Enjoy the best of the Berkshires from this beautifully maintained Contemporary Colonial, privately set on more than 2.5 acres with deeded access to Otis Reservoir, Massachusetts' largest recreational lake. Spend your summers boating, swimming, and fishing, then return home to relax in the peace and privacy of your own wooded retreat.Built in 2000, this spacious home offers four bedrooms and three full baths, including a first-floor primary suite with a private en suite bath. The open-concept living area features soaring cathedral ceilings, a cozy gas stove, and a seamless flow into the well-appointed kitchen, creating an inviting space for everyday living and entertaining. A generous screened porch overlooks the expansive yard, while the stone terrace and newer hot tub

Don't miss this rare opportunity to own this private, meticulously maintained waterfront sanctuary. The grounds feature a charming English garden, an expansive deck and a private dock for launching kayaks, offering outdoor living at its best. The main level features an eat-in kitchen with custom cabinetry, a living room, sunroom ideal for gatherings, an office, mudroom with laundry and a first-floor primary suite with full bath, providing convenient single-level living. This home includes central AC and a backup generator for year round comfort and peace of mind. With beautiful views and just moments from downtown, this property blends privacy, comfort and convenience in a truly special setting.

STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a one car oversized garage, Association pool, tennis and pickle ball courts. All of this in a most desirable location near cultural attractions in the Berkshires.

Welcome home! This magnificent 13.3-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons, while trails through the meadows and woods offer four season hiking and riding opportunities. A large, private office area with high-speed internet provides a productive ''work from home'' environment. The first floor features an eat-in country kitchen with an antique Glenwood stove. The formal living room, with its wood-burning fireplace, is ideal for cozy evenings.

Big, 2800 square foot log home privately set on a seven plus acres. The great room, framed with massive log timbers, opens onto the large deck leading to the hot tub and fire pit. Kitchen features include granite & butcher block counters and an eat in island. Two bedrooms - each with private half baths - plus a full bath in the hallway complete the main level. The upper level loft is used as an office and extra sleeping area. The primary bedroom, cathedral ceiling, walk in closet, has an ensuite bath with soaking tub and separate shower. The game room on the lower level can also be used as an overflow sleeping area with the full bath including a jet tub and sauna. Laundry area, mud room, garage access & utility room Are located n this level. The 7+ acre lot includes a surveyed 2nd lot.

Investors take Notice!! Just about 8.3 acres with 360 degree of views. Architectural designs done in 2004 with the intent to construct up to 16 condominiums (2 per building) approved by the town. Current owner has already installed a 20 ft wide 640 ft length paved driveway. Utility hookups to each proposed building (electric, gas, and fiber optic cable) have been done. Hookups to each of the eight buildings for public water and sewer are also done. This could also be used for possibly a tiny home development, apartment buildings, single family home or divided into separate lots with town approval . If you're looking for paradise, it's right here. Owner is motivated to sell! The source of all representations are from the seller or a public source; broker has not verified same.

'ON THE HILL' Cozy 4 bedroom 1925 Cape, OPEN HOUSE JULY 4th SATURDAY 11:00-2:00. WALK TO CENTER OF GREAT BARRINGTON AND LAKE MANSFIELD. Living room with mini split, custom built in cabinets in dining room, Large primary bedroom with mini split, large family room, OPEN FRONT PORCH WITH VIEWS. BACK YARD PATIO FOR COOK OUTS. Attached 1 car garage, town water and sewer, So much charm, house needs updating. DONT MISS THIS GEM !!

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking.

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking.

Move-in-ready Colonial offering 3 bedrooms and 2.5 baths on a sunny, picturesque lot with a beautiful stone wall, it is just seconds from the charming downtown. The main level features a living room with a striking fieldstone fireplace, formal dining room, kitchen, a family room ,an office, a heated sunroom and a full bath with a lovely soaking tub, and a powder room. The second level has three bedrooms and a full bath. Warm wood-paneled walls crafted from timber harvested on the property add distinctive character throughout. An oversized garage with workshop and upper level provides excellent storage or hobby space, complemented by a barn & shed. Ideally located minutes from all that the Berkshires has to offer. A special home built with craftsmanship and a whole lot of love.

LAKEFRONT: Classic 3BR/2B plus loft, lakefront cottage. Enjoy the private boat dock and grassy beach area for swimming, sailing, kayaking and canoeing on lovely (no motor boats) Benton Pond, plus deeded rights to Big Pond for motor-boating. Four season contemporary Cape with an open plan featuring a window wall overlooking the lake and a brick fireplace. The screened porch is next to the kitchen, convenient for al fresco dining. Exterior access to the basement is perfect for storage of your canoes and kayaks. This home is located on over an acre and is the 2nd to the last on the road so very quiet. Less than 3 hours to NYC and 2 1/2 to Boston, near Tanglewood, Jacobs Pillow and most other Berkshire cultural attractions. MOTIVATED SELLER.

Escape to your own private retreat in the Berkshires with this beautifully updated 4-bedroom, 3.5 -bath modern farmhouse bungalow, where contemporary style meets timeless comfort. Designed for effortless living, the sun-filled open floor plan creates a warm and inviting atmosphere, perfect for both everyday life and entertaining. At the heart of the home is a stunning chef's kitchen featuring elegant quartz countertops, a classic farmhouse sink, stainless steel appliances, and generous workspace that will inspire every meal. Thoughtful details throughout the home enhance both comfort and convenience, including a first-floor laundry room with a half bath, mini-split cooling on the main level, a cozy wood pellet stove for crisp Berkshire evenings, and radiant heated floors in the primary

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity. Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room. The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room. Enjoy the association pool, Bousquet Mountain next door and all of the

This custom-built home seamlessly blends country tranquility with modern convenience. Inside, a gracious foyer leads to formal and informal first floor living spaces designed for comfortable living and gracious entertaining. 4 bedrooms, 3 full and 2 half baths, including a large spacious primary suite, guest room with en suite bath, private home office, well appointed eat- in kitchen with sliders to deck and yard, a screened porch and 2 fireplaces that add warmth and character. The partially finished lower level offers a spacious family room and home gym while the unfinished space provides ample storage. 3 -car garage and spacious mudroom and first floor laundry. A rare opportunity to enjoy privacy, space, and the very best of Berkshire living.

Set in the foothills of the Berkshires, this beautifully restored 1930s cottage blends timeless character with thoughtful modern updates. The sleek, updated kitchen and baths complement the home's original warmth and charm, creating an inviting balance of old and new.Surrounded by five picturesque acres of mature trees and established gardens, the property feels both peaceful and deeply rooted in its setting. A classic rocking-chair front porch welcomes you home, while the screened porch overlooks the backyard -- the perfect spot for quiet mornings, summer evenings, or gathering with friends after a day in the garden.Inside, the home offers four bedrooms and two baths, along with rich details that make farmhouse living so enduringly appealing: a wood-burning fireplace, a cozy wood stov

Looking to enjoy lakeside living year round? This one bedroom home sits on three contiguous lots which provide the opportunity to expand your living space in the future. It overlooks it's own private lake lot allowing you to enjoy lakefront activities and everything that Ashmere Lake has to offer The home features an open floor plan with large windows overlooking the lake. At one end of the cathedral ceiling, a ship's ladder leads to an enclosed bonus room above the large bedroom The lower level walkout has a foyer entrance, multipurpose room, including the laundry room and a mechanical room Outside you'll find a separate deck, fire pit, and a large grassy yard with plenty of room for a garden. This property includes four lots totaling .37 acres. Water Front on Ashmere Lake!

Light-filled contemporary cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area & living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom & a balcony overlooking the living area. The four-season sunroom (heated & cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge & Lenox. A quick drive to Tanglewood, cultural venues, & abundant outdoor recreation including hiking & lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location.

Enjoy lakefront living in this charming 3-bedroom, 1-bath home offering beautiful water views and comfortable indoor-outdoor living. The inviting living room features a cozy fireplace and sliding glass doors that open to a spacious deck, complete with a screened-in room--perfect for relaxing, entertaining, or enjoying peaceful mornings overlooking the lake.The updated kitchen provides modern convenience while maintaining the home's welcoming character. Additional features include a one-car garage and a full basement offering abundant storage. Whether you're looking for a year-round residence or a weekend getaway, this waterfront property offers the perfect blend of comfort, scenic beauty, and outdoor enjoyment.

Rare opportunity to own a substantial two-family home in one of the most desirable locations in the Berkshires. Overlooking meadows, sheep pastures, mountains, and Naumkeag, this special property is also just a short walk to Stockbridge Main Street. Each spacious unit offers 3 bedrooms, 1.5 baths, and hardwood floors throughout. The grounds are truly magical, with mature trees and a peaceful setting that feels tucked away while remaining close to everything. Currently fully tenant occupied, one unit will become vacant in September, creating the perfect opportunity for owner occupancy while generating rental income from the second side. Multi-family properties in this area are exceptionally rare. See Supplement

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.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532