PRIME BERKSHIRE LAND - FEEL 'AWAY FROM IT ALL' YET YOU ARE MOMENTS FROM THE BEST OF THE BERKSHIRES. $158,000+ UNDER ASSESSED VALUESet on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the Berkshires just minutes to Stockbridge & Lenox, Tanglewood, The Bowl, The Mount, Kripalu, Great Barrington, the Pike, shopping & more. The single home site & septic area are already cleared, wetlands approvals are in place, and rough-in driveway cut in.This 7.8 acre parcel offers peace & quiet, beauty, and low Stockbridge taxes. With an assessed value of $397,600 this land offers a tremendous value for those looking to build on PRIME Berkshire land. This is so close to 'ready to go' - plan your design, drill a well, and finish permit!

Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra acreage, an additional dwelling/guest house or to sell off in the future. Driveway to two sites. Excellent perc results and soil analyses from 2005 and engineered plans available. Great opportunity in Stockbridge.

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.

Bring your contractors and your imagination to this unique fixer-upper, an old carriage barn with an attached apartment. The spacious barn features original beams with large open areas. The lush grounds are complemented by charming rock walls and rustic outbuildings. With a convenient location close to all the Berkshire attractions, this property is ideal for transformation into a one-of-a-kind retreat!!

Log Cabin in Stockbridge! Tucked away at the end of a country road, this charming log home offers warmth, privacy, and convenience - and it's close to Tanglewood. Beautifully maintained inside and out, it sits on two wooded acres with a welcoming front porch. Inside you will find a cozy retreat - a living room with cathedral ceilings, pine floors, and a working fireplace. The updated kitchen features stainless Whirlpool appliances and generous cabinet space. Loft-style bedroom with wide pine floors, updated bath with tub and shower. Spiral staircase leads to a lower level with slate floors, office or hobby room, laundry with GE washer/dryer, and walkout to the backyard. Move right in and enjoy your own Berkshire hideaway.

Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The setting is exceptional, stroll just minutes to the Red Lion Inn, cafes, shops, and the library; at the end of the street, pick up beloved local trails toward Laura's Tower for quick nature escapes. A manageable 6,970 sq ft lot keeps weekends free for play, gardening, or launching out to the Berkshires' cultural highlights: Tanglewood, Norman Rockwell Museum, Naumkeag, and more.

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect you to the landscape. Your backyard is a protected nature preserve, guaranteeing permanent privacy. The property features a handsome 24x30 horse barn with 2+ acres of paddocks, plus a separate lower-level guest apartment--perfect for weekend visitors or a private home office. A complete package blending modern convenience with pastoral beauty and cultural access.

Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry closet. The second level features the primary bedroom with en suite full bath, walk in closet and bonus loft space; Guest bedroom and en suite full bath. Association beach rights to the Stockbridge Bowl, tennis courts, indoor pool, gym and hiking paths. All of this while being conveniently located near Tangelwood, Lenox Village and many cultural attractions here in the Berkshires.

WHITE PINES IN STOCKBRIDGE Tasteful 2 bed 2 full and 2 half bath home offers generous great room with windows showcasing beautiful views. Wood burning fireplace graces open living/dining room with beautiful hardwood floors. Large en-suite primary has spa-like bath. Community amenities include private beach at Stockbridge Bowl, indoor pool, HarTru tennis courts and fitness center. Covered parking. Meticulously maintained grounds with abundant flowers and mature landscaping. Minutes to Tanglewood, dining, art, music, swimming, boating and golf in charming Berkshires.

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

Welcome to this stunning one level living, 3 bedroom, 3 bathroom home on a serene 4 acre lot. Designed for comfort and style, it features a bright first floor living area with large picture windows and a charming fireplace. The spacious kitchen offers a skylight, breakfast nook, and access to a screened porch perfect for relaxing. Cherry Floors flow throughout (except the kitchen and baths), and the large dining room is ideal for entertaining. Enjoy a generous deck, two car garage, brand new Buderus Boiler, and new air conditioning system.This Berkshire escape could be yours to enjoy and is minutes from Tanglewood, Norman Rockwell, Chesterwood, Berkshire Theatre, and minutes to the charming towns of Stockbridge, Great Barrington, Lee, Lenox, West Stockbridge!

This White Pines Garden Unit is a must see if you are considering condominium living in this sought after community. Open living Great Room/kitchen/dining with double volume glass to take in the view, fireplace & guest bath on main level. The lower level greets you with a tiled floor sunroom w/direct access to the spacious decking w/private courtyard outdoor space. The primary ensuite, guest bedroom w/full bath & laundry & office/flex space complete this level. This unit boasts a most convenient covered carport space. Assoc. amenities include a clubhouse w/exercise rm, indoor heated pool, 2 Har Tru tennis courts, hiking and walking trails, private beachfront on the Stockbridge Bowl with swimming and kayak & canoe storage or anchor your boat... ..all this and only minutes to Tanglewood

Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated, blending original character with contemporary upgrades. Post and beam construction adds warmth and architectural texture, while a sleek gas fireplace anchors the open living and dining areas. The updated kitchen is ideal for gatherings both casual and festive. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two additional bedrooms and a full bath complete the

RARE BERKSHIRE OPPORTUNITY: READY-TO-BUILD MODERN RETREAT ON A PRIVATE POND + DEEDED STOCKBRIDGE BOWL BEACH RIGHTSDiscover a truly extraordinary offering in the heart of the Berkshires--9.1 pristine acres with direct frontage on Lily Pond, a private, non-motorized body of water celebrated for its serenity, protected natural setting, and sweeping views. Occupying the entire southern end of the pond, this estate parcel enjoys a commanding, unobstructed panorama over the water, creating an intimate, one-of-a-kind backdrop for your future home.A long, gently winding driveway follows a picturesque babbling brook and sets the stage for a memorable arrival. A **brand-new bridge--now fully completed--**leads to the exceptionally private, pond-front building site.

WHITE PINES COUNTRY VILLA WITH DEEDED STOCKBRIDGE BOWL BEACHFRONT!! This sought after end unit is the one you've been waiting for if you are looking for the ease of condominium living with a striking Great Room with vaulted ceiling, open dining/kitchen living, fireplace, wall of windows that take in the meadow view and direct access to decking along with the primary bedroom with a wall of closets plus a walk-in and an ensuite primary bath all on the main level with the bonus of a guest half bath and direct access to the attached garage. The lower level has two guest bedrooms, one with an ensuite bath; the other with a hallway full bath; a spacious family room and in home office space with direct access to private ground level decking, and a wonderful laundry room with lots of storage.

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal, boxwood garden, all of which have been meticulously maintained. There are two stone patios which look out over four acres of pasture to the west. This home is fueled by gas heat and is serviced by town water and sewer. Perhaps the famous Reverend, Johnathan Edwards and Chief Kondapot of the Stockbridge-Munsee Indians met in the front parlor a time or two.

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Garages for 5+ cars, perfect pool site, and privacy ensured by abutting protected land.

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 enter through classic stone walls and manicured hedgerows, you'll be welcomed by sweeping meadows and lush gardens. Time slows as you meander along stone pathways that lead to a charming red barn and a quaint stone summer cottage--perfect for painting or relaxing. The estate is oriented towards cultural and natural beauty with walking trails

Prime Owner-User/Investment Property in the heart of historic Stockbridge. Currently an Educational Facility with Retail, Office and Residential Units. Can be combined to Office, 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 Accessability.

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 Bedrooms,, 3 Baths, has a lovely brookside courtyard w/Pergola, rustic charm maintained. Quiet your mind and embody perfect country living. Overlook the Kampoosa Brook, with private swimming area from your backyard! Cultural & recreational activities nearby. Great income potential. Solar powers Main house, car charger & Mill House. A MUST SEE!