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Newest Homes for Sale in Stockbridge, MA

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  • /37

    $2,295,000

    • 31 Beds
    • 29 Baths
    • 38,415 Sq Ft

    349 Old Stockbridge Rd, Lenox, MA 01240

    A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    349 Old Stockbridge Rd, Lenox, MA 01240
  • /60

    $1,999,999

    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    14 Old Tree Farm Rd, Stockbridge, MA 01262

    Some homes offer extraordinary settings. Others offer exceptional living. Rarely does one offer both. Embracing its extraordinary setting, this classic center hall Colonial is all about the way it lives. The heart of the home is an inviting open kitchen with a breakfast nook and a beautiful sitting area where walls of glass and French doors open to a stunning stone patio, tranquil waterfall, and

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    14 Old Tree Farm Rd, Stockbridge, MA 01262
  • /55

    $995,000

    • 2 Beds
    • 2 Baths
    • 1,125 Sq Ft

    10 Mahkeenac Terrace, Stockbridge, MA 01262

    Bring your BOAT and enjoy all that the Stockbridge Bowl has to offer. This charming home has deeded rights to the lake, as well as its own dock space!The house was recently renovated with all top of the line mechanicals and appliances. Bosch, Miele, & Fisher Paykel. Central AC. One level living with two bedrooms and two full baths. Open concept living with a large front deck and yard for

    Lawrence Reilly THE KINDERHOOK GROUP

    10 Mahkeenac Terrace, Stockbridge, MA 01262
  • /47

    $1,125,000

    • 4 Beds
    • 3.5 Baths
    • 2,859 Sq Ft

    2 Goodrich St, Stockbridge, MA 01262

    Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage. Second floor

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    2 Goodrich St, Stockbridge, MA 01262
  • /43

    $750,000

    • 3 Beds
    • 2 Baths
    • 2,446 Sq Ft

    2 Fox Meadow Rd, Stockbridge, MA 01262

    Don't miss this hard to find single floor living opportunity in the highly sought after town of Stockbridge. Offering nearly 2500 sq ft of thoughtful living space, this 3 bedroom, 2 full bath home blends main level convenience and genuine rustic warmth and modern versatility. Inside the home features multiple cozy heat sources for New England winters, including a classic wood burning fireplace as

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    2 Fox Meadow Rd, Stockbridge, MA 01262
  • /46

    $4,975,000

    • 3 Beds
    • 3.5 Baths
    • 4,359 Sq Ft

    5 Deer Hill Rd, West Stockbridge, MA 01266

    Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    5 Deer Hill Rd, West Stockbridge, MA 01266
  • /12

    $475,000

    • Land
    • 7.1 Acres
    • $66,901 per Acre

    8 Stone Ridge Rd, Stockbridge, MA 01262

    This alluring seven acre parcel is nested between two gentle, fern filled, wooded slopes to the east and west of the site. A spacious meadow, with an intimate connection to wooded shade, is filled with bright southern light. Approaching from the Campion Farms entrance, Stone Ridge Rd curves gently upward, leading to a lovely meandering drive which takes you to the partially cleared building site.

    Claudia Crane COMPASS MASSACHUSETTS , LLC GB

    8 Stone Ridge Rd, Stockbridge, MA 01262
  • /17

    $360,000

    • 3 Beds
    • 1 Bath
    • 1,298 Sq Ft

    17 High St, West Stockbridge, MA 01236

    This home is the perfect chance to live in a sweet neighborhood with a short stroll to the village. With solid bones, a welcoming front porch, and a detached garage ideal for work shop/studio/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 away. Lovely back yard!

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    17 High St, West Stockbridge, MA 01236
  • /28

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 2,088 Sq Ft

    5 Apple St, Stockbridge, MA 01262

    Great potential in a lovely setting. Located on a dead end, this property offers a gracious living room with wood floors, open kitchen and dining, mudroom/laundry room, half bath and serene sitting front porch. The second level has three bedrooms and full bath. It awaits the Buyers new vision and thoughtfulness to bring it back to it's original glory. Great location near cultural attractions in

    Cortney Dupont COHEN & WHITE ASSOCIATES

    5 Apple St, Stockbridge, MA 01262
  • /37

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262

    STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a

    Cortney Dupont COHEN & WHITE ASSOCIATES

    200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262
  • /56

    $1,490,000

    $260K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    5 Glendale Rd, Stockbridge, MA 01262

    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 sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage,

    Martha Piper THE KINDERHOOK GROUP

    5 Glendale Rd, 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
  • /42

    $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
  • /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
  • /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
  • /42

    $2,950,000

    $450K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 3,432 Sq Ft

    36 Yale Hill Rd, Stockbridge, MA 01262

    EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, 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
  • /49

    $950,000

    $110K PRICE DROP
    • 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
  • /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
  • /88

    $2,950,000

    $300K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 5,696 Sq Ft

    7 Wheatley Dr, Stockbridge, MA 01262

    At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    7 Wheatley Dr, 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
  • /35

    $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
  • /19

    $865,000

    $35K PRICE DROP
    • 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
  • /42

    $3,195,000

    $555K PRICE DROP
    • 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

    349 Old Stockbridge Rd, Lenox, MA 01240
  • /50

    $1,999,000

    $996K 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
  • /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
  • /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
  • /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
  • /20

    $4,250

    • 3 Beds
    • 2 Baths

    44 Main St Unit 1, Stockbridge, MA 01262

    STOCKBRIDGE IN-TOWN LOCATION. SUMMER RENTAL! Fully Furnished, Like New. 3 Bedroom Apartment. Must be seen to be appreciated. Location, Location, Location. It doesn't get any better than this. 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
  • /12

    $4,500

    $3K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    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. JULY & AUGUST @ $9,000/month. 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
  • /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
  • /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

Frequently Asked Questions

What is the average home price in Stockbridge, MA?
Homes for sale in Stockbridge, MA have an average home price of $1,882,204.
Are home prices dropping in Stockbridge?
Yes, home prices in Stockbridge are down 11% in the last 12 months.
How many homes have sold over the last 12 months in Stockbridge, MA?
43 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 $895,000. If you put a 20% down payment of $179,000 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $4,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $197K 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
$670,000
Median Single Family Sale Price
$955,000
Median 2 Bedroom Sale Price
$497,500
Median 1 Bedroom Sale Price
$214,500
Average Price Per Sq Ft
$465
Number of Homes for Sale
19
Last 12 months Home Sales
43
Months of Supply
5.30
Median List Price
$895,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-29%
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