1,881

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
    /48

    $820,000

    $64K PRICE DROP
    • 4 Beds
    • 4 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

    9 Castle Hill Rd, Stockbridge, MA 01262
  • 12 Main St Unit SI ID1546057P, Stockbridge, MA 01262
    12 Main St Unit SI ID1546057P, Stockbridge, MA 01262
    12 Main St Unit SI ID1546057P, Stockbridge, MA 01262
    /20

    $4,652

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    12 Main St Unit SI ID1546057P, Stockbridge, MA 01262

    The advertised rate of $4,652/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 12, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    12 Main St Unit SI ID1546057P, 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
    • 3 Willard Hill Rd, Stockbridge, MA 01262
      3 Willard Hill Rd, Stockbridge, MA 01262
      3 Willard Hill Rd, Stockbridge, MA 01262
      /34

      Est $915,658

      Not Listed For Sale

      3 Willard Hill Rd, Stockbridge, MA 01262

      • 4 Beds
      • 3.5 Baths
      • 2,189 Sq Ft
      • Built 1996
      3 Willard Hill Rd, Stockbridge, MA 01262

      Last Sold Summary

      • 17 Days On Market

  • 10 Prospect Hill, Stockbridge, MA 01263
    10 Prospect Hill, Stockbridge, MA 01263
    10 Prospect Hill, Stockbridge, MA 01263
    /36

    $895,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,515 Sq Ft

    10 Prospect Hill, Stockbridge, MA 01263

    Rare opportunity on coveted Prospect Hill Road in Stockbridge. Offered for the first time in more than 40 years, this c.1880 residence is privately set on 3.5 acres just moments from downtown Stockbridge, the Red Lion Inn, Tanglewood, Lenox, and the Berkshires' renowned cultural attractions. The home offers approximately 2,515 square feet with wide-plank floors, exposed brick, wood beams,

    Agent Photo

    Selina Lamb

    Birch Properties

    10 Prospect Hill, Stockbridge, MA 01263
  • 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 Per Month

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

    $350,000

    Sold May 08, 2026

    9 Wheatleigh Dr, Stockbridge, MA 01262

    • Land
    • 3.3 Acres
    • $106,061 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 708 Days On Market

    Last Listing Agent Selina Lamb Birch Properties

    9 Wheatleigh Dr, Stockbridge, MA 01262
    • 14 Interlaken Rd, Stockbridge, MA 01262
      14 Interlaken Rd, Stockbridge, MA 01262
      14 Interlaken Rd, Stockbridge, MA 01262
      /27

      Est $590,423

      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

      • 49 Days On Market

  • 10 Prospect Hill Rd, Stockbridge, MA 01262
    10 Prospect Hill Rd, Stockbridge, MA 01262
    10 Prospect Hill Rd, Stockbridge, MA 01262
    /39

    $895,000

    • 4 Beds
    • 2 Baths
    • 2,515 Sq Ft

    10 Prospect Hill Rd, Stockbridge, MA 01262

    Offered for the first time in more than forty years, this c.1880 residence presents a rare opportunity to own a substantial property on coveted Prospect Hill Road, one of Stockbridge's most desirable addresses. Set privately on 3.5 acres just moments from the center of Stockbridge, the property offers the increasingly rare combination of privacy, acreage, and location that defines some of the

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    10 Prospect Hill Rd, Stockbridge, MA 01262
  • 12 Main St Unit SI ID1546058P, Stockbridge, MA 01262
    12 Main St Unit SI ID1546058P, Stockbridge, MA 01262
    12 Main St Unit SI ID1546058P, Stockbridge, MA 01262
    /20

    $3,803

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 699 Sq Ft
    • Condo for Rent

    12 Main St Unit SI ID1546058P, Stockbridge, MA 01262

    The advertised rate of $3,804/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    12 Main St Unit SI ID1546058P, 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
    • 16 Interlaken Rd, Stockbridge, MA 01262
      16 Interlaken Rd, Stockbridge, MA 01262
      16 Interlaken Rd, Stockbridge, MA 01262
      /42

      Est $876,404

      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

      • 4 Days On Market

  • 6 East St, Stockbridge, MA 01262
    6 East St, Stockbridge, MA 01262
    6 East St, Stockbridge, MA 01262
    /23

    $445,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,664 Sq Ft

    6 East St, Stockbridge, MA 01262

    Spacious and filled with natural light, this four bedroom, two bath home offers incredible potential and timeless charm. Featuring large windows throughout the home makes it bright and inviting, with a comfortable layout with a full kitchen, formal dining room, cozy sitting room, and a charming fireplace in the living room which is perfect for relaxing evenings. Generously sized rooms provide

    Patricia Andrew STONE HOUSE PROPERTIES, LLC

    6 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 Per Month

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

    $513,000

    Sold May 11, 2026

    86 E Main St, Stockbridge, MA 01262

    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft
    • Built 1870

    Last Sold Summary

    • 14% Below List Price
    • $224/SF
    • 42 Days On Market

    Current Estimated Value $586,713

    Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

    86 E Main St, Stockbridge, MA 01262
    • 40 Interlaken Rd, Stockbridge, MA 01262
      40 Interlaken Rd, Stockbridge, MA 01262
      40 Interlaken Rd, Stockbridge, MA 01262
      /23

      Est $258,966

      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

      • 79 Days On Market

  • 46 Glendale Rd, Stockbridge, MA 01262
    46 Glendale Rd, Stockbridge, MA 01262
    46 Glendale Rd, Stockbridge, MA 01262
    /29

    $719,000

    $30K PRICE DROP
    • 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
  • 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 $536,261

      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

      • 3 Days On Market

  • 34 Church St, Stockbridge, MA 01262
    34 Church St, Stockbridge, MA 01262
    34 Church St, Stockbridge, MA 01262
    /25

    $699,999

    $45K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,730 Sq Ft

    34 Church St, Stockbridge, MA 01262

    Rare opportunity to own a substantial two-family home in one of the most desirable locations in the Berkshires. Overlooking meadows, sheep pastures, mountains, and Naumkeag, this special property is also just a short walk to Stockbridge Main Street. Each spacious unit offers 3 bedrooms, 1.5 baths, and hardwood floors throughout. The grounds are truly magical, with mature trees and a peaceful

    Lisa Kelley MACCARO REAL ESTATE

    34 Church St, Stockbridge, MA 01262
  • 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

    $270,000

    Sold May 11, 2026

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

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

    Last Sold Summary

    • 3% Below List Price
    • $410/SF
    • 84 Days On Market

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

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
    • 25 Mahkeenac Terrace, Stockbridge, MA 01262
      25 Mahkeenac Terrace, Stockbridge, MA 01262
      25 Mahkeenac Terrace, Stockbridge, MA 01262
      /77

      Not Listed For Sale

      25 Mahkeenac Terrace, Stockbridge, MA 01262

      • 4 Beds
      • 3.5 Baths
      • 2,882 Sq Ft
      • Built 2011
      25 Mahkeenac Terrace, Stockbridge, MA 01262

      Last Sold Summary

      • 4 Days On Market

  • 22 Goodrich St, Stockbridge, MA 01262
    22 Goodrich St, Stockbridge, MA 01262
    22 Goodrich St, Stockbridge, MA 01262
    /29

    $599,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    22 Goodrich St, Stockbridge, MA 01262

    Fall in love with this renovated 3BED 2BATH house located just a stone's throw from downtown Stockbridge on nearly half an acre. Inside, the open layout features a cozy living room anchored by a classic fireplace. The kitchen has granite countertops and an expanded pantry with new custom shelving. The primary suite boasts a custom walk-in closet, an updated bathroom and direct access to the

    Kate Lascar COMPASS MASSACHUSETTS , LLC GB

    22 Goodrich St, 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
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    /47

    $530,000

    Sold Jun 12, 2026

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

    • 2 Beds
    • 3 Baths
    • 1,935 Sq Ft
    • Built 1985

    Last Sold Summary

    • 22% Below List Price
    • $274/SF
    • 241 Days On Market

    Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit Carriage Barn E-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 $1,422,283

      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

      • 5 Days On Market

  • 41 Main St Unit 7, Stockbridge, MA 01262
    41 Main St Unit 7, Stockbridge, MA 01262
    41 Main St Unit 7, Stockbridge, MA 01262
    /16

    $190,000

    • 1 Bed
    • 1 Bath
    • 383 Sq Ft

    41 Main St Unit 7, Stockbridge, MA 01262

    Welcome to Stone Court Condominium #7, a charming second-floor studio located in the heart of Stockbridge. Set within an historic Berkshire property, this inviting 383-square-foot residence features a fireplace, large windows for natural light, a Pullman kitchen, and a full bath with tub and shower.Thoughtfully designed to make the most of its space, this studio offers a comfortable,

    Elisabeth Wheeler WILLIAM RAVEIS - BERKSHIRE

    41 Main St Unit 7, 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 $166,062

    Last Listing Agent Elisabeth Wheeler WILLIAM RAVEIS - BERKSHIRE

    41 Main St Unit 2, 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 $372,971

      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

      • 25 Days On Market

  • 200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262
    200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262
    200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262
    /30

    $795,000

    • 3 Beds
    • 3 Baths
    • 2,218 Sq Ft

    200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262

    Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. This sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    200 Vanna #3 Old Stockbridge 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 $219,500

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

    13 Rattlesnake Mountain Rd, 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

  • 21A Interlaken Rd, Stockbridge, MA 01262
    21A Interlaken Rd, Stockbridge, MA 01262
    21A Interlaken Rd, Stockbridge, MA 01262
    /41

    $3,850,000

    Under Contract
    • 4 Beds
    • 4 Baths
    • 4,000 Sq Ft

    21A Interlaken Rd, Stockbridge, MA 01262

    A newly built modern country home of rare quality and quiet sophistication, set on five private acres in the heart of Stockbridge. Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. Newly completed and never before lived in, this 4,000 sq ft residence sits on 5 private acres, just minutes to Lenox, downtown Stockbridge, and the Mass

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    21A Interlaken 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
    • 82 E Main St, Stockbridge, MA 01262
      82 E Main St, Stockbridge, MA 01262
      82 E Main St, Stockbridge, MA 01262
      /52

      Est $1,455,372

      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

      • 49 Days On Market

  • 200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
    /30

    $795,000

    • 3 Beds
    • 3 Baths
    • 2,218 Sq Ft

    200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262

    Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    200 Old Stockbridge Rd Unit Vanna 3, 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
    • 44 East St, Stockbridge, MA 01262
      44 East St, Stockbridge, MA 01262
      44 East St, Stockbridge, MA 01262
      /30

      Est $537,474

      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

      • 5 Days On Market

  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /19

    $900,000

    • 11 Beds
    • 6 Baths
    • 4,863 Sq Ft

    Unlisted Address

    Stockbridge Investment Opportunity Fully Rented In Town 5-Family Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures. Can also be purchased as part of a investment portfolio 35 Main Street West Stockbridge ,Ma MLS# 249539

    Matt Carlino MACCARO REAL ESTATE

    Unlisted Address
  • 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 $1,255,051

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

    16 Glendale Middle Rd, Stockbridge, MA 01262
    • 47 Main St, Stockbridge, MA 01262
      47 Main St, Stockbridge, MA 01262
      47 Main St, Stockbridge, MA 01262
      /41

      Est $1,575,709

      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

      • 37 Days On Market

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County Stockbridge

Real Estate & Homes

Home Prices in Stockbridge, MA

The median home sale price in Stockbridge, MA is $750,000, down 20% year-over-year. Homes in Stockbridge sell in 79 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$750,000
Median Single Family Sale Price
$870,000
Median Townhouse Sale Price
$660,000
Median 2 Bedroom Sale Price
$497,500
Median 1 Bedroom Sale Price
$214,500
Average Price Per Sq Ft
$446
Number of Homes for Sale
19
Last 12 months Home Sales
41
Months of Supply
5.60
Median List Price
$845,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-20%
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