27

Homes for Sale in 01262

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  • 11 Hawthorne Rd, Stockbridge, MA 01262
    11 Hawthorne Rd, Stockbridge, MA 01262
    11 Hawthorne Rd, Stockbridge, MA 01262
    /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
  • 53 Main St, Stockbridge, MA 01262
    53 Main St, Stockbridge, MA 01262
    53 Main St, Stockbridge, MA 01262
    /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
  • 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
  • 36 Yale Hill Rd, Stockbridge, MA 01262
    36 Yale Hill Rd, Stockbridge, MA 01262
    36 Yale Hill Rd, Stockbridge, MA 01262
    /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
  • 6 Manitauk Heights, Stockbridge, MA 01262
    6 Manitauk Heights, Stockbridge, MA 01262
    6 Manitauk Heights, Stockbridge, MA 01262
    /49

    $1,060,200

    • 4 Beds
    • 4 Baths
    • 2,052 Sq Ft

    6 Manitauk Heights, Stockbridge, MA 01262

    Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the

    Patricia Andrew STONE HOUSE PROPERTIES, LLC

    6 Manitauk Heights, Stockbridge, MA 01262
  • 15 Goodrich St, Stockbridge, MA 01262
    15 Goodrich St, Stockbridge, MA 01262
    15 Goodrich St, Stockbridge, MA 01262
    /20

    $10,000

    • 1 Bed
    • 2 Baths
    • 4,200 Sq Ft

    15 Goodrich St, Stockbridge, MA 01262

    Escape the city heat and spend August in an unbeatable, walk-to-town Stockbridge location. This striking, artist-loft-style residence perfectly blends vibrant, colorful design with modern country comfort. Situated just a short stroll from historic Main Street, it offers a sophisticated, high-design summer sanctuary. Enjoy radiant heated, polished concrete floors, expansive ceiling height, and

    John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    15 Goodrich St, Stockbridge, MA 01262
  • 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
  • 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
  • 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
  • 7 Wheatley Dr, Stockbridge, MA 01262
    7 Wheatley Dr, Stockbridge, MA 01262
    7 Wheatley Dr, Stockbridge, MA 01262
    /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
  • 17 Beachwood Dr, Stockbridge, MA 01262
    17 Beachwood Dr, Stockbridge, MA 01262
    17 Beachwood Dr, Stockbridge, MA 01262
    /15

    $649,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    17 Beachwood Dr, Stockbridge, MA 01262

    Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves. Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents enjoy steps to a private beach,

    Franz Forster FRANZ J. FORSTER R. E.

    17 Beachwood Dr, Stockbridge, MA 01262
  • 8 Shamrock St, Stockbridge, MA 01262
    8 Shamrock St, Stockbridge, MA 01262
    8 Shamrock St, Stockbridge, MA 01262
    /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
  • 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
  • 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 2E, Stockbridge, MA 01262
    2 Wallace Rd Unit 2E, Stockbridge, MA 01262
    2 Wallace Rd Unit 2E, Stockbridge, MA 01262
    /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
  • 10 Mahkeenac Shores Rd, Stockbridge, MA 01262
    10 Mahkeenac Shores Rd, Stockbridge, MA 01262
    10 Mahkeenac Shores Rd, Stockbridge, MA 01262
    /50

    $2,750,000

    $245K PRICE DROP
    • 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
  • 9 Interlaken Rd, Stockbridge, MA 01262
    9 Interlaken Rd, Stockbridge, MA 01262
    9 Interlaken Rd, Stockbridge, MA 01262
    /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
  • 8 Lukeman Ln, Stockbridge, MA 01262
    8 Lukeman Ln, Stockbridge, MA 01262
    8 Lukeman Ln, Stockbridge, MA 01262
    /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
  • 1 Devon Rd, Stockbridge, MA 01262
    1 Devon Rd, Stockbridge, MA 01262
    1 Devon Rd, Stockbridge, MA 01262
    /59

    $1,595,000

    $255K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 4,952 Sq Ft

    1 Devon Rd, Stockbridge, MA 01262

    A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1 Devon Rd, Stockbridge, MA 01262
  • 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
  • 0 Mohawk Lake Rd, Stockbridge, MA 01262
    0 Mohawk Lake Rd, Stockbridge, MA 01262
    0 Mohawk Lake Rd, Stockbridge, MA 01262
    /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
  • 14 Old Tree Farm Rd, Stockbridge, MA 01262
    14 Old Tree Farm Rd, Stockbridge, MA 01262
    14 Old Tree Farm Rd, Stockbridge, MA 01262
    /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
  • 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
  • 5 Glendale Rd, Stockbridge, MA 01262
    5 Glendale Rd, Stockbridge, MA 01262
    5 Glendale Rd, Stockbridge, MA 01262
    /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
  • 8 Yale Hill Rd, Stockbridge, MA 01262
    8 Yale Hill Rd, Stockbridge, MA 01262
    8 Yale Hill Rd, Stockbridge, MA 01262
    /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
  • 0 Glendale Rd Unit 248566, Stockbridge, MA 01262
    0 Glendale Rd Unit 248566, Stockbridge, MA 01262
    0 Glendale Rd Unit 248566, Stockbridge, MA 01262
    /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
  • 0 Interlaken Cross Rd, Stockbridge, MA 01262
    0 Interlaken Cross Rd, Stockbridge, MA 01262
    /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
Massachusetts Berkshire County Stockbridge 01262

Real Estate & Homes for Sale in 01262

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