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Berkshire Single Family Properties

Discover single family homes for sale in the Southern Berkshires of Massachusetts. Find homes in Great Barrington, Egremont, Lee, and beyond. Search through a variety of current listings, including lakeside homes, antique luxury homes, and many more! Whether you're looking for multimillion dollar estates or modest cabins and camps, Southern Berkshire homes are truly diverse and offer options for most any homebuyer. Enjoy the mountains, lakes, and the area's many natural wonders from your new home!

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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)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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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319 Under Mountain Road Lenox MA 01240

Lenox, MA319 Under Mountain Road

Price$13,500,000

Est. Mortgage: $/month

Pending

MLS Number 244657

  • Residential
  • Bathroom 6
  • Bedrooms 7
  • Square Feet 13,261
  • Acreage 218.11

Pine needles built in 1903, this very private berkshire cottage epitomizes the area- past and present. Built in the arts and crafts style, surrounded by hundreds of acres of land, with magnificent southern views, one can enjoy nature, sports, and a relaxed lifestyle. Unspoiled, original detailing in place. Settle right in and be transported back to an earlier age. Paneled public rooms overlook the unspoiled views. Logias beckon to the out of doors. Seven bedrooms and 9 baths, two sleeping porches . The eat in kitchen offers space to gather, cook, enjoy the wildlife. This east wing also contains a butler's pantry, formal dining room, a summer dining room and one of the loggias.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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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1175 County Route 27a Road Copake NY 12516

Copake, NY1175 County Route 27a Road

Price$9,995,000

Est. Mortgage: $/month

MLS Number 243487

  • Residential
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 8,384
  • Acreage 133.04

Nestled in the heart of the hudson valley, this unparalleled 133 acre compound in copake, ny is a masterpiece of luxury and sophistication. The sprawling private grounds are a haven of natural beauty, with serene water frontage on 46 acre chrysler pond, lush woodlands for outdoor adventures and farm facilities, each corner of the property offers breathtaking mountain views and a sense of tranquility.The masterfully handcrafted 6-bedroom lodge, constructed with timber from british columbia, offers over 8000 sf for year round entertainment. The residence exudes elegance with a chef's kitchen, gracious dining room and exquisite living room, complete with commanding fireplace - see supplement for full remarks

Listed by Karen Climo and Jennifer Capala of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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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77 Seekonk Cross Road Great Barrington MA 01230

MLS Number 243158

  • Residential
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,474
  • Acreage 30.93

Welcome to meadow woodthis elegant property on a secluded reach of the green river epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays, a barn, and cutting gardens.

Listed by Elvia Gignoux and Lenore Mallett of WILLIAM PITT SOTHEBY'S - SALISBURY ((860) 435-2400)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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 Sullivan Road Sandisfield MA 01255

Sandisfield, MA14 Sullivan Road

Price$6,500,000

Est. Mortgage: $/month

MLS Number 242546

  • Residential
  • Bathroom 6
  • Bedrooms 3
  • Square Feet 3,000
  • Acreage 321

Atwater pond is a remarkable 321-acre retreat in southern berkshire county. An immaculately renovated mid-century house and 1920's guest cottage sit on the edge of a 32-acre, spring-fed pond, surrounded by hundreds of acres of pristine forest. Year-round recreational opportunities abound and a 4+ mile trail system winds through the property. Additional features include multiple docks, historic boathouse, deep water swimming hole, paddock with run-in shed, and 23' airstream trailer. Truly the best of both worlds, the property is supremely private, yet conveniently located to take full advantage of everything the berkshires offer. Boston and new york city can be reached in 2.5 hours or less, bradley international airport is only 45 min away. Offered turnkey.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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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25 Sheffield Road Egremont MA 01230

Egremont, MA25 Sheffield Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 243036

  • Residential
  • Bathroom 10
  • Bedrooms 11
  • Square Feet 9,748
  • Acreage 67

Listed by Elyse Harney Morris and Lauren A. Molk of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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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Monterey MA 01245

Monterey, MA

Price$5,500,000

Est. Mortgage: $/month

Pending

MLS Number 243798

  • Residential
  • Bathroom 7
  • Bedrooms 8
  • Square Feet 9,300
  • Acreage 51.55

Crow house - an enchanting private stone-and-timber compound in monterey.One of berkshire county's most atmospheric and luxurious properties, this stone-and-timber 52-acre compound, which abuts thirteen thousand acres of protected state forest, is a magical world unto itself. A winding driveway through horse pastures leads under a porte cochere to a european-style courtyard, where a pergola draped in wisteria links the entrances to the five-bedroom, five-bath main house, the three-bedroom, two-bath guest house and a terrace with an outdoor dining pavilion.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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 Kemble Street Lenox MA 01240

Lenox, MA2 Kemble Street

Price$5,485,000

Est. Mortgage: $/month

MLS Number 242956

  • Residential
  • Bathroom 14
  • Bedrooms 13
  • Square Feet 9,556
  • Acreage 3

The kemble, a registered ''great estate'' built in 1881 is located in the heart of the thriving downtown lenox business district. This classic colonial revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate groups of 20+ and is frequently rented to wedding parties, corporate retreat groups, and multi-generational family retreats. Stays can vary from a weekend to month or longer. Guests can choose to bring in cooks, bartenders, and waitstaff, if desired. Manicured lawns and gardens. Breathtaking views to the west. Fully ada compliant.

Listed by Cameron Volastro and Lori J Rose of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Oct 31, 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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Based on information submitted to BCMLS  as of November 4, 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.