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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: 7.02% last updated on May 16, 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

MLS Number 237753

  • 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: 7.02% last updated on May 16, 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: 7.02% last updated on May 16, 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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890 Bald Mountain Road Austerlitz NY 12017

Austerlitz, NY890 Bald Mountain Road

Price$9,750,000

Est. Mortgage: $/month

MLS Number 239939

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,438
  • Acreage 85.51

Located in a gated community of large acreage land holders and highlighted in interior design magazine, sits this exquisite and truly special property. The main house is a stunning post and beam contemporary masterpiece built with the highest quality materials and a curated aesthetic that draws the outdoors within. Glass, wood, steel and textiles compliment each other to create a space that is inviting and cozy while also being edgy and hip. A gunite pool encased by stone walls sits just beyond a wall of glass. Two equally designed and inviting guest cottages sitting just steps away are perfect for friends and family. Continue beyond the complex, past a couple crystal clear swim ponds and you'll end up at one of the most jaw dropping premier building sites in the hudson valley with views

Listed by Nikki Carchedi of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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2080 South Undermountain Road Sheffield MA 01257
Pending

MLS Number 234183

  • Residential
  • Bathroom 6
  • Bedrooms 11
  • Square Feet 5,850
  • Acreage 85

This spectacular 85+/- acre property is a destination educational center. It offers a magnificent 1880 manor house, with spectacular distant views, a pond, and 11 additional buildings which house an auditorium, group meeting areas, breakout private offices, a fitness center, pondside cottage, huge dining hall with commercial kitchen, and accommodations in over 56 guest rooms. The land is made up of 70+/- acres in the southern berkshires and 15+/- abutting acres in salisbury, ct - the entire ct side runs along sage's ravine. There are walking trails throughout the land and access to the appalachian trail. You will be smitten by this property and totally taken with the possibilities... Building and property tax details are for the main house only. Please contact agent for more details.

Listed by Juliet Moore and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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181 Golf Course Road Craryville NY 12521

Craryville, NY181 Golf Course Road

Price$6,950,000

Est. Mortgage: $/month

MLS Number 240682

  • Residential
  • Bedrooms 7
  • Square Feet 4,035
  • Acreage 134.39

Unparalleled 134 acre estate fronted on copake lake and adjacent to the copake country club. Spacious, 7 br 6 ba stone & wood home surrounded by dramatic stonework and lush landscaping. Great room with fireplace, chef's kitchen and 4 season sun-room. Grotto-like swimming pool with multi-level terraces and outdoor kitchen. Tennis court is beyond a wooden foot bridge. Past the stocked pond are the horse stables with a fenced in pasture, & a 3,600 square foot heated hangar, perfectly suited for an artist's work space, recording studio or a classic car collection. Several dramatic building sites have been thoughtfully cleared revealing jaw-dropping panoramic views of the hudson valley and the catskills & some w views of lake. 2,200 ft of lake frontage & trails throughout the wooded hillside.

Listed by Russ Stein of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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390 Tamaridge Way New Marlborough MA 01259

New Marlborough, MA390 Tamaridge Way

Price$6,900,000

Est. Mortgage: $/month

MLS Number 240324

  • Residential
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 5,890
  • Acreage 330

Rare 330 acre parcel with stunning long views, abutting conservation land. Total seclusion and privacy, bucolic countryside with open meadows. Once a grand berkshire estate, the property consists of the main tudor style residence with indoor pool, shingled barn, dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all in need of extensive work. Divided into distinct areas, the sunken gardens feature several different design elements. A unique and wonderful opportunity, within close proximity to gedney farm, old inn on the green, southfield store, and just minutes to ski butternut and great barrington. Seller financing available.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC ((413) 429-7733)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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: 7.02% last updated on May 16, 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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250 Long Pond Road Great Barrington MA 01230

Great Barrington, MA250 Long Pond Road

Price$6,500,000

Est. Mortgage: $/month

MLS Number 240514

  • Residential
  • Bathroom 9
  • Bedrooms 7
  • Square Feet 11,714
  • Acreage 119.73

Price improvement: this unique architecturally designed contemporary offers the perfect blend of sophisticated esthetics with easy country living sited beautifully on 119+ acres of privacy and tranquility. The main residence and guest quarters are surrounded by nature and sweeping views in all seasons. Sorpetaler sliding glass walls and expansive decking overlook the 25 meter heated saltwater lap pool, hot tub, stone fire pit and striking rock outcroppings. The 3,000 sq ft finished barn with double volume height ceiling offers numerous uses on your way to the hiking & bike trails to the frontage on the williams river...All just a short drive to the sought after town of great barrington for dining, shopping & entertainment!

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES ((413) 637-1086)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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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67, 71, 73 Blunt Road Egremont MA 01230

Egremont, MA67, 71, 73 Blunt Road

Price$6,500,000

Est. Mortgage: $/month

MLS Number 242753

  • Residential
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 12,047
  • Acreage 20

Eight building estate compound for discriminating buyers on quiet country road. Three parcels combined. Created exclusively with custom, high-end designer elements & imported materials in 2021-22. #71: main house features 3 brs, 2 1/2 baths, tiled fireplace, first floor primary br, club house/guest house w/kitchen (no stove), living room, loft office or br, extensive landscaping, heated gunite pool, pickleball court. Pink house: office/playhouse. #67: under construction: 6,000+/- post & beam luxury 3-level, 3-br home with inground pool & 2-br guest house. Unique sanctuary w/indonesian tub, fountain, antique fireplace, jeweled floor, koi pond.#73 guest house: custom 3-br 1 bath retreat over 3 bay garage. Closing preferred in october. September 27 wedding confirmed.

Listed by Rosemary Ann Baumann of WHEELER & TAYLOR REALTY CO.,INC. ((413) 528-1006)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 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 May 22, 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.