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
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: -0.14% Traditional cash on cash: 1.27% Airbnb Rental Income: $3537 Traditional Rental Income: $5729 Airbnb ROI: -0.14% Traditional ROI: 1.27%
9 Forest Row Great Barrington, MA Why rent when you can own in a delightful neighborhood. Immaculate ground level unit in th...	2 beds \| 1 baths \| 1,008 sq.ft.	$307,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.37% Airbnb Rental Income: $1730 Traditional Rental Income: $1728 Airbnb ROI: 1.73% Traditional ROI: 3.37%
Thrushwood Ln lot: 10 Great Barrington, MA POOL COMMUNITY: BUILD YOUR DREAM HOME: Open plan living with, first floor master, fireplac...	5 beds \| 5 baths \| 3,808 sq.ft.	$829,000	Airbnb cash on cash: 5.92% Traditional cash on cash: 4.78% Airbnb Rental Income: $7924 Traditional Rental Income: $5532 Airbnb ROI: 5.92% Traditional ROI: 4.78%
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: -0.29% Traditional cash on cash: 1.68% Airbnb Rental Income: $2838 Traditional Rental Income: $4000 Airbnb ROI: -0.29% 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: 0.57% Traditional cash on cash: 3% Airbnb Rental Income: $2838 Traditional Rental Income: $4096 Airbnb ROI: 0.57% 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 \| 5 baths \| 2,900 sq.ft.	$1,290,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.59% Airbnb Rental Income: $7924 Traditional Rental Income: $6057 Airbnb ROI: 3.89% Traditional ROI: 3.59%
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: 2.69% Traditional cash on cash: 2.61% Airbnb Rental Income: $7924 Traditional Rental Income: $6304 Airbnb ROI: 2.69% 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: 0.62% Traditional cash on cash: 1.43% Airbnb Rental Income: $3537 Traditional Rental Income: $3662 Airbnb ROI: 0.62% Traditional ROI: 1.43%
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: 4.09% Traditional cash on cash: 5.8% Airbnb Rental Income: $3537 Traditional Rental Income: $3478 Airbnb ROI: 4.09% Traditional ROI: 5.8%
73 Christian Hill Rd Great Barrington, MA Investors zoom in on this property, we have an income producing property. 3 of the 4 units...	5 beds \| 4 baths \| 2,499 sq.ft.	$650,000	Airbnb cash on cash: 8.45% Traditional cash on cash: 6.75% Airbnb Rental Income: $7924 Traditional Rental Income: $5384 Airbnb ROI: 8.45% Traditional ROI: 6.75%
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: -0.7% Traditional cash on cash: 2.44% Airbnb Rental Income: $1180 Traditional Rental Income: $2109 Airbnb ROI: -0.7% 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.	$545,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 4.5% Airbnb Rental Income: $2838 Traditional Rental Income: $3352 Airbnb ROI: 2.19% Traditional ROI: 4.5%
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: 0.8% Traditional cash on cash: 5.24% Airbnb Rental Income: $1730 Traditional Rental Income: $3063 Airbnb ROI: 0.8% Traditional ROI: 5.24%
360 Park St #4 Great Barrington, MA Easy condo living in a prime location! This townhouse-style unit features two bedrooms and...	2 beds \| 2 baths \| 1,126 sq.ft.	$245,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 10.12% Airbnb Rental Income: $1730 Traditional Rental Income: $2967 Airbnb ROI: 2.71% Traditional ROI: 10.12%
39 Castle St Great Barrington, MA Within walking distance to Main Street, this adorable home has been lovingly cared for. Im...	2 beds \| 1 baths \| 1,296 sq.ft.	$599,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.15% Airbnb Rental Income: $1730 Traditional Rental Income: $2363 Airbnb ROI: 0.17% 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: 0.83% Traditional cash on cash: 2.5% Airbnb Rental Income: $2838 Traditional Rental Income: $3410 Airbnb ROI: 0.83% 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: 1.96% Traditional cash on cash: 2.35% Airbnb Rental Income: $7924 Traditional Rental Income: $6989 Airbnb ROI: 1.96% 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.	$325,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 5.36% Airbnb Rental Income: $2838 Traditional Rental Income: $2446 Airbnb ROI: 4.48% Traditional ROI: 5.36%
11 Muddy Brook Cir Great Barrington, MA Well-maintained contemporary home in an exceptionally convenient location set on 5+ wooded...	3 beds \| 4 baths \| 3,236 sq.ft.	$995,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 3.08% Airbnb Rental Income: $2838 Traditional Rental Income: $5095 Airbnb ROI: -0.07% Traditional ROI: 3.08%
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: 0.06% Traditional cash on cash: 1.67% Airbnb Rental Income: $2838 Traditional Rental Income: $4113 Airbnb ROI: 0.06% Traditional ROI: 1.67%

Real Estate investment in Great-barrington, MA

There are 22 properties for sale in the city of Great Barrington . The median list price in Great Barrington is $699,639 and the average price per square foot is $300. In June 2026, the average monthly cash on cash return in Great Barrington is 3.00%. The average monthly rental income in Great Barrington is $3,492.

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

There are 22 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 $3,492.

Your search for investment property begins and ends here

Investment Property for Sale in Great Barrington, MA

10 Berkshire Heights Rd

Great Barrington, MA

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

$2,265,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $3537

Traditional Rental Income: $5729

Airbnb ROI: -0.14%

Traditional ROI: 1.27%

9 Forest Row

Great Barrington, MA

2 beds | 1 baths | 1,008 sq.ft.

$307,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $1730

Traditional Rental Income: $1728

Airbnb ROI: 1.73%

Traditional ROI: 3.37%

Thrushwood Ln lot: 10

Great Barrington, MA

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

$829,000

Airbnb cash on cash: 5.92%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $7924

Traditional Rental Income: $5532

Airbnb ROI: 5.92%

Traditional ROI: 4.78%

6 Muddy Brook Cir

Great Barrington, MA

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

$995,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $2838

Traditional Rental Income: $4000

Airbnb ROI: -0.29%

Traditional ROI: 1.68%

211 Cottage St

Great Barrington, MA

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

$849,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 3%

Airbnb Rental Income: $2838

Traditional Rental Income: $4096

Airbnb ROI: 0.57%

Traditional ROI: 3%

228 East St

Great Barrington, MA

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

$1,290,000

Airbnb cash on cash: 3.89%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $7924

Traditional Rental Income: $6057

Airbnb ROI: 3.89%

Traditional ROI: 3.59%

6 Thrushwood Ln

Great Barrington, MA

5 beds | 4 baths | 4,200 sq.ft.

$1,375,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $7924

Traditional Rental Income: $6304

Airbnb ROI: 2.69%

Traditional ROI: 2.61%

127 Monument Valley Rd

Great Barrington, MA

4 beds | 3 baths | 1,860 sq.ft.

$1,195,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $3537

Traditional Rental Income: $3662

Airbnb ROI: 0.62%