1,871

Stockbridge, MA Homes

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  • 9 Castle Hill Rd, Stockbridge, MA 01262
    9 Castle Hill Rd, Stockbridge, MA 01262
    9 Castle Hill Rd, Stockbridge, MA 01262
    /50

    $845,000

    • 4 Beds
    • 3.5 Baths
    • 2,955 Sq Ft

    9 Castle Hill Rd, Stockbridge, MA 01262

    Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated,

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 269-8632

    9 Castle Hill Rd, Stockbridge, MA 01262
  • 44 Main St Unit 3, Stockbridge, MA 01262
    44 Main St Unit 3, Stockbridge, MA 01262
    44 Main St Unit 3, Stockbridge, MA 01262
    /13

    $2,250 total monthly price

    • 2 Beds
    • 1 Bath
    • 583 Sq Ft
    • Condo for Rent

    44 Main St Unit 3, Stockbridge, MA 01262

    Totally Renovated, Newly Furnished, Stockbridge In-Town Location. Truly a ''renter's dream come true.''Must be seen!Rent is $2,250/Month September to June and $4500/month for July and August.No pets.

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    44 Main St Unit 3, Stockbridge, MA 01262
  • 176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
    176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
    176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
    /40

    $660,000 Sold Jul 10, 2025

    176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262

    • 2 Beds
    • 2.5 Baths
    • 1,853 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $356/SF
    • 133 Days On Market

    Last Listing Agent Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /17

      Est $238,000 Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 6% Above List Price
      • 661 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Gary Johnston STONE HOUSE PROPERTIES, LLC

  • 17 East St, Stockbridge, MA 01262
    17 East St, Stockbridge, MA 01262
    17 East St, Stockbridge, MA 01262
    /42

    $1,650,000 Pending

    • 4 Beds
    • 3 Baths
    • 7,027 Sq Ft

    17 East St, Stockbridge, MA 01262

    Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with an addition that respects the original proportions while opening new possibilities for contemporary living. Set along the Stockbridge–Lenox corridor on 13+/- acres (9

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 300-6860

    17 East St, Stockbridge, MA 01262
  • 44 Main St Unit 1, Stockbridge, MA 01262
    44 Main St Unit 1, Stockbridge, MA 01262
    44 Main St Unit 1, Stockbridge, MA 01262
    /20

    $8,500 total monthly price

    • 3 Beds
    • 2 Baths
    • Condo for Rent

    44 Main St Unit 1, Stockbridge, MA 01262

    STOCKBRIDGE IN-TOWN LOCATION. SUMMER RENTAL! Fully Furnished, Like New. 3 Bedroom Apartment. Must be seen to be appreciated. Location, Location, Location. It doesn't get any better than this. JULY AND AUGUST RENTS ARE $8500 per Month. Monthly rents outside of July and August will be $4,250 per month.

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    44 Main St Unit 1, Stockbridge, MA 01262
  • 3 Willard Hill Rd, Stockbridge, MA 01262
    3 Willard Hill Rd, Stockbridge, MA 01262
    3 Willard Hill Rd, Stockbridge, MA 01262
    /34

    $885,000 Sold Jun 30, 2025

    3 Willard Hill Rd, Stockbridge, MA 01262

    • 4 Beds
    • 3.5 Baths
    • 2,189 Sq Ft
    • Built 1996

    Last Sold Summary

    • $404/SF
    • 17 Days On Market

    Current Estimated Value $906,981

    Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB

    3 Willard Hill Rd, Stockbridge, MA 01262
    • 14 Interlaken Rd, Stockbridge, MA 01262
      14 Interlaken Rd, Stockbridge, MA 01262
      14 Interlaken Rd, Stockbridge, MA 01262
      /27

      Est $609,284 Not Listed For Sale

      14 Interlaken Rd, Stockbridge, MA 01262

      • 4 Beds
      • 2 Baths
      • 2,132 Sq Ft
      • Built 1969
      14 Interlaken Rd, Stockbridge, MA 01262

      Last Sold Summary

      • 52% Above List Price
      • $188/SF
      • 49 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Patricia Andrew STONE HOUSE PROPERTIES, LLC

  • 9 Wheatleigh Dr, Stockbridge, MA 01262
    9 Wheatleigh Dr, Stockbridge, MA 01262
    9 Wheatleigh Dr, Stockbridge, MA 01262
    /6

    $395,000

    • Land
    • 3.3 Acres
    • $119,697 per Acre

    9 Wheatleigh Dr, Stockbridge, MA 01262

    RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 343-5283

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • 44 Main St Unit 4, Stockbridge, MA 01262
    44 Main St Unit 4, Stockbridge, MA 01262
    44 Main St Unit 4, Stockbridge, MA 01262
    /12

    $9,500 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    44 Main St Unit 4, Stockbridge, MA 01262

    Outstanding fully renovated 3 Bedroom, 2 bathroom apartment in the heart of Stockbridge. Walk to restaurants, shops, library, etc. The best apartment in the building even though it is on the third level. Fully furnished with all new quality appointments. Must be seen to be appreciated. Terrific Summer Rental! No pets. JULY & AUGUST @ $9,000/month. Rent reduces to $4500 per month on September 1,

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    44 Main St Unit 4, Stockbridge, MA 01262
  • 3 Apple St, Stockbridge, MA 01236
    3 Apple St, Stockbridge, MA 01236
    3 Apple St, Stockbridge, MA 01236
    /18

    $180,000 Sold Apr 25, 2025

    3 Apple St, Stockbridge, MA 01236

    • 6 Beds
    • 2 Baths
    • 2,700 Sq Ft
    • Built 1858

    Last Sold Summary

    • 28% Below List Price
    • $67/SF
    • 14 Days On Market

    Last Listing Agent John Segalla HOUSATONIC REAL ESTATE

    3 Apple St, Stockbridge, MA 01236
    • 16 Interlaken Rd, Stockbridge, MA 01262
      16 Interlaken Rd, Stockbridge, MA 01262
      16 Interlaken Rd, Stockbridge, MA 01262
      /42

      Est $868,019 Not Listed For Sale

      16 Interlaken Rd, Stockbridge, MA 01262

      • 3 Beds
      • 2 Baths
      • 2,014 Sq Ft
      • Built 1983
      16 Interlaken Rd, Stockbridge, MA 01262

      Last Sold Summary

      • 19% Above List Price
      • $362/SF
      • 4 Days On Market

      Last Sold Price $730,000

      Last Listing Agent Katie Williams STONE HOUSE PROPERTIES, LLC

  • 9 Wheatleigh Dr, Stockbridge, MA 01262
    9 Wheatleigh Dr, Stockbridge, MA 01262
    9 Wheatleigh Dr, Stockbridge, MA 01262
    /6

    $395,000

    • Land
    • 3.3 Acres
    • $119,697 per Acre

    9 Wheatleigh Dr, Stockbridge, MA 01262

    RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 722-5098

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • 19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262
    19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262
    19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262
    /64

    $1,383,000 Sold Jan 15, 2026

    19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262

    • 3 Beds
    • 3.5 Baths
    • 3,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Above List Price
    • $421/SF
    • 8 Days On Market

    Last Listing Agent Mary Jane White COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit CV 7-A, Stockbridge, MA 01262
    • 40 Interlaken Rd, Stockbridge, MA 01262
      40 Interlaken Rd, Stockbridge, MA 01262
      40 Interlaken Rd, Stockbridge, MA 01262
      /23

      Est $221,379 Not Listed For Sale

      40 Interlaken Rd, Stockbridge, MA 01262

      • 2 Beds
      • 1 Bath
      • 749 Sq Ft
      • Built 1800
      40 Interlaken Rd, Stockbridge, MA 01262

      Last Sold Summary

      • 27% Above List Price
      • $234/SF
      • 79 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Shelley Cozzaglio LAMACCHIA REALTY, INC

  • 18 Goodrich St, Stockbridge, MA 01262
    18 Goodrich St, Stockbridge, MA 01262
    18 Goodrich St, Stockbridge, MA 01262
    /63

    $1,300,000

    • 4 Beds
    • 2 Baths
    • 2,548 Sq Ft

    18 Goodrich St, Stockbridge, MA 01262

    This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal,

    Lance Vermeulen LANCE VERMEULEN RE, INC

    18 Goodrich St, Stockbridge, MA 01262
  • 19 Hawthorne Rd Unit GH 8, West Stockbridge, MA 01266
    19 Hawthorne Rd Unit GH 8, West Stockbridge, MA 01266
    /2

    $814,000 Sold Nov 03, 2025

    19 Hawthorne Rd Unit GH 8, West Stockbridge, MA 01266

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft
    • Built 1984

    Last Sold Summary

    • $424/SF

    Last Listing Agent Comparable Listing COMPARABLE LISTING ONLY

    19 Hawthorne Rd Unit GH 8, West Stockbridge, MA 01266
    • 72 Interlaken Rd Unit 1, West Stockbridge, MA 01266
      72 Interlaken Rd Unit 1, West Stockbridge, MA 01266
      72 Interlaken Rd Unit 1, West Stockbridge, MA 01266
      /16

      Est $569,723 Not Listed For Sale

      72 Interlaken Rd Unit 1, West Stockbridge, MA 01266

      • 2 Beds
      • 2 Baths
      • 1,162 Sq Ft
      • Built 1900
      72 Interlaken Rd Unit 1, West Stockbridge, MA 01266

      Last Sold Summary

      • 15% Above List Price
      • $425/SF
      • 3 Days On Market

      Last Sold Price $494,100

      Last Listing Agent Selina Lamb BIRCH PROPERTIES

  • 5 Glendale Rd, Stockbridge, MA 01262
    5 Glendale Rd, Stockbridge, MA 01262
    5 Glendale Rd, Stockbridge, MA 01262
    /55

    $1,490,000

    • 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
  • 41 Main St Unit 2, Stockbridge, MA 01262
    41 Main St Unit 2, Stockbridge, MA 01262
    41 Main St Unit 2, Stockbridge, MA 01262
    /18

    $159,000 Sold Oct 15, 2025

    41 Main St Unit 2, Stockbridge, MA 01262

    • 1 Bed
    • 1 Bath
    • 349 Sq Ft
    • Built 1900

    Last Sold Summary

    • $456/SF
    • 2 Days On Market

    Current Estimated Value $159,514

    Last Listing Agent Elisabeth Wheeler WILLIAM RAVEIS - BERKSHIRE

    41 Main St Unit 2, Stockbridge, MA 01262
    • 8 Bean Hill Rd, Stockbridge, MA 01262
      8 Bean Hill Rd, Stockbridge, MA 01262
      8 Bean Hill Rd, Stockbridge, MA 01262
      /36

      Est $1,573,172 Not Listed For Sale

      8 Bean Hill Rd, Stockbridge, MA 01262

      • 3 Beds
      • 2.5 Baths
      • 2,498 Sq Ft
      • Built 2008
      8 Bean Hill Rd, Stockbridge, MA 01262

      Last Sold Summary

      • 1% Above List Price
      • $620/SF
      • 5 Days On Market

      Last Sold Price $1,550,000

      Last Listing Agent Selina Lamb BIRCH PROPERTIES

  • 14 Old Tree Farm Rd, Stockbridge, MA 01262
    14 Old Tree Farm Rd, Stockbridge, MA 01262
    14 Old Tree Farm Rd, Stockbridge, MA 01262
    /59

    $2,185,000

    • 3 Beds
    • 3.5 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
  • 13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
    13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
    13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
    /26

    $220,000 Sold Dec 05, 2025

    13 Rattlesnake Mountain Rd, Stockbridge, MA 01262

    • Land
    • 7.83 Acres
    • $28,083 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 259 Days On Market

    Current Estimated Value $220,000

    Last Listing Agent Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
    • 57 Main St Unit 4, Stockbridge, MA 01262
      57 Main St Unit 4, Stockbridge, MA 01262
      57 Main St Unit 4, Stockbridge, MA 01262
      /12

      Est $377,770 Not Listed For Sale

      57 Main St Unit 4, Stockbridge, MA 01262

      • 2 Beds
      • 1 Bath
      • 872 Sq Ft
      • Built 1850
      57 Main St Unit 4, Stockbridge, MA 01262

      Last Sold Summary

      • 8% Above List Price
      • $401/SF
      • 25 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Susan Calkins STONE HOUSE PROPERTIES, LLC

  • 8 Yale Hill Rd, Stockbridge, MA 01262
    8 Yale Hill Rd, Stockbridge, MA 01262
    8 Yale Hill Rd, Stockbridge, MA 01262
    /51

    $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
  • 11 Prospect Unit F, Stockbridge, MA 01262
    11 Prospect Unit F, Stockbridge, MA 01262
    11 Prospect Unit F, Stockbridge, MA 01262
    /51

    $635,000 Sold Oct 27, 2025

    11 Prospect Unit F, Stockbridge, MA 01262

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1886

    Last Sold Summary

    • 2% Above List Price
    • $353/SF
    • 3 Days On Market

    Last Listing Agent Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

    11 Prospect Unit F, Stockbridge, MA 01262
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /12

      Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 15 Days On Market

      Last Sold Price $145,000

      Last Listing Agent Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  • 46 Glendale Rd, Stockbridge, MA 01262
    46 Glendale Rd, Stockbridge, MA 01262
    46 Glendale Rd, Stockbridge, MA 01262
    /24

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,015 Sq Ft

    46 Glendale Rd, Stockbridge, MA 01262

    Light-filled contemporary cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area & living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom & a balcony overlooking the living area. The four-season sunroom (heated & cooled for

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    46 Glendale Rd, Stockbridge, MA 01262
  • 15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
    15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
    15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
    /34

    $840,000 Sold Nov 17, 2025

    15 Mahkeenac Heights Rd, West Stockbridge, MA 01266

    • 2 Beds
    • 1.5 Baths
    • 1,294 Sq Ft
    • Built 1950

    Last Sold Summary

    • 4% Above List Price
    • $649/SF
    • 7 Days On Market

    Last Listing Agent Selina Lamb BIRCH PROPERTIES

    15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
    • 82 E Main St, Stockbridge, MA 01262
      82 E Main St, Stockbridge, MA 01262
      82 E Main St, Stockbridge, MA 01262
      /52

      Est $1,435,305 Not Listed For Sale

      82 E Main St, Stockbridge, MA 01262

      • 5 Beds
      • 4 Baths
      • 3,891 Sq Ft
      • Built 1826
      82 E Main St, Stockbridge, MA 01262

      Last Sold Summary

      • 6% Above List Price
      • $347/SF
      • 49 Days On Market

      Last Sold Price $1,350,000

      Last Listing Agent Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  • 86 E Main St, Stockbridge, MA 01262
    86 E Main St, Stockbridge, MA 01262
    86 E Main St, Stockbridge, MA 01262
    /55

    $579,000

    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    86 E Main St, Stockbridge, MA 01262

    Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area.

    Cortney Dupont COHEN & WHITE ASSOCIATES

    86 E Main St, Stockbridge, MA 01262
  • 16 Glendale Middle Rd, Stockbridge, MA 01262
    16 Glendale Middle Rd, Stockbridge, MA 01262
    16 Glendale Middle Rd, Stockbridge, MA 01262
    /34

    $1,275,000 Sold Oct 29, 2025

    16 Glendale Middle Rd, Stockbridge, MA 01262

    • 4 Beds
    • 2.5 Baths
    • 2,511 Sq Ft
    • Built 1801

    Last Sold Summary

    • 8% Below List Price
    • $508/SF
    • 61 Days On Market

    Current Estimated Value $1,268,404

    Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    16 Glendale Middle Rd, Stockbridge, MA 01262
    • 44 East St, Stockbridge, MA 01262
      44 East St, Stockbridge, MA 01262
      44 East St, Stockbridge, MA 01262
      /30

      Est $547,167 Not Listed For Sale

      44 East St, Stockbridge, MA 01262

      • 3 Beds
      • 2 Baths
      • 1,721 Sq Ft
      • Built 1948
      44 East St, Stockbridge, MA 01262

      Last Sold Summary

      • 123% Above List Price
      • $142/SF
      • 5 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  • 2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
    /36

    $278,800

    • 1 Bed
    • 1 Bath
    • 658 Sq Ft

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

    Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move-in-ready appeal is what you'll find at this Heron Pond condo! Well-maintained, 1 br/1ba unit filled with natural light includes living room, separate dining room, updated bath and galley kitchen. Outside, relax on your own stone patio. Enjoy peaceful surroundings, the pond, and beautifully kept grounds.

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
  • 19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
    /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
    • 47 Main St, Stockbridge, MA 01262
      47 Main St, Stockbridge, MA 01262
      47 Main St, Stockbridge, MA 01262
      /41

      Est $1,524,749 Not Listed For Sale

      47 Main St, Stockbridge, MA 01262

      • 5 Beds
      • 5.5 Baths
      • 4,977 Sq Ft
      • Built 1860
      47 Main St, Stockbridge, MA 01262

      Last Sold Summary

      • 20% Above List Price
      • $256/SF
      • 37 Days On Market

      Last Sold Price $1,275,000

      Last Listing Agent Elle Villetto William Pitt

  • 19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    /47

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 1,935 Sq Ft

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

    MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry

    Cortney Dupont COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
  • 85 E Main St, Stockbridge, MA 01262
    85 E Main St, Stockbridge, MA 01262
    85 E Main 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 $773,492

    Last Listing Agent Susan Laidlaw COMPASS MASSACHUSETTS , LLC GB

    85 E Main St, Stockbridge, MA 01262
    • 19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262
      19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262
      19 Hawthorne Rd Unit S-2C, 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

      • $373/SF
      • 6 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

  • 21A Interlaken Rd, Stockbridge, MA 01262
    21A Interlaken Rd, Stockbridge, MA 01262
    21A Interlaken Rd, Stockbridge, MA 01262
    /43

    $3,850,000

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    21A Interlaken Rd, Stockbridge, MA 01262

    Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    21A Interlaken Rd, Stockbridge, MA 01262

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County Stockbridge

Real Estate & Homes

Home Trends in Stockbridge, MA

On average, homes in Stockbridge, MA sell after 46 days on the market compared to the national average of 55 days. The median sale price for homes in Stockbridge, MA over the last 12 months is $775,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$775,000
Median Single Family Sale Price
$845,000
Median Townhouse Sale Price
$660,000
Median 2 Bedroom Sale Price
$585,000
Median 1 Bedroom Sale Price
$278,800
Average Price Per Sq Ft
$419
Number of Homes for Sale
12
Last 12 months Home Sales
31
Months of Supply
4.60
Median List Price
$792,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-3%
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