Found 170 Listings

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30 Photos
ASHMERE REALTY, INC.
$560,000
4 BD | 2 BA
Residential - Single Family

Nestled on a serene private 5.52 -acre lot with a picturesque brook running through, this beautifully updated brick ranch offers the perfect blend of comfort, style, and nature. Located in desirable Dalton, this home features 4 spacious bedrooms with a versatile office space ideal for remote work -- and 2 full bathrooms. Step into the heart of the home with a chef's kitchen with stunning granite countertops, ideal for cooking and entertaining. Recent updates include a new roof (2018), new furnace (2025) and fresh paint throughout, giving the home a warm, bright and welcoming feel. The finished lower level provides a generous family room perfect for gatherings with a wood burning fireplace insert, along with laundry hookups and a two-car garage tucked beneath the house.


33 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$569,000
3 BD | 3 BA
Residential - Single Family

Charm. You'll find it in this 3BR, 2.5BA West Stockbridge home. The charm of a farmhouse fence, lush with white hydrangeas, roses, and day lilies, set along a peaceful street where neighbors jog, push strollers, or walk their dogs. The charm of luminous freshly painted interiors and windows framing views of greenery on all sides--mists atop Lenox Mountain, vivid sunsets, and star-spangled night skies. The charm of a spacious enclosed porch for relaxing and entertaining, a 400sf insulated, 'do-with-it-what-you-will' barn with French doors and patio, perennial gardens, overarching maples. Practical charms, too: new roof, new primary bath, updated systems, 2-car garage, 2 minutes to Six Depot, 10 to Tanglewood, 16 to Guidos. Charm and privacy, with room to dream, create. Make it your own.


45 Photos
STEEPLEVIEW REALTY - ADAMS BRANCH
$574,900
3 BD | 2 BA
Residential - Single Family

DEEDED LAKE RIGHTS to Onota lake with access to a private beach on Blythwood Drive. This unique Brick colonial home has many high end finishes and recent updates. The kitchen boasts a Wolf gas range, granite counter tops, an island, a new touch screen refrigerator (2023) new dishwasher, recessed lighting, plus ceiling height cabinets for tons of storage The living room has a gas fireplace creating a cozy ambience. Plus there is a library/den with marble floors and tons of storage. The primary bedroom is spacious with 2 closets. There are wood floors through out the home, new vinyl windows/roof (2023). The lower level is partially finished & has radiant heat for winter comfort. The outdoor space is wonderful for entertaining highlighted by a patio with pergola & brick fireplace.


53 Photos
ROBERTS & ASSOC. REALTY, INC
$575,000
5 BD | 3 BA
Residential - Single Family

An inviting 5 bedroom, 3 bath Contemporary home nestled on almost 6 acres of woodland. Open floorplan, Master suite on 2nd floor, cozy wood burning fireplace and expansive family room on basement level. Plenty of storage throughout, including walk in closets & 2 cedar closets. 2 large decks both with built in seating- one on the south side of the house, accessible by 2 sliding glass doors & one stand alone with a 6 person hot tub, large seating area, a fridge & storage space, accessible via a lighted stone walkway. Solar roof panels & a Tesla battery power the property. Lovingly cared for home with mature landscaping & irrigation system. All the best that Becket offers including Right of Way access to nearby Horn Pond & the residents only beach on gorgeous Center Pond.


57 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$575,000
4 BD | 3 BA
Residential - Single Family

Step into a piece of Adams history with the beautifully preserved Simmons Cottage, on the market for the first time in generations. Built in 1901, this elegant Victorian residence offers a rare in-town opportunity, blending architectural charm with modern comfort.Set on a .24 acre lot, just a short stroll to the vibrant center of Adams, with its restaurants, shops, and small town charm, this 9 room, 4 bedroom, 2.5 bath home is rich with original detail and character. From the moment you step onto the welcoming front porch, ideal for lazy summer days, you'll appreciate the timeless appeal of this property.


58 Photos
ROBERTS & ASSOC. REALTY, INC
$584,900
4 BD | 3 BA
Residential - Single Family

Showings begin on December 1st. If you are looking for privacy and acreage, this Dalton expanded cape is a must see! So much to come home to. First floor flows nicely with fireplaced-formal living, formal dining and open kitchen/family room. Additionally, private first floor office (or bedroom) with full bath, first floor laundry and a pellet-stove heated sunroom making it a usable year-round space. The second floor features a private primary suite accessed with its own staircase. It includes spacious dressing area, bath with soaking tub, and tiled shower. The main stairway leads to three bedrooms, full bath and walk-in attic. The land (over five acres!!) has so many possibilities for the gardening enthusiast. Open and cleared!


42 Photos
LANCE VERMEULEN RE, INC
$589,000
3 BD | 2 BA
Residential - Single Family

The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original detail. The wood-paneled living room features a handsome brick hearth with beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large window overlooks the lush backyard, framed by towering hydrangeas. The 1st-floor bedroom has a closed off fireplace and sits conveniently across the hall from a full bath. The rear entry mudroom has sliding doors that lead to an enclosed wood deck, an ideal spot for summer gatherings. Upstairs 2 bedrooms with wide-plank pine floors share a full bath, completing this timeless gem. Seller to install new heating system.


31 Photos
HOUSATONIC REAL ESTATE
$589,000
4 BD | 2 BA
Residential - Single Family

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 minutes away. Mature gardens, a new roof (3 years), fresh exterior paint, and a recently installed septic system add value. The interior, full of historic character, awaits your personal touch.


67 Photos
RED HORSE REAL ESTATE
$599,000
3 BD | 2 BA
Residential - Single Family

Country Farm: Sixty Acre cattle Farm. Remodeled country Home with beautiful open fields and Yokum Brook running through the back lot were the cows use to sip cool water and graze. The farm consists of 5 different parcels of land with the barn across from the main house. You'll find a modern Kitchen and bath. The main Bedroom has a low deck and full-length windows looking out to the pastures and Apple trees were deer frolic and feed. A rock count yard with a fireplace and trellises holding grapevines makes a lovely entertainment area Most of the land is open fields.The barn has two garages, and the lower level has a feeding station. A shop and 2 hay lofts Although the cows are gone the farmer remains in the home, please respect his privacy. Showing by request only.


37 Photos
LANCE VERMEULEN RE, INC
$600,000
6 BD | 5 BA
Multi-Family

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 grocery stores and the hospital, while ample on-site parking provides a crucial amenity for all residents. Adding to its value, a detached garage/workshop offers the flexibility to be rented separately for additional income or used as a storage amenity for tenants.


43 Photos
RED HORSE REAL ESTATE
$625,000
3 BD | 4 BA
Residential - Single Family

Stunning contemporary high-tech home. Custom built. Ideal for entertaining and large gathering. The spacious living room flows into an open dining and large kitchen with stainless & granite. Primary bedroom and full bath along with a 2nd bedroom and full bath plus laundry are all on the first floor. 3rd bedroom and full bath are in the loft and 2 extra rooms; full bath and a huge family room are downstairs. This also would be a perfect Air B & B. Charging station, fiber optics. Beautiful creamy wood floors and vaulted high ceilings, custom shaped windows throughout the house bring in beautiful day light. Two Ponds for kayaking & swimming are walking distance. Central A/C, propane heat. Circular driveway, Southern exposure. Roof solar system owned. MUST SEE.


28 Photos
RE/MAX TRANSITIONS
$625,000
4 BD | 2 BA
Residential - Single Family

Experience the ultimate in lakeside living with this stunning 4-bedroom, 2-bath home in the coveted Otis Wood Lands community. This property offers a perfect blend of comfort and entertainment, featuring spacious sun-filled rooms and a sprawling deck ideal for relaxation and gatherings. Enjoy the convenience of a fully furnished home, complete with game room favorites like pool and air hockey tables. Modern amenities include energy-efficient heat pumps, remote-controlled security systems, and Alexa-compatible features for added convenience. Step outside only seconds away to discover the private beach and swimming area, perfect for launching your canoe or kayak. The community boasts a wealth of recreational options, including a great lodge for social events, a fitness center, tennis and


29 Photos
LANCE VERMEULEN RE, INC
$629,000
3 BD | 2 BA
Residential - Single Family

The private drive into this property says it all... Set well off a quiet cul-de-sac in a sought-after Egremont neighborhood on nearly 6 acres of lush, mature landscaping, this charming raised ranch offers the perfect blend of privacy and proximity. This beautifully maintained property is neat as a pin and move-in ready. With 3 bedrooms and 2 full baths, the main level features a light-filled open kitchen & dining area that flows out to a spacious deck overlooking the tranquil back yard. A finished room on the walkout lower level provides flexible bonus space for a family room, media room, or home office. Located just minutes from French Park, Prospect Lake, downtown Great Barrington, and Catamount Ski Resort, this home is a true Berkshires retreat with convenience in every direction.


52 Photos
RED HORSE REAL ESTATE, LLC
$639,000
4 BD | 4 BA
Residential - Single Family

There's room for everyone in this four bedroom contemporary cape set on 13+ acres. Designed by the owner for one level living, the lower and upper levels feature full baths, additional bedrooms and a second living area. Highlights of the main level include a private office, screened porch, deck, laundry & attached garage. The main floor living area incorporates a living room with gas fireplace, a defined dining area, the kitchen with granite counters, stainless steel appliances, an island with breakfast bar and a pantry. French doors open on to the deck, a hallway leads the primary bedroom suite with walk in closet. A few minutes walk to the Harrington Woods inground swimming pool and tennis/pickleball court, less than one mile to downhill skiing at Otis Ridge.


51 Photos
LAMACCHIA REALTY, INC
$639,900
3 BD | 2 BA
Residential - Single Family

Welcome to 106 Stoney Brook Road in the hills of Becket Massachusetts. This 3 bedroom 2 bath ranch offers an open concept living area including a spacious living room with pellet stove, eat in kitchen, and den just filled with natural light. The main floor offers a generously sized primary en suite complete with custom shower and walk-in closet. An additional 2 bedrooms and a full bath nicely round out the first floor. A partially finished basement adds to the charm and space within this beautiful home. On the exterior you will find a large deck off of the kitchen that overlooks the private and peaceful yard complete with fire pit that is perfect for anyone looking for a serene retreat that is minutes from many local attractions. You won't want to miss this beautiful home!


54 Photos
LANCE VERMEULEN RE, INC
$649,000
5 BD | 3 BA
Multi-Family

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 storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.


15 Photos
FRANZ J. FORSTER R. E.
$649,000
3 BD | 1 BA
Residential - Single Family

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, tranquil surroundings, and proximity to the region's finest cultural destinations.The home's inviting open-concept layout features a bright kitchen, dining, and living area centered around a cozy fireplace. Cathedral ceilings, updated appliances, and thoughtful upgrades throughout add modern comfort to this classic retreat


32 Photos
JIMINY REALTY
$689,000
3 BD | 3 BA
Residential - Condo/Townhouse

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 top-of-the-line stainless steel appliances, perfect for entertaining. The primary suite offers a spa-inspired bathroom with a walk-in shower. Outside, the meticulously landscaped, fenced-in patio provides a private sanctuary, complete with plenty of room for al fresco dining. Enjoy the convenience of being just a short walk from the slopes and local shops. This captivating property won't last long.


43 Photos
COMPASS MASSACHUSETTS , LLC GB
$695,000
4 BD | 2 BA
Residential - Single Family

Contemporary home nestled on over 7 acres minutes to Great Barrington center. The entry level of this home has a large boot room with a nice size laundry room off of it. The stairs lead you up into the main living space with an open plan kitchen, dining and living. The outside very much becomes part of the living space during the warmer months with doors to a front porch and a side open deck. Down the hall there are two guest rooms and a hall bath. Upstairs off a small landing there are two generous guest rooms with vaulted ceilings and a hall full bath. New heating system, new windows in most of the house,


44 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$695,000
3 BD | 2 BA
Residential - Single Family

An Heirloom Timber-Frame Home with Artisan Barn!This property is as much a story as it is a homestead. Rooted in the 1820s Greek Revival farmhouse that once stood near the road, the home was reimagined in 2002 when the original hand-hewn Dutch-style timber frame was preserved and given new life. Set on a new foundation deeper into the land, and meticulously rebuilt over the past two decades by a renowned master builder, the result is a turnkey home that combines history with modern craftsmanship.Behind the residence stands an extraordinary 5,200-square-foot timber-frame barn, built by the same master builder as his own workshop. Designed with both beauty and utility in mind, it offers the scale and flexibility to serve as a studio, recreational retreat, or professional space.

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