Homes for Sale near Mt. Everett High School

/19
$795,000
- Land
- 26 Acres
- $30,577 per Acre
0 Whites Hill Rd Unit 250028, Alford, MA 01266

Gorgeous and private 26 acre subdividable parcel in one of the most desirable locations in Alford. The land comprises approximately 21 acres in Alford and 5 acres in Egremont. Diverse topography includes lush hardwood trees and pine forest, ledge outcroppings, an overgrown pasture, a couple micro ponds, seasonal wetlands and a lovely understory of ferns and wildflowers. The 5-acre Egremont

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

0 Whites Hill Rd Unit 250028, Alford, MA 01266
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/53
$1,200,000
- 3 Beds
- 2 Baths
- 2,148 Sq Ft
468 East St, Mount Washington, MA 01258

Elevated Living - Inside and Out!Exceptional design and craftsmanship distinguish this stunning home. The single-level interior is warm, sophisticated and filled with natural light, with the kitchen, dining and living areas flowing together in one open space surrounded by specialty windows and French doors. Set on four private acres amid the highest peaks in South County, the home offers

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

468 East St, Mount Washington, MA 01258
/64
$685,000
- 4 Beds
- 2.5 Baths
- 2,333 Sq Ft
138 Hillsdale Rd, Great Barrington, MA 01230

Set on over 2 acres in beautiful Egremont, this lovingly maintained four-bedroom, 2½-bath home blends classic character with thoughtful updates and additions made over the years. Built in 1920's, the house retains the warmth and craftsmanship of its era, including charming built-ins and inviting spaces that make it feel truly like home.A large deck provides the perfect setting for morning

Lauren Rosen WILLIAM RAVEIS - BERKSHIRE

138 Hillsdale Rd, Great Barrington, MA 01230
/30
$649,000
- 5 Beds
- 3 Baths
- 2,710 Sq Ft
6 Redwood Ln, Sheffield, MA 01257

A compelling multi-family opportunity in move-in condition, offering comfortable living space with the added flexibility of rental income or accommodations for extended family. The property also features a barn and access to a nearby pond for fishing and kayaking. Sheffield Center is approximately two miles away, offering local restaurants, the Bushnell-Sage Library, the Sheffield Historical

Timothy Wighton STONE HOUSE PROPERTIES, LLC

6 Redwood Ln, Sheffield, MA 01257
/14
$99,500

$20K PRICE DROP
- Land
- 1.17 Acres
- $85,043 per Acre
2 Terra Ferma Dr, Egremont, MA 01230

Build your dream home on Terra Ferma Drive—arguably the best dead-end road in the Berkshires. Located in Egremont and just a short drive to South Egremont village, Great Barrington, and Catamount Ski Area, this is the ideal location to stake your ground. The road hosts a quiet neighborhood that leads directly to state hiking trails, putting the outdoors just steps from your door. The lot is

Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

2 Terra Ferma Dr, Egremont, MA 01230
/62
$2,495,000
- 5 Beds
- 3.5 Baths
- 6,254 Sq Ft
84B N Undermountain Rd, Egremont, MA 01230

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it

Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

84B N Undermountain Rd, Egremont, MA 01230
/7
$299,000

$50K PRICE DROP
- Land
- 19.73 Acres
- $15,155 per Acre
0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244

Just shy of 20 acres. Make your way to the top for views, you won't be disappointed. An abundance of wildlife, and not a building in sight. Come take a look and make this your Berkshire retreat!

Lawrence Reilly THE KINDERHOOK GROUP

0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244
/44
$959,000

$20K PRICE DROP
- 4 Beds
- 2.5 Baths
- 1,986 Sq Ft
12 Harrison Calkins Rd, Alford, MA 01266

Discover a peaceful retreat in Alford with this charming 4-bedroom, 2.5-bath Contemporary Cape set on more than 8 acres. Relax on the spacious screened-in porch while listening to the birdsong and the gentle flow of Scribner Brook.Offering an upscale cabin feel in every season, this inviting home provides the perfect escape from the pace of everyday life. Enjoy privacy, natural beauty, and

Matt Carlino MACCARO REAL ESTATE

12 Harrison Calkins Rd, Alford, MA 01266
/7
$995,000
- Land
- 17.97 Acres
- $55,370 per Acre
59 Whites Hill Rd, Egremont, MA 01230

Perched atop a breathtaking ridgeline with some of the most extraordinary panoramic views in the Berkshires, this remarkable almost 18-acre estate parcel is one of only seven exclusive homesites within this private enclave. With the most recent neighboring estate having changed hands for $5.6 million, the property's exceptional pedigree and enduring value are unmistakable.Surrounded by more

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

59 Whites Hill Rd, Egremont, MA 01230
/42
$9,500,000

$4M PRICE DROP
- 7 Beds
- 9 Baths
- 10,429 Sq Ft
30 East Rd, West Stockbridge, MA 01266

Offered fully furnished and ready to enjoy, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and

Steven Weisz William Pitt Sotheby's International Realty

30 East Rd, West Stockbridge, MA 01266
/23
$699,000
- 5 Beds
- 3 Baths
- 4,127 Sq Ft
43 Main St, Egremont, MA 01258

Versatile mixed-use property pairing a sophisticated second-floor apartment with a flexible first-floor residence that doubles as an ideal commercial or gallery space. Overlooking a tranquil year-round brook and a private backyard, the offering sits right downtown Egremont and includes the convenience of an ample garage.Property HighlightsSecond-Floor Apartment: Sophisticated, charming

Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

43 Main St, Egremont, MA 01258
/30
$673,000

$22K PRICE DROP
- 3 Beds
- 6 Baths
- 4,044 Sq Ft
1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
/35
$449,000
- 2 Beds
- 1 Bath
- 660 Sq Ft
25 Pine St, New Marlborough, MA 01230

Year round retreat in the Lake Buel Community. Thoughtfully designed spaces, cozy & unpretentious. The living area, comfortable for family & guests, has vaulted ceiling and Gas Fireplace, making this home just as inviting in the cooler months. Kitchen is functional, attractive and updated. Simple lines, wainscoting, wood floors, ductless A/C units. The Sunroom is perfect for Dining, board games

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

25 Pine St, New Marlborough, MA 01230
/72
$1,185,000

$15K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,800 Sq Ft
249 Boardman St, Sheffield, MA 01257

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the

Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

249 Boardman St, Sheffield, MA 01257
/11
$450,000
- Land
- 8.59 Acres
- $52,386 per Acre
Lot #19 Stratford Rd, New Marlborou, MA 01230

Settle into the quiet charm of the Windemere Lake community with this 8.592-acre building lot. Tucked away on a peaceful road and embraced by natural woodland, the property offers a sense of seclusion while remaining part of a thoughtfully maintained private enclave. Though it doesn't sit directly on the water, owners enjoy shared access to Windemere Lake—a pristine, non-motorized lake perfect

Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

Lot #19 Stratford Rd, New Marlborou, MA 01230
/12
$885,000
- 1 Bed
- 1 Bath
- 1,377 Sq Ft
190 Egremont Plain Rd, Egremont, MA 01230

Originally built in the 19th century, this Egremont schoolhouse has undergone a radical,''down-to-the-studs'' transformation, and has been thoughtfully designed to create a high-performance home for modern living, while honoring its historic character.Sound structural integrity, with state of the art insulation, custom engineered windows, a new HVAC system, and a solar array for near zero

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

190 Egremont Plain Rd, Egremont, MA 01230
/10
$329,000
- Land
- 8.69 Acres
- $37,860 per Acre
10 Mountain Rd, Mount Washington, MA 01258

RARE OPPORTUNITY. Private parcel with open views potential, atarting from the idyllic cul-de-sac, on Mountain Rd. in Mt. Washington, MA. This exclusive, private land parcel has 8.69 level and gently rolling acres.: Septic Field has been partially installed, Well has been drilled , and rough driveway installed. Fiber Optic is available. The plans for 4BR+4BA house with an in-law suite have been

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

10 Mountain Rd, Mount Washington, MA 01258
/45
$3,490,000

$410K PRICE DROP
- 10 Beds
- 5.5 Baths
- 7,864 Sq Ft
535 Main Rd, Monterey, MA 01245

Welcome to NEWGRANGE, a grand 1920s Manor House capturing the golden age of lakeside country living. This historic estate echoes the effortless elegance of an early 20th-century summer retreat. Imagine hosting lavish gatherings in the formal dining room, or retiring by original, roaring stone fireplaces after a leisurely day on the water or the slopes.Encompassing over 10,000 sqft, the

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

535 Main Rd, Monterey, MA 01245
/71
$875,000

$275K PRICE DROP
- 3 Beds
- 4 Baths
- 2,900 Sq Ft
29 Old Village Rd, Great Barrington, MA 01230

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first

Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

29 Old Village Rd, Great Barrington, MA 01230
/2
$2,400,000
- Land
- 38.2 Acres
- $62,827 per Acre
3 Jenssen Rd, Great Barrington, MA 01230

3 lots available to develop in EgremontParcels, 008.0-0000-0123.0, 008.0-0000-0283.0, 008.0-0000-0048.0

Jeremy Casey SR Commercial Realty

3 Jenssen Rd, Great Barrington, MA 01230
/40
$695,000
- 5 Beds
- 2 Baths
- 2,741 Sq Ft
189 New Marlboro-Southfield Rd, New Marlborough, MA 01230

Loads of room for family and friends in this semi-private country home near The Old Inn on the Green and The Southfield Store Café.The first floor features spacious living areas, including a living room with a wood-burning fireplace, a large eat-in kitchen and dining area, and a paneled den, along with an attached two-car garage. Two of the six bedrooms are on this level, including the

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

189 New Marlboro-Southfield Rd, New Marlborough, MA 01230
/4
$425,000
- Land
- 17.93 Acres
- $23,703 per Acre
99 Creamery Rd, Egremont, MA 01230

NORTH EGREMONT - Almost 18 elevated acres with sweeping views of the Berkshire Hills that has been surveyed, flagged with enough road frontage to subdivide once. An open meadow with woodlands as a backdrop make this parcel most desirable....a must see!

Cortney Dupont COHEN & WHITE ASSOCIATES

99 Creamery Rd, Egremont, MA 01230
/56
$1,300,000
- 4 Beds
- 5 Baths
- 2,524 Sq Ft
9 Prospect Lake Rd, Egremont, MA 01230

LOCATION, LOCATION, LOCATION. This terrific home is in low-tax Egremont, setback from road, & is a short walk to French Park which sports new tennis/pickleball courts, a playground, hiking trails, a basketball court, and a dog park. The town also features two of the more popular restaurants in the Berkshires. But, what about the house? This well maintained 4 bedroom/3 bathroom home is wheelchair

George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

9 Prospect Lake Rd, Egremont, MA 01230
/55
$549,000

$100K PRICE DROP
- 5 Beds
- 2.5 Baths
- 2,750 Sq Ft
168 Main St, Sheffield, MA 01257

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

168 Main St, Sheffield, MA 01257
/57
$2,200,000
- 5 Beds
- 3 Baths
- 3,073 Sq Ft
630 Main Rd, Monterey, MA 01245

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

630 Main Rd, Monterey, MA 01245
/17
$399,000
- 3 Beds
- 2 Baths
- 1,564 Sq Ft
1415 Canaan Southfield Rd, Southfield, MA 01259

3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

1415 Canaan Southfield Rd, Southfield, MA 01259
/41
$995,000

$155K PRICE DROP
- 4 Beds
- 3 Baths
- 3,349 Sq Ft
120 Hupi Rd, Monterey, MA 01245

Perched on Mount Hunger is this lovely, private, contemporary four-bedroom, three-bath home located near Lake Garfield, of which there are winter views. The current owners added a huge, beautiful living/dining room with a fieldstone fireplace, cathedral ceiling and huge windows. The renovated kitchen has granite counters with a Viking cooktop and Bosch double wall ovens. A first floor primary

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

120 Hupi Rd, Monterey, MA 01245
/26
$429,000

$30K PRICE DROP
- 3 Beds
- 2 Baths
- 2,258 Sq Ft
689 N Main St, Sheffield, MA 01257

Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a .50-acre commercially zoned lot just a 5 minute drive to downtown GB, the property offers outstanding live/work, investment, or business potential.The 2,258 sq. ft. main residence features 3 spacious bedrooms, a large new kitchen, full bath, washer/dryer, and

Judi Panzano HOUSATONIC REAL ESTATE

689 N Main St, Sheffield, MA 01257
/108
$1,725,000
- 5 Beds
- 4.5 Baths
- 5,127 Sq Ft
293 New Marlboro Sandisfield Center, New Marlborough, MA 01230

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular

Vashti Poor WILLIAM RAVEIS - BERKSHIRE

293 New Marlboro Sandisfield Center, New Marlborough, MA 01230
/22
$799,000

$50K PRICE DROP
- Land
- 29 Acres
- $27,552 per Acre
416 West Rd, Alford, MA 01266

Experience the Berkshires Like Never BeforeNestled on West Road in Alford, this exceptional 29-acre estate offers a rare blend of natural beauty, flexibility, and investment potential. A meandering brook, Alford Brook gently courses through the property, creating serene waterside vistas and the soothing soundtrack of flowing water day and night.From the open meadows and wooded glens, enjoy

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

416 West Rd, Alford, MA 01266
/75
$2,875,000

$375K PRICE DROP
- 6 Beds
- 5.5 Baths
- 3,416 Sq Ft
651 Hayes Hill Rd, New Marlborough, MA 01230

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape

Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

651 Hayes Hill Rd, New Marlborough, MA 01230
/71
$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 direct Green River waterfront.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
/36
$799,000

$126K PRICE DROP
- 4 Beds
- 3 Baths
- 2,155 Sq Ft
19 Sackman Way, Monterey, MA 01245

Private Lake Buel access is just steps from this one-level, 4-bedroom, 3-bath ranch--your perfect year-round getaway or full-time retreat. Inside, you'll find a striking two-sided fieldstone fireplace anchoring the living and dining areas, complemented by warm wood floors that add timeless charm. Step outside to a spacious back deck overlooking your own private bird sanctuary--an ideal setting

Rosemary Baumann HOUSATONIC REAL ESTATE

19 Sackman Way, Monterey, MA 01245
/33
$565,000

$40K PRICE INCREASE
- 3 Beds
- 3.5 Baths
- 2,000 Sq Ft
4 Plantain Pond Rd, Mount Washington, MA 01258

Nestled on scenic Mount Washington, this beautifully maintained contemporary home offers the perfect blend of privacy, comfort, and modern updates. The thoughtfully designed floor plan features 3 bedrooms, including a desirable first-floor primary suite with a private bath and direct access to a secluded deck. With 3.5 bathrooms, this home provides exceptional space for family and guests.The

Suzann Ward HOUSATONIC REAL ESTATE

4 Plantain Pond Rd, Mount Washington, MA 01258
/70
$3,750,000
- 5 Beds
- 4.5 Baths
- 3,200 Sq Ft
1015 Sisson Hill Rd, New Marlborough, MA 01230

As seen in Architectural Digest, this meticulously reimagined 1875 farmhouse compound unfolds across 11.5 lush acres on a quiet, bucolic dead-end country road, with protected views. Brought to life in collaboration with AD100 design firm Sachs Lindores and landscape design by Judy Murphy, the property is full of historic character with refined modern comfort. The compound includes a four-bedroom,

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

1015 Sisson Hill Rd, New Marlborough, MA 01230
/65
$2,095,000

$55K PRICE DROP
- 4 Beds
- 3 Baths
- 3,461 Sq Ft
304 Hickey Hill Rd, Sheffield, MA 01257

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added.Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

304 Hickey Hill Rd, Sheffield, MA 01257
/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
/57
$2,400,000
- 5 Beds
- 5 Baths
- 6,092 Sq Ft
89 N Undermountain Rd, Egremont, MA 01258

Welcome to Treetops. A long private driveway passing a large pond sets the scene for this impressive hilltop retreat with 6,000 square feet across three levels and seasonal views of the Taconic Hills. Built with wood hewn from trees on the property, including the distinctive stairway, the home offers a huge open-plan main level ideal for gatherings, along with an indoor pool, hot tub, sauna and a

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

89 N Undermountain Rd, Egremont, MA 01258
/6
$265,000

$30K PRICE DROP
- Land
- 1.97 Acres
- $134,518 per Acre
14 McGee Rd, Egremont, MA 01230

Lovely building lot on a quiet road in bucolic Egremont. Well has been drilled, septic design done for two structures and power is brought to site. Truly ready for your design/build.

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

14 McGee Rd, Egremont, MA 01230
/31
$494,999

$26K PRICE INCREASE
- 3 Beds
- 2 Baths
- 1,920 Sq Ft
184 Old Hitchcock Rd, New Marlborough, MA 01230

Tucked away deep in the quiet woods of New Marlborough, a low tax town, this distinctive property sits on 18+ very private acres. Perfect for anyone seeking true seclusion, natural beauty, and a life off the beaten trail. Surrounded by mature trees and untouched wilderness, it offers exceptional privacy and a peaceful atmosphere where the only sounds are birdsong, flowing breeze, and the soft

William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

184 Old Hitchcock Rd, New Marlborough, MA 01230

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