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.

17 Prospect Hill Stockbridge MA 01262

Stockbridge, MA17 Prospect Hill Rd

Price$4,450,000

Est. Mortgage: $/month

MLS Number 236486

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Acreage 15.6

Enjoy all the berkshire seasons. Winter brings sledding, cross country skiing, access to downhill runs or enjoy the fire pit or get cozy by one of thefour fireplaces. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular. Thought to be one the first of the large 'cottages' on prospect hill. A wraparound glass porch overlooks the walled sunken garden. Three floors of living spaces with almost every room open to the views. Beautiful detailing with marble fireplaces and antique woodwork. Four bedroom and four and a half baths. A large game room with full bath occupies the third floor. There is a gunite pool. Golf tee/driving area. Minutes from tanglewood . May be purchased without the building lot for 4,150,000.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Stockbridge MA 01262

Stockbridge, MA1 Lahey Cross Rd

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: 5.81% last updated on Jun 23, 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 Stockbridge MA 01262

Stockbridge, MA108 Interlaken Rd

Price$2,500,000

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: 5.81% last updated on Jun 23, 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 Stockbridge MA 01262

Stockbridge, MA30 East St

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: 5.81% last updated on Jun 23, 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

7 Interlaken Cross Stockbridge MA 01262

Stockbridge, MA7 Interlaken Cross Rd

Price$1,500,000

Est. Mortgage: $/month

MLS Number 238072

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,000
  • Acreage 1.8

Ready to move-into fully furnished, exceptionally well maintained, stockbridge home with 4 bedrooms/3bathrooms, an open floor plan, and an easy walk to stockbridge bowl. Enjoy the comforts of a wrap-around deck, screened porch and a 3-car garage. Investors note: this property has a terrific vrbo and airb&b rental history. Must be seen to be fully appreciated. Schedule your showings today.

Listed by George Cain of WILLIAM PITT SOTHEBY'S - GT BARRINGTON'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

15 East Stockbridge MA 01262

Stockbridge, MA15 East St

Price$1,200,000

Est. Mortgage: $/month

MLS Number 237693

  • Residential
  • Bathroom 8
  • Bedrooms 25
  • Square Feet 12,672
  • Acreage 6.11

A unique development opportunity in the center of historic stockbridge, close to so many area attractions, including the national shrine of the divine mercy. Six acres on busy route 7 with existing residential and theater buildings ready for renovation. Various past iterations include a grand hotel, dance theater, and theater rehearsal and residences. Main building with over 12,000 square feet, 2 ranch homes, 2 small cottages, 2 theater studios and a pole barn.

Listed by Marnie Garzone and Natalie Rose Weissbrod of THE KINDERHOOK GROUP - PITTSFIELD'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

5 Main Stockbridge MA 01262

Stockbridge, MA5 Main St

Price$993,000

Est. Mortgage: $/month

MLS Number 237917

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,600
  • Acreage 0.66

Quintessential late 1700''s historic new england colonial. Situated on a private level corner lot close to the village of stockbridge ma., home of the norman rockwell museum, chesterwood, wheatleigh, tanglewood and the iconic red lion inn. This 3600 sq. Ft lovely home offers 4 or 5 bedrooms, 2 full 2 half baths, sitting room, den, office, dining room, sun room eat in kitchen with great light and space for a huge island, two car attached garage, full basement. Hidden behind an established hedge the yard opens to a secret garden of established garden beds and speciman trees and stone walls.Many systems have been updated. A true pleasure to show.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

2 Lake Stockbridge MA 01262

Stockbridge, MA2 Lake Dr

Price$849,000

Est. Mortgage: $/month

MLS Number 238007

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,500
  • Acreage 1.46

Fabulous stockbridge location: mid century light and bright contemporary with open plan, large great room with cathedral ceiling and cast iron free standing fireplace, updated kitchen with granite and center island, first floor master with ensuite bath and it's very own screened porch, family room, three additional bedrooms, privacy, large decks minutes to the stockbridge bowl. This lovely home is minutes to downtowns of lenox, stockbridge and west stockbridge. Minutes to kirpalu, museums, restaurants, tanglewood, and all the berkshires has to offer.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

2 South Hill Stockbridge MA 01262

Stockbridge, MA2 South Hill Rd

Price$749,000

Est. Mortgage: $/month

Pending

MLS Number 237430

  • Residential
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2,111
  • Acreage 3.1

Fabulous location in stockbridge, close to all the best berkshire attractions. This pristine home sits back from a private road & is 1 of 2 homes on a dead end street. Manicured grass, landscaping & stone driveway, lead you to this 2111 square foot contemporary home with attached barn structure. Light abounds in the large open living room with tall ceilings & many windows that bring in the beauty of the outdoors. Eat in kitchen attaches to formal dining room. First floor has a den that can be used as bedroom for extra guests. Full bathroom on first floor & laundry. Upstairs has a large open loft that is used as an office (or for more sleeping space). 2 more spacious bedrooms & large bathroom with shower & free standing bathtub. The attached barn is a perfect place for summer soirees.

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S - GT BARRINGTON'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

58 Interlaken Stockbridge MA 01262

Stockbridge, MA58 Interlaken Rd

Price$599,000

Est. Mortgage: $/month

MLS Number 237960

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,430
  • Acreage 2.1

This 3 bedroom ranch is recently renovated and located on a desirable stockbridge road close to kripalu , only 1/2 mile from the boat ramp, and 5 minutes to tanglewood. The house sits well back from the road for a private setting. First floor consists of a mudroom entry, full bath and primary bedroom. The fully appointed kitchen with adjacent dining room flows to a large living room with oversized picture windows and a wood burning fireplace. The lower floor offers 2 more bedrooms with walk out , full bath , and potential full kitchen w/ sink and refrigerator a bonus is the deeded limited access to the stockbridge bowl for boat launching . A simple house easy to maintain home so you can enjoy the berkshires!

Listed by Cindy Welch of LANDVEST,INC.'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

5 Cherry Hill Stockbridge MA 01262

Stockbridge, MA5 Cherry Hill Rd

Price$595,000

Est. Mortgage: $/month

MLS Number 238076

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,031
  • Acreage 2

Beautifully kept mid century ranch on two acres in stockbridge. Set off the main room to enjoy the privacy of this lovely street, you are only a short distance to down town stockbridge, golfing, restaurants, and the many cultural institutions of the area. With a fully updated kitchen and laundry, this house has an easy to maintain single floor living area to make your own. The living room with wood burning fireplace looks out onto a fenced in patio and garden to enjoy the berkshire weather and entertain. Or, enjoy the screened in patio off the kitchen for summer dining. The yard extends further to include a small barn with stall and storage, perfect for the urban homesteader or gardening enthusiast. Loved for 30 years by the current owner, come find your new home for the next 30.

Listed by Claire Shomphe of HOUSATONIC REAL ESTATE'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 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 and Pamela Roberts of ROBERTS & ASSOC. REALTY,INC'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

22 Goodrich Stockbridge MA 01262

Stockbridge, MA22 Goodrich St

Price$549,000

Est. Mortgage: $/month

Pending

MLS Number 237637

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,152
  • Acreage 0.39

Open house canceled. Offer accepted. Be prepared to fall in love with this charming, renovated home located in the heart of the berkshires. Imagine cooking gourmet dinners in the recently-updated kitchen and sharing the meal on your screened porch while watching fireflies go by. The master bedroom has an attached, updated bathroom as well as a door that leads directly to the back deck, so you may sip your morning coffee in peace. On the other side of the house are two bedrooms and another full bath. Set on nearly 1/2 acre, the property has plenty of room for puttering in the garden and other outdoor fun. Downtown stockbridge is 1 mile away, with sidewalks much of the way. Perfect condo alternative

Listed by Jessica Tyler of NON-MEMBER: Reciprocal'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

326 Old Stockbridge Stockbridge MA 01262

MLS Number 238055

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,400
  • Acreage 1.9

Charming converted turn-of-the-century, tri-level, two horse barn on almost two acres.Original beams, hardwood floors, skylights and vaulted ceilings throughout main living level. This unique home has 3 bedrooms and 2 full baths. Kitchen features ceramic tile floor, newer appliances and granite counters. Separate dining room with soaring ceiling and french doors leading to a delightful patio. Screened sleeping/reading porch off the main level bedroom with perennial garden and woodland views. Second bedroom is located in the second level hayloft. Additionally, there is a third bedroom with a full bath on the lower level with kitchenette and separate entrance that allows for great flexibility. Highly desirable stockbridge location

Listed by Cortney K Dupont and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

38 Interlaken Stockbridge MA 01262

Stockbridge, MA38 Interlaken Rd

Price$499,000

Est. Mortgage: $/month

MLS Number 238103

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,912
  • Acreage 0.24

Historic, move in ready home in the charming interlaken neighborhood of stockbridge.This updated home has 3 bedrooms, 2 baths, lovely gardens, and a paved drive. Just the right size for easy care, and close to all the best things the berkshires has to offer. Within 10 minutes or less to stockbridge and lenox, as well as the stockbridge bowl, and tanglewood. Walk to is 183 art school, as well as sweet averic park across the street. The home was owned by the well known american painter, ammi phillips from 1859 to 1865.

Listed by Robin Ban of BERKSHIRE PROPERTY AGENTS,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

15 Stockbridge Stockbridge MA 01262

Stockbridge, MA15 Stockbridge Rd

Price$449,000

Est. Mortgage: $/month

Pending

MLS Number 237450

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,600
  • Acreage 5.15

This is the location! Right between stockbridge and west stockbridge, moments to town, tanglewood and all of what the berkshires have to offer. This spacious four bedroom, three bath home abuts a protected nature preserve full of life! The recently replaced, large and highly efficient windows flood this home with light and serenity. Lifetime metal roof and recently installed buderus boiler makes it easy to just move in and enjoy. Bring the horses! 24'' by 30'' horse barn complete with comfort stalls, tack room, hay loft and a paddock of over 2 acres for your four legged family members to enjoy. The lower level boasts an in-law efficiency apartment ready for guests. This is a special property loved by its current owners for over 25 years and is ready for its next chapter.

Listed by Ryan Lane of GILCREST PROPERTIES'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

17 Beachwood Stockbridge MA 01262

Stockbridge, MA17 Beachwood Dr

Price$425,000

Est. Mortgage: $/month

MLS Number 237945

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,120
  • Acreage 1.3

Prime stockbridge bowl access cottagecharming seasonal stockbridge bowl access cottage, with open kitchen/dining/living room, delightful screened porch, and large deck just steps from your private association beach, on one of the area's finest recreational lakes. Property is exceptionally private sitting over 200ft back from the road on 1.3 acres. Minutes away from downtown stockbridge, lenox and many cultural attractions.

Listed by Allison Rada of STONE HOUSE PROPERTIES,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

5 Lake Stockbridge MA 01262

Stockbridge, MA5 Lake Dr

Price$419,000

Est. Mortgage: $/month

MLS Number 238079

  • Residential
  • Bathroom 1
  • Bedrooms 1
  • Square Feet 650
  • Acreage 0.99

Privately situated this ''manhattan loft style'' cabin in the woods meticulously designed & fully renovated w/ ease of living in mind. Directly opposite the access to the stockbridge bowl outlet for canoeing & kayaking. The entrance foyer leads into a double volume great room w/ bed, seating area, gas fp, hw floors, built-ins and cabinets, split-unit ac/heating and a writer's loft. The kitchen is well equipped and ba w/ walk-in shower. A large vaulted screened-in porch provides for outdoor entertaining and greatly expands the living space to relax and enjoy. A superb berkshires pied-a-terre and as a rental (airbnb) property--has been used as both. Perfectly located in stockbridge near lenox & tanglewood. Includes all of the furniture, furnishings & electronics. Just bring your toothbrush!

Listed by Levin + Lazarus Team of BERKSHIRE PROPERTY AGENTS,LLC'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Beachwood Stockbridge MA 01262

Stockbridge, MA11 Beachwood Dr

Price$389,900

Est. Mortgage: $/month

Pending

MLS Number 237370

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 704
  • Acreage 0.25

Welcome to beachwood! This cozy three season cottage is ready for your enjoyment this summer in one of the most sought after communities. Three bedrooms, fireplace, screened porch located on a level corner sun filled lot. Stroll across the street to a path that is seconds away from the spectacular srockbridge bowl private beach with views for days. Short drive to tanglewood and minutes away from downtown stockbridge, lenox and many cultural attractions.

Listed by Tiffany Roberts of ROBERTS & ASSOC. REALTY,INC'

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 June 30, 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.