Stockbridge, MA Homes

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  $998,000 Under Contract

  • Land
  • 9.1 Acres
  • $109,670 per Acre

  19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

  RARE BERKSHIRE OPPORTUNITY: READY-TO-BUILD MODERN RETREAT ON A PRIVATE POND + DEEDED STOCKBRIDGE BOWL BEACH RIGHTSDiscover a truly extraordinary offering in the heart of the Berkshires--9.1 pristine acres with direct frontage on Lily Pond, a private, non-motorized body of water celebrated for its serenity, protected natural setting, and sweeping views. Occupying the entire southern end of the

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 343-4919

  19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
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  $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
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  /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
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  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  $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.

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 722-5098

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  /20

  $4,500 total monthly price

  • 3 Beds
  • 2 Baths
  • Condo for Rent

  44 Main St Unit 1, Stockbridge, MA 01262

  STOCKBRIDGE IN-TOWN LOCATION. Fully Renovated as of April 1, 2025, 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 $8000 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
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  /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 $911,193

  Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  3 Willard Hill Rd, Stockbridge, MA 01262
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  /27

  Est $558,259 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,132 Sq Ft

  14 Interlaken Rd, Stockbridge, MA 01262

  14 Interlaken Rd, Stockbridge, MA 01262
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  /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,

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 269-8632

  9 Castle Hill Rd, Stockbridge, MA 01262
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  $25 total monthly price

  • 2 Baths
  • 1,632 Sq Ft
  • Property for Rent

  2 Depot Rd, Stockbridge, MA 01262

  Physician, Dentist, Attorney, Architect, Engineer, Accountant or other professional office use with a long-term lease, minimum of 5 years. Berkshire Scenic Railway Museum has decided to lease their historic train station located in Stockbridge. Built in 1893, the building is listed on the National Registry of Historic Places. It was purchased by the Jack and Jane Fitzpatrick charitable High

  Rich Aldrich WILLIAM PITT SOTHEBY'S - LENOX

  2 Depot Rd, Stockbridge, MA 01262
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  /23

  $175,000 Sold Feb 28, 2025

  40 Interlaken Rd, Stockbridge, MA 01262

  • 2 Beds
  • 1 Bath
  • 749 Sq Ft
  • Built 1800

  Last Sold Summary

  • 20% Below List Price
  • $234/SF
  • 79 Days On Market

  Current Estimated Value $229,314

  Last Listing Agent Shelley Cozzaglio LAMACCHIA REALTY, INC

  40 Interlaken Rd, Stockbridge, MA 01262
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  /42

  Est $883,419 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,014 Sq Ft

  16 Interlaken Rd, Stockbridge, MA 01262

  16 Interlaken Rd, Stockbridge, MA 01262
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  /42

  $1,650,000

  • 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

  

  Selina Lamb

  Birch Properties

  (413) 300-6860

  17 East St, Stockbridge, MA 01262
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  /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. AVAILABLE JULY 1, 2026. Summer 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
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  /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
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  /16

  Est $571,364 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft

  72 Interlaken Rd Unit 1, West Stockbridge, MA 01266

  72 Interlaken Rd Unit 1, West Stockbridge, MA 01266
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  $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.

  

  Selina Lamb

  Birch Properties

  (413) 343-5283

  9 Wheatleigh Dr, Stockbridge, MA 01262
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  $8,000 total monthly price

  • 5 Beds
  • 5.5 Baths
  • 4,952 Sq Ft
  • House for Rent

  1 Devon Rd, Stockbridge, MA 01262

  Located in Stockbridge with very recent renovations and excellent furnishings. There's no place like home, but this property might well be better than your home. No detail has been overlooked. A true rental master piece. Must be seen to be fully appreciated. Six bedrooms, 5 and one half bathrooms, SIX fireplaces, in-ground pool, 4 acres,...who could ask for anything more??? Call for a showing

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1 Devon Rd, Stockbridge, MA 01262
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  /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
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  /52

  Est $1,442,515 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,891 Sq Ft

  82 E Main St, Stockbridge, MA 01262

  82 E Main St, Stockbridge, MA 01262
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  /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,

  Robert Doerr LANCE VERMEULEN RE, INC., LENOX

  18 Goodrich St, Stockbridge, MA 01262
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  /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
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  /41

  Est $1,488,404 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,977 Sq Ft

  47 Main St, Stockbridge, MA 01262

  47 Main St, Stockbridge, MA 01262
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  /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
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  /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 $158,273

  Last Listing Agent Elisabeth Wheeler LANCE VERMEULEN RE, INC., LENOX

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

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,768 Sq Ft

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

  19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262
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  /51

  $2,100,000 Under Contract

  • 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
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  /12

  $350,000 Sold Mar 03, 2025

  57 Main St Unit 4, Stockbridge, MA 01262

  • 2 Beds
  • 1 Bath
  • 872 Sq Ft
  • Built 1850

  Last Sold Summary

  • 7% Below List Price
  • $401/SF
  • 25 Days On Market

  Current Estimated Value $380,203

  Last Listing Agent Susan Calkins STONE HOUSE PROPERTIES, LLC

  57 Main St Unit 4, Stockbridge, MA 01262
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  /37

  Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,088 Sq Ft

  11a Interlaken Cross Rd, West Stockbridge, MA 01266

  11a Interlaken Cross Rd, West Stockbridge, MA 01266
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  $2,185,000

  • 3 Beds
  • 2.5 Baths
  • 2,952 Sq Ft

  14 Old Tree Farm Rd, Stockbridge, MA 01262

  Set on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access

  Claire Pollart LANCE VERMEULEN RE, INC

  14 Old Tree Farm Rd, Stockbridge, MA 01262
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  /30

  $245,000 Sold Feb 18, 2025

  44 East St, Stockbridge, MA 01262

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 1948

  Last Sold Summary

  • 40% Above List Price
  • $142/SF
  • 5 Days On Market

  Current Estimated Value $554,806

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

  44 East St, Stockbridge, MA 01262
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  /29

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft

  8 Arthur Fiedler Ln, Stockbridge, MA 01262

  8 Arthur Fiedler Ln, Stockbridge, MA 01262
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  /55

  $599,000

  • 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
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  $225,000 Sold Mar 24, 2025

  Unlisted Address

  • Land
  • 10.4 Acres
  • $21,635 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 661 Days On Market

  Current Estimated Value $238,500

  Last Listing Agent Gary Johnston STONE HOUSE PROPERTIES, LLC

  Unlisted Address
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  /20

  Est $525,055 Not Listed For Sale

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

  3 N Church St, Stockbridge, MA 01262

  3 N Church St, Stockbridge, MA 01262
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  /30

  $895,000

  • 3 Beds
  • 2.5 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
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  $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

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

  13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
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  Est $1,071,822 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,446 Sq Ft

  42 Lake Dr, Stockbridge, MA 01262

  42 Lake Dr, Stockbridge, MA 01262
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  /35

  $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
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  $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

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