1,870

Stockbridge, MA Homes

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  • /43

    $3,850,000

    • 4 Beds
    • 3.5 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
  • /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 $959,506

    Last Listing Agent Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    66 Interlaken Rd, 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

      • $350/SF
      • 14 Days On Market
      • Last Sold Price $1,429,000
      • Oct 07, 2024

      Last Listing Agent Altaluxre Group William Pitt Sotheby's International Realty

  • /47

    $2,998,000 Pending

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

    11 Mahkeenac Terrace, Stockbridge, MA 01262

    Welcome to a lakefront retreat where timeless charm meets breath taking natural beauty. This four bedroom, two bath cottage is perfectly positioned to capture stunning water views and an abundance of natural light throughout the day. Inside, you will find beautifully preserved, rare chestnut floors that add warmth and character, complemented by a cozy fireplace that creates the perfect gathering

    Patricia Andrew STONE HOUSE PROPERTIES, LLC

    11 Mahkeenac Terrace, 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
    • 709 Days On Market

    Last Listing Agent Selina Lamb BIRCH PROPERTIES

    9 Wheatleigh Dr, 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

      • $535/SF
      • 0 Days On Market
      • Last Sold Price $650,000
      • Sep 30, 2024

      Last Listing Agent Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

  • /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
  • /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 $2,904,858

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

    55 Main St, Stockbridge, MA 01262
    • /20

      Est $545,176 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

      • 28% Above List Price
      • $371/SF
      • 2 Days On Market
      • Last Sold Price $427,000
      • Oct 04, 2024

      Last Listing Agent Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  • /30

    $895,000

    • 3 Beds
    • 2.5 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
  • /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 $1,051,333 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

      • 11% Above List Price
      • $657/SF
      • 78 Days On Market
      • Last Sold Price $950,000
      • Sep 27, 2024

      Last Listing Agent Selina Lamb BIRCH PROPERTIES

  • /19

    $550,000 Under Contract

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

    15 W Stockbridge, Stockbridge, MA 01262

    The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect

    C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

    15 W Stockbridge, 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

    Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

    49 Main St, Stockbridge, MA 01262
    • /30

      Est $600,157 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

      • 22% Above List Price
      • $348/SF
      • 3 Days On Market
      • Last Sold Price $491,000
      • Jul 08, 2024

      Last Listing Agent Selina Lamb Birch Properties

  • /27

    $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
  • /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

      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

      • $410/SF
      • 39 Days On Market
      • Last Sold Price $660,000
      • May 28, 2024

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

  • /54

    $795,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,731 Sq Ft

    11 Sergeant St, Stockbridge, MA 01262

    Welcome to 11 Sergeant, ideally located on a quiet side street around the corner from Stockbridge's historic Main Street. This property includes a well-maintained main house and a separate barn with ADU potential. The main house features an updated kitchen that opens to a bright den overlooking the backyard. The first floor also includes a powder room, dining room, and formal living room.

    Katie Williams STONE HOUSE PROPERTIES, LLC

    11 Sergeant St, 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
    • /34

      Est $948,527 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

      • 5% Above List Price
      • $423/SF
      • 4 Days On Market
      • Last Sold Price $900,000
      • Mar 22, 2024

      Last Listing Agent Mary Jo Piretti PIRETTI REAL ESTATE

  • /30

    $752,000

    • 3 Beds
    • 1.5 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
  • /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 $480,758

    Last Listing Agent Conor Meehan STONE HOUSE PROPERTIES, LLC

    42 East St, Stockbridge, MA 01262
    • /57

      Est $1,384,520 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

      • 14% Above List Price
      • $367/SF
      • 244 Days On Market
      • Last Sold Price $1,210,000
      • Nov 22, 2024

      Last Listing Agent Randy Thunfors STONE HOUSE PROPERTIES, LLC

  • /22

    $695,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,715 Sq Ft

    4 Fox Meadow Ln, Stockbridge, MA 01262

    Convenient one-level ranch in a prime location close to town. This well-maintained home offers four bedrooms and two full bathrooms, ideal for comfortable living. The updated kitchen features modern finishes and plenty of workspace. Enjoy energy efficiency with owned solar panels that significantly reduce utility costs, plus a pellet stove for supplemental heating. A generator ensures

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    4 Fox Meadow Ln, 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 $963,696

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

    9 Yale Hill Rd, Stockbridge, MA 01262
    • /31

      Est $746,972 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

      • 12% Above List Price
      • $349/SF
      • 14 Days On Market
      • Last Sold Price $666,750
      • Feb 15, 2024

      Last Listing Agent Katie Williams STONE HOUSE PROPERTIES, LLC

  • /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
  • /22

    $450,000 Sold Oct 03, 2025

    7 N Church St, Stockbridge, MA 01262

    • 2 Beds
    • 2 Baths
    • 1,298 Sq Ft
    • Built 1900

    Last Sold Summary

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

    Current Estimated Value $1,181,873

    Last Listing Agent Nikki Carchedi STONE HOUSE PROPERTIES, LLC

    7 N Church St, Stockbridge, MA 01262
    • /26

      Est $589,101 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

      • 16% Above List Price
      • $455/SF
      • 18 Days On Market
      • Last Sold Price $510,000
      • Jan 29, 2024

      Last Listing Agent Tanya Shepardson LAMACCHIA REALTY, INC

  • /2

    $289,000

    • Land
    • 3.69 Acres
    • $78,320 per Acre

    0 Interlaken Cross Rd, Stockbridge, MA 01262

    A pristine building lot in the heart of the Berkshires! Parcel B at Echo Valley is a 3.69-acre wooded, buildable lot offering a beautiful blank canvas for your dream home. Located off Interlaken Cross Road in Stockbridge, MA, this level parcel is easy to work with and provides excellent flexibility for siting your house, garage, and outdoor living spaces. Just minutes from Tanglewood, Stockbridge

    Lisa Berry Simply Sell Realty

    0 Interlaken Cross Rd, Stockbridge, MA 01262
  • /12

    $371,000 Sold Jun 18, 2025

    57 Main St Unit 10, Stockbridge, MA 01262

    • 1 Bed
    • 1 Bath
    • 837 Sq Ft
    • Built 1850

    Last Sold Summary

    • 1% Below List Price
    • $443/SF
    • 57 Days On Market

    Current Estimated Value $370,715

    Last Listing Agent Kathleen Hopkins CARRIAGE HOUSE REAL ESTATE

    57 Main St Unit 10, Stockbridge, MA 01262
    • /43

      Est $1,328,281 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

      • 11% Above List Price
      • $296/SF
      • 678 Days On Market
      • Last Sold Price $1,200,000
      • Dec 06, 2024

      Last Listing Agent Patricia Andrew STONE HOUSE PROPERTIES, LLC

  • /55

    $485,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 904 Sq Ft

    22 Mahkeenac Heights Rd, Stockbridge, MA 01262

    Tucked away on a quiet 2.1 acre lot in Mahkeenac Heights--a true rarity for this area--this charming 1940s seasonal cottage in need of updating sits elevated close to the Stockbridge Bowl. Access is up a verdant driveway. Enter the cottage through a long screened-in porch, the perfect setting for outside dining and relaxation. Once inside it opens into a cathedral-style living room anchored by a

    Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

    22 Mahkeenac Heights Rd, Stockbridge, MA 01262
  • /38

    $895,000 Sold Sep 25, 2025

    33 Interlaken Rd, Stockbridge, MA 01262

    • 5 Beds
    • 3.5 Baths
    • 3,194 Sq Ft
    • Built 1979

    Last Sold Summary

    • 19% Below List Price
    • $280/SF
    • 43 Days On Market

    Current Estimated Value $959,296

    Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

    33 Interlaken Rd, Stockbridge, MA 01262
    • /28

      Est $606,984 Not Listed For Sale

      27 Park St, Stockbridge, MA 01262

      • 4 Beds
      • 2 Baths
      • 1,607 Sq Ft
      • Built 1932
      27 Park St, Stockbridge, MA 01262

      Last Sold Summary

      • 20% Above List Price
      • $314/SF
      • 4 Days On Market
      • Last Sold Price $505,000
      • Dec 15, 2023

      Last Listing Agent Elisabeth Wheeler WILLIAM RAVEIS - BERKSHIRE

  • /50

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,647 Sq Ft

    2 Wallace Rd Unit 2E, Stockbridge, MA 01262

    Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening

    Paula McLean PAULA MCLEAN REALTORS INC.

    2 Wallace Rd Unit 2E, Stockbridge, MA 01262
  • /17

    $475,000 Sold Mar 13, 2026

    18 Hill Rd, Stockbridge, MA 01262

    • 2 Beds
    • 1 Bath
    • 1,015 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $468/SF
    • 8 Days On Market

    Current Estimated Value $502,082

    Last Listing Agent Marie Bourassa SIGNATURE ASSOCIATES

    18 Hill Rd, Stockbridge, MA 01262
    • /32

      Est $935,757 Not Listed For Sale

      3 Yale Hill Rd, Stockbridge, MA 01262

      • 3 Beds
      • 2 Baths
      • 2,395 Sq Ft
      • Built 1975
      3 Yale Hill Rd, Stockbridge, MA 01262

      Last Sold Summary

      • 26% Above List Price
      • $311/SF
      • 5 Days On Market
      • Last Sold Price $745,000
      • Nov 17, 2023

      Last Listing Agent Jared Kelly William Pitt

  • /50

    $2,995,000

    • 4 Beds
    • 3 Baths
    • 1,932 Sq Ft

    10 Mahkeenac Shores Rd, Stockbridge, MA 01262

    Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full bath year 'round home offers a seamless blend of modern comfort and natural beauty! Sunlight pours through expansive windows, framing breathtaking water views from nearly every room. The open concept living space is anchored by a striking double sided

    Mary Jo Piretti PIRETTI REAL ESTATE

    10 Mahkeenac Shores Rd, Stockbridge, MA 01262

Showing Results 41 - 80, Page 2 of 18

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