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Stockbridge, MA Homes for Sale

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  • /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
  • /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
  • /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
  • /47

    $1,175,000

    • 4 Beds
    • 3 Baths
    • 3,242 Sq Ft

    15 Interlaken Cross Rd, Stockbridge, MA 01262

    Stockbridge Contemporary surrounded by 5+ acres of privacy and deeded rights to the Beachwood Association private beach is just waiting for you to rebrand this mid century jewel. Open common spaces to gather and take in the nature surrounding the house, four bedrooms and three baths; main floor primary is en suite. The location of this property is perfect in all directions, conveniently located

    Mary Jane White COHEN & WHITE ASSOCIATES

    15 Interlaken Cross Rd, Stockbridge, MA 01262
  • /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
  • /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
  • /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 -one a four bedroom home and a 1000 sq ft guest house-both surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with

    Martha Piper THE KINDERHOOK GROUP

    5 Glendale Rd, Stockbridge, MA 01262
  • /33

    $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
  • /50

    $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
  • /46

    $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 Sothebys Intn'l

    11 Hawthorne Rd, Stockbridge, MA 01262
  • /23

    $549,000

    • 3 Beds
    • 1 Bath
    • 1,188 Sq Ft

    26 Mahkeenac Rd, Stockbridge, MA 01262

    Have you been dreaming of year round fun on Stockbridge Bowl? The time is now! Built in 2011, this lovely home is directly across the street from the beloved town beach and affords water views from most windows. Offering single-level living, 3 BR, 1 full BA, a well appointed kitchen and gracious living spaces. The unfinished walk-out lower level is the perfect place to store your kayaks, and

    John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    26 Mahkeenac Rd, Stockbridge, MA 01262
  • /52

    $1,995,000

    $105K PRICE DROP
    • 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
  • /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
  • /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
  • /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
  • /47

    $3,495,000

    • 5 Beds
    • 4.5 Baths
    • 3,862 Sq Ft

    16 Old Tree Farm Rd, Stockbridge, MA 01262

    Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    16 Old Tree Farm 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
  • /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
  • /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
  • /52

    $350,000

    • 6 Beds
    • 4 Baths
    • 2,700 Sq Ft

    3 Apple St, Stockbridge, MA 01236

    Rare opportunity to acquire a updated two-family property in Stockbridge with nearly 1.9 acres across two included lots. Come take a look to add your finishing touches to this project. Situated on a dead-end street on a spacious and clear lot. Each unit features three bedrooms and one-and-a-half baths, across approximately 2,700 square feet. Separate utilities for each unit, off street parking,

    Cory Evangelisto NOCHER REALTY

    3 Apple St, Stockbridge, MA 01236
  • /15

    $649,000

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

    17 Beachwood Dr, Stockbridge, MA 01262

    OPEN HOUSE - Saturday, July 11, 11-1. 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

    Franz Forster FRANZ J. FORSTER R. E.

    17 Beachwood Dr, 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
  • /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
  • /49

    $1,060,200

    • 4 Beds
    • 3.5 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
  • /50

    $2,500,000

    $495K 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
  • /59

    $1,595,000

    $255K PRICE DROP
    • 6 Beds
    • 5.5 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
  • /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
  • /43

    $1,550,000

    • 4 Beds
    • 4.5 Baths
    • 3,542 Sq Ft

    650 Mallard Ln, Lee, MA 01238

    Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout.The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's

    Paula McLean PAULA MCLEAN REALTORS INC.

    650 Mallard Ln, Lee, MA 01238
  • /26

    $835,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft

    90 Hawthorne St, Lenox, MA 01240

    Beautiful historic farm house available in Lenox Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst'', one of the famed Berkshire ''cottages'', this formerguest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2 car garage.. Luxurious traditional

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    90 Hawthorne St, Lenox, MA 01240

Why Live in Stockbridge

Stockbridge, MA, a small community in the Berkshires, is known for its sweeping mountain vistas, historic estates, and vibrant art scene. The town's Main Street is lined with local businesses, cozy coffee shops, and art galleries, anchored by the iconic Red Lion Inn. Stockbridge is a cultural hub, home to the Norman Rockwell Museum, which houses the world's largest collection of Rockwell's work, and other historic sites like Naumkeag and Chesterwood. The Berkshire Theatre Group and Tanglewood music venue offer a variety of performances, while nearby attractions like Jacob's Pillow and Mass MOCA provide additional cultural experiences. Outdoor recreation is abundant, with Monument Mountain Reservation and October Mountain State Forest offering hiking, fishing, and camping. Winter activities include snowmobiling and skiing at nearby resorts like Ski Butternut. The Stockbridge Golf Club and Stockbridge Bowl cater to golfers, boaters, and beachgoers. Housing options range from colonial-style farmhouses and Victorian-style homes to modern custom-built estates. The Berkshire Hills Regional School District serves the area, with highly rated schools such as Muddy Brook Regional Elementary and Monument Mountain Regional High School. Stockbridge is primarily car-dependent, with U.S. Route 7 and Interstate 90 providing access to nearby towns and Albany International Airport, 50 miles away.

Frequently Asked Questions

What is the average home price in Stockbridge, MA?
Homes for sale in Stockbridge, MA have an average home price of $1,859,624.
Are home prices dropping in Stockbridge?
Yes, home prices in Stockbridge are down 10% in the last 12 months.
How many homes have sold over the last 12 months in Stockbridge, MA?
41 homes have sold in Stockbridge, MA over the last 12 months.
What is the average household income in Stockbridge, MA?
The average household income in Stockbridge, MA is $105K.
What are the most popular zip codes in Stockbridge, MA?
The most popular zip codes in Stockbridge, MA include 01262, 01266, 01238, 01240 and 01236.
How much do you need to make to afford a house in Stockbridge?
The median home price in Stockbridge is $882,000. If you put a 20% down payment of $176,400 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $4,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $191K a year to afford the median home price in Stockbridge. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Stockbridge is $105K.
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 Price Trends

Median Sale Price
$750,000
Median Single Family Sale Price
$925,000
Median 2 Bedroom Sale Price
$475,000
Median 1 Bedroom Sale Price
$214,500
Average Price Per Sq Ft
$462
Number of Homes for Sale
20
Last 12 months Home Sales
41
Months of Supply
5.90
Median List Price
$882,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-21%
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