66 Stockbridge, MA 01262 Real Estate Listings

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$2,550,000Est. Payment
5 Beds | 4 Baths | 3,424 Sqft

78 Interlaken Rd, Stockbridge, MA 01262

House For Sale

Spacious 1800's Colonial tastefully updated on 8 acres of land with 296 ft of waterfront on Stockbridge Bowl! A private dock for your boat. A secluded flat grass area for picnics and sunbathing. Swim from the sandy water front. The house offers 4 or 5 bedrooms, 4 updated baths, expansive eat in kitchen with butcher block counters, an island, stainless appliances and walk in pantry/laundry room. The kitchen opens to the cozy family room with French doors to a covered porch and views of acres of fields. The living space includes a 25 ft living room with fireplace, large dining room currently being used as a pool room! Time for a game? Enjoy out door living in style; porches, decks, gardens, stone walls, gorgeous lawn and basketball court. More than enough space for pool and or tennis!

$835,000Est. Payment
3 Beds | 2 Baths | 219,542 Sqft

32 Prospect Hill Rd, Stockbridge, MA 01262

House For Sale

This Circa 1930's colonial w/classic gambrel roof located on one of the most picturesque roads in the Berkshires is just minutes from Main St. Stockbridge, the Stockbridge Bowl beachfront and Tanglewood just down the road. The addition of a Great Room where all can gather with direct access to a vaulted ceiling dining area overlooking the fabulous acreage with mountain view make this a most welcoming home. Wonderful spacious decking is the perfect spot to enjoy the privacy and magnificent mature trees and landscaping with a backdrop of rolling hills. Formal living and dining rooms, spacious eat in country kitchen, three bedrooms and two full baths with lovely pastoral vistas from all, offer you the opportunity to enjoy living in a most comfortable home in a fantastic Berkshire location!

$599,000Est. Payment
6 Beds | 4 Baths | 3,638 Sqft

74 East Main St, Stockbridge, MA 01262

House For Sale

Charming In-Town Victorian. Close to all downtown Stockbridge attractions including The Red Lion Inn and Berkshire Theatre Festival. Close to the town tennis courts and playground. This historic home has 6 bedrooms and 4 bathrooms, which includes a separate one bedroom apartment with its own kitchen and entrance, perfect for additional rental income or an in-law suite for guests. The main house has a sunny south-facing addition that opens up to a large deck overlooking the parklike, fenced in backyard. This home could easily be updated with modern amenities while maintaining the historic charm, with its wide plank wood floors, large fireplaces, and beautiful built-ins.

$425,000Est. Payment
3.3 Acres

9 Wheatley Dr, Stockbridge, MA 01262

Lots Land For Sale

Serene Lilly Pond waterfront 3.3 acre building lot with deeded rights to a private beach on Stockbridge Bowl. This wooded lot is perfectly situated on a quiet street just minutes to Tanglewood and downtown Lenox/Stockbridge.

$269,500Est. Payment
2 Beds | 1 Bath | 33,541 Sqft

2 Massasoit Rd, Stockbridge, MA 01262

House For Sale

Drive down an unpaved country lane just 2 miles from Tanglewood and a short walk from the town beach on Stockbridge Bowl and you'll enter a world of its own. Park in the circular driveway, walk through lovely hosta gardens and arrive at a meticulously maintained rustic cottage! You'll find two large decks (sun and shade) separated by a 25 ft screened-in porch. Enter the great room featuring hardwood floors, a soaring fieldstone fireplace, and a cathedral ceiling with large skylights. You'll have two bedrooms plus a charming sleep-in loft, bathroom with corner shower unit, and a compact, efficient kitchen that opens to a bluestone patio! This unique Mahkeenac Heights cottage sits on a 3/4 acre wooded lot providing lots of privacy, but owners enjoy belonging to a friendly community.

$900,000Est. Payment
12.49 Acres

Prospect Hill Rd, Stockbridge, MA 01262

Lots Land For Sale

Build your perfect home on this land sited along one of the most prestigious roads in Stockbridge. The property encompasses the entire corner running along Prospect Hill, Larrywaug and to North Church St. or divide into three lots. Four acre zoning and this property has enough frontage and acreage for three building lots. With clearing there is the possibility of views from different sites on the property.

$745,000Est. Payment
3 Beds | 3 Baths | 36,155 Sqft

29 Mahkeenac Rd, Stockbridge, MA 01262

House For Sale

A convenient location in Stockbridge with Lenox nearby, too! This property is part of the Mahkeenac Terrace association on the east shore of Stockbridge Bowl. Single level living. Large master suite with sitting area, gas fireplace. Open kitchen living room with 14!ft eating island, floor to ceiling windows, gas fireplace. Large private patio with built in grill and refrigerator. Out building provides additional entertainment space plus storage for winter months. Swim or dock boat ( annual fee) at private association beach.

$449,000Est. Payment
4 Beds | 2 Baths | 15,682 Sqft

71 East Main St, Stockbridge, MA 01262

House For Sale

Historic 1840 Main Street Stockbridge home with unique architectural detail being offered for the first time in over 70 Years! This 2,877 sq/ft home features a sun-filled living room, formal dining room, family room, and sitting room within the first floor of the original home. A modern addition has created a spacious kitchen/dining area with a full bath and laundry area. The second floor completes the home with 4 bedrooms and a full bath. This in-town home on .36 of an acre also contains a historic barn for endless possibilities. Walk to Red Lion Inn for dining & cocktails and Berkshire Theatre Festival for performing arts!

$1,050,000Est. Payment
6 Beds | 4 Baths | 47,045 Sqft

17 Willard Hill Rd, Stockbridge, MA 01262

House For Sale

New England Refuge: space to live, work from home, play, and learn. On the picturesque banks of the Larrywaug Brook this stunning, welcoming compound awaits. Wonderful living spaces, indoors and out, a fantastic vegetable garden and sugaring shack to sustain you and share with family and friends, office spaces, schoolroom and fitness area comprise the light-filled third floor.At Willard Hill, you can unwind in your magical gardens, convene by the brook, books or work in hand, attend to calls from either the upper or lower porches, use local byroads and the wide open third floor for exercise, gather and cook with supplies from your own garden. In a word - life here can be private and independent and nourishing all within 10 minutes of delightful Stockbridge, Lenox and West Stockbridge.

$349,000Est. Payment
6 Beds | 3 Baths | 30,492 Sqft

23 Glendale Rd, Stockbridge, MA 01262

Multi Family For Sale

Say goodbye to your landlord. Move in to one side of this renovated two family home and let your tenant help pay your mortgage. On a corner lot by a little park. Put your kayak on the river in back of your home. Two 3 bedroom apartments in move in condition in a great location, Five minutes to Stockbridge Village , ten minutes to Tanglewood and Stockbridge Bowl for swimming and boating.

$350,000Est. Payment
3 Beds | 2 Baths | 60,984 Sqft

13 Cherry Hill Rd, Stockbridge, MA 01262

House For Sale

Situated on a quiet country road in the heart of the Berkshires, this roomy ranch is located just south of the Red Lion Inn. Close to Tanglewood, Stockbridge Bowl, and Kripalu. Take advantage of local skiing, horseback riding, and area cultural attractions, yet still be only 2 1/2 hours from NYC or Boston. Enjoy your Berkshires getaway in a storied New England town and be a part of village life in charming Stockbridge!

$504,000Est. Payment
3 Beds | 4 Baths | 56,628 Sqft

328 Old Stockbridge Rd, Stockbridge, MA 01262

House For Sale

Welcome home to Serendipity! Originally part of the Elm Court Estates this charming home has hand-hewn Chestnut beams that add gorgeous character throughout the home. This home was thoughtfully expanded to preserve the sight lines and original character while modernizing for todays essentials. The expansive private backyard is meticulously landscaped with a blue stone patio, stone waterfall and mature Magnolia trees. The first floor includes an open dining room to kitchen with granite counter tops, family room, living room with glass doors to the patio, office, laundry room, first floor bedroom, full bathroom, and guest half bath. The second floor separate master suite includes a large bedroom with wood floors and vaulted ceiling, walk-in closet, and master bathroom with soaking tub

$525,000Est. Payment
3 Beds | 3 Baths | 2,130 Sqft

29 Rattlesnake Mountain Rd, Stockbridge, MA 01262

House For Sale

NEW REDUCED PRICE! Live in true Berkshires splendor with magnificent mountain views! This contemporary 3 bedroom has it all. Open floor plan with loads of sunlight, gourmet kitchen and large deck for entertaining. Level property with tranquil meadows. Ideally located very close to Tanglewood and Stockbridge Bowl town beach. Very close to vibrant downtown Lenox and so many of the Berkshires' world class cultural attractions. Don't miss this gem!

$1,200,000Est. Payment
5 Beds | 3 Baths | 960,934 Sqft

20-A Goodrich St, Stockbridge, MA 01262

House For Sale

Perfection in America's ''most charming'' townBuilt in 2010 by local craftsman Gregg Wellenkamp, this five bedroom, three and half bath contemporary is the definition of turn key. Bright, inviting, and warm, with amenities galore. First floor or second floor master/guest suite depending on your preference. Modern chef's kitchen, saltwater pool, hot tub spa, music room, basketball court, heated garage, fenced garden, and screened porch are highlights of this modern oasis. Set back from the road, it is private yet conveniently located just minutes to downtown GB and Stockbridge, and a short drive to Tanglewood, Norman Rockwell Museum, Chesterwood, Stockbridge Bowl and more! NO SHOWINGS 7/16-7/20.--

$495,000Est. Payment
2 Beds | 2 Baths | -- Sqft

11 Prospect Hill Rd Rd #C, Stockbridge, MA 01262

Condominium For Sale

This condo combines the charm and elegance of the original 1880s mansion with the modern layout and amenities of pool, tennis court, gym. Large windows bathe the two-story, floor-through unit in natural light throughout the day. The main floor offers a beautiful, formal living space open to a high-end kitchen featuring granite counters and custom cherry cabinetry. The southwest facing terrace, with stunning panoramic views of the Berkshire Hills, is the perfect spot to enjoy casual meals and watch the sunset. The main floor includes a family room, second bedroom and hall bath that affords private guest accommodations, washer and dryer, and ample storage space. The large master suite upstairs features a walk-in closet and spacious bathroom. Community amenities include an in-ground poo

$1,200,000Est. Payment
6 Beds | 6 Baths | 174,240 Sqft

1 Devon Rd, Stockbridge, MA 01262

House For Sale

The Historic General Williams House circa 1795, has been lovingly restored and improved and now provides modern day comfort in quintessential Stockbridge MA. Featuring 6 inviting bedrooms, 5.5 modern baths, 6 elaborate wood burning fireplaces, two cook's kitchens, spacious dining and living areas, a sparkling new in-ground pool and separate ''Ice House'' that is ideal for group gatherings with it's own kitchen and full bath. Ideally situated on 4 acres this delightful residence is only 2 miles from Rockwell's famous Stockbridge Main Street and only 5 miles to Lenox township and Tanglewood Music Center. Bask in the Berkshire sunshine poolside, invite friends to chat on one of the stone terraces, or simply rock the afternoon away on a tree top porch.One can enjoy this grand property as a

$459,000Est. Payment
2 Beds | 3 Baths | -- Sqft

19 Hawthorne Rd #Cb D2, Stockbridge, MA 01262

Condominium For Sale

Beautiful Carriage Barn Unit in White Pines; Gracious common spaces with wall of windows flooding the unit with natural light, renovated kitchen w/new counters and backsplash, sunroom/bedroom with closet; great room with fireplace, powder room, second level master en suite and guest bedroom en suite. Stunning views of natural beauty from every window; Association indoor pool, Har tru tennis courts, association beach on the Stockbridge Bowl, exercise room and walking trails. All of this in a convenient location within walking distance to Tangelwood, Lenox Village and Berkshire cultural attractions!

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