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. engineered plans available. Great opportunity in Stockbridge.

Not for the faint of heart, this unique 2BR/2BA property near downtown Stockbridge is pulled back to the studs and ready for a total revival. Currently uninhabitable, but brimming with whimsical potential, its one-of-a-kind footprint features unique octagonal rooms, a central fireplace and a detached garage with an adjacent mini studio--perfect for an artist nook or home office. Located in a highly sought-after prime location, the heavy demo is done, leaving a blank canvas for your contractor and imagination. Grab this tremendous opportunity to create a bespoke masterpiece in the heart of the Berkshires. Bring your creative spirit!

Rare opportunity to acquire a updated two-family property in Stockbridge with nearly 1.9 acres across two included lots. Come take a look to add your finishing touches to this project. Situated on a dead-end street on a spacious and clear lot. Each unit features three bedrooms and one-and-a-half baths, across approximately 2,700 square feet. Separate utilities for each unit, off street parking, and two new heating systems are ready for installation. Extensive recent updates include a new roof, renovated kitchens, updated flooring, and fresh interior/exterior paint. Conveniently located near downtown Stockbridge, the property offers easy access to some of the Berkshires' most recognized cultural destinations, including Tanglewood, the Norman Rockwell Museum

Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening breezes. The flexible floor plan allows you to choose between 2 or 3 bedrooms to best fit your needs - perfect for guests, an office, or extra sleeping space. Two stylish full bathrooms ensure everyone has plenty of space and comfort. Nestled in Stockbridge, you'll have easy access to all the charm and amenities the area has to offer, with nature at your doorstep. Offered fully furnished.

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!!

Spacious and filled with natural light, this four bedroom, two bath home offers incredible potential and timeless charm. Featuring large windows throughout the home makes it bright and inviting, with a comfortable layout with a full kitchen, formal dining room, cozy sitting room, and a charming fireplace in the living room which is perfect for relaxing evenings. Generously sized rooms provide plenty of space to make your own. Ideally located within walking distance to town, this property is a wonderful opportunity for a first-time homebuyer or investor to bring fresh vision and updates to an already solid home. Enjoy just minutes away from the best of all the Berkshires cultural attractions, Berkshire Theatre Norman Rockwell Museum, Tanglewood, Historic Red Lion Inn and more!

Wonderful opportunity to own 19 acres in Stockbridge for your dream home! The parcel features acres of deciduous trees with an abundance of peacefulness and tranquility. Gentle upward slope from the street then levels off. Providing several options for building. Freestanding fireplace/chimney remains from a former homestead. Norman Rockwell Museum, Chesterwood and Berkshire Botanical Gardens down the street. Charming downtown Stockbridge within 3 miles. Close proximity to Tanglewood, Lenox and Great Barrington. Presently in Chapter 61 for tax benefits. Sellers to complete a perc test upon accepted offer.

Tranquil Berkshire Retreat: Cottage with Screened Porch and River Sounds Embrace the ease of single-level living in this enchanting 3-bedroom, 2-full-bath cottage nestled in historic Stockbridge. Perfect as a year-round residence or a peaceful weekend getaway, this home perfectly blends cozy charm with modern convenience.

Fall in love with this renovated 3BED 2BATH house located just a stone's throw from downtown Stockbridge on nearly half an acre. Inside, the open layout features a cozy living room anchored by a classic fireplace. The kitchen has granite countertops and an expanded pantry with new custom shelving. The primary suite boasts a custom walk-in closet, an updated bathroom and direct access to the backyard. Two additional bedrooms share a 2nd full bathroom. Excellent functionality extends to the basement, which has new custom storage closets. Enjoy your morning coffee from the screened-in porch or step out onto the newly refinished back deck. Entertain in the the partially fenced yard with a new paver patio and built-in fire pit. Move-in-ready at its finest. Furnishings available to purchase

This move-in ready, sunny Cape next to the Botanical Garden offers significant upgrades, a four-season sunroom, private fenced backyard, attached garage, patio, first-floor bedroom & full bath, and low Stockbridge taxes. Hardwood floors, updated kitchen with pantry, mini-splits for heat & AC, new roof, gutters, windows, insulation, primary bath, and electric hot water heater make this truly turnkey. Minutes to Norman Rockwell (3), Tanglewood (9), The Mount (13), Shakespeare & Co (13), Ski Butternut (17), downtown Stockbridge (5), Lenox (12), Great Barrington (16) & I-90 (13). Cozy, year-round retreat on a quiet street -- won't last long!

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

Rare opportunity to own a substantial two-family home with a potential bonus Airbnb cottage 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

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.

Quitessential 1830's side hall Colonial....charming home located in the village of Interlaken in the town of Stockbridge, MA....just minutes to Lenox, Stockbridge center and the Berkshire Botanical Center. Listen to the babbeling water from the Larrywaug Brook and walk just steps to the small town park.....sit on the deck or around the firepit to soak in the atmosphere of privacy and peacefullness.This 3 bedroom, 1.5 bath house has been miticulously updated including: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer.....garage is partitioned for a workshop but can easily be converted to a one car garage again.

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

Offered for the first time in more than forty years, this c.1880 residence presents a rare opportunity to own a substantial property on coveted Prospect Hill Road, one of Stockbridge's most desirable addresses. Set privately on 3.5 acres just moments from the center of Stockbridge, the property offers the increasingly rare combination of privacy, acreage, and location that defines some of the most sought-after luxury real estate in the Berkshires and Berkshire County.

''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.

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income? This property has a very nice history of rental income! Who could ask for anything more? Call for a showing today.

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!

A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking a peaceful Berkshire retreat. This location offers easy access to hiking, yoga & wellness centers, boating, skiing, & excellent dining & shopping. Inside, bright & inviting spaces include a living room w/ cathedral ceiling, fireplace, & abundant natural light. A renovated kitchen opens to a cozy den & breakfast nook, pantry, laundry, mudroom & garage.