South Berkshire Homes for Sale & Real Estate
1-40 of 476 Homes
![$565,000 | 32 Hillside Avenue | Great Barrington Center](http://www.compass.com/m/7d839bf3b32223952d0e9a7fb3be1aae2946582f_img_0_731e8/640x480.jpg)
2
Beds
2
Baths
1,728
Sq. Ft.
![$499,000 | 10 Prospect Street | Great Barrington Center](http://www.compass.com/m/53584b05e5cf3e9adc2708c66ab6e3ceb9df96fa_img_0_861fc/640x480.jpg)
4
Beds
2.5
Baths
2,161
Sq. Ft.
![$369,000 | 52 Shunpike Road | New Marlborough](http://www.compass.com/m/e509e75e61cc1c5f62f7c1029325d379f98b4e01_img_0_d8a59/640x480.jpg)
2
Beds
2
Baths
1,659
Sq. Ft.
![$205,000 | 73 Porcupine Court | Becket](http://www.compass.com/m/330ef9f49869b647876be139cd4ac1ed643bbbec_img_0_06c43/640x480.jpg)
2
Beds
1
Bath
852
Sq. Ft.
![$1,230,000 | 20 Brewer Hill Road | New Marlborough](http://www.compass.com/m/901e4112b5b08cdfa7c86cd79807078290b308f8_img_0_18803/640x480.jpg)
4
Beds
2.5
Baths
2,720
Sq. Ft.
![$2,300,000 | 263 Long Pond Road | Great Barrington](http://www.compass.com/m/d438ff0e9c6d4506afe07e417f646cea741a9097_img_0_2f38b/640x480.jpg)
5
Beds
4
Baths
3,256
Sq. Ft.
![$215,000 | 260 Pittsfield Road, Unit C7 | Lenox](http://www.compass.com/m/e442ceea96d7c5f24fd57e6a3c781ca76d9d3722_img_0_d431e/640x480.jpg)
1
Bed
1
Bath
670
Sq. Ft.
![$3,995,000 | 32 Oxbow Road | Egremont](http://www.compass.com/m/e46b91364b7f6ea9aeb533dbd5bd14a608ff31ae_img_0_941a7/640x480.jpg)
$3,995,000
32 Oxbow Road
Egremont, MA 01230
5
Beds
6
Baths
5,667
Sq. Ft.
![$1,250,000 | 248 Water Farm Road | Sheffield](http://www.compass.com/m/55a3f9408a0e46d20a105ea3c916906610249c95_img_0_53d69/640x480.jpg)
Open: 7/27 12:00PM - 02:00PM
$1,250,000
248 Water Farm Road
Sheffield, MA 01257
3
Beds
2.5
Baths
2,195
Sq. Ft.
![$445,000 | 585 Leonhardt Road | Becket](http://www.compass.com/m/32031d684719969afdb5061d84a08ba487c3eeac_img_0_2bab8/640x480.jpg)
2
Beds
2
Baths
1,672
Sq. Ft.
![$40,000 | 0 West Center Road | Otis](http://www.compass.com/m/3bdfc53f144e59b0c0737131cb843aa9fddf97c0_img_0_7aba2/640x480.jpg)
-
Beds
-
Baths
-
Sq. Ft.
![$625,000 | 18 East Hill Road | New Marlborough](http://www.compass.com/m/00624ab0f05e95c4af9033120945d56a36457fd3_img_0_0de37/640x480.jpg)
4
Beds
2
Baths
1,944
Sq. Ft.
![$412,000 | 10 Stanley Drive | Great Barrington](http://www.compass.com/m/c6ee3fc3d324f3456ebb09d4b38735deb9089169_img_0_d12fa/640x480.jpg)
3
Beds
1.5
Baths
1,512
Sq. Ft.
![$589,000 | 2 Park Street | Lee Village](http://www.compass.com/m/dc9b29a479c9d76a79777a7b5fcdc40e5369ccc5_img_0_af944/640x480.jpg)
$589,000
2 Park Street
Lee, MA 01238
6
Beds
1.5
Baths
3,792
Sq. Ft.
![$400,000 | 268 E Road | Alford](http://www.compass.com/m/3b51ca8542ed38e4fc3517206bb81908bb7daeb1_img_0_3c849/640x480.jpg)
$400,000
268 E Road
Alford, MA 01266
4
Beds
3
Baths
2,775
Sq. Ft.
![$89,900 | 850 Chester Road | Becket](http://www.compass.com/m/846235c1edd5cdb26b6e9e59834381ac782ba9a2_img_0_37074/640x480.jpg)
6
Beds
2.5
Baths
1,884
Sq. Ft.
![$1,100,000 | 1 Prospect Lake Road | Egremont](http://www.compass.com/m/2c1e7e93845f89bdd84350f578f5b0279c6d6468_img_0_f8a09/640x480.jpg)
$1,100,000
1 Prospect Lake Road
Egremont, MA 01230
8
Beds
10
Baths
4,840
Sq. Ft.
![$1,650,000 | 82 Stockbridge Terrace, Unit 82 | Lee](http://www.compass.com/m/e0a78d08af9122de9be2506ecc15280211151aab_img_0_4cc7b/640x480.jpg)
4
Beds
4.5
Baths
3,395
Sq. Ft.
![$400,000 | 268 E Road | Alford](http://www.compass.com/m/d423fda390bec7dae5b852077be23811e49f2f4d_img_0_3c849/640x480.jpg)
$400,000
268 E Road
Alford, MA 01266
4
Beds
3
Baths
2,775
Sq. Ft.
![$1,200,000 | 300 E Road | Alford](http://www.compass.com/m/13d7fff9b8c27f5fd3ca0869eab61a7bb34cd6bb_img_0_fbc4a/640x480.jpg)
$1,200,000
300 E Road
Alford, MA 01266
2
Beds
2
Baths
1,968
Sq. Ft.
![$899,000 | 6 Tyringham Road | Monterey](http://www.compass.com/m/05d2db775033a62aeeddd2cb7e918ffe70359b63_img_0_7315e/640x480.jpg)
4
Beds
3.5
Baths
4,188
Sq. Ft.
![$1,495,000 | 221 Egremont Plain Road | Egremont](http://www.compass.com/m/d1655ae869d67a6c9e6bc8a42a64893ea2b99a2f_img_0_54825/640x480.jpg)
5
Beds
4.5
Baths
3,716
Sq. Ft.
![$2,050,000 | 751 E Road | Lenox](http://www.compass.com/m/552b9b166bdc2e7fa90c88814afc763428e73268_img_0_ff11b/640x480.jpg)
$2,050,000
751 E Road
Richmond, MA 01254
3
Beds
2.5
Baths
2,862
Sq. Ft.
![$450,000 | 203 High Street, Unit 2 | Housatonic](http://www.compass.com/m/76a4b3a1dea6fd1f5be11214248b3b65126e257a_img_0_e7ded/640x480.jpg)
7
Beds
3
Baths
2,294
Sq. Ft.
![$349,000 | 1242 Main Street | Becket](http://www.compass.com/m/36aeeb9f9e6edb36ce7af1a4ff93bacfe1a6c259_img_0_7d291/640x480.jpg)
$349,000
1242 Main Street
Becket, MA 01223
3
Beds
1
Bath
1,260
Sq. Ft.
![$569,000 | 163 Main Street | Sheffield](http://www.compass.com/m/d3337bf13f1293e34df86bc5068a1c1fe30fd7b7_img_0_7fd24/640x480.jpg)
3
Beds
2
Baths
2,152
Sq. Ft.
![$565,000 | 170 High Street | Lee Village](http://www.compass.com/m/3ee1848b673edfa864e4ba623cce6786b89cb003_img_0_06d58/640x480.jpg)
$565,000
170 High Street
Lee, MA 01238
5
Beds
4.5
Baths
2,562
Sq. Ft.
![$310,000 | 880 East Street, Unit 100D | Lee](http://www.compass.com/m/54707722046432b497c2c07fa1f4ce5c046932f7_img_0_4187c/640x480.jpg)
2
Beds
1.5
Baths
1,056
Sq. Ft.
![$1,444,250 | 165 Kemble Street, Unit 1 | Lenox](http://www.compass.com/m/ac0b7ee345ee2f7b5b9767848f5b8ffbaac16dc4_img_0_e6db8/640x480.jpg)
$1,444,250
165 Kemble Street, Unit 1
Lenox, MA 01240
1
Bed
1.5
Baths
1,180
Sq. Ft.
![$229,750 | 14 Mahkeenac Road | Stockbridge](http://www.compass.com/m/5354b795376daaf1d0cb44ff5f7c8eae6a22675c_img_0_8a64a/640x480.jpg)
3
Beds
1
Bath
900
Sq. Ft.
![$999,000 | 485 Pine Road | Otis](http://www.compass.com/m/2b6f28ee8c72737a8f900dd32074a6ef2c7568fe_img_0_1c85b/640x480.jpg)
$999,000
485 Pine Road
Otis, MA 01253
4
Beds
2
Baths
1,843
Sq. Ft.
![$1,100,000 | 16 Woodland Hl Road | Great Barrington](http://www.compass.com/m/a59afbdc7fae163b7765eb25624e2bf9ab64b6d4_img_0_250b3/640x480.jpg)
5
Beds
3.5
Baths
4,232
Sq. Ft.
![$175,000 | 170-180 King Richard Drive | Becket](http://www.compass.com/m/ab680501c7bdd4c37a8357c05c98e00234135e7d_img_0_da321/640x480.jpg)
-
Beds
-
Baths
-
Sq. Ft.
![$315,000 | 20 Moscow Road | West Stockbridge](http://www.compass.com/m/0e7249a812995efbd8fef50c5f26d9cad54870ea_img_0_c76cb/640x480.jpg)
3
Beds
1.5
Baths
1,677
Sq. Ft.
![$650,000 | 424 Cooper Hill Road | Sheffield](http://www.compass.com/m/15c3c031822dd6997d7312e1add9bf567a059e8b_img_0_b8e06/640x480.jpg)
2
Beds
1.5
Baths
1,728
Sq. Ft.
![$795,000 | 367 North Plain Road | Great Barrington](http://www.compass.com/m/0ff9314c013d3428d61505e6fb1dc29355361913_img_0_0bb6d/640x480.jpg)
4
Beds
2.5
Baths
2,422
Sq. Ft.
![$299,750 | 15 Holmeswood Terrace | Lenox](http://www.compass.com/m/b177883eaaa4ead65bbf9480f81b227ef0044f7f_img_0_25912/640x480.jpg)
2
Beds
1
Bath
1,272
Sq. Ft.
...