Real Estate Investment Properties for Sale in Great Barrington, MA
Looking for investment property in Great Barrington, MA with high ROI ?
Explore a variety of short-term homes & houses in Great Barrington, MA. Invest wisely with VRBO & Great Barrington, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Great Barrington, MA
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
10 Berkshire Heights RdGreat Barrington, MALuxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, fou... |
4 beds | 5 baths | 3,600 sq.ft. |
$2,149,000 |
Airbnb cash on cash: -0.26%
|
Thrushwood Ln lot: 10Great Barrington, MATHIS HOME HAS BEEN UNDER CONSTRICTION SINCE 2018. PRICE DOES NOT REFLECT CURRENT MARKET CO... |
5 beds | 5 baths | 3,808 sq.ft. |
$829,000 |
Airbnb cash on cash: 3.35%
|
41 Pearl St #1-2Great Barrington, MAWelcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just mo... |
4 beds | 2 baths | 1,964 sq.ft. |
$365,000 |
Airbnb cash on cash: 4.29%
|
148 Maple Ave #12Great Barrington, MANestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of ... |
1 beds | 1 baths | 568 sq.ft. |
$447,300 |
Airbnb cash on cash: 0.47%
|
402 Park StGreat Barrington, MAThis well-maintained mixed-use property offers excellent flexibility for both commercial a... |
3 beds | 2 baths | 2,438 sq.ft. |
$489,000 |
Airbnb cash on cash: 2.39%
|
39 Castle StGreat Barrington, MATHE BEST OF GREAT BARRINGTON RIGHT OUTSIDE YOUR DOOR! Set high up on a knoll, this home bo... |
2 beds | 1 baths | 1,296 sq.ft. |
$549,000 |
Airbnb cash on cash: 2.02%
|
80 Taconic Ave #12Great Barrington, MA''ON THE HILL'' Condo at The Oakwoood! Town-House style unit in a prime location. Located ... |
3 beds | 2 baths | 1,898 sq.ft. |
$795,000 |
Airbnb cash on cash: 0.73%
|
11 Muddy Brook CirGreat Barrington, MAImmaculate and well-maintained contemporary home in an exceptionally convenient location s... |
3 beds | 4 baths | 3,236 sq.ft. |
$749,000 |
Airbnb cash on cash: 0.12%
|
164 Alford RdGreat Barrington, MASINGLE LEVEL BERKSHIRE RETREAT tucked away on 5.91 peaceful acres just minutes from downto... |
3 beds | 3 baths | 2,400 sq.ft. |
$998,500 |
Airbnb cash on cash: 0.28%
|
15 Cone AveGreat Barrington, MAMotivated sellers are ready to move! Built in 2019 on 1.73 private acres in Housatonic, th... |
3 beds | 3 baths | 2,257 sq.ft. |
$539,900 |
Airbnb cash on cash: 1.48%
|
134 Hurlburt RdGreat Barrington, MA*** MOTIVATED SELLER**Nestled in the heart of Great Barrington, this spacious 4 bedroom, 4... |
4 beds | 4 baths | 3,100 sq.ft. |
$995,000 |
Airbnb cash on cash: 0.82%
|
14 Prospect StGreat Barrington, MA'ON THE HILL' Cozy 4 bedroom 1925 Cape, HOUSE BEING SOLD ''AS IS'' WALK TO TOWN AND LAKE M... |
4 beds | 2 baths | 1,600 sq.ft. |
$475,000 |
Airbnb cash on cash: 3.01%
|
5 Thrushwood LnGreat Barrington, MAPUBLIC OPEN HOUSE: Saturday October 10 from 10-1. See you there!! Enjoy the relaxing Berks... |
5 beds | 4 baths | 3,800 sq.ft. |
$1,599,000 |
Airbnb cash on cash: 1.03%
|
247 Park StGreat Barrington, MAImmaculate 3-bedroom ranch with additional 750 square feet of finished living space in low... |
3 beds | 2 baths | 2,050 sq.ft. |
$449,000 |
Airbnb cash on cash: 2.66%
|
3 Thrushwood LnGreat Barrington, MATO BE BUILT: Gorgeous neighborhood setting with lush landscaping and Indulge in refined Be... |
5 beds | 5 baths | 3,808 sq.ft. |
$1,498,000 |
Airbnb cash on cash: 1.92%
|
12 Mountain StGreat Barrington, MAWelcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elega... |
5 beds | 4 baths | 3,068 sq.ft. |
$623,000 |
Airbnb cash on cash: 5.44%
|
18 Hemlock Hill RdGreat Barrington, MA'Located in Great Barrington's coveted residential neighborhood surrounded by million-doll... |
3 beds | 3 baths | 1,790 sq.ft. |
$705,000 |
Airbnb cash on cash: 1.25%
|
25 Cottage StGreat Barrington, MABeautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bri... |
3 beds | 2 baths | 1,700 sq.ft. |
$849,000 |
Airbnb cash on cash: 0.79%
|
238 East StGreat Barrington, MAThis meticulously maintained 1900 farmhouse seamlessly blends timeless historic character ... |
3 beds | 2 baths | 1,544 sq.ft. |
$749,000 |
Airbnb cash on cash: 1.14%
|
279 North Plain RdGreat Barrington, MAEl Refugio, ''The Refuge'', a hidden gem minutes from downtown Great Barrington. A 2-bedro... |
2 beds | 2 baths | 1,233 sq.ft. |
$569,000 |
Airbnb cash on cash: 1.76%
|
312 Park StGreat Barrington, MAThis inviting, move-in-ready Colonial blends classic New England character with comfortabl... |
3 beds | 1 baths | 1,739 sq.ft. |
$575,000 |
Airbnb cash on cash: 1.82%
|
14 Woodland Hill RdGreat Barrington, MATucked away in a peaceful, private setting, this charming mid-century ranch offers easy on... |
3 beds | 2 baths | 1,562 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.48%
|
14 Hemlock Hill RdGreat Barrington, MAYour private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 be... |
4 beds | 5 baths | 3,600 sq.ft. |
$1,295,000 |
Airbnb cash on cash: -0.06%
|
5 Crimson LnGreat Barrington, MASet in a lovely neighborhood just outside downtown Great Barrington, this center-hall Colo... |
5 beds | 4 baths | 3,454 sq.ft. |
$949,000 |
Airbnb cash on cash: 2.57%
|
202 Oak StGreat Barrington, MASet on a quiet corner lot in the village of Housatonic, this cozy cape has 3 bedrooms 2.5 ... |
3 beds | 3 baths | 2,121 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.21%
|
Real Estate investment in Great-barrington, MA
There are 27 properties for sale in the city of Great Barrington . The median list price in Great Barrington is $544,741 and the average price per square foot is $228. In November 2026, the average monthly cash on cash return in Great Barrington is 4.00%. The average monthly rental income in Great Barrington is $3,506.