796 Listings
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$9,950,000
7 Prospect Hill Rd, Stockbridge, MA 01262
9,339 SqFt
5 Beds | 9 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$5,995,000
390 Tamaridge Rd, New Marlborough, MA 01259
5,890 SqFt
5 Beds | 7 Baths
Listing Provided By Helen Mullany Real Estate

$5,900,000
Virtual Tour
25 Sheffield Rd, Egremont, MA 01230
9,748 SqFt
11 Beds | 10 Baths
Listing Provided By Elyse Harney Real Estate

$5,500,000
1175 County Rte 27a Rd, Copake, NY 12516
8,384 SqFt
6 Beds | 7 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$4,999,999
14 Sullivan Rd, Sandisfield, MA 01255
3,000 SqFt
3 Beds | 6 Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$4,300,000
165 Kemble St Unit 18, Lenox, MA 01240
3,348 SqFt
3 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$4,290,000
113 Brush Hill Rd, Great Barrington, MA 01230
5,800 SqFt
4 Beds | 5 Baths
Listing Provided By Cohen & White Associates

$4,200,000
Virtual Tour
662 Brewer Hill Rd, New Marlborough, MA 01244
6,915 SqFt
5 Beds | 7 Baths
Listing Provided By Lance Vermeulen RE

$3,995,000
615 Laurel St, Lee, MA 01238
11,945 SqFt
15 Beds | 17 Baths
Listing Provided By East Coast Inn Brokers

$3,785,000
185 Keyes Hill Rd, New Marlborough, MA 01230
4,386 SqFt
7 Beds | 3 Baths
Listing Provided By Compass Massachusetts

$3,575,000
19 Mill Rd, Egremont, MA 01258
3,940 SqFt
5 Beds | 6 Baths
Listing Provided By Housatonic Real Estate

$3,575,000
19 Mill Rd, Egremont, MA 01230
n/a SqFt
-- Beds | -- Baths
Listing Provided By Housatonic Real Estate

$3,495,000
685 S Egremont Rd, Great Barrington, MA 01230
n/a SqFt
-- Beds | -- Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$3,495,000
32 Oxbow Rd, Egremont, MA 01230
5,667 SqFt
5 Beds | 7 Baths
Listing Provided By Compass Massachusetts

$3,495,000
84a Undermountain Rd, Egremont, MA 01230
6,000 SqFt
5 Beds | 8 Baths
Listing Provided By Cohen & White Associates

$3,490,000
350 Old Cheshire Rd, Lanesborough, MA 01237
12,225 SqFt
-- Beds | -- Baths
Listing Provided By The Kinderhook Group - Pittsfield

$3,400,000
802 State Rd, Richmond, MA 01254
6,232 SqFt
-- Beds | -- Baths
Listing Provided By William Pitt Sotheby's - Salisbury

$3,295,000
56 Crooked Hill Rd, Alford, MA 01230
5,238 SqFt
5 Beds | 5 Baths
Listing Provided By William Pitt Sotheby's - Lenox

$3,250,000
146-156 North St, Pittsfield, MA 01201
17,150 SqFt
-- Beds | -- Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$3,195,000
184a Cambridge Rd, Hillsdale, NY 12529
4,130 SqFt
5 Beds | 5 Baths
Listing Provided By Four Seasons Sotheby's International Realty

$3,100,000
349 Old Stockbridge Rd, Lenox, MA 01240
38,415 SqFt
32 Beds | 30 Baths
Listing Provided By Stone House Properties

$2,999,000
470 Harrington Dr, Austerlitz, NY 12017
3,000 SqFt
5 Beds | 5 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$2,995,000
813 East St, Lenox, MA 01240
6,578 SqFt
7 Beds | 9 Baths
Listing Provided By Piretti Real Estate

$2,750,000
300 Alcott Rd, Great Barrington, MA 01230
7,008 SqFt
7 Beds | 6 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$2,700,000
490 Main St, Great Barrington, MA 01230
13,656 SqFt
-- Beds | -- Baths
Listing Provided By Lance Vermeulen RE

$2,595,000
1 Lahey Cross Rd, Stockbridge, MA 01262
4,847 SqFt
5 Beds | 5 Baths
Listing Provided By Non-Member / Reciprocal

$2,500,000
1373 Boardman St, Sheffield, MA 01257
3,100 SqFt
4 Beds | 5 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$2,500,000
Virtual Tour
1 Devon Rd, Stockbridge, MA 01262
4,952 SqFt
6 Beds | 6 Baths
Listing Provided By Signature Associates

$2,500,000
0 Stanley Dr, Great Barrington, MA 01230
n/a SqFt
-- Beds | -- Baths
Listing Provided By Lance Vermeulen RE

$2,495,000
84 B Undermountain Rd, Egremont, MA 01258
6,254 SqFt
5 Beds | 4 Baths
Listing Provided By Lance Vermeulen RE

$2,475,000
49 Sky Top Rd, Copake, NY 12516
3,886 SqFt
4 Beds | 3 Baths
Listing Provided By Four Seasons Sotheby's International Realty

$2,400,000
111 Park St, Williamstown, MA 01267
4,840 SqFt
5 Beds | 4 Baths
Listing Provided By Alton & Westall Real Estate Agency

$2,399,990
Virtual Tour
141 Stevens Lake Way, Monterey, MA 01245
6,000 SqFt
6 Beds | 6 Baths
Listing Provided By Nocher Realty

$2,299,999
978 Clayton Mill River Rd, New Marlborough, MA 01259
5,000 SqFt
4 Beds | 5 Baths
Listing Provided By Lance Vermeulen RE

$2,295,000
14 Pinecrest Cross Rd, Egremont, MA 01258
4,060 SqFt
5 Beds | 6 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$2,200,000
20 Keeler St, Pittsfield, MA 01201
228,611 SqFt
-- Beds | -- Baths
Listing Provided By Lamacchia Realty

$2,170,000
290 Cole Ave, Williamstown, MA 01267
19,395 SqFt
-- Beds | -- Baths
Listing Provided By Non-Member / Reciprocal

$2,130,000
140 Blythewood Dr, Pittsfield, MA 01201
3,850 SqFt
3 Beds | 4 Baths
Listing Provided By Lamacchia Realty

$2,100,000
137 North St, Pittsfield, MA 01201
26,000 SqFt
-- Beds | 9 Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$2,100,000
Homestead Farm 15 Ln, Millerton, NY 12546
n/a SqFt
-- Beds | -- Baths
Listing Provided By Houlihan Lawrence

$2,000,000
Hubbard Ave, Pittsfield, MA 01201
1,935,370 SqFt
-- Beds | -- Baths
Listing Provided By Berkshire Business Properties

$1,999,000
885 Washington Mountain Rd, Washington, MA 01223
9,018 SqFt
-- Beds | -- Baths
Listing Provided By RE/MAX Compass

$1,999,000
71 Blunt Rd, Egremont, MA 01230
4,850 SqFt
6 Beds | 6 Baths
Listing Provided By Gilcrest Properties

$1,995,000
87 Alford Rd, Great Barrington, MA 01230
2,990 SqFt
3 Beds | 2 Baths
Listing Provided By Lance Vermeulen RE

$1,995,000
350 Old Cheshire Rd, Lanesborough, MA 01224
12,225 SqFt
5 Beds | 2 Baths
Listing Provided By The Kinderhook Group - Pittsfield

$1,975,000
Virtual Tour
248 East Rd, Alford, MA 01266
6,000 SqFt
5 Beds | 5 Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$1,950,000
112 W 114 St Whousatonic, Pittsfield, MA 01201
3,500 SqFt
-- Beds | -- Baths
Listing Provided By Berkshire Real Estate

$1,925,000
Virtual Tour
17 East St, Stockbridge, MA 01262
5,469 SqFt
4 Beds | 3 Baths
Listing Provided By Birch Properties

$1,895,000
129 Harrington Dr, Austerlitz, NY 12017
4,500 SqFt
4 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,890,000
775 Williamstown Rd, Lanesborough, MA 01237
5,878 SqFt
11 Beds | 7 Baths
Listing Provided By Berkshire Business Properties

$1,880,000
105 Norton Rd, Canaan, NY 12029
n/a SqFt
-- Beds | -- Baths
Listing Provided By Stone House Properties

$1,800,000
Virtual Tour
593 Lakeway Dr, Pittsfield, MA 01201
3,043 SqFt
4 Beds | 3 Baths
Listing Provided By Mockingbird Real Estate

$1,795,000
155 Edwards Rd, Westhampton, MA 01027
4,341 SqFt
5 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,785,000
206 Hillsdale Rd, Egremont, MA 01258
4,632 SqFt
5 Beds | 5 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,775,000
850 Old Wendell Rd, Northfield, MA 01360
4,258 SqFt
7 Beds | 5 Baths
Listing Provided By Equine Homes Real Estate

$1,750,000
200 Elm St, Pittsfield, MA 01201
8,240 SqFt
-- Beds | -- Baths
Listing Provided By Lance Vermeulen RE

$1,695,000
Virtual Tour
112 Tyringham Rd, Monterey, MA 01245
3,495 SqFt
4 Beds | 4 Baths
Listing Provided By Compass Massachusetts

$1,695,000
Virtual Tour
9 East Mountain Rd, Great Barrington, MA 01230
3,305 SqFt
4 Beds | 4 Baths
Listing Provided By Compass Massachusetts

$1,695,000
4 Thrushwood Ln, Great Barrington, MA 01230
4,200 SqFt
5 Beds | 4 Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$1,675,000
29 Main St, West Stockbridge, MA 01266
8,881 SqFt
12 Beds | 7 Baths
Listing Provided By Housatonic Real Estate

$1,650,000
460 Silvernails Rd, Pine Plains, NY 12567
3,802 SqFt
5 Beds | 3 Baths
Listing Provided By Four Seasons Sotheby's International Realty

$1,610,000
37 Fairwynds Dr, Lenox, MA 01240
3,044 SqFt
3 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Lenox

$1,595,000
15 Bridge St, Great Barrington, MA 01230
9,696 SqFt
-- Beds | -- Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$1,595,000
82 West Ave, Great Barrington, MA 01230
4,000 SqFt
5 Beds | 4 Baths
Listing Provided By Lance Vermeulen RE

$1,590,000
518 Main St, Great Barrington, MA 01230
8,134 SqFt
11 Beds | 13 Baths
Listing Provided By The Kinderhook Group - Pittsfield

$1,590,000
469 Fairview Ave, Hudson, NY 12534
5,340 SqFt
-- Beds | -- Baths
Listing Provided By Gilcrest Properties

$1,550,000
Virtual Tour
485 Oblong Rd, Williamstown, MA 01267
3,966 SqFt
4 Beds | 4 Baths
Listing Provided By Burnham Gold Real Estate

$1,525,000
82 Stockbridge Ter Unit 82, Lee, MA 01238
3,395 SqFt
4 Beds | 5 Baths
Listing Provided By Roberts & Assoc. Realty

$1,500,000
5 Homestead Farm Ln, Millerton, NY 12546
n/a SqFt
-- Beds | -- Baths
Listing Provided By Houlihan Lawrence

$1,500,000
S 685b 685 Rd Segremont, Great Barrington, MA 01230
n/a SqFt
-- Beds | -- Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,500,000
8 Lot 144 Eastbrook Ln, Pittsfield, MA 01201
3,100 SqFt
4 Beds | 3 Baths
Listing Provided By Bishop West Real Estate

$1,499,900
Virtual Tour
45 Forest St, Lee, MA 01238
7,956 SqFt
13 Beds | 7 Baths
Listing Provided By Lamacchia Realty

$1,499,000
Virtual Tour
12 Bishop Estate Rd, Lenox, MA 01240
2,185 SqFt
3 Beds | 5 Baths
Listing Provided By Stone House Properties

$1,495,000
19 Lynne Ct, Lanesborough, MA 01237
4,320 SqFt
4 Beds | 4 Baths
Listing Provided By Kempf-Vanderburgh Realty Consultants

$1,495,000
124 Egremont Plain Rd, Egremont, MA 01230
3,185 SqFt
4 Beds | 5 Baths
Listing Provided By Berkshire Hathaway Homeservices Barnbrook Realty

$1,495,000
1669 Silver St, Sheffield, MA 01257
3,528 SqFt
4 Beds | 5 Baths
Listing Provided By Elyse Harney Real Estate

$1,495,000
1-1a George Canon Rd, Tyringham, MA 01264
4,952 SqFt
8 Beds | 4 Baths
Listing Provided By Helen Mullany Real Estate

$1,475,000
481 Shunpike Rd, Sheffield, MA 01257
1,296 SqFt
1 Bed | 2 Baths
Listing Provided By Housatonic Real Estate

$1,475,000
125 Old Stockbridge Rd, Lenox, MA 01240
4,800 SqFt
4 Beds | 6 Baths
Listing Provided By Stone House Properties

$1,450,000
142 Main Rd, Monterey, MA 01245
2,754 SqFt
4 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,450,000
2 Oak St, West Stockbridge, MA 01266
6,054 SqFt
-- Beds | 10 Baths
Listing Provided By Lance Vermeulen RE

$1,400,000
426 424 Stockbridge - Unit 5 Rd, Great Barrington, MA 01230
6,707 SqFt
-- Beds | 2 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,395,000
Virtual Tour
223 Cardinal Way, Northampton, MA 01062
4,644 SqFt
5 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,350,000
41 Warner Crossing Rd, Canaan, NY 12029
3,415 SqFt
4 Beds | 3 Baths
Listing Provided By Preferred Country Properties

$1,306,895
77a Belgo Rd, Salisbury, CT 06039
1,846 SqFt
3 Beds | 2 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,300,000
168 Main St, Great Barrington, MA 01230
6,121 SqFt
-- Beds | -- Baths
Listing Provided By Stone House Properties

$1,295,000
1955 N Main St, Sheffield, MA 01257
5,540 SqFt
-- Beds | 2 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,279,000
97 Brush Hill Rd, Great Barrington, MA 01230
2,322 SqFt
4 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington

$1,275,000
1166 Rannapo Rd, Sheffield, MA 01257
2,878 SqFt
3 Beds | 3 Baths
Listing Provided By Equine Homes Real Estate

$1,270,000
25 Nobletown Rd, Hillsdale, NY 12529
1,344 SqFt
4 Beds | 3 Baths
Listing Provided By Houlihan Lawrence

$1,250,000
460-475 Norfolk Rd, New Marlborough, MA 01259
2,900 SqFt
3 Beds | 4 Baths
Listing Provided By Elyse Harney Real Estate

$1,250,000
311 Woodmere Rd, Becket, MA 01223
3,775 SqFt
4 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Lenox

$1,250,000
39 Main St, Egremont, MA 01258
11,991 SqFt
-- Beds | -- Baths
Listing Provided By Lance Vermeulen RE

$1,245,000
132 North Rd, Tolland, MA 01034
1,908 SqFt
3 Beds | 3 Baths
Listing Provided By Carriage House Real Estate

$1,245,000
584 Water St, Williamstown, MA 01267
2,511 SqFt
4 Beds | 4 Baths
Listing Provided By William Pitt Sotheby's - Lenox

$1,234,000
163 Fourth St, Pittsfield, MA 01201
11,395 SqFt
-- Beds | -- Baths
Listing Provided By Allegrone Real Estate

$1,200,000
179 South St, Pittsfield, MA 01201
2,320 SqFt
-- Beds | 2 Baths
Listing Provided By Stone House Properties

$1,200,000
0 Route 57, New Marlborough, MA 01230
n/a SqFt
-- Beds | -- Baths
Listing Provided By William Pitt Sotheby's - Gt Barrington