Stockbridge MA Single Family Homes

View a list of Stockbridge Massachusetts homes currently for sale below and let us know if you would like to learn more or schedule a tour.  If you would like to save your favorite Stockbridge MA property listings, you can register with our website.  You may also be interested in Great Barrington MA homes or Stockbridge MA homes.

7 Prospect Hill Road Stockbridge MA 01262

Stockbridge, MA7 Prospect Hill Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 239285

  • Residential
  • Bathroom 9
  • Bedrooms 5
  • Square Feet 9,339
  • Acreage 6.2

One of the berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media)room, wine cellar, fitness studio. Elevator, computerized systems. 9,339 sf with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house

Listed by Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

23 Prospect Hill Road Stockbridge MA 01262

Stockbridge, MA23 Prospect Hill Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 238266

  • Residential
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 8,200
  • Acreage 57

Privacy and elegant simplicity in a home for all seasons this exquisitely designed house, set upon 55+ acres, has sweeping linear forms, large expanses of glass & an open yet cozy floor plan. Dozens of sliding glass doors & windows as well as the extensive indoor use of natural materials like wood, brick & stone tile adds a warmth & beauty to the space & allows it to merge with the surrounding landscape of well-established gardens & woodlands. The layout of the common areas permits an easy & organic flow of movement & while well defined, these areas live in an intentional & casual relationship with each other. This offers a flexible use of space, whether for intimate conversations or large gatherings

Listed by Leslie G Chesloff and Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1 Lahey Cross Road Stockbridge MA 01262

Stockbridge, MA1 Lahey Cross Road

Price$2,595,000

Est. Mortgage: $/month

Pending

MLS Number 237363

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,847
  • Acreage 22.63

Custom built estate on a 22+ acre picturesque lot. Thoughtfully designed with exceptional detail and quality. Enjoy a winding tree-lined driveway, seasonally blooming landscape, renowned goshen stonework, in-ground pool, & guest house w/ private deck. In the main house, a 2-story foyer leads you to a grand living room w/ superb views, & a library perfect for book lovers. Farmhouse kitchen, dining room w/ fireplace, & sweeping windows lead you to a screened porch. A 2nd-floor primary suite includes walk-in closets, european style bath & dual pedestal sinks. Perfect for entertaining w/ 5 total bedrooms, butlers pantry, wine cellar, & plenty of outdoor space overlooking the manicured landscape. Nearby attractions: norman rockwell museum, berkshire botanical garden, tanglewood, & chesterwood.

Listed by Joshua Stephens of NON-MEMBER: Reciprocal'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

30 East Street Stockbridge MA 01262

Stockbridge, MA30 East Street

Price$2,450,000

Est. Mortgage: $/month

MLS Number 237413

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 9,337
  • Acreage 6.98

Move right in and take over this successful well established business in the heart of the berkshires. This beautiful property is complete with a heated in-ground pool, mature landscaping, and distant mountain views. The private location is perfectly situated between the picturesque towns of lenox, stockbridge and lee, close to tanglewood and many other berkshire attractions.This property would also be perfect for a large family compound.

Listed by Lauren Rosen and Lance Vermeulen of LANCE VERMEULEN RE,INC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

108 Interlaken Road Stockbridge MA 01262

Stockbridge, MA108 Interlaken Road

Price$2,375,000

Est. Mortgage: $/month

MLS Number 236514

  • Residential
  • Square Feet 500
  • Acreage 1.34

279' of frontage on stockbridge bowl. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well. Utilities easily accessible. Design plans for a 5,000+ square foot home with garage available. A rare opportunity to own a large parcel of land with frontage on deep lakefront on stockbridge bowl.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

12 Castle Hill Road Stockbridge MA 01262

Stockbridge, MA12 Castle Hill Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 238412

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,224
  • Acreage 8.81

Welcome to 12 castle hill rd!Creative building solutions designed & built this beautiful home in 2004, and it has been lovingly cared for by the same owner since. As you meander up the long drive, you will find yourself perched atop a hill with incredible views spanning to ski butternut. As you enter this exquisite home, you are greeted by an expansive kitchen that leads to a incredible family room that offers excellent natural light, a study with beautiful built ins and a gorgeous fireplace. The kitchen features a viking range, hand selected vermont soapstone counters, and plenty of space for cooking and entertaining. Off of the family room, you can either catch some sun on the graciously sized back deck, or enjoy evening dinners al fresco on the screened in porch.

Listed by John J Burns of BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

6 Wheatley Drive Stockbridge MA 01262

Stockbridge, MA6 Wheatley Drive

Price$995,000

Est. Mortgage: $/month

Pending

MLS Number 238931

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,851
  • Acreage 2.6

Hand crafted architectural work of art in the design tradition of famed new zealand architect maurice k. Smith. Extraordinary use of masonry, wood and glass. Delightful unique details at every turn. One's eye is continually brought to the next level and the out of doors. A wonderful retreat on a wooded setting a short walk to tanglewood and a quick drive to downtown lenox. Deeded beach rights at white pines beach on stockbridge bowl. Recent updates of furnace, oil tank, water heater, windows and more add to this rare find.Furniture available.

Listed by Suzanne Crerar and Cameron Volastro of STONE HOUSE PROPERTIES,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

21 Interlaken Cross Road Stockbridge MA 01262
Pending

MLS Number 235817

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,216
  • Acreage 2.6

This wonderful one-level home features beautiful grounds, and a wonderful, private location walking distance to stockbridge bowl. The house consists of a well maintained mid-century ranch, plus a dramatic primary suite addition with sleeping and living areas, adobe fireplace, cathedral ceilings, built-in cherry cabinetry, and a nicely appointed bathroom. There is a wood-paneled living room with propane fireplace and built-ins, open kitchen/dining area, screened porch, expansive trex decking, two-car garage, and lovely gardens with pond. Minutes to stockbridge, lenox, and all the berkshires has to offer, this unique oasis would make a wonderful getaway or full-time home.

Listed by Claire Naylor Pollart and Lance Vermeulen of LANCE VERMEULEN RE,INC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

14 Yale Hill Road Stockbridge MA 01262

Stockbridge, MA14 Yale Hill Road

Price$659,000

Est. Mortgage: $/month

Pending

MLS Number 238934

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,518
  • Acreage 0.31

This recently renovated bungalow is a sanctuary in the coveted neighborhood of yale hill. Listen to the sounds of the babbling kampoosa brook while enjoying a peaceful day in the garden, yard or on the deck. This house has 3 bedrooms, 2 full baths. A sunny kitchen appointed with high end appliances and combined dining area opens out to a large deck. The living room with fireplace has distant views of bear mountain. First floor bedroom could double as office space if working from home. Upper level has two bedrooms and full bath with double sinks. Laundry is situated off the kitchen. The front porch is the perfect spot to enjoy a good book. A 1 car garage is under the deck. Walk to town, and access to town beach and tennis courts. Low stockbridge taxes.

Listed by Susan Laidlaw of BERKSHIRE PROPERTY AGENTS,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

20 Church Street Stockbridge MA 01262

Stockbridge, MA20 Church Street

Price$575,000

Est. Mortgage: $/month

Pending

MLS Number 239315

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,984
  • Acreage 0.4

Location!! Walk to downtown stockbridge and naumkeag is your neighbor! Charm abounds in this adorable 4-bedroom home with so much to offer - light and bright kitchen/great room with double doors to the backyard and views of naumkeag, first floor primary, classic 3-season front porch and light landscaping for ease. The second floor includes 3 bedrooms, full bath, and washer/dryer. Close to berkshire botanical garden, 10 minutes to lenox and great barrington.

Listed by Katie Soules and Kelley Ryan Vickery of STONE HOUSE PROPERTIES,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

11 Mahkeenac Shores Road Stockbridge MA 01262

MLS Number 237824

  • Residential
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 950
  • Acreage 0.14

You don't want to miss the chance to own this three-season cabin, in a ''rare to market'' community on the stockbridge bowl. Perfect summer retreat!! Just minutes away from tanglewood and only a few short steps away from the private community beach and swimming dock. This adorable cabin has a signature fieldstone fireplace, a large screen porch, 2 bedrooms with sleeping loft and a stone patio. Lovely perennial beds enhance the grounds. Be in for summer 2022!

Listed by Molly E Thomas of ROBERTS & ASSOC. REALTY,INC'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

27 Cherry Hill Road Stockbridge MA 01262

Stockbridge, MA27 Cherry Hill Road

Price$450,000

Est. Mortgage: $/month

MLS Number 239266

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,440
  • Acreage 4.5

A most rare find to be within nature. A gift to discover oneself in stockbridge, the very heart and soul of country living. This property is still full of timeless beauty. The changing light filters in between the trees. Let time slow down. Leave chaos elsewhere and open the door to new possibilities.

Listed by Maggie C Merelle and George Cain of WILLIAM PITT SOTHEBY'S - GT BARRINGTON'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

11 Park Street Stockbridge MA 01262

Stockbridge, MA11 Park Street

Price$425,000

Est. Mortgage: $/month

MLS Number 238968

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,722
  • Acreage 0.19

The charming downtown stockbridge home you have been waiting for! Situated on just under a quarter acre, the property sits across from the stockbridge town park; down the road from miles of hiking trails at goodrich memorial park; and around the corner from the quaint village of stockbridge with cafes, shops, restaurants & museums. The first floor includes a light-filled living room, formal dining room, large eat-in kitchen with granite countertops, first floor laundry room and a first floor primary suite. The second floor includes three additional bedrooms and a full bathroom. The flat backyard is filled with mature pear, peach & apple trees. With a newer furnace, roof, windows and recently painted exterior - it's ready for you to move right in!

Listed by Maggie Gavin of WILLIAM PITT SOTHEBY'S - LENOX'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

12 Mahkeenac Heights Road Stockbridge MA 01262

MLS Number 239162

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,592
  • Acreage 0.41

Three season bungalow with three bedrooms, two full bathrooms along with loft for additional sleeping space. Living room boast a floor to ceiling field stone fireplace creating that perfect cool night atmosphere. The primary bedroom and bath is in the silo section of the house with the other two bedrooms in the main section of the house that has access to their own full bathroom. There is an ample sized kitchen that can accommodate a small table for eating. The rear of the house has two separate decks for morning sun along with a nice back yard. There also is a front deck for the afternoon sun. House is currently on the association water source that is shut off around the end of october for the winter season. Other houses in the area have drilled their own wells to enable year-round use.

Listed by Michael A Sorrentino of BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD'

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of December 2, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.