23

Newest Homes for Sale in Stockbridge, MA

Section Image Section Image
  • 215 Old Stockbridge Rd, Lenox, MA 01240
    215 Old Stockbridge Rd, Lenox, MA 01240
    215 Old Stockbridge Rd, Lenox, MA 01240
    /31

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    215 Old Stockbridge Rd, Lenox, MA 01240

    An exceptional architect-designed home in the heart of the Berkshires, privately sited within the conservation landscape of Bishop Estates and just minutes from Tanglewood and the center of Lenox.Thoughtfully positioned to preserve complete privacy, the home is surrounded by protected natural beauty without neighboring homes in view. Expansive walls of glass frame sweeping meadow and mountain

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    215 Old Stockbridge Rd, Lenox, MA 01240
  • 22 Goodrich St, Stockbridge, MA 01262
    22 Goodrich St, Stockbridge, MA 01262
    22 Goodrich St, Stockbridge, MA 01262
    /29

    $599,000

    • 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
  • 8 Shamrock St, Stockbridge, MA 01262
    8 Shamrock St, Stockbridge, MA 01262
    8 Shamrock St, Stockbridge, MA 01262
    /18

    $2,650,000

    New Construction
    • 5 Beds
    • 4.5 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
  • 349 Old Stockbridge Rd, Lenox, MA 01240
    349 Old Stockbridge Rd, Lenox, MA 01240
    349 Old Stockbridge Rd, Lenox, MA 01240
    /42

    $3,750,000

    • 34 Beds
    • 31 Baths
    • 40,241 Sq Ft

    349 Old Stockbridge Rd, Lenox, MA 01240

    Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways,

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 343-7496

    349 Old Stockbridge Rd, Lenox, MA 01240
  • 34 Church St, Stockbridge, MA 01262
    34 Church St, Stockbridge, MA 01262
    34 Church St, Stockbridge, MA 01262
    /17

    $745,000

    • 6 Beds
    • 4 Baths
    • 2,730 Sq Ft

    34 Church St, Stockbridge, MA 01262

    Rare opportunity to own a substantial two-family home with a potential bonus Airbnb cottage 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,

    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

    $2,995,000

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

    $729,000

    $20K 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
  • 8 Lukeman Ln, Stockbridge, MA 01262
    8 Lukeman Ln, Stockbridge, MA 01262
    8 Lukeman Ln, Stockbridge, MA 01262
    /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 High St, West Stockbridge, MA 01236
    17 High St, West Stockbridge, MA 01236
    17 High St, West Stockbridge, MA 01236
    /17

    $385,000

    $14K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,298 Sq Ft

    17 High St, West Stockbridge, MA 01236

    Charming small home with a cozy feel.This home is the perfect chance for a first time buyer to create a home of their own. With solid bones, a welcoming front porch, and a detached garage ideal for work shop or extra storage. Located in a convenient setting, it's ready for your vision, with opportunities for modern updates. A little work could mean a big reward.Housatonic Village a few steps

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    17 High St, West Stockbridge, MA 01236
  • 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

    $825,000

    $70K PRICE DROP
    • 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
  • 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

    $825,000

    $70K PRICE DROP
    • 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
  • 14 Old Tree Farm Rd, Stockbridge, MA 01262
    14 Old Tree Farm Rd, Stockbridge, MA 01262
    14 Old Tree Farm Rd, Stockbridge, MA 01262
    /67

    $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
  • 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

    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
  • 1 Devon Rd, Stockbridge, MA 01262
    1 Devon Rd, Stockbridge, MA 01262
    1 Devon Rd, Stockbridge, MA 01262
    /61

    $1,695,000

    $155K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 4,952 Sq Ft

    1 Devon Rd, Stockbridge, MA 01262

    Located in Stockbridge, this 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 own kitchen and bath, for family gatherings or as Artist Studio. A sparkling

    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
    /50

    $820,000

    $64K PRICE DROP
    • 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
  • 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
  • 5 Glendale Rd, Stockbridge, MA 01262
    5 Glendale Rd, Stockbridge, MA 01262
    5 Glendale Rd, Stockbridge, MA 01262
    /55

    $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
    /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
  • 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
Massachusetts Berkshire County Stockbridge

Newest Listings for Sale in Stockbridge, MA

Frequently Asked Questions

What is the average home price in Stockbridge, MA?
Homes for sale in Stockbridge, MA have an average home price of $1,157,527.
How many homes have sold over the last 12 months in Stockbridge, MA?
38 homes have sold in Stockbridge, MA over the last 12 months.
What are the most popular zip codes in Stockbridge, MA?
The most popular zip codes in Stockbridge, MA include 01262, 01266, 01240, 01238 and 01236.
How much do you need to make to afford a house in Stockbridge?
The median home price in Stockbridge is $822,000. If you put a 20% down payment of $164,400 and had a 30-year fixed mortgage with an interest rate of 6.51%, your estimated principal and interest payment would be $4,160 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $178K a year to afford the median home price in Stockbridge. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Stockbridge, MA?
Stockbridge, MA has highly rated public and private schools. Some of the best schools in Stockbridge based on Niche Grades are Berkshire Waldorf High School, The Montessori School of the Berkshires and Morris Elementary School. Browse all the schools in Stockbridge, MA to learn more.

Home Trends in Stockbridge, MA

On average, homes in Stockbridge, MA sell after 90 days on the market compared to the national average of 58 days. The median sale price for homes in Stockbridge, MA over the last 12 months is $762,500, down 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$762,500
Median Single Family Sale Price
$845,000
Median Townhouse Sale Price
$660,000
Median 2 Bedroom Sale Price
$548,000
Median 1 Bedroom Sale Price
$270,000
Average Price Per Sq Ft
$434
Number of Homes for Sale
15
Last 12 months Home Sales
38
Months of Supply
4.70
Median List Price
$822,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-19%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group