Stockbridge MA Real Estate & Homes for Sale

Introducing a meticulously well-maintained and charming colonial home. Situated on a highly sought-after dead-end street just a short walk to downtown Stockbridge. The first floor features a cook's kitchen with ample storage, cozy breakfast nook, half bath w/ laundry, a dining room with gleaming wood floors which opens to a comfortable living room with a gas fireplace. Additionally, there is a three season sunroom that provides a peaceful retreat. Upstairs you'll find two inviting guest rooms and a full bathroom - accessed by the hallway and primary bedroom. The primary bedroom boasts of abundant natural light, cathedral ceilings, exposed beams with plenty of closet space. Fenced in yard, heated garage, walk-up attic and a heated basement. This home is not to be missed!

Looking for a peaceful and picturesque place to call home? Look no further than Heron Pond! This beautiful second floor end unit is situated on the serene grounds of Heron Pond and offers water views and a large screened-in porch, so you can feel like you're living in your own private oasis. The open floor plan and vaulted ceilings create a light-filled great room, perfect for entertaining guests or relaxing after a long day. Cozy up by the fireplace on chilly evenings and enjoy the tranquil atmosphere of your new home. This unit features not one, but two primary bedrooms, making it perfect for couples or small families. And with its convenient location just three minutes from Main St., you'll have easy access to all the best Berkshire attractions.

Step into the charm of history with this renovated exceptional property nestled in the picturesque town of Stockbridge, just off Main Street. A meticulously renovated 4-bedroom, 4-bath historic home offers elegant living spaces with the convenience of modern amenities such a solar array providing all electricity, a car charger and central air. The new eat-in kitchen offers SubZero, BlueStar, Vent-A-Hood and Bosch appliances, while overlooking the Kampoosa Brook and a private swimming hole. The Millhouse, as it's known, one of the first in Stockbridge is a 3-bedroom, 3-bath guest house with a great summer rental history. There's also a two-car garage and a fruit orchard. Enjoy the sound of the rushing brook from almost any window along with walking to town for an espresso, food or theater.

Ideally situated in the heart of downtown Stockbridge, this 1860 colonial home has been stylishly updated and is move-in ready. The stunning first floor has three spacious adjoining living areas, including a central dining area and a family room with fireplace. The renovated kitchen has a chef's range and a large island perfect for gathering around. In the rear of the first floor is one of the home's two primary en-suite bedrooms, both with gas fireplaces. Take the back or front staircase to the second floor, which has the second primary en-suite bedroom, a central sitting area, and three more bedrooms, each with their own bathroom. A light filled loft/office and a vaulted-ceiling media room are found at the rear of the second floor - a perfect place for work or entertainment. Outside, this property features all of the Berkshire outdoor essentials. Enjoy summers on the large screened porch, eat al fresco on a lovely patio, and hold summer soir es or pursue one's creative pursuits in the charming two-story timber frame barn. With 5 bedrooms, 6 bathrooms, and multiple living and creative/work areas - indoors and out - this 4,900 sq ft home welcomes the possibilities of today's lifestyles while captivating the heritage of this classic colonial. A short stroll to eateries, groceries, and entertainment, and just minutes to Lenox and Great Barrington. See it now and be in before the summer!

Wonderful opportunity to enjoy summer in the Berkshires! Panoramic westerly views from this Stockbridge condo that is conveniently located to Lenox village and a short drive to Tanglewood. Enjoy beautiful sunsets and glorious foliage. Two bedrooms each with private bath; the open floor plan includes fireplace open kitchen and slider to the rear deck. The den tucked off from the kitchen serves as a third sleeping space. Central a/c; gas heat, stack laundry. The community includes swimming pool and tennis/pickleball.

Introducing an exquisite Colonial masterpiece in the heart of historic Stockbridge. Nestled amidst the picturesque Berkshire Mountains, this charming residence is situated on 0.74 acres with a bonus cottage. Close to many local attractions including Tanglewood, Norman Rockwell Museum, and Chesterwood. Inside, you'll discover a harmonious fusion of old-world charm and contemporary convenience. The spacious living areas exude warmth and sophistication, with gleaming wide-plank hardwood floors, and a cozy fireplace off the remolded kitchen and dining area. The main home has been completely renovated with a new roof, windows, siding, heating and electrical. Including one full bathroom, three bedrooms, one on the first floor and two on the second. Additional cottage included on the lot with endless possibilities! Could be used as an in-law suite, artist studio, or rental for additional income. Also renovated to mirror the main home.

Just a very special property. Located between the Rockwell Museum and the Botanical Garden. You are moments from Tanglewood. Equidistant from Lenox and Great Barrington so it's easy to access the Berkshires wonderful restaurants. The main house has three bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. Gracious grounds are well landscaped. Adorable play house for little ones. Several various outbuildings. Garages for at least 5 cars.

A classic Main St Stockbridge residence on a remarkable 4.3 acres. Walk to shops, restaurants, town tennis courts, the library, the Stockbridge Golf Club, the Berkshire Theatre Festival and more. The David Dudley Field house c.1824 is steeped in history remaining in the Field family until 1984. The current owners have lovingly maintained and cherished this exceptional property for 40 yrs. The gracious interior is bathed in natural light and full of beautiful period details. Front and back staircases, pocket doors, built-in shelving, exceptional fireplace mantels, beautiful floors, etc. The carriage barn is a delight. An exceptional property perfectly located in the center of Berkshire activities. Lenox and Great Barrington are only a quick 10 minutes away.

A Magnificent 6 bedroom stucco residence less than a mile to the center of Stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out beautiful French doors to your screened in patio which leads to a well lit and heated pool. A 20 ft hallway wall of built in cabinets and closets leading to the primary bedroom. Three en suite bedroom areas for guests and family. Electric car charger in the heated garage. Majestic stonewalls. Not far to all attractions Tanglewood, Norman Rockwell, ski areas etc. A must see!

Waterfront! A year round vacation home with 158 feet of frontage on the Stockbridge Bowl. Two bedroom contemporary including a 2 story living room with vaulted ceiling and double sided wood burning fireplace. Dining room with deck and water views is off an efficient kitchen. Cozy bedroom and bath on main level. Open staircase to the second floor overlooks the spacious living room. Primary bedroom has a fireplace, private deck, and bath with steam shower. Oversized windows, skylights, glass sliders and a glass solarium bring the view inside. Come and enjoy all the Berkshires has to offer including Tanglewood, Jacob's Pillow, Norman Rockwell Museum. Sail, swim or kayak on the lake, hike at Olivia's Overlook, ski at Butternut, Catamount. Close proximity to both Stockbridge and Lenox

GREAT STOCKBRIDGE-LENOX HOME with POOL For TANGLEWOOD + STOCKBRIDGE BOWL (lake) fans - stroll to the Music Shed at Tanglewood in just over 5 minutes, or 10 minutes to YOUR DEEDED ACCESS AT THE BOWL for picnics or kayaking! The back yard is your own summer resort! This 2,829 sq ft home has been substantially renovated & improved since it was purchased in 2018. It now features all the coveted features one seeks in a BERKSHIRE GETAWAY OR FULL-TIME HOME: pool (w/ new liner & systems); beautifully landscaped, very private backyard, patio, fire pit, hot tub & space for outdoor games; screened porch; 1st floor primary suite with fireplace; new kitchen & new great room with gas fireplace since 2018 + 3 ENSUITE BEDROOMS & 5 baths, office/den/add'l sleeping space + a bonus basement area.

One of the Berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media)room, wine cellar, fitness studio. elevator, computerized systems. 9,339 SF with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house