Stockbridge Real Estate

Stockbridge is the quintessence of small-town New England charm, untainted by large-scale development. It is also the blueprint for small-town America as represented on the covers of the Saturday Evening Post by painter Norman Rockwell (the official state artist of Massachusetts). From 1953 until his death in 1978, Rockwell lived in Stockbridge and painted the simple charm of its buildings and residents. James Taylor sang about the town in his hit "Sweet Baby James," as did balladeer Arlo Guthrie in his famous Thanksgiving anthem "Alice's Restaurant," in which he tells what ensued when he tossed some garbage out the back of his Volkswagen bus down a Stockbridge hillside.

Search new real estate in the Berkshires town of Stockbridge, MA. Discover hundreds of current listings, including single-family homes, luxury estates, and residential land. Love what you see? Register with us to save your favorites, and receive notifications when similar properties are listed. Contact us to see any of the homes below!

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11 Hawthorne Street Stockbridge MA 01262

Stockbridge, MA11 Hawthorne Street

Price$15,000,000

Est. Mortgage: $/month

MLS Number 243138

  • Residential
  • Bathroom 23
  • Bedrooms 19
  • Square Feet 22,000
  • Acreage 21

Wheatleigh is the perfect marriage of the grandeur of a 16th century florentine palazzo and the comfort and elegance of the twenty first century. Imagine living in desirable lenox on 22 acres overlooking stockbridge bowl and the mountains and being within a short stroll to tanglewood! Henry cook in 1893 commissioned peabody and sterns to construct this italianate style home. It has since been updated by famed architects tsao and mckown for contemporary living. The 19 suites, guest rooms and baths set a new standard of style and sophistication and can accommodate many friends, business guests and family. Each of the bedrooms have high speed internet and bang and olufsen tv's . The state of the art fitness center, heated pool, and tennis court keep every one active.

Listed by Cindy Welch of LANDVEST,INC. ((978) 544-5767)

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$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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11 Hawthorne Street Stockbridge MA 01262

MLS Number 243137

  • Commercial
  • Acreage 21
  • Parking Spaces 100

Rarely does a property of such landmark significance, fully restored and in impeccable condition grace the market. Situated on 21.25 acres in desirable stockbridge on grounds landscaped by frederick law olmstead with views of stockbridge bowl and a short walk to tanglewood. This italianate building has been upgraded by famed architects tsao and mckown. The property offers 33 rooms, 19 ensuite bed rooms with high ceilings, luxurious baths and grand common rooms awaiting your imagination for a new life .

Listed by Cindy Welch of LANDVEST,INC. ((978) 544-5767)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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7 Prospect Hill Road Stockbridge MA 01262

Stockbridge, MA7 Prospect Hill Road

Price$9,950,000

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 ((413) 528-4192)

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$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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18 Main Street Stockbridge MA 01262

Stockbridge, MA18 Main Street

Price$6,200,000

Est. Mortgage: $/month

MLS Number 243879

  • Residential
  • Bathroom 15
  • Bedrooms 11
  • Square Feet 13,426
  • Acreage 2.7

Houses like this do not come along often! Two magnificent houses on 2.7 acres of serenity. The 17 room mansion boasts victorian architecture with modern luxuries. Named the taggart house, this property has hosted celebrities and guests for many years. Almost 9000 square feet including a ballroom! Continue operating the business or live in it as your dream home. The rear guest house is a 4,500 square foot modern post and beam farmhouse built in 2006 with many beautiful recent renovations. Kayak from your private beach on the housatonic river, stroll into town and all that stockbridge has to offer.

Listed by Dina B Browne of NEPONSET VALLEY REAL ESTATE,INC. ((508) 561-4448)

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%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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23 Prospect Hill Road Stockbridge MA 01262

Stockbridge, MA23 Prospect Hill Road

Price$4,750,000

Est. Mortgage: $/month

MLS Number 243745

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

Significantly restored in 2024! Sellers have masterfully updated this legacy home w/ a cool & fresh aesthetic that preserves the integrity of its mid-century modern design. Updates to the 1st floor primary suite, kit, entertainment kit, bathrooms & freshly painted interiors are just a few of the improvements. The airy main living spaces w/ their expansive sliding glass doors offer sublime views of the resort-like grounds complete w/ manicured lawns, patios, in-ground pool, playground, newly resurfaced tennis/pickle ball court, gardens curated by a master gardener & distant mountain views. The 7 bedroom, 7 bathroom estate w/ 8200 sq ft of versatile living space prominently sited on 57+ acres is 3 hours to nyc and 2 hours to boston!

Listed by Nancy Cole of COMPASS MASSACHUSETTS,LLC. ((617) 206-3333)

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$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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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 ((413) 442-8049)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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8 Yale Hill Road Stockbridge MA 01262

Stockbridge, MA8 Yale Hill Road

Price$2,400,000

Est. Mortgage: $/month

MLS Number 243017

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,738
  • Acreage 1.8

Step into the charm of history with this renovated exceptional property nestled in the picturesque town of stockbridge, just off main street. A meticulously renovated 4-bedroom, 4-bath historic home offers elegant living spaces with the convenience of modern amenities such a solar array providing all electricity, a car charger and central air. The new eat-in kitchen offers subzero, bluestar, vent-a-hood and bosch appliances, while overlooking the kampoosa brook and a private swimming hole. The millhouse, as it's known, one of the first in stockbridge is a 3-bedroom, 3-bath guest house with a great summer rental history. There's also a two-car garage and a fruit orchard. Enjoy the sound of the rushing brook from almost any window along with walking to town for an espresso, food or theater.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

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$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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14 Pine Street Stockbridge MA 01262

Stockbridge, MA14 Pine Street

Price$2,150,000

Est. Mortgage: $/month

MLS Number 243783

  • MultiFamily
  • Acreage 0.49
  • Year Built 1900
  • Parking Spaces 24

Welcome to 14 pine street, a unique and vibrant property nestled in the heart of picturesque stockbridge, ma. This versatile building offers an ideal blend of commercial and residential spaces, making it an outstanding investment opportunity for those seeking a dynamic property in a central location. The property went through extensive renovations in 2019, including the following upgrades: installation of upper parking lot, sidewalks and ramps, retaining wall and landscaping, drainage and rain garden, roof, updated all 4 boilers, repainted exterior, and a full renovation of the ground floor (new bathrooms, kitchenette, lighting, and two new egresses). The main floor offers a flexible commercial space, boasting a large assembly room with vaulted ceilings and oversized windows that flood

Listed by Katie Williams of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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14 Pine Street Stockbridge MA 01262

MLS Number 243782

  • Commercial
  • Acreage 0.49
  • Parking Spaces 24

Welcome to 14 pine street, a unique and vibrant property nestled in the heart of picturesque stockbridge, ma. This versatile building offers an ideal blend of commercial and residential spaces, making it an outstanding investment opportunity for those seeking a dynamic property in a central location. The property went through extensive renovations in 2019, including the following upgrades: installation of upper parking lot, sidewalks and ramps, retaining wall and landscaping, drainage and rain garden, roof, updated all 4 boilers, repainted exterior, and a full renovation of the ground floor (new bathrooms, kitchenette, lighting, and two new egresses). The main floor offers a flexible commercial space, boasting a large assembly room with vaulted ceilings and oversized windows that flood

Listed by Katie Williams of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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5 Glendale Road Stockbridge MA 01262

Stockbridge, MA5 Glendale Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 242787

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,200
  • Acreage 3.6

Two dwellings on almost four acres.Just a very special property. Located between the rockwell museum and the botanical garden. You are moments from tanglewood. Equidistant from lenox and great barrington providing easy access to the berkshires wonderful restaurants. The main house has four bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. Gracious grounds are beautifully landscaped. Adorable play house for little ones. Several outbuildings. Garages for at least 5 cars. First floor primary bedroom with sunroom. Perfect site for a pool. Abuts protected land.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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2 Laurel Lane Stockbridge MA 01262

Stockbridge, MA2 Laurel Lane

Price$1,475,000

Est. Mortgage: $/month

MLS Number 243586

  • Residential
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 3,878
  • Acreage 0.69

Rare; a renovated historic farmhouse abutting conserved land in the center of stockbridge at the end of a private, quiet lane. The 3 season front porch with new pella windows looks over a sunny lawn. The flow of first floor rooms allow for space and togetherness. There is a proper mudroom and butler's pantry. The bedrooms on the second floor are sun drenched, with tall ceilings and lovely restored wood floors. All 4.5 baths in the house have been remodeled with elegant detail. The third floor remains a fun recreational space for overflow family, guests, office or exercise. With utility upgrades, owned solar panels, and new windows, this is a highly functional 21st century house with the softness and warmth of an antique. Walk to tennis, golf, ice glen, dining, and the library. Glorious.

Listed by Kenzie Fields and David W Taylor of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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.

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2 Cherry Street Stockbridge MA 01262

Stockbridge, MA2 Cherry Street

Price$1,395,000

Est. Mortgage: $/month

MLS Number 242048

  • Residential
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,057
  • Acreage 0.91

A magnificent 6 bedroom stucco residence less than a mile to the center of stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out beautiful french doors to your screened in patio which leads to a well lit and heated pool. A 20 ft hallway wall of built in cabinets and closets leading to the primary bedroom. Three en suite bedroom areas for guests and family. Electric car charger in the heated garage. Majestic stonewalls. Not far to all attractions tanglewood, norman rockwell, ski areas etc. A must see!

Listed by Patricia Andrew of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 2024
* 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 July 21, 2024 . 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.