Homes for Sale near Hillcrest Educational Center - Brookside

/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

(413) 613-4139

445 Monterey Rd, Great Barrington, MA 01230
/61
$1,280,000
- 3 Beds
- 3 Baths
- 2,002 Sq Ft
276 Great Barrington Rd, West Stockbridge, MA 01236

Price Improvement! Motivated Seller!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, 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
/27
$499,000
- 4 Beds
- 2 Baths
- 1,634 Sq Ft
1068 Main St, Housatonic, MA 01236

Very unique duplex in the heart of Housatonic! This very cool house combines antique charm, contemporary style, and a convenient village location to suit many uses and lifestyles. Currently configured as two leased 2 br/1ba apartments, it could easily be converted back to a single-family residence or provide income to an owner-occupant. Each unit offers a bright & cheery eat-in kitchen, living

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 728-1160

1068 Main St, Housatonic, MA 01236
/28
$515,000
- 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
/47
$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
/69
$5,900,000
- 11 Beds
- 10 Baths
- 9,748 Sq Ft
25 W Sheffield Rd, Great Barrington, MA 01230

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

Lauren Molk ELYSE HARNEY REAL ESTATE

25 W Sheffield Rd, Great Barrington, MA 01230
/58
$1,799,900
- 4 Beds
- 3.5 Baths
- 3,800 Sq Ft
105 Christian Hill Rd, Great Barrington, MA 01230

CLASSIC ARCHITECTURE WITH CONTEMPORARY ELEGANCE! A beautifully maintained home set back from the road. Exceptional landscaping embraces the property, offering a private sanctuary. A front porch welcomes you to the first floor. A light-filled,capacious living room, dining room with a fireplace opened to both main rooms, a primary suite with two walk-in closets, a 1/2 bath, and study open to a

Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

105 Christian Hill Rd, Great Barrington, MA 01230
/70
$1,299,000
- 5 Beds
- 4 Baths
- 3,289 Sq Ft
49 Main St, Stockbridge, MA 01262

Improved stunning Stockbridge Village property that boasts an updated main house and includes a separate three apartment carriage house. The main property offers great natural light and ample common spaces that are gracious in size, updated lovely kitchen, five bedrooms, four baths, screened porch and inviting outdoor spaces. It has been thoughtfully updated while keeping the charm and character

Cortney Dupont COHEN & WHITE ASSOCIATES

49 Main St, Stockbridge, MA 01262
/38
$1,100,000
- 5 Beds
- 3.5 Baths
- 3,194 Sq Ft
33 Interlaken Rd, Stockbridge, MA 01262

Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

Lori Rose STONE HOUSE PROPERTIES, LLC

33 Interlaken Rd, Stockbridge, MA 01262
/36
$850,000
- 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
/59
$949,000
- 4 Beds
- 3.5 Baths
- 4,072 Sq Ft
311 N Plain Rd, Housatonic, MA 01236

This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an

Vashti Poor LANCE VERMEULEN RE, INC

311 N Plain Rd, Housatonic, MA 01236
/34
$1,295,000
- 4 Beds
- 2.5 Baths
- 2,511 Sq Ft
16 Glendale Middle Rd, Stockbridge, MA 01262

VINTAGE EYEBROW COLONIAL WITH VIEWS & A POST AND BEAM ADDITION. Updated and renovated open concept plan dripping with charm in pristine condition. 2013 addition by renowned builder David Lanoue. Systems updated at that time. Gorgeous wide pine flooring, a chef's kitchen with custom cabinets a Viking Range, a stone farmers sink with windows overlooking the beautiful view. 4 Bedrooms, 2.5 baths,

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

16 Glendale Middle Rd, Stockbridge, MA 01262
/45
$1,495,000
- 3 Beds
- 2.5 Baths
- 2,900 Sq Ft
21 Kalliste Hill, Great Barrington, MA 01230

SWEEPING MOUNTAIN VIEWS less than 5 minutes to Main Street. Sited on 5+ acres, this stylish contemporary is located in the most desirable section of Great Barrington. The home has an open living/dining/kitchen floor plan with a gas fireplace and huge windows taking in the view. A screened porch is conveniently located off the kitchen. The first floor also has a primary bedroom suite with full

Tom Lynch COMPASS MASSACHUSETTS , LLC GB

21 Kalliste Hill, Great Barrington, MA 01230
/76
$1,075,000
- 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
/43
$885,000
- 3 Beds
- 2 Baths
- 1,964 Sq Ft
126 Christian Hill Rd, Great Barrington, MA 01230

HIDDEN GEM!!! Enjoy the best of both worlds with privacy in a country setting, only minutes from town. Thisbeautiful property is set back off the road in a lovely clearing, surrounded by 2 acres of woodsfor privacy. Mature perennial gardens enhance the natural beauty of this saltbox-style home.Solidly built in the 1980s with many upgrades including; A new kitchen (2021) with all newappliances,

Suzann Ward HOUSATONIC REAL ESTATE

126 Christian Hill Rd, Great Barrington, MA 01230
/34
$969,000
- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
10 Terra Ferma Dr, Egremont, MA 01230

Escape the expected and discover the art of effortless living on Terra Ferma Drive. Tucked away on a private dead-end road in coveted South Egremont, this nearly new (built within 5 years) residence redefines one-level luxury. Imagine a home where every detail is designed for comfort and ease - no steps, just seamless flow leading you first to a beautifully appointed kitchen, the true heart of

Tony Segalla LANCE VERMEULEN RE, INC

10 Terra Ferma Dr, Egremont, MA 01230
/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
/28
$799,000
- 3 Beds
- 2 Baths
- 1,773 Sq Ft
11 Prospect Hill Rd Unit 1, Stockbridge, MA 01262

This 3 Bedroom, 2 Bath unit on the historic grounds of Oronoque Estate checks off all the boxes. Only 14 units in complex, this Villa offers one floor living, attached garage, high ceilings, recently renovated natural cherry custom cabinetry, walk in shower in primary bath, low Stockbridge taxes, propane heat, central air conditioning, wood burning fireplace. Two guest bedrooms, a screened in

Susan Baum BERKSHIRE HOMES AND CONDOS

11 Prospect Hill Rd Unit 1, Stockbridge, MA 01262
/21
$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
/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
/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
/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
/25
$698,000 Open Sat 11AM - 1PM
- 2 Beds
- 2 Baths
- 1,137 Sq Ft
34 Bridge St, Great Barrington, MA 01230

A unique offering, this 2BR, 2BA condo, built in 2019, offers modern convenience & elegant details throughout. Walk out the door into iconic downtown Great Barrington &have all that the town has to offer at your fingertips. Shopping, restaurants, & groceries are less than a minute away. Take in the mountains & the historic Mahaiwe marquee from the French Door balcony opening onto Bridge Street.

Lauren Rosen LANCE VERMEULEN RE, INC

34 Bridge St, Great Barrington, MA 01230
/24
$698,000 Open Sat 11AM - 1PM
- 2 Beds
- 2 Baths
- 1,137 Sq Ft
34 Bridge St Unit 201, Great Barrington, MA 01230

A unique offering, this 2BR, 2BA condo, built in 2019, offers modern convenience & elegant details throughout. Walk out the door into iconic downtown Great Barrington &have all that the town has to offer at your fingertips. Shopping, restaurants, & groceries are less than a minute away. Take in the mountains & the historic Mahaiwe marquee from the French Door balcony opening onto Bridge Street.

Lauren Rosen LANCE VERMEULEN RE, INC

34 Bridge St Unit 201, Great Barrington, MA 01230
/71
$2,200,000
- 5 Beds
- 4.5 Baths
- 3,354 Sq Ft
176 W Center Rd, West Stockbridge, MA 01266

The lovely approach to this gorgeous estate property ensures serenity, privacy, and the beauty of living in the country and includes a 3 bed 2 1/2 bath main house and a gorgeous architect designed guest house. Offering 2 ensuite bedrooms with balconies, dramatic exposed beams, vaulted ceilings, and gas fireplace the guest house is an extraordinary place to host family and friends both

Lori Rose STONE HOUSE PROPERTIES, LLC

176 W Center Rd, West Stockbridge, MA 01266
/16
$199,000
- 2 Beds
- 1 Bath
- 1,092 Sq Ft
386 N Plain Rd, Great Barrington, MA 01230

Charming 1930s Bungalow with Privacy and Potential! Tucked away on nearly an acre (.93 acres) of land with direct access to the scenic Rail Trail, this classic 1930s bungalow is an opportunity for investors, contractors, or anyone looking to restore a gem. Terrific bones and a tranquil setting--perfect for a weekend retreat or full-time residence. Located within walking distance to the heart of

John Segalla HOUSATONIC REAL ESTATE

386 N Plain Rd, Great Barrington, MA 01230
/6
$650,000
- Land
- 19 Acres
- $34,211 per Acre
0 Mohawk Lake Rd, Stockbridge, MA 01262

Discover a rare opportunity to own a piece of history in Stockbridge, available for the first time in over 120 years. This stunning land offers a private setting perfect for building your dream home, while being just moments away from the renowned Norman Rockwell Museum, Chesterwood, the enchanting Berkshire Botanical Gardens, and the charming downtown Stockbridge, all within a 3-mile radius.

Gary Fuls Jr RE/MAX TRANSITIONS

0 Mohawk Lake Rd, Stockbridge, MA 01262
/27
$439,000
- 3 Beds
- 1 Bath
- 1,192 Sq Ft
370 Park St, Great Barrington, MA 01230

Charming New England farmhouse featuring some modern updates and newer mechanical systems. Enjoy the perfect blend of rustic character and warmth of country living with modern conveniences in this delightful home. New full house insulation, Heat/ AC splits, updated electrical system. Large open backyard offers endless possibilities of outdoor activities and enjoyment. With a Berkshire Mountain

Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

370 Park St, Great Barrington, MA 01230
/19
$949,000
- 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
/15
$999,999
- 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
/48
$5,775,000
- 5 Beds
- 8 Baths
- 9,400 Sq Ft
Unlisted Address

Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

Elyse Morris ELYSE HARNEY REAL ESTATE

Unlisted Address
/20
$299,900 Open Sat 1PM - 2:30PM
- 1 Bed
- 1 Bath
- 658 Sq Ft
2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

Heron Pond Condominiums in Stockbridge (at intersection of 2 Wallace Rd. also known as 26 East St.) is adjacent to the village and the Red Lion Inn. Famous for having been the former Shaggy Dog Recording Studio, that was a location for prominent musicians of the 60's and 70's. Come experience the beauty of the four seasons in the center of the Berkshires. Enjoy 1-level living, 1-bed, 1-bath

Susan Calkins STONE HOUSE PROPERTIES, LLC

2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
/43
$749,000
- 4 Beds
- 2 Baths
- 2,328 Sq Ft
119 Egremont Plain Rd, Egremont, MA 01230

Stylish Farmhouse on 1.5 Acres in Coveted Low-Tax EgremontThis updated c.1912 farmhouse blends classic charm with modern function on a scenic 1.5-acre parcel in low-tax Egremont--just minutes from downtown Great Barrington. With four bedrooms, two full baths, and a flowing 2,328 sq ft layout, the home is move-in ready for summer in the Berkshires.Light-filled rooms and wide-plank wood floors

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

119 Egremont Plain Rd, Egremont, MA 01230
/46
$649,900
- 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
/36
$799,000
- 3 Beds
- 3 Baths
- 2,272 Sq Ft
204 Cottage St, Great Barrington, MA 01236

TWO HOMES FOR FAMILY LIVING OR INVESTMENT! So much to love about this property. The Main House exudes charm & warmth, and across the way a 2004 Cottage was added, creating the perfect income producer, family dwelling or Guest house. The Main house is tastefully updated preserving the cozy esthetic. 2 Bedroom, 2 Bath, Den, Great Room, and Country Kitchen. The Cottage, w/open plan living has

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

204 Cottage St, Great Barrington, MA 01236
/53
$849,000
- 8 Beds
- 4 Baths
- 3,044 Sq Ft
328 Park St, Great Barrington, MA 01230

Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

328 Park St, Great Barrington, MA 01230
/50
$2,250,000
- 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
/31
$499,000
- 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. Walk to town of Great Barrington with all it has to offer, 1/2 block to Co-op and Main St. Utilities are included in rent as electric and heat is combined. 1 car garage

Mark Rosengren LANCE VERMEULEN RE, INC

115 Bridge St, Great Barrington, MA 01230
/26
$660,000
- 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
/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

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