Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move-in-ready appeal is what you'll find at this Heron Pond condo! Well-maintained, 1 br/1ba unit filled with natural light includes living room, separate dining room, updated bath and galley kitchen. Outside, relax on your own stone patio. Enjoy peaceful surroundings, the pond, and beautifully kept grounds. Perfect for full-time living, weekend retreat, or investment property. Low-maintenance living gives plenty of time to enjoy the benefit of being minutes from Stockbridge, Berkshire Theater Festival, Tanglewood and other area attractions. Quick access to hiking, nature trails, and recreation on Stockbridge Bowl. Whether you're looking for a cozy escape or turn-key purchase don't miss this one!

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.

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!

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!!

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.

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.

Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area. Additionally there is an attached first floor In-law apartment with living room, kitchen, bedroom and full bath. Included with the house is a multi level barn with electricity. Lovely setting to relax on the back deck and take in the views or stroll into town to enjoy the cultural amenities This gem has great potential and is ready for the new owners vision

MOTIVATED SELLER! 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.

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!

Location is everything with this light-filled contemporary ranch on Prospect Hill. Ready for quick occupancy! Five minutes from downtown Stockbridge or to Tanglewood and so close to the town beach on Stockbridge Bowl. This three bedroom, two bath home has been lovingly cared for. Living room and dining with hardwood floors, built-in shelving and built-in storage. Quality updates in the primary bath. Almost two acres of land with garden shed, many perennials and raised vegetable garden beds. Bonus features: spacious attached two car garage, back-up generator, first floor laundry for truly one-level living. The three-season sunroom and outdoor deck add to the charm of this Stockbridge home that's priced to sell!

Convenient one-level ranch in a prime location close to town. This well-maintained home offers four bedrooms and two full bathrooms, ideal for comfortable living. The updated kitchen features modern finishes and plenty of workspace. Enjoy energy efficiency with owned solar panels that significantly reduce utility costs, plus a pellet stove for supplemental heating. A generator ensures uninterrupted power during outages--peace of mind year-round. Situated on a private road, the property provides tranquility while remaining minutes from shopping and dining. Additional highlights include ample storage, a functional layout and move-in-ready condition. Whether you're downsizing, seeking your first home or looking for a smart investment, this turnkey property delivers.

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 1831 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.

Welcome to 11 Sergeant, ideally located on a quiet side street around the corner from Stockbridge's historic Main Street. This property includes a well-maintained main house and a separate barn with ADU potential. The main house features an updated kitchen that opens to a bright den overlooking the backyard. The first floor also includes a powder room, dining room, and formal living room. Upstairs are 2 spacious bedrooms and 2 full bathrooms, with additional finished space on the third floor. The barn offers flexible use with one garage bay, a first floor studio space, and separate guest quarters on the 2nd floor with a large living room/kitchenette and ensuite bedroom.

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

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. This sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite comes with an oversized walk out deck large enough to place your summer lounge furniture, the perfect spot for your morning coffee. Amenities at Winden Hill include a heated pool and a tennis and pickleball court....all this and and only a 20 minute stroll to the center of Lenox. This truly is the perfect place to call home.

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.