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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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310 Old Stockbridge Lenox MA 01240

Lenox, MA310 Old Stockbridge Rd

Price$12,500,000

Est. Mortgage: $/month

MLS Number 232689

  • Residential
  • Bathroom 15
  • Bedrooms 33
  • Square Feet 20,821
  • Acreage 89

The elm court estate retains the title of the largest american shingle style home in the united states. The extraordinary gilded age berkshire cottage was built by william douglas sloane and emily vanderbilt, (granddaughter of cornelius vanderbilt), along with architects peabody & stearns in 1886. The gardens and landscape were designed by frederick law olmsted. In 1919, the elm court talks held at the home ultimately led to the creation of the treaty of versailles and league of nations. Outbuildings include butler and gardener cottages, carriage house & stable, greenhouses & caretaker's house and two barns. Significant renovations were accomplished in the early 2000s and continued work is necessary with an additional 8,000 sq. Ft. Of unrestored living space.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Undermountain Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$12,500,000

Est. Mortgage: $/month

MLS Number 229173

  • Residential
  • Bathroom 7
  • Bedrooms 11
  • Square Feet 7,946
  • Acreage 85

The jewel of new england... Offered for the first time in four decades, this 85 acre berkshire mountainside campus awaits your imagination. This property offers an atmosphere for breakout creative expression with great potential for an enterprise for retreats, wellness center, writers/ artists workshops, educational endeavors or your family's private estate. The property consists of 12 buildings; conference halls, dining/ meeting facilities, lodging accommodations, offices and an historic queen anne manor house sitting on a knoll with breathtaking views. 40 years of stewarding this campus where thousands of participants made life long memories, the owners are ready to pass it on. Let their growth be your opportunity. For details & digital brochure please see jewelinnewengland.Com

Listed by Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Craryville NY 12521

Craryville, NY181 Golf Course Rd

Price$9,500,000

Est. Mortgage: $/month

MLS Number 231864

  • Residential
  • Bathroom 6
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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6 Seekonk Cross Alford MA 01230

Alford, MA6 Seekonk Cross Rd

Price$6,800,000

Est. Mortgage: $/month

MLS Number 233896

  • Residential
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 7,000
  • Acreage 17.62

When the interior design hall of famers were commissioned to build a family compound in the beautiful berkshires, they first started by getting acquainted with the land. Calvin tsao and zack mckown walked the many acres of open fields often to take in the magnificent views from all angles. The almost 18 acres was on the slope of the hill with the berkshire hills in the distance and forefront. To capture the postcard panorama, they designed the 7000' house to follow the sun with angles and very large windows. The end result is a c configuration. The winding 1/2 mile drive is lined with a long allee of trees and mature landscaping leading to the house. Stone walls delineate the lawn from the woodlands. Views looking out to the mountains are visible even at ground level.

Listed by Cindy Welch of LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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199 Dawson Hillsdale NY 12529

Hillsdale, NY199 Dawson Rd

Price$5,250,000

Est. Mortgage: $/month

MLS Number 233547

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 7,600
  • Acreage 230

Sitting atop 230 tranquil acres consisting of fields, woods and expansive views, the home was built in 2006, is 7000+/- sqft, with 5 bedroom and 5 bath has everything one could want in either a full time residence or get away retreat. Miles of trails encompass the property perfect for hiking, biking or atv's. Tennis court, treehouse, basketball court, and large patio surround a nearly 3 acre spring fed swimming pond. Inside one will find the kitchen with top of the line appliances and informal dining area. Library and sitting room parallel each other on either side of the first floor with a billiard room and exterior doors leading to the patio located in the north west corner. The second floor is accessed from the central hall with two bedrooms sharing a full bath on one end and primary

Listed by Nikki Carchedi of STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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399 Under Mountain Lenox MA 01240

Lenox, MA399 Under Mountain Rd

Price$4,935,000

Est. Mortgage: $/month

MLS Number 233680

  • Residential
  • Bathroom 7
  • Bedrooms 8
  • Square Feet 9,364
  • Acreage 11.45

Highwick farm manor house is nearing its 3 year restoration/renovation in time for the summer of 2021. Meticulously preserving and restoring the magnificent original details of this berkshire cottage from the infrastructure to the doorknobs, while renovating it with only the finest of materials for the sought after amenities of a modern lifestyle today, makes this distinctive lenox home shine in its original grandeur, designed to be luxurious yet cozy and unpretentious. Generously proportioned rooms with walls of windows flooding the house with natural light and taking in the view, with open flow from room to room and the spectacular kitchen/family room not often seen in homes of this era. Perched high above the country road taking in the sweeping southern vista of parsons marsh and

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Great Barrington MA 01230

MLS Number 232672

  • 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: 3.04% last updated on Apr 15, 2021
* 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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179 Mt Hunger Monterey MA 01245

Monterey, MA179 Mt Hunger Rd

Price$4,850,000

Est. Mortgage: $/month

MLS Number 231972

  • Residential
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 8,374
  • Acreage 5.21

Casa tramonti.....House of the sunset...Life's reminder that whatever happens every day can end beautifully, says it all for this sophisticated contemporary, built by one of berkshire's premier builders. Offered for the first time, it has the necessary amenities of broadband fiber optic & great cell phone service. From the approach this home captures stunning westerly views to the catskills, keeping the viewer mesmerized with walls of glass. The sleek & sophisticated design of a most comfortable and ''livable'' space features open common living, decking for 80*, 5 br's en suite, an amazing sunroom & screened porch with waterfall sounds. A home theatre, gym & specimen plantings, organic vegetable garden, a multiple fruit orchard & fire pit to gather around.....Reason to never leave home!!

Listed by Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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

802 MA-41 Richmond MA 01254

Richmond, MA802 MA-41 Rd

Price$4,600,000

Est. Mortgage: $/month

MLS Number 232610

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,000
  • Acreage 27

Options abound for a lifestyle change at what is now known as the inn at richmond and the berkshire equestrian center. This magnificent 27 acre property includes a charming colonial era 7 bedroom inn, 5 cottages, 2 event barns, 1 shaker horse barn, 26 horse stalls, 15 grazing paddocks, a 16,000 sf multi-purpose heated indoor arena with offices and a two bed apartment with spa, 1 outdoor arena, and the possibility to develop three building lots. With its casual elegance and charm, this colonial equestrian estate will allow your long held passion to blossom whether you use the property as a stunning family compound, an event destination, and/or a first class equestrian facility. The prime central berkshire county location will graciously support your new found lifestyle,

Listed by Jennifer Capala of WILLIAM PITT SOTHEBY'S - LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Stone Hill Stockbridge MA 01262

Stockbridge, MA14 Stone Hill Rd

Price$3,995,000

Est. Mortgage: $/month

MLS Number 233847

  • Residential
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 6,623
  • Acreage 18.25

A one-of-a-kind stockbridge luxury home. Mansion design. Every room features quality touches throughout. The living room/great room boasts two fireplaces and terrific exterior views from expansive decorative windows. The first floor master bedroom suite includes a very comfortable sitting room and a state-of-the art master bath. Conveniently placed off the master bedroom on the nearby deck is a wonderful gunite-lined hot-tub. The formal dining room boasts a fireplace along with impressive exterior views. The spacious eat-in kitchen features top-of-the-line appliances neatly positioned amongst attractive custom cabinetry. Leave the kitchen, go out and notice the delightful gunite heated pool with its attractive waterfall feature. While outside, also notice the perennial gardens

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 April 22, 2021 . 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.