1,881

Stockbridge, MA Homes

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  • /5

    $495,000

    • Land
    • 19 Acres
    • $26,053 per Acre

    0 Mohawk Lake Rd, Stockbridge, MA 01262

    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

    Debra Petrovsky DONOVAN REAL ESTATE

    0 Mohawk Lake Rd, Stockbridge, MA 01262
  • /7

    $825,000

    Sold Mar 13, 2026

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

    • Land
    • 9.1 Acres
    • $90,659 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 303 Days On Market

    Last Listing Agent Selina Lamb BIRCH PROPERTIES

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
    • /11

      Est $488,339

      Not Listed For Sale

      14 Partridge Way, Stockbridge, MA 01262

      • 3 Beds
      • Built 1947
      14 Partridge Way, Stockbridge, MA 01262

      Last Sold Summary

      • 16 Days On Market

  • /56

    $1,490,000

    $260K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    5 Glendale Rd, Stockbridge, MA 01262

    ''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage'' Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

    Martha Piper THE KINDERHOOK GROUP

    5 Glendale Rd, Stockbridge, MA 01262
  • /47

    $2,575,000

    Sold May 29, 2026

    11 Mahkeenac Terrace, Stockbridge, MA 01262

    • 4 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 1952

    Last Sold Summary

    • 14% Below List Price
    • $1,617/SF
    • 11 Days On Market

    Current Estimated Value $2,288,350

    Last Listing Agent Patricia Andrew STONE HOUSE PROPERTIES, LLC

    11 Mahkeenac Terrace, Stockbridge, MA 01262
    • /41

      Not Listed For Sale

      19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262

      • 2 Beds
      • 2 Baths
      • 1,768 Sq Ft
      • Built 1986
      19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262

      Last Sold Summary

      • 6 Days On Market

  • /30

    $2,650,000

    • 5 Beds
    • 5 Baths
    • 3,700 Sq Ft

    8 Shamrock St, Stockbridge, MA 01262

    A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTSHistoric Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage--crafted with

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    8 Shamrock St, Stockbridge, MA 01262
  • /53

    $750,000

    Sold Aug 26, 2025

    85 E Main St, Stockbridge, MA 01262

    • 4 Beds
    • 4 Baths
    • 2,688 Sq Ft
    • Built 1735

    Last Sold Summary

    • 4% Below List Price
    • $279/SF
    • 36 Days On Market

    Current Estimated Value $795,898

    Last Listing Agent Susan Laidlaw COMPASS MASSACHUSETTS , LLC GB

    85 E Main St, Stockbridge, MA 01262
    • /37

      Not Listed For Sale

      11a Interlaken Cross Rd, West Stockbridge, MA 01266

      • 4 Beds
      • 5 Baths
      • 4,088 Sq Ft
      • Built 2003
      11a Interlaken Cross Rd, West Stockbridge, MA 01266

      Last Sold Summary

      • 14 Days On Market

  • /50

    $2,185,000

    • 3 Beds
    • 4 Baths
    • 4,752 Sq Ft

    14 Old Tree Farm Rd, Stockbridge, MA 01262

    A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking

    Claire Pollart WILLIAM RAVEIS - BERKSHIRE

    14 Old Tree Farm Rd, Stockbridge, MA 01262
  • /52

    $975,000

    Sold Jul 25, 2025

    66 Interlaken Rd, Stockbridge, MA 01262

    • 4 Beds
    • 3 Baths
    • 2,010 Sq Ft
    • Built 1948

    Last Sold Summary

    • $485/SF
    • 10 Days On Market

    Current Estimated Value $968,188

    Last Listing Agent Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    66 Interlaken Rd, Stockbridge, MA 01262
    • /29

      Not Listed For Sale

      8 Arthur Fiedler Ln, Stockbridge, MA 01262

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 1965
      8 Arthur Fiedler Ln, Stockbridge, MA 01262

      Last Sold Summary

      • 0 Days On Market

  • /52

    $2,100,000

    • 4 Beds
    • 4 Baths
    • 2,738 Sq Ft

    8 Yale Hill Rd, Stockbridge, MA 01262

    A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    8 Yale Hill Rd, Stockbridge, MA 01262
  • /54

    $2,600,000

    Sold Dec 30, 2025

    55 Main St, Stockbridge, MA 01262

    • 5 Beds
    • 4.5 Baths
    • 5,233 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Above List Price
    • $497/SF
    • 140 Days On Market

    Current Estimated Value $3,210,375

    Last Listing Agent Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    55 Main St, Stockbridge, MA 01262
    • /20

      Est $528,637

      Not Listed For Sale

      3 N Church St, Stockbridge, MA 01262

      • 2 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1982
      3 N Church St, Stockbridge, MA 01262

      Last Sold Summary

      • 2 Days On Market

  • /23

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft

    8 Lukeman Ln, Stockbridge, MA 01262

    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

    Jesse Dimitropolis RE/MAX COMPASS

    8 Lukeman Ln, Stockbridge, MA 01262
  • /64

    $1,205,000

    Sold Aug 11, 2025

    44 Prospect Hill Rd, Stockbridge, MA 01263

    • 5 Beds
    • 4 Baths
    • 2,976 Sq Ft
    • Built 1980

    Last Sold Summary

    • 7% Below List Price
    • $405/SF
    • 32 Days On Market

    Last Listing Agent Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

    44 Prospect Hill Rd, Stockbridge, MA 01263
    • /34

      Est $1,056,658

      Not Listed For Sale

      42 Lake Dr, Stockbridge, MA 01262

      • 3 Beds
      • 3 Baths
      • 1,446 Sq Ft
      • Built 2001
      42 Lake Dr, Stockbridge, MA 01262

      Last Sold Summary

      • 78 Days On Market

  • /42

    $14,500,000

    • 19 Beds
    • 25 Baths
    • 19,364 Sq Ft

    11 Hawthorne Rd, Stockbridge, MA 01262

    The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century

    Steven Weisz William Pitt Sotheby's International Realty

    11 Hawthorne Rd, Stockbridge, MA 01262
  • /70

    $1,200,000

    Sold Sep 05, 2025

    49 Main St, Stockbridge, MA 01262

    • 5 Beds
    • 4 Baths
    • 3,289 Sq Ft
    • Built 1850

    Last Sold Summary

    • 8% Below List Price
    • $365/SF
    • 27 Days On Market

    Current Estimated Value $1,216,359

    Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

    49 Main St, Stockbridge, MA 01262
    • /30

      Est $600,484

      Not Listed For Sale

      23 Church St, Stockbridge, MA 01262

      • 4 Beds
      • 2 Baths
      • 1,409 Sq Ft
      • Built 1900
      23 Church St, Stockbridge, MA 01262

      Last Sold Summary

      • 3 Days On Market

  • /88

    $3,250,000

    • 4 Beds
    • 4 Baths
    • 5,696 Sq Ft

    7 Wheatley Dr, Stockbridge, MA 01262

    A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    7 Wheatley Dr, Stockbridge, MA 01262
  • /19

    $490,000

    Sold May 15, 2026

    15 W Stockbridge, Stockbridge, MA 01262

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft
    • Built 1956

    Last Sold Summary

    • 11% Below List Price
    • $188/SF
    • 229 Days On Market

    Last Listing Agent C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

    15 W Stockbridge, Stockbridge, MA 01262
    • /34

      Not Listed For Sale

      176 Old Stockbridge Rd Unit Smith 4, Stockbridge, MA 01262

      • 2 Beds
      • 2.5 Baths
      • 1,610 Sq Ft
      • Built 1988
      176 Old Stockbridge Rd Unit Smith 4, Stockbridge, MA 01262

      Last Sold Summary

      • 39 Days On Market

  • /61

    $1,900,000

    • 5 Beds
    • 6 Baths
    • 4,670 Sq Ft

    53 Main St, Stockbridge, MA 01262

    Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three

    Paula McLean PAULA MCLEAN REALTORS INC.

    53 Main St, Stockbridge, MA 01262
  • /17

    $403,000

    Sold Nov 07, 2025

    7 Mahkeenac Heights Rd, Stockbridge, MA 01263

    • 3 Beds
    • 1.5 Baths
    • 1,171 Sq Ft
    • Built 1940

    Last Sold Summary

    • 6% Above List Price
    • $344/SF
    • 40 Days On Market

    Last Listing Agent Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    7 Mahkeenac Heights Rd, Stockbridge, MA 01263
    • /34

      Est $945,619

      Not Listed For Sale

      25 Nielsen Ln, Lenox, MA 01240

      • 4 Beds
      • 2.5 Baths
      • 2,127 Sq Ft
      • Built 1951
      25 Nielsen Ln, Lenox, MA 01240

      Last Sold Summary

      • 4 Days On Market

  • /30

    $752,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    9 Interlaken Rd, Stockbridge, MA 01262

    Quitessential 1830's 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

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    9 Interlaken Rd, Stockbridge, MA 01262
  • /38

    $548,000

    Sold Dec 18, 2025

    19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262

    • 2 Beds
    • 4 Baths
    • 1,870 Sq Ft
    • Built 1986

    Last Sold Summary

    • 16% Below List Price
    • $293/SF
    • 88 Days On Market

    Last Listing Agent Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262
    • /57

      Est $1,427,105

      Not Listed For Sale

      17 Main St, Stockbridge, MA 01262

      • 4 Beds
      • 2.5 Baths
      • 3,300 Sq Ft
      • Built 1824
      17 Main St, Stockbridge, MA 01262

      Last Sold Summary

      • 244 Days On Market

  • /60

    $3,150,000

    $250K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 3,432 Sq Ft

    36 Yale Hill Rd, Stockbridge, MA 01262

    EXPANDED CONTEMPORARY CAPE Appointed with elegant detail and masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for

    Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

    36 Yale Hill Rd, Stockbridge, MA 01262
  • /42

    $445,000

    Sold Nov 06, 2025

    42 East St, Stockbridge, MA 01262

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $343/SF
    • 71 Days On Market

    Current Estimated Value $483,321

    Last Listing Agent Conor Meehan STONE HOUSE PROPERTIES, LLC

    42 East St, Stockbridge, MA 01262
    • /31

      Est $705,343

      Not Listed For Sale

      10 Church St, Stockbridge, MA 01262

      • 3 Beds
      • 2 Baths
      • 1,909 Sq Ft
      • Built 1900
      10 Church St, Stockbridge, MA 01262

      Last Sold Summary

      • 14 Days On Market

  • /16

    $295,000

    • Land
    • 25.22 Acres
    • $11,697 per Acre

    0 Glendale Rd Unit 248566, Stockbridge, MA 01262

    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

    Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    0 Glendale Rd Unit 248566, Stockbridge, MA 01262
  • /29

    $955,000

    Sold Sep 12, 2025

    9 Yale Hill Rd, Stockbridge, MA 01262

    • 4 Beds
    • 2.5 Baths
    • 2,008 Sq Ft
    • Built 1880

    Last Sold Summary

    • 4% Below List Price
    • $476/SF
    • 20 Days On Market

    Current Estimated Value $970,477

    Last Listing Agent Annabel Taylor Four Seasons Sotheby's International Realty

    9 Yale Hill Rd, Stockbridge, MA 01262
    • /26

      Est $589,079

      Not Listed For Sale

      7 Birch Ln, Stockbridge, MA 01262

      • 3 Beds
      • 1.5 Baths
      • 1,120 Sq Ft
      • Built 1949
      7 Birch Ln, Stockbridge, MA 01262

      Last Sold Summary

      • 18 Days On Market

  • /51

    $350,000

    • 6 Beds
    • 4 Baths
    • 2,700 Sq Ft

    3 Apple St, Stockbridge, MA 01236

    Rare opportunity to acquire a updated two-family property in Stockbridge with nearly 1.9 acres across two included lots. Come take a look to add your finishing touches to this project. Situated on a dead-end street on a spacious and clear lot. Each unit features three bedrooms and one-and-a-half baths, across approximately 2,700 square feet. Separate utilities for each unit, off street parking,

    Cory Evangelisto NOCHER REALTY

    3 Apple St, Stockbridge, MA 01236
  • /2

    $1,250,100

    Sold May 11, 2026

    1 S Hill Rd, Stockbridge, MA 01262

    • 5 Beds
    • 3 Baths
    • 2,870 Sq Ft
    • Built 1780

    Last Sold Summary

    • 4% Above List Price
    • $436/SF
    • 1 Day On Market

    Current Estimated Value $1,146,326

    Last Listing Agent Comparable Listing COMPARABLE LISTING ONLY

    1 S Hill Rd, Stockbridge, MA 01262
    • /43

      Est $1,161,882

      Not Listed For Sale

      2 Cherry St, Stockbridge, MA 01262

      • 6 Beds
      • 4.5 Baths
      • 4,057 Sq Ft
      • Built 1900
      2 Cherry St, Stockbridge, MA 01262

      Last Sold Summary

      • 678 Days On Market

  • /27

    $595,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft

    1 Pixley Hill Rd, Stockbridge, MA 01262

    Tranquil Berkshire Retreat: Cottage with Screened Porch and River Sounds Embrace the ease of single-level living in this enchanting 3-bedroom, 2-full-bath cottage nestled in historic Stockbridge. Perfect as a year-round residence or a peaceful weekend getaway, this home perfectly blends cozy charm with modern convenience.

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1 Pixley Hill Rd, Stockbridge, MA 01262

Showing Results 41 - 80, Page 2 of 18

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