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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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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$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: 6.79% last updated on Jun 1, 2023
* 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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New Marlborough MA 01259

New Marlborough, MA

Price$12,000,000

Est. Mortgage: $/month

MLS Number 240336

  • Residential
  • Bathroom 12
  • Bedrooms 9
  • Square Feet 8,623
  • Acreage 298

Cross a covered bridge over the konkapot river, pass a red barn and the caretaker cottage, follow the land's arc as it rises through rolling green fields with fruit trees until you reach the crest of a hill. Here, on 298 private acres, is a contemporary masterwork by world-renown architect tom kundig. In collaboration with acclaimed landscape architect tom stuart-smith, kundig has created a bold, innovative, yet intimate home where line and form embrace light and the landscape. Set on a spectacular parcel of land in berkshire county, facing sunsets over the taconic mountains, this astounding property includes two guest cottages, a caretaker's home, luxurious 6-stall barn, paddocks, indoor and outdoor riding arenas with olympic-grade footing, climate-controlled storage facility with office,

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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$7,250,000

Est. Mortgage: $/month

MLS Number 240514

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

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 house 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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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24 & 30 Berkshire Heights Road Great Barrington MA 01230
Pending

MLS Number 239716

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 6,240
  • Acreage 46.25

A rare estate offering in the berkshires. Breathtaking southern and western views from this historically important great barrington estate. Designed by charles platt for charles freer of the renowned freer gallery in dc, and constructed of stone quarried from the property, this one floor layout was well ahead of its time. The main house has a large, comfortable living room with views from massive windows, a library, a gracious dining room, all with fireplaces. The property encompasses a stable and riding ring, pool, orchard, vineyard and two fully equipped guest houses and a caretaker's home. This is a rare opportunity to own a unique nearly 50 acre estate with magnificent views - all close to great barrington.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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$5,840,000

Est. Mortgage: $/month

MLS Number 238388

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

The kemble, a registered ''great estate'' built in 1881 is located within walking distance to the wonderful array of shops and restaurants in downtown lenox. This classic colonial revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury estate, and is being offered as a turn key property. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and 13 en-suite bedrooms, the property can easily accommodate parties and guests of 20+. Property qualifies as a ''great estate'' allowing for special uses in the residential district. When not using the property, enjoy the benefits of short/long term rental. Manicured lawns and gardens, stone walls, breathtaking views to the west, and fully ada compliant.

Listed by Lori J Rose and Cameron Volastro of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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

49 Chanterwood Road Lee MA 01238

Lee, MA49 Chanterwood Road

Price$4,999,000

Est. Mortgage: $/month

MLS Number 240075

  • Residential
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 6,000
  • Acreage 35

Eagles roost: 877 feet of lake frontage and 35 acres on goose pond. Complete privacy. This quintessential berkshire lake lodge, nestled among ancient boulders along the shore of the most pristine lake in the massachusetts berkshire mountains provides unparalleled, gated privacy only moments from all activities the berkshires' has to offer. Designed and constructed for the private use of the builder, no expense has been spared. This five bedroom, 6 1/2 bath, energy efficient home features soaring stone fireplaces, two primary suites on the first level, two guest rooms with en suite baths, an in-law suite and a huge screened porch all with tremendous water views and access to stone patios with fire pits overlooking the lake front.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 8, 2023 . 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.