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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
80 Taconic Ave Great Barrington, MA Welcome to Oakwood Condominium. A one car garage comes with unit. Plenty of additional par...	2 beds \| 2 baths \| 1,308 sq.ft.	$629,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.31% Airbnb Rental Income: $2379 Traditional Rental Income: $3267 Airbnb ROI: 0.8% Traditional ROI: 3.31%
10 Berkshire Heights Rd Great Barrington, MA Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, fou...	4 beds \| 5 baths \| 3,600 sq.ft.	$2,265,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.27% Airbnb Rental Income: $3784 Traditional Rental Income: $5729 Airbnb ROI: -0.05% Traditional ROI: 1.27%
Thrushwood Ln lot: 10 Great Barrington, MA THIS 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: 1.6% Traditional cash on cash: 4.78% Airbnb Rental Income: $3918 Traditional Rental Income: $5532 Airbnb ROI: 1.6% Traditional ROI: 4.78%
153 State Rd Great Barrington, MA Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home ...	4 beds \| 1 baths \| 1,336 sq.ft.	$399,900	Airbnb cash on cash: 5.41% Traditional cash on cash: 5.77% Airbnb Rental Income: $3784 Traditional Rental Income: $3097 Airbnb ROI: 5.41% Traditional ROI: 5.77%
53 Mahaiwe St Great Barrington, MA	6 beds \| 5 baths \| 3,502 sq.ft.	$600,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 9.66% Airbnb Rental Income: $3784 Traditional Rental Income: $6829 Airbnb ROI: 2.76% Traditional ROI: 9.66%
6 Muddy Brook Cir Great Barrington, MA Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and Convenience ...	3 beds \| 4 baths \| 2,447 sq.ft.	$995,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.68% Airbnb Rental Income: $2744 Traditional Rental Income: $4000 Airbnb ROI: -0.38% Traditional ROI: 1.68%
211 Cottage St Great Barrington, MA Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian s...	3 beds \| 3 baths \| 3,204 sq.ft.	$849,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3% Airbnb Rental Income: $2744 Traditional Rental Income: $4096 Airbnb ROI: 0.47% Traditional ROI: 3%
228 East St Great Barrington, MA Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold...	5 beds \| 4 baths \| 2,900 sq.ft.	$1,250,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.74% Airbnb Rental Income: $3918 Traditional Rental Income: $6057 Airbnb ROI: 1.17% Traditional ROI: 3.74%
6 Thrushwood Ln Great Barrington, MA MOTIVATED SELLER. Indulge in refined Berkshire living on an exclusive cul-de-sac, where ef...	5 beds \| 4 baths \| 4,200 sq.ft.	$1,375,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.61% Airbnb Rental Income: $3918 Traditional Rental Income: $6304 Airbnb ROI: 0.08% Traditional ROI: 2.61%
127 Monument Valley Rd Great Barrington, MA Beautifully renovated New England Farmhouse with thoughtful modern updates! The home retai...	4 beds \| 3 baths \| 1,860 sq.ft.	$1,195,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 1.43% Airbnb Rental Income: $3784 Traditional Rental Income: $3662 Airbnb ROI: 0.81% Traditional ROI: 1.43%
264 Main St #B Great Barrington, MA 264 Main St #B, Great Barrington, MA 01230 \| Condo/Coop	2 beds \| 1 baths \| 1,860 sq.ft.	$425,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 2.24% Airbnb Rental Income: $2379 Traditional Rental Income: $2869 Airbnb ROI: -0.46% Traditional ROI: 2.24%
41 Pearl St #1-2 Great Barrington, MA Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just mo...	4 beds \| 2 baths \| 1,964 sq.ft.	$449,900	Airbnb cash on cash: 4.58% Traditional cash on cash: 5.8% Airbnb Rental Income: $3784 Traditional Rental Income: $3478 Airbnb ROI: 4.58% Traditional ROI: 5.8%
406 Main St Great Barrington, MA 406 Main St, Great Barrington, MA 01230 \| Multi Family	N/A beds \| 1 baths \| 5,180 sq.ft.	$950,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 3.12% Airbnb Rental Income: $3784 Traditional Rental Income: $4815 Airbnb ROI: 1.02% Traditional ROI: 3.12%
88-90 Main St Great Barrington, MA 88-90 Main St, Great Barrington, MA 01230 \| Single Family Residential	4 beds \| 2 baths \| 2,346 sq.ft.	$550,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 4.64% Airbnb Rental Income: $3784 Traditional Rental Income: $3617 Airbnb ROI: 3.37% Traditional ROI: 4.64%
185 A State Rd Great Barrington, MA 185 A State Rd, Great Barrington, MA 01230 \| Other	N/A beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 1.45% Airbnb Rental Income: $928 Traditional Rental Income: $1639 Airbnb ROI: -1.05% Traditional ROI: 1.45%
148 Maple Ave #12 Great Barrington, MA Nestled 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: -0.57% Traditional cash on cash: 2.44% Airbnb Rental Income: $1245 Traditional Rental Income: $2109 Airbnb ROI: -0.57% Traditional ROI: 2.44%
402 Park St Great Barrington, MA This well-maintained mixed-use property offers excellent flexibility for both commercial a...	3 beds \| 2 baths \| 2,438 sq.ft.	$510,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 4.87% Airbnb Rental Income: $2744 Traditional Rental Income: $3352 Airbnb ROI: 2.24% Traditional ROI: 4.87%
43 Hart St Great Barrington, MA Nestled on a quiet setback lot in the desirable Housatonic Village of Great Barrington, th...	2 beds \| 2 baths \| 1,970 sq.ft.	$435,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.24% Airbnb Rental Income: $2379 Traditional Rental Income: $3063 Airbnb ROI: 2.12% Traditional ROI: 5.24%
39 Castle St Great Barrington, MA Set high up on a knoll, this home boasts good, solid construction, wood floors throughout ...	2 beds \| 1 baths \| 1,296 sq.ft.	$599,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 2.15% Airbnb Rental Income: $2379 Traditional Rental Income: $2363 Airbnb ROI: 1.14% Traditional ROI: 2.15%
80 Taconic Ave #12 Great 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% Traditional cash on cash: 2.5% Airbnb Rental Income: $2744 Traditional Rental Income: $3410 Airbnb ROI: 0.73% Traditional ROI: 2.5%
7 Thrushwood Ln Great Barrington, MA IMMACULATE, LIKE-NEW DESIGNER CONTEMPORARY HOME tucked away on a quiet country cul-de-sac ...	5 beds \| 5 baths \| 3,800 sq.ft.	$1,625,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.35% Airbnb Rental Income: $3918 Traditional Rental Income: $6989 Airbnb ROI: -0.25% Traditional ROI: 2.35%
34 Fairview Ter Great Barrington, MA Charming single-level 1987 home set on one of the nicest streets in town--quiet, convenien...	3 beds \| 1 baths \| 960 sq.ft.	$299,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 5.9% Airbnb Rental Income: $2744 Traditional Rental Income: $2446 Airbnb ROI: 4.67% Traditional ROI: 5.9%
11 Muddy Brook Cir Great Barrington, MA Immaculate and well-maintained contemporary home in an exceptionally convenient location s...	3 beds \| 4 baths \| 3,236 sq.ft.	$799,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.07% Airbnb Rental Income: $2744 Traditional Rental Income: $5095 Airbnb ROI: 0.05% Traditional ROI: 4.07%
164 Alford Rd Great Barrington, MA Single level Berkshire retreat tucked away on 5.91 peaceful acres just minutes from downto...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,295,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.67% Airbnb Rental Income: $2744 Traditional Rental Income: $4113 Airbnb ROI: 0% Traditional ROI: 1.67%
15 Cone Ave Great Barrington, MA Built in 2019 and tucked away on 1.73 private acres in Housatonic, this beautifully mainta...	3 beds \| 3 baths \| 2,257 sq.ft.	$574,999	Airbnb cash on cash: 1.32% Traditional cash on cash: 5.09% Airbnb Rental Income: $2744 Traditional Rental Income: $4119 Airbnb ROI: 1.32% Traditional ROI: 5.09%
134 Hurlburt Rd Great Barrington, MA Nestled in the heart of Great Barrington, this spacious 4 bedroom, 4 bathroom residence of...	4 beds \| 4 baths \| 3,100 sq.ft.	$1,795,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 1.81% Airbnb Rental Income: $3784 Traditional Rental Income: $5426 Airbnb ROI: 0.33% Traditional ROI: 1.81%
14 Prospect St Great Barrington, MA 'ON THE HILL' Cozy 4 bedroom 1925 Cape, OPEN HOUSE JULY 4th SATURDAY 11:00-2:00. WALK TO C...	4 beds \| 1 baths \| 1,600 sq.ft.	$615,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.29% Airbnb Rental Income: $3784 Traditional Rental Income: $3685 Airbnb ROI: 3.04% Traditional ROI: 4.29%
15 Monument Valley Rd Great Barrington, MA Create your own Berkshire homestead starting with this diamond-in-the-rough log cabin prop...	2 beds \| 1 baths \| 704 sq.ft.	$225,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 5.88% Airbnb Rental Income: $2379 Traditional Rental Income: $2068 Airbnb ROI: 4.59% Traditional ROI: 5.88%
80 Taconic Ave #2 Great Barrington, MA 80 Taconic Ave #2, Great Barrington, MA 01230 \| Condo/Coop	2 beds \| 2 baths \| 1,308 sq.ft.	$629,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.68% Airbnb Rental Income: $2379 Traditional Rental Income: $2848 Airbnb ROI: -0.11% Traditional ROI: 1.68%
80 Taconic Ave #8 Great Barrington, MA 80 Taconic Ave #8, Great Barrington, MA 01230 \| Condo/Coop	2 beds \| 2 baths \| 1,308 sq.ft.	$679,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.4% Airbnb Rental Income: $2379 Traditional Rental Income: $2848 Airbnb ROI: -0.27% Traditional ROI: 1.4%
165 Maple Ave Great Barrington, MA 165 Maple Ave, Great Barrington, MA 01230 \| Single Family Residential	3 beds \| 2 baths \| 1,771 sq.ft.	$734,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 2.7% Airbnb Rental Income: $2744 Traditional Rental Income: $3467 Airbnb ROI: 0.7% Traditional ROI: 2.7%
165 Maple Ave #D Great Barrington, MA 165 Maple Ave #D, Great Barrington, MA 01230 \| Condo/Coop	3 beds \| 2 baths \| 1,771 sq.ft.	$734,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.84% Airbnb Rental Income: $2744 Traditional Rental Income: $3543 Airbnb ROI: -0.27% Traditional ROI: 1.84%
Lake Mansfield Rd Great Barrington, MA Lake Mansfield Rd, Great Barrington, MA 01230 \| Other	N/A beds \| N/A baths \| N/A	$825,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.38% Airbnb Rental Income: $928 Traditional Rental Income: $1511 Airbnb ROI: -1.58% Traditional ROI: -0.38%
0 Lake Mansfield Rd Great Barrington, MA 0 Lake Mansfield Rd, Great Barrington, MA 01230 \| Other	N/A beds \| N/A baths \| N/A	$825,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.38% Airbnb Rental Income: $928 Traditional Rental Income: $1511 Airbnb ROI: -1.58% Traditional ROI: -0.38%
0 Christian Hill Rd Great Barrington, MA 0 Christian Hill Rd, Great Barrington, MA 01230 \| Other	N/A beds \| N/A baths \| N/A	$185,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.85% Airbnb Rental Income: $928 Traditional Rental Income: $1511 Airbnb ROI: 0.58% Traditional ROI: 5.85%

Real Estate investment in Great-barrington, MA

There are 36 properties for sale in the city of Great Barrington . The median list price in Great Barrington is $746,303 and the average price per square foot is $326. In September 2026, the average monthly cash on cash return in Great Barrington is 3.00%. The average monthly rental income in Great Barrington is $3,439.

Great-barrington, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 36 investment properties available for sale in Great-barrington.

In 2026, the best neighborhood to buy investment property is Great Barrington.

The ROI for Long-Term is higher than the Short-Term in Great-barrington with average rental income of $3,439.

Your search for investment property begins and ends here

Investment Property for Sale in Great Barrington, MA

80 Taconic Ave

Great Barrington, MA

2 beds | 2 baths | 1,308 sq.ft.

$629,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $2379

Traditional Rental Income: $3267

Airbnb ROI: 0.8%

Traditional ROI: 3.31%

10 Berkshire Heights Rd

Great Barrington, MA

4 beds | 5 baths | 3,600 sq.ft.

$2,265,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $3784

Traditional Rental Income: $5729

Airbnb ROI: -0.05%

Traditional ROI: 1.27%

Thrushwood Ln lot: 10

Great Barrington, MA

5 beds | 5 baths | 3,808 sq.ft.

$829,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $3918

Traditional Rental Income: $5532

Airbnb ROI: 1.6%

Traditional ROI: 4.78%

153 State Rd

Great Barrington, MA

4 beds | 1 baths | 1,336 sq.ft.

$399,900

Airbnb cash on cash: 5.41%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $3784

Traditional Rental Income: $3097

Airbnb ROI: 5.41%

Traditional ROI: 5.77%

53 Mahaiwe St

Great Barrington, MA

6 beds | 5 baths | 3,502 sq.ft.

$600,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 9.66%

Airbnb Rental Income: $3784

Traditional Rental Income: $6829

Airbnb ROI: 2.76%

Traditional ROI: 9.66%

6 Muddy Brook Cir

Great Barrington, MA

3 beds | 4 baths | 2,447 sq.ft.

$995,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $2744

Traditional Rental Income: $4000

Airbnb ROI: -0.38%

Traditional ROI: 1.68%

211 Cottage St

Great Barrington, MA

3 beds | 3 baths | 3,204 sq.ft.

$849,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 3%

Airbnb Rental Income: $2744

Traditional Rental Income: $4096

Airbnb ROI: 0.47%

Traditional ROI: 3%

228 East St

Great Barrington, MA

5 beds | 4 baths | 2,900 sq.ft.

$1,250,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $3918

Traditional Rental Income: $6057

Airbnb ROI: 1.17%