Stockbridge, Massachusetts is a small town that is mostly still the same as it was in the 1950s when Norman Rockwell painted it. The Red Lion Inn is the centerpiece of Main Street. Along Main Street in Stockbridge, you will also find the Berkshire Botanical Garden and the Norman Rockwell Museum. Stockbridge’s largest lake is the Stockbridge Bowl.
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SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool, , 3 bedroom guest house, barn complex and paddocks, a magnificent maze, and additional formal gardens. See documents file for detail of each building, room and floor plan.
Listing courtesy of Cindy Welch and Keith Ross of LANDVEST, INC.
Spectacular 36-acre estate steps from Tanglewood's Hawthorne Gate. Enjoy the relaxed elegance of the impeccable New Traditional brick manor house, which combines 21st-century conveniences with exquisite top-quality custom details and graceful elements of another era. In a jewel-like setting with beautiful landscaping and views of emerald lawns and hills. Custom furnishings available separately.
Listing courtesy of Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
A once-in-a-lifetime opportunity to renovate or potentially to build on an existing 6, 328sf footprint, in a prime 8.63-acre spot with significant lake frontage on the west side of the Stockbridge Bowl (Lake Mahkeenac). The existing six-bedroom home has been gutted and awaits a new owner with a new vision. Two architectural plans, one Arts & Crafts, one Modernist, both customized to the site, are available for review. This is a gorgeous building site on the lake and an ideal location, minutes from restaurants, galleries and shops in Lenox and Stockbridge; close to Kripalu, Tanglewood, and all the cultural, culinary and outdoor amenities for which the Berkshires are known; and just 2.5-hours drive from Boston and New York.
Listing courtesy of Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
Exquisitely renovated late 1700 antique home w/ perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded with light. Beautifully sited on over 9 acres on one of the most prestigious roads in the county. Barn, apple orchard, specimen trees, masterful stonework. Secluded and private heated Gunite pool w/ classic pool house & adventurous boardwalk.
Listing courtesy of Christian Deckert of Berkshire Property Agents
Living is easy in this impressive Stockbridge contemporary located on a fantastic plot of land with western view, blazing sunsets and heated pool all minutes from Tanglewood. Three levels of thoughtful living spaces with soaring two level Great Room open to informal dining and gourmet kitchen make the perfect gathering space around the fireplace on cool fall days while taking in the view from the walls of glass. Wander out to the extensive decking on those warm fall days that overlook the heated pool and look forward to making memories of Berkshire summers. The master bedroom, with "His & Her" baths, are on the main level; guests have their own floor. Lower level family room with fireplace and galley kitchen with bar make this wonderful family space most convenient for exercising,
Listing courtesy of Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES
Total privacy on 22 acres with back country roads for strolling. Within a couple of miles you will find fresh baked bread, a pub, the Norman Rockwell Museum, the Berkshire Botanical Garden and Chesterwood. And within 6 or 7 miles you will find the boat ramp at Stockbridge Bowl, Kripalu Yoga Center and Tanglewood. Wonderful setting with mature trees, landscaped gardens, extensive stonework and in-gorund pool. Beautifully designed home with dramatic two-story foyer, spacious living room, exceptional library, dining room and porch each with fireplace, country kitchen. Great wall space to display art. A covered colonnade joins the main house to the guest house with 2 bedrooms, bath and gathering room plus a large office/studio and a garden workshop. A FABULOUS place to live! A winding driveway through dappled sunlight and mature trees leads to the picturesque setting for this exceptional home. The house is surrounded by expansive landscaped gardens, with seasonally blooming perennials, rock garden plants, rare species, and extensive stonework. Enter the gracious spacious two-story foyer. Step down into the sun filled living room with fireplace. The exceptional library is lined with bookshelves. Dining room has its own fireplace as does the adjacent dining porch. The large eat-in country kitchen has a wall of windows looking out to the gardens. The butler's pantry and the large back mudroom provide terrific work spaces for household activities and entertaining. Complete with wine cellar in the basement. The flow of spaces is excellent and there are multiple accesses to the outdoors. On the second floor is the master suite with a sunny southern exposure, his and her walk-in closets with custom cabinetry, and a grand European styled bath. Two other bedrooms, one with a fireplace, open onto an open balcony porch overlooking the gardens. The rooms are beautifully sized and have a dedicated bath. Two more bedrooms with a sitting area are easily available just steps away in the charming guesthouse reached by a covered stone colonnade. This building also contains a large open office space that could be used as a family game space or studio. On the lower of the three levels is a garden studio/workshop. Through the gardens and stone paths is the in-ground swimming pool for summer enjoyment. Take walks on the country back roads, stroll to Chesterwood. Terrific location near the Norman Rockwell Museum and the Berkshire Botanical Garden. 7 miles to Great Barrington and 6 miles to Tanglewood.
Listing courtesy of Martha Piper and Sheila Thunfors of STONE HOUSE PROPERTIES, LLC
Quiet, serene and beautiful - a retreat or a place for magnificent entertaining - it's your choice. One of a kind home, built by the current owners in 1994 & lovingly maintained. Enter the foyer & take in a view across the great room through two stories of windows to the gunite pool, Lily Pond and views beyond. Living room, 1st floor master bedroom, atrium dining all take in the view. A custom paneled office is nestled away for privacy. The second floor offers three more bedrooms & 2 full baths. The lower lever has spacious media & game rooms & extra all purpose rooms with a full bath. Your dock on Lily Pond is great for canoes & kayaks. Less than 5 minutes to Lenox and Stockbridge. Deeded rights to private beach on Stockbridge Bowl.
Listing courtesy of Anthony C Blair and Suzanne Crerar of STONE HOUSE PROPERTIES, LLC
Set on 4.2 acres in a prestigious neighborhood, this 5 bedroom contemporary has sensational pastoral views overlooking a farm and two mountain ridges. A spacious, open floor plan, large country kitchen, privately placed ensuite guest rooms and expansive patio and porch facing unending views, make this home perfect for entertaining. Within walking distance to Lenox for shopping and dining.
Listing courtesy of Sheila Thunfors of STONE HOUSE PROPERTIES, LLC
Exquisite home with winter views. Walk to the town beach to your stored kayaks. Entertain with style in this open, bright and beautiful contemporary home. A grand center fireplace will warm you on cold winter evenings. A beautiful first floor master bedroom has a raised gas fireplace and a glorious master bathroom. Share food with love from the delightful gourmet kitchen with center island, gorgeous granite counters and stainless steel appliances. Relax with a glass of wine on the peaceful screened porch and listen to the music drifting from Tanglewood just minutes away. Minutes to the downtowns of Stockbridge, Lenox, Great Barrington, and West Stockbridge This is a perfect home in a perfect Stockbridge location. Please see supplement for specifications.
Listing courtesy of Maureen White Kirkby of BARNBROOK REALTY, INC.
Secluded & private, yet conveniently located in scenic Stockbridge, w/in minutes drive of the Berkshires' premier cultural attractions. Magnificent setting offers tranquil retreat in stunning landscape. Beautiful natural features create an intimate sense of connection with nature & the seasons. Over 30 conservation acres & pvt walking trails ensure this beauty & tranquility will remain forever.
Listing courtesy of Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
''A Merchants Home'' The Best of New World and Old. Inspired French Country Estate this exceptional home tells a story. A private driveway leads to this remarkable residence. The first floor of this lovely house includes a Chef's kitchen with Separate eating area, Office, Library with Fireplace, Laundry Room, Powder room, Mud room, Screen Porch, with a Formal Living Room with Fireplace. Temperature controlled master wine cellar. The second floor offers the Master Bedroom with sitting area, large bath and River views, 2 guest rooms with en suite bath, one large fireplace.2 Lincoln Lane is truly an address of prestige, located within walking distance to many restaurants and cultural attractions. Separate charming guest house. Private entrance. The grounds features a landscape plan thoughtfully designed by Windy Hill. This beautiful home and grounds make this property a must see. The privacy, space, and proximity to both river and main street Stockbridge make it a one-of-a kind opportunity. This location is secluded and quiet as though living in the country yet close enough to walk to town and get a cup of coffee. 2.5 hours to NYC and 2 hours to Boston . 45 minutes to Hartford Int'l Airport or Albany Int'l Airport.
Listing courtesy of Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
Rated #1 in Mass. and #9 in the US by Trip Advisor Seasons on Main is a nationally recognized top rated 1862 Greek revival B&B in the center of Stockbridge and has been lovingly restored to its original grandeur and maintained with the utmost care.This is your opportunity to own a turnkey business with a proven record of success, or to have as your own exquisite homestead.
Listing courtesy of Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES
Founded in 2007 by long-time Berkshire residents Tim Lovett and Jen Harvey, Berkshire Property Agents is an independent, locally-owned real-estate agency that caters to both full-time residents and second-home owners in Berkshire, Columbia and Litchfield counties. Based in Great Barrington, Massachusetts, BPA is committed to preserving the rural landscape and supporting the cultural organizations that contribute to the region’s exceptional quality of life. Whether representing buyers or sellers, BPA’s team of agents maintain the highest professional standards with a focus on extraordinary customer service.
*Based on Berkshire Board of REALTORS figures. All data and representations herein are derived from public records, client represenations and other general sources of information. Berkshire Property Agents makes its best effort to assure the completeness of such information, but makes no warranty or assertion as to the accuracy of the information presented. BPA recommends that all information be verified by clients and their representatives.