MA 01230
/33
$515,000
- 4 Beds
- 3.5 Baths
- 2,330 Sq Ft
230 Prospect St, Great Barrington, MA 01236

Tucked at the end of a dead-end street, this sun-drenched 4 bedroom is set on a corner lot w/ direct access to scenic trails - a rare find just minutes from local amenities. Step inside through a practical mudroom w/ a tiled floor, oversized closet, & powder room. The main level features an open-concept layout, seamlessly connecting the living, dining & kitchen w/ granite countertops and

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

230 Prospect St, Great Barrington, MA 01236
/3
$325,000
- Land
- 15 Acres
- $22,049 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
/46
$699,000
- 5 Beds
- 2 Baths
- 2,765 Sq Ft
120 Maple Ave, Great Barrington, MA 01230

Nestled at the end of a private drive, this 5-Bedroom home offers charm and comfort. The spacious Living Room has warm wood floors, a cozy fireplace, and expansive windows filling the space with natural light. A thoughtful layout features a first-floor Primary Bedroom for convenience and privacy. The open Dining Room, flows from the Living space, defined by custom built-in bookshelves, perfect

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

120 Maple Ave, Great Barrington, MA 01230
/3
$975,000
- Land
- 132 Acres
- $7,404 per Acre
0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

This is a generous hillside parcel with 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
$739,000
- 5 Beds
- 3 Baths
- 3,035 Sq Ft
133 Front St Unit 1 & 2, Great Barrington, MA 01236

OPEN HOUSE: Sat, May 3rd 11-1PMUnique 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

Judi Panzano HOUSATONIC REAL ESTATE

133 Front St Unit 1 & 2, Great Barrington, MA 01236
/41
$695,000
- 8 Baths
- 18,157 Sq Ft
445 Monterey Rd, Great Barrington, MA 01230

Unique property with potential for a wide range of educational, recreational, residential or other potential re-development uses. Formerly part of an residential school facility, the property consists of over 11 acres with extensive road frontage on both sides of Route 23. The buildings include: 1) 10,560 sq. ft. gymnasium w/ levels of office/conference rooms, 750 lb elevator, 4 bathrooms, and

Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

445 Monterey Rd, Great Barrington, MA 01230
/5
$150,000
- Land
- 1.96 Acres
- $76,530 per Acre
275 Mill River Southfield Rd, New Marlborough, MA 01230

A rare find, nearly 2 acres of flat land, ready for your dream home! Located in a peaceful setting with easy access to utilities, this property has already passed percolation testing and is fully prepared for construction. Whether you're looking to build now or invest for the future, this is a prime opportunity.

Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

275 Mill River Southfield Rd, New Marlborough, MA 01230
/3
$349,000
- Land
- 73 Acres
- $4,782 per Acre
0 Lake Buel Rd, Great Barrington, MA 01230

Beautiful Building Site - 72.98 acres in Great Barrington. Gently sloping land abuts the Appalachian Trail and East Mountain State Forest. Shared driveway off Aberdeen Road in New Marlborough. Cleared spot with a partially built barn/workshop on site. Rough driveway in place. Tranquil spot for your dream home!

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

0 Lake Buel Rd, Great Barrington, MA 01230
/53
$615,000
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
6 Bryan Rd, West Stockbridge, MA 01266

Nature Lover's Paradise on 17+ Acres - Private Forests, Manicured Lawns, and Protected Wetlands!Entirely private, 6 Bryan Road features spectacular wetland vistas, green meadows, and serene untouched woods.Stunning west-facing views from your deck overlook 8+ acres of protected wetlands, including a pond frequented by geese, ducks, and blue herons. To the south, the grand lawn is perfect for

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

6 Bryan Rd, West Stockbridge, MA 01266
/33
$548,500
- 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
/57
$2,950,000
- 5 Beds
- 4.5 Baths
- 4,468 Sq Ft
180 W Center Rd, West Stockbridge, MA 01266

Experience serene living at the end of a picturesque tree-lined driveway in a secluded family estate in the heart of West Stockbridge. Crafted as a berm home artfully built into the rolling hillside, this turnkey residence glows with natural light in its park-like setting. Ideal for both grand entertaining and quiet retreats, the multi-level home features over five bedrooms or flexible sleeping

Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

180 W Center Rd, West Stockbridge, MA 01266
/32
$695,000
- 5 Beds
- 2 Baths
- 2,060 Sq Ft
57 South St, Great Barrington, MA 01230

A charming historic home nestled in the heart of Great Barrington, moved to it's location from Main Street in 1858. This delightful detached residence boasts 2,060 square feet of living space across 10 rooms. The living area features a wood-burning fireplace and space for formal dining. The eat-in kitchen, complete with built-ins, adds character. With four bedrooms and two baths, there's ample

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

57 South St, Great Barrington, MA 01230
/40
$1,995,000
- 6 Beds
- 8 Baths
- 10,507 Sq Ft
14 Pine St, Stockbridge, MA 01262

Prime Owner-User/Investment Property in the heart of historic Stockbridge. Currently an Educational Facility with Retail, Office and Residential Units. Can be combined for Offices, Medical, Educational, Gallery, Apartments/Condos, or any use that demands a location in one of the most well known and loved towns in America. Fully upgraded mechanicals, large Parking facilities and Handicapped

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

14 Pine St, Stockbridge, MA 01262
/11
$315,000
- Land
- 1.50 Acres
- $210,000 per Acre
14 Partridge Way, Stockbridge, MA 01262

A rare opportunity to own a 1.5-acre parcel on a quiet road in the highly sought-after Beachwood community, available only once in many decades. This property is ideally located in a peaceful, nature-filled setting with deeded rights to the Stockbridge Bowl, and is just minutes from the private Beachwood beach and swimming area and is connected to town sewer. It's also conveniently close to

Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

14 Partridge Way, Stockbridge, MA 01262

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