Stockbridge Real Estate

Stockbridge is the quintessence of small-town New England charm, untainted by large-scale development. It is also the blueprint for small-town America as represented on the covers of the Saturday Evening Post by painter Norman Rockwell (the official state artist of Massachusetts). From 1953 until his death in 1978, Rockwell lived in Stockbridge and painted the simple charm of its buildings and residents. James Taylor sang about the town in his hit "Sweet Baby James," as did balladeer Arlo Guthrie in his famous Thanksgiving anthem "Alice's Restaurant," in which he tells what ensued when he tossed some garbage out the back of his Volkswagen bus down a Stockbridge hillside.

Search new real estate in the Berkshires town of Stockbridge, MA. Discover hundreds of current listings, including single-family homes, luxury estates, and residential land. Love what you see? Register with us to save your favorites, and receive notifications when similar properties are listed. Contact us to see any of the homes below!

3 Ice Glen Stockbridge MA 01262

Stockbridge, MA3 Ice Glen Rd

Price$8,500,000

Est. Mortgage: $/month

MLS Number 225549

  • Residential
  • Bathroom 15
  • Bedrooms 13
  • Square Feet 12,253
  • Acreage 58.8

Built in 1915 believed to be the last of the berkshire cottages. This stunning home on 58.8 acres is just minutes to the village of stockbridge ma. Restored to its original splendor with black and white marble floor entry, curved marble staircase, loggia with painted ceiling and fountain. The library includes book shelves flanking 3 walls and two fireplaces. The room is used as an office/family space with tv and electronics hidden behind custom doors. Main salon with fireplace and views of the terrace and eastern light. Dining room with fireplace custom table seats 14 easily. Modern kitchen with corian topped island and comfortable table spaces. A work area as well as tv space off of kitchen. Nine bedrooms. Six baths on second and third floors. See additional info

Listed by Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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82 Interlaken Stockbridge MA 01262

Stockbridge, MA82 Interlaken Rd

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number 222056

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,000
  • Acreage 11.11

Rare waterfront opportunity on the stockbridge bowl: a paradise for your family. 11 acres on the beautiful bowl. Over 400 feet of pristine lake frontage looking across the ''belly'' of the bowl. Two beautiful site specific modern style plans have been drawn with walls of windows from every room facing the lake. Amazing mountain and water views in every season. Build one private home or a family compound. Three home sites with existing structure for rare opportunity to have your dream home within 71 feet of the lake. Minutes to tanglewood, kripalu, and canyon ranch.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12 Prospect Hill Stockbridge MA 01262

Stockbridge, MA12 Prospect Hill Rd

Price$1,850,000

Est. Mortgage: $/month

Pending

MLS Number 232169

  • Residential
  • Bathroom 5
  • Bedrooms 7
  • Square Feet 4,320
  • Acreage 1.82

Located on the most picturesque road in stockbridge, this completely renovated colonial is on almost 2 acres of level lawn w/ heated in-ground pool and awesome firepit. Central a/c, radiant heat, sparkling & open marble kitchen, a brilliant screened in porch w/ built in chefs grill. Huge media room w/ wet bar above the 3 bay garage. Master suite w/ fireplace and office space. 1 gb/s internet. Minutes from downtown stockbridge and lenox, tanglewood & the public beach at stockbridge bowl. Enjoy sunsets from the awesome front porch.

Listed by Christian G Deckert of BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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44 Main Stockbridge MA 01262

Stockbridge, MA44 Main St

Price$1,500,000

Est. Mortgage: $/month

MLS Number 228073

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 8,770

Rare opportunity to own a berkshire landmark. Known as ''the antique shop'' in norman rockwell's main street painting, this iconic building is famous worldwide. Classic victorian style with acres of charm. 3 stories with on-site parking. 3 'main street' retail spaces, a large (and vacant) second floor residential / office space and an income producing third floor. Owned and well-maintained by the same family since the 1960's and steps away from the red lion inn and former ''alice's restaurant''. Minutes to tanglewood and all berkshire attractions. Ideal for investment, office, residential or retail use. A true 'once in a life-time opportunity' to be part of stockbridge history.

Listed by Steven J. Weisz and Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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44 Main Stockbridge MA 01262

MLS Number 228072

  • Commercial

Rare opportunity to own a berkshire landmark. Known as ''the antique shop'' in norman rockwell's main street painting, this iconic building is famous worldwide. Classic victorian style with acres of charm. 3 stories with on-site parking. 3 'main street' retail spaces, a large (and vacant) second floor residential/office space and an income producing third floor. Owned and well-maintained by the same family since the 1960's and steps away from the red lion inn and former ''alice's restaurant''. Minutes to tanglewood and all berkshire attractions. Ideal for investment, office, residential or retail use. A true 'once in a life-time opportunity' to be part of stockbridge history.

Listed by Maggie C Merelle and Steven J. Weisz of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Brookside Stockbridge MA 01262

Stockbridge, MA2 Brookside Ln

Price$1,295,000

Est. Mortgage: $/month

MLS Number 232160

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,980
  • Acreage 3.33

Magnificent contemporary in spectacular setting. This move-in ready home has it all! Sun filled living room w/ double height, cathedral ceilings & floor to ceiling windows, great room that opens to a 4 season, enclosed, heated porch plus a large outdoor deck, perfect for entertaining friends. 1st floor also includes large first floor master suite w/ luxurious master bath & a state-of-the-art, open chef's kitchen. 2 spacious bedrooms upstairs plus an office. Fully finished, walk-out lower level w/ bedroom & full bath. Beautifully manicured grounds w/ mature plantings, lush lawns & waterfall. Deeded access to pvt. Dock on stockbridge bowl, just across the road - perfect for a kayak or paddleboard. Plus, additional deeded rights to private beachwood beach, just a short walk away.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Glendale and Butler Stockbridge MA 01262

Stockbridge, MAGlendale and Butler Rd

Price$1,200,000

Est. Mortgage: $/month

MLS Number 221926

  • Land
  • Acreage 45.83

Price reduced and now also available as 4 lots: 35 acres at $950,000 and 2 one acre lots for $125,000 along butler rd. Longfellow's oxbow consists of 45 acres within walking distance of the center of stockbridge. This large undeveloped parcel offers views, privacy, open space and a mile of river frontage. Ideal for a premiere home or homes with vast open maintained hayfields, and views to naumkeag, the back meadows of norman rockwell museum and overlooking the stockbridge golf club. Once used as a polo field, there is a run-in shed for horses. Longfellow's oxbow is named after the poet henry wadsworth longfellow , who once owned the land.With high conservation potential, it is possible to both build and conserve in this highly desired stockbridge location.

Listed by Keith Ross and Cindy Welch of LANDVEST, INC.

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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47 Main Stockbridge MA 01262

MLS Number 228609

  • Commercial
  • Acreage 0.32

Rated #2 in the country in 2018 and #16 in the world, 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.

Listed by Cortney K Dupont and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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47 Main Stockbridge MA 01262

Stockbridge, MA47 Main St

Price$998,500

Est. Mortgage: $/month

MLS Number 228608

  • Residential
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 4,977
  • Acreage 0.33

What a beautiful home for today! Set in the heart of stockbridge -- that most gracious and iconic of berkshire towns -- ''seasons'' is a new england classic, a lovingly detailed, superbly renovated 1862 greek revival mansion, warm and welcoming. From the restful length of its shady porch to the elegantly appointed front parlor, from the serene formal dining room to its secluded bedroom retreats, ''seasons'' manages to both welcome the world, while offering friends and family a perfect refuge. This spectacular all-season ''getaway'' home, part 19th century, part 21st, generously arranged, with elegantly designed public rooms, and the pleasures of a spacious modern chef's kitchen with multi-zone air conditioning throughout. In perfect order, it's waiting for your fortunate family!

Listed by Cortney K Dupont and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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49 Main Stockbridge MA 01262

Stockbridge, MA49 Main St

Price$995,000

Est. Mortgage: $/month

MLS Number 227978

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,289
  • Acreage 0.69

Gracious 1890 residence with carriage barn income property, graces the charming main street of stockbridge. The main house is comprised of 4 bedrooms, double parlors w/fireplace, formal dining room, country kitchen and the most delightful screened porch. An attached 2 bedroom apartment with separate entrance, is ideal for extended family and guests. Distanced from the main house by a circular drive, the converted carriage barn sets behind, housing three apartments. Mature landscaping, perennial gardens, stone patios, and a 3 bay garage complete this idyllic compound. Red lion inn, stockbridge golf club and theatre nearby.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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49 Main Stockbridge MA 01262

Stockbridge, MA49 Main St

Price$995,000

Est. Mortgage: $/month

MLS Number 228624

  • MultiFamily
  • Acreage 0.69
  • Year Built 1821

A gracious main street property with four rental apartments, a main house with four bedrooms, double parlors, country kitchen, two full baths, a wonderful screened porch and a three bay garage. The yard has wonderful out door spaces for the residents, and all a short walk to everything the town offers. Perfect for an investor owner occupier.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Prospect Hill Stockbridge MA 01262

Stockbridge, MAProspect Hill Rd

Price$900,000

Est. Mortgage: $/month

MLS Number 231106

  • Land
  • Acreage 12.49

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.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to BCMLS  as of November 27, 2020 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.