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.	$695,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.9% Airbnb Rental Income: $1976 Traditional Rental Income: $3267 Airbnb ROI: 0.11% Traditional ROI: 2.9%
63 Division St Great Barrington, MA Antonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC	3 beds \| 2 baths \| 2,066 sq.ft.	$625,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 4.16% Airbnb Rental Income: $3379 Traditional Rental Income: $3759 Airbnb ROI: 2.22% Traditional ROI: 4.16%
4 West Rose Ct Great Barrington, MA David Carlson [email protected] 413-329-1279 FAIRGROUND REAL ESTATE, INC	3 beds \| 3 baths \| 2,034 sq.ft.	$399,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 7.09% Airbnb Rental Income: $3379 Traditional Rental Income: $3612 Airbnb ROI: 4.46% Traditional ROI: 7.09%
34 Bridge St Great Barrington, MA Paige Lang Paluch [email protected] 518-821-4063 LANCE VERMEULEN RE, INC	1 beds \| 1 baths \| 717 sq.ft.	$495,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.89% Airbnb Rental Income: $1408 Traditional Rental Income: $2992 Airbnb ROI: -0.45% Traditional ROI: 3.89%
26 Prospect St Great Barrington, MA Helen Mullany [email protected] 413-429-7733 HELEN MULLANY REAL ESTATE, LLC	2 beds \| 2 baths \| 1,125 sq.ft.	$675,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.31% Airbnb Rental Income: $1976 Traditional Rental Income: $2902 Airbnb ROI: 0.02% Traditional ROI: 2.31%
8 Stillwell St Great Barrington, MA Antonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC	3 beds \| 1 baths \| 1,025 sq.ft.	$445,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 4% Airbnb Rental Income: $3379 Traditional Rental Income: $2560 Airbnb ROI: 4.16% Traditional ROI: 4%
Lot 10 Thrushwood Ln Great Barrington, MA Maureen White Kirkby [email protected] 413-446-5634 BERKSHIRE HATHAWAY HOMESERVI...	5 beds \| 5 baths \| 3,808 sq.ft.	$829,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.78% Airbnb Rental Income: $4484 Traditional Rental Income: $5532 Airbnb ROI: 2.21% Traditional ROI: 4.78%
16 Depot St Great Barrington, MA	N/A beds \| N/A baths \| 2,950 sq.ft.	$315,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.73% Airbnb Rental Income: $954 Traditional Rental Income: $2193 Airbnb ROI: 0.38% Traditional ROI: 5.73%
26 Manville St Great Barrington, MA Charming Updated Cape Style Home in Prime Great Barrington LocationDiscover this beautiful...	3 beds \| 2 baths \| 1,479 sq.ft.	$485,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 4.69% Airbnb Rental Income: $3379 Traditional Rental Income: $3173 Airbnb ROI: 3.49% Traditional ROI: 4.69%
82 West Ave Great Barrington, MA Classic turn-of-the-century Berkshire residence on the Hill. Rich w/ history & ready for n...	5 beds \| 4 baths \| 4,000 sq.ft.	$1,295,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 2.54% Airbnb Rental Income: $4484 Traditional Rental Income: $5580 Airbnb ROI: 0.86% Traditional ROI: 2.54%
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.	$419,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 5.46% Airbnb Rental Income: $3620 Traditional Rental Income: $3097 Airbnb ROI: 4.78% Traditional ROI: 5.46%
54 Division St Great Barrington, MA Opportunity to Finish Your Dream Home! This newly renovated home is awaiting your final to...	2 beds \| 2 baths \| 1,792 sq.ft.	$300,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 9.43% Airbnb Rental Income: $1976 Traditional Rental Income: $3346 Airbnb ROI: 2.75% Traditional ROI: 9.43%
133 Front St Great Barrington, MA	5 beds \| 3 baths \| 3,035 sq.ft.	$655,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 5.36% Airbnb Rental Income: $4484 Traditional Rental Income: $4535 Airbnb ROI: 3.74% Traditional ROI: 5.36%
165 Maple Ave Great Barrington, MA Beautiful open plan concept with wide pine flooring and so much light. Upscale kitchen, f...	3 beds \| 2 baths \| 1,771 sq.ft.	$795,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.56% Airbnb Rental Income: $3379 Traditional Rental Income: $3473 Airbnb ROI: 1.42% Traditional ROI: 2.56%
328-332 Park St Great Barrington, MA	8 beds \| 4 baths \| 3,044 sq.ft.	$849,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 4.9% Airbnb Rental Income: $4484 Traditional Rental Income: $5257 Airbnb ROI: 2.74% Traditional ROI: 4.9%
204 Cottage St Great Barrington, MA Helen Mullany [email protected] 413-429-7733 HELEN MULLANY REAL ESTATE, LLC	3 beds \| 3 baths \| 2,272 sq.ft.	$699,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.05% Airbnb Rental Income: $3379 Traditional Rental Income: $3515 Airbnb ROI: 1.69% Traditional ROI: 3.05%
126 Christian Hill Rd Great Barrington, MA Suzann Laverack Ward [email protected] 413-329-3031 HOUSATONIC REAL ESTATE	3 beds \| 2 baths \| 1,964 sq.ft.	$875,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 2.53% Airbnb Rental Income: $3379 Traditional Rental Income: $3648 Airbnb ROI: 1.27% Traditional ROI: 2.53%
311 North Plain Rd Great Barrington, MA The Giddings House, c. 1800. Historic Great Barrington home just 3 miles north of Main Str...	4 beds \| 4 baths \| 4,072 sq.ft.	$899,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.47% Airbnb Rental Income: $3620 Traditional Rental Income: $5557 Airbnb ROI: 1.21% Traditional ROI: 4.47%
114 Brush Hill Rd Great Barrington, MA New Build Contemporary Mark Rosengren [email protected] 413-329-0049 LANCE VERMEULEN ...	2 beds \| 2 baths \| 1,584 sq.ft.	$1,250,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 1.8% Airbnb Rental Income: $1976 Traditional Rental Income: $3366 Airbnb ROI: 0.15% Traditional ROI: 1.8%
42 Seekonk Rd Great Barrington, MA Timothy J Harrigan [email protected] 413-429-7042 BERKSHIRE HATHAWAY HOMESERVICES BA...	4 beds \| 4 baths \| 4,968 sq.ft.	$1,849,235	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.51% Airbnb Rental Income: $3620 Traditional Rental Income: $5572 Airbnb ROI: -0.08% Traditional ROI: 1.51%
386 North Plain Rd Great Barrington, MA Charming 1930s Bungalow with Privacy and Potential! Tucked away on nearly an acre (.93 acr...	2 beds \| 1 baths \| 1,092 sq.ft.	$199,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 8.79% Airbnb Rental Income: $1976 Traditional Rental Income: $2347 Airbnb ROI: 4.08% Traditional ROI: 8.79%
6-10 Manville St Great Barrington, MA	16 beds \| 10 baths \| 8,870 sq.ft.	$1,330,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.7% Airbnb Rental Income: $4484 Traditional Rental Income: $7501 Airbnb ROI: 0.5% Traditional ROI: 3.7%
53 Mahaiwe St Great Barrington, MA	6 beds \| 5 baths \| 3,502 sq.ft.	$600,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 9.66% Airbnb Rental Income: $4484 Traditional Rental Income: $6829 Airbnb ROI: 3.81% 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.	$1,200,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.22% Airbnb Rental Income: $3379 Traditional Rental Income: $4000 Airbnb ROI: -0.01% Traditional ROI: 1.22%
20 Cooper Rd Great Barrington, MA Antonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC	4 beds \| 3 baths \| 2,631 sq.ft.	$935,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.53% Airbnb Rental Income: $3620 Traditional Rental Income: $4873 Airbnb ROI: 1.18% Traditional ROI: 3.53%
324 Park St Great Barrington, MA Claudia Laslie [email protected] 413-854-7422 LANCE VERMEULEN RE, INC. 413-528-6011	2 beds \| 2 baths \| 1,622 sq.ft.	$796,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.17% Airbnb Rental Income: $1976 Traditional Rental Income: $3387 Airbnb ROI: -0.43% Traditional ROI: 2.17%
2 Lake Ave Great Barrington, MA WONDERFUL CONTEMPORARY HOME '''' ON THE HILL'''' IN GB. CONSIDERED ONE OF GB'S MOST DESIRE...	3 beds \| 2 baths \| 1,618 sq.ft.	$650,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 3.53% Airbnb Rental Income: $3379 Traditional Rental Income: $3597 Airbnb ROI: 1.93% Traditional ROI: 3.53%
1 Stanley Dr Great Barrington, MA Nicely maintained stand alone Condo unit with first floor Bed & Bath. Bath has new floorin...	3 beds \| 3 baths \| 1,444 sq.ft.	$485,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 5.13% Airbnb Rental Income: $3379 Traditional Rental Income: $3288 Airbnb ROI: 3.67% Traditional ROI: 5.13%
375 North Plain Rd Great Barrington, MA Cortney K Dupont [email protected] COHEN & WHITE ASSOCIATES	3 beds \| 2 baths \| 1,425 sq.ft.	$399,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 6.21% Airbnb Rental Income: $3379 Traditional Rental Income: $3335 Airbnb ROI: 4.31% Traditional ROI: 6.21%
3 Benton Ave Great Barrington, MA Adam J Dingman [email protected] 413-464-1381 BERKSHIRE HATHAWAY HOMESERVICES BARNB...	4 beds \| 1 baths \| 1,500 sq.ft.	$450,000	Airbnb cash on cash: 4.29% Traditional cash on cash: 4.62% Airbnb Rental Income: $3620 Traditional Rental Income: $2968 Airbnb ROI: 4.29% Traditional ROI: 4.62%
416 Monterey Rd Great Barrington, MA Michael Harrigan [email protected] 413-429-7788 BERKSHIRE HATHAWAY HOMESERVICES ...	3 beds \| 3 baths \| 1,708 sq.ft.	$675,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.44% Airbnb Rental Income: $3379 Traditional Rental Income: $3465 Airbnb ROI: 2.11% Traditional ROI: 3.44%
69 Welcome St Great Barrington, MA Rosemary Ann Baumann [email protected] 413-329-1219 LANCE VERMEULEN RE, INC	4 beds \| 3 baths \| 2,885 sq.ft.	$625,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 5.93% Airbnb Rental Income: $3620 Traditional Rental Income: $4831 Airbnb ROI: 2.49% Traditional ROI: 5.93%
302 A Egremont Plain Rd Great Barrington, MA Maureen White-Kirkby [email protected] 413-446-5634 BERKSHIRE HATHAWAY HOMESERVI...	4 beds \| 6 baths \| 4,846 sq.ft.	$2,300,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 2.71% Airbnb Rental Income: $3620 Traditional Rental Income: $8224 Airbnb ROI: 0.18% Traditional ROI: 2.71%
6 Locust St Great Barrington, MA Paige Lang Paluch [email protected] 518-821-4063 LANCE VERMEULEN RE, INC	3 beds \| 1 baths \| 1,075 sq.ft.	$550,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.42% Airbnb Rental Income: $3379 Traditional Rental Income: $2392 Airbnb ROI: 3.88% Traditional ROI: 3.42%

Real Estate investment in Great-barrington, MA

There are 34 properties for sale in the city of Great Barrington . The median list price in Great Barrington is $665,000 and the average price per square foot is $272. In September 2025, the average monthly cash on cash return in Great Barrington is 4.00%. The average monthly rental income in Great Barrington is $3,473.

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

There are 34 investment properties available for sale in Great-barrington.

In 2025, 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 $3,473.

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.

$695,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $1976

Traditional Rental Income: $3267

Airbnb ROI: 0.11%

Traditional ROI: 2.9%

63 Division St

Great Barrington, MA

3 beds | 2 baths | 2,066 sq.ft.

$625,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $3379

Traditional Rental Income: $3759

Airbnb ROI: 2.22%

Traditional ROI: 4.16%

4 West Rose Ct

Great Barrington, MA

3 beds | 3 baths | 2,034 sq.ft.

$399,900

Airbnb cash on cash: 4.46%

Traditional cash on cash: 7.09%

Airbnb Rental Income: $3379

Traditional Rental Income: $3612

Airbnb ROI: 4.46%

Traditional ROI: 7.09%

34 Bridge St

Great Barrington, MA

1 beds | 1 baths | 717 sq.ft.

$495,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1408

Traditional Rental Income: $2992

Airbnb ROI: -0.45%

Traditional ROI: 3.89%

26 Prospect St

Great Barrington, MA

2 beds | 2 baths | 1,125 sq.ft.

$675,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $1976

Traditional Rental Income: $2902

Airbnb ROI: 0.02%

Traditional ROI: 2.31%

8 Stillwell St

Great Barrington, MA

3 beds | 1 baths | 1,025 sq.ft.

$445,000

Airbnb cash on cash: 4.16%

Traditional cash on cash: 4%

Airbnb Rental Income: $3379

Traditional Rental Income: $2560

Airbnb ROI: 4.16%

Traditional ROI: 4%

Lot 10 Thrushwood Ln

Great Barrington, MA

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

$829,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $4484

Traditional Rental Income: $5532

Airbnb ROI: 2.21%

Traditional ROI: 4.78%

16 Depot St

Great Barrington, MA

N/A beds | N/A baths | 2,950 sq.ft.

$315,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $954

Traditional Rental Income: $2193

Airbnb ROI: 0.38%