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
497 S Main St Great Barrington, MA Multi-family in a convenient location, walking distance to town and shopping, bus line nea...	3 beds \| 3 baths \| 2,480 sq.ft.	$465,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 6.57% Airbnb Rental Income: $2423 Traditional Rental Income: $3914 Airbnb ROI: 1.78% Traditional ROI: 6.57%
6 Lake Ave Great Barrington, MA Perched ''on the hill'' this fully renovated cottage is bright, chic, and effortlessly liv...	2 beds \| 1 baths \| 1,107 sq.ft.	$599,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.07% Airbnb Rental Income: $2080 Traditional Rental Income: $2373 Airbnb ROI: 0.59% Traditional ROI: 2.07%
119 Hollenbeck Ave Great Barrington, MA Beautifully renovated one-level ranch offers the perfect blend of modern convenience and c...	3 beds \| 1 baths \| 1,031 sq.ft.	$595,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 1.97% Airbnb Rental Income: $2423 Traditional Rental Income: $2196 Airbnb ROI: 1.32% Traditional ROI: 1.97%
2 Walnut St Great Barrington, MA 4 bed / 2 bath Cape - clean, modern kitchen, 2 bedrooms and 1 full bath on first floor - g...	4 beds \| 2 baths \| 1,588 sq.ft.	$399,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 6.08% Airbnb Rental Income: $2461 Traditional Rental Income: $3111 Airbnb ROI: 2.74% Traditional ROI: 6.08%
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: 2.74% Traditional cash on cash: 3.37% Airbnb Rental Income: $2080 Traditional Rental Income: $1728 Airbnb ROI: 2.74% 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: 1.64% Traditional cash on cash: 4.78% Airbnb Rental Income: $3954 Traditional Rental Income: $5532 Airbnb ROI: 1.64% 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 \| 1,337 sq.ft.	$399,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 5.77% Airbnb Rental Income: $2461 Traditional Rental Income: $3097 Airbnb ROI: 2.47% Traditional ROI: 5.77%
165 Maple Ave unit: D Great Barrington, MA Experience the ease of downtown living in this immaculate Maple Grove condominium. Positio...	3 beds \| 2 baths \| 1,771 sq.ft.	$779,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.63% Airbnb Rental Income: $2423 Traditional Rental Income: $3473 Airbnb ROI: 0.37% Traditional ROI: 2.63%
114 Brush Hill Rd Great Barrington, MA New Build Contemporary. Timbercraft Homes & Rosengren Architects collaborated to create th...	2 beds \| 2 baths \| 1,584 sq.ft.	$1,250,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 1.8% Airbnb Rental Income: $2080 Traditional Rental Income: $3366 Airbnb ROI: 0.23% Traditional ROI: 1.8%
6-10 Manville St Great Barrington, MA A prime investment opportunity in the heart of downtown Great Barrington. This 10-unit res...	16 beds \| 10 baths \| 8,870 sq.ft.	$1,330,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.7% Airbnb Rental Income: $3954 Traditional Rental Income: $7501 Airbnb ROI: 0.14% Traditional ROI: 3.7%
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: -0.66% Traditional cash on cash: 1.68% Airbnb Rental Income: $2423 Traditional Rental Income: $4000 Airbnb ROI: -0.66% Traditional ROI: 1.68%
20 Cooper Rd Great Barrington, MA This is the one you've been waiting for. A classic mid-century home on over 4 private acre...	4 beds \| 3 baths \| 2,631 sq.ft.	$935,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.53% Airbnb Rental Income: $2461 Traditional Rental Income: $4873 Airbnb ROI: 0.07% Traditional ROI: 3.53%
324 Park St Great Barrington, MA Architectural gem with lots of glass perched like a treehouse on the backside of Monument ...	2 beds \| 2 baths \| 1,622 sq.ft.	$796,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.17% Airbnb Rental Income: $2080 Traditional Rental Income: $3387 Airbnb ROI: -0.32% Traditional ROI: 2.17%
2 Lake Ave Great Barrington, MA WONDERFUL CONTEMPORARY HOME '' ON THE HILL'' IN GB. CONSIDERED ONE OF GB'S MOST DESIRED AR...	3 beds \| 2 baths \| 1,618 sq.ft.	$550,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 4.35% Airbnb Rental Income: $2423 Traditional Rental Income: $3597 Airbnb ROI: 0.91% Traditional ROI: 4.35%
416 Monterey Rd Great Barrington, MA This charming ranch is perfect for easy one level living! It is a well maintained home fea...	3 beds \| 3 baths \| 1,708 sq.ft.	$675,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.44% Airbnb Rental Income: $2423 Traditional Rental Income: $3465 Airbnb ROI: 0.84% Traditional ROI: 3.44%
6 Locust St Great Barrington, MA Tucked away in a vibrant, walkable east-side neighborhood, this custom 3-bedroom bungalow ...	3 beds \| 1 baths \| 1,075 sq.ft.	$495,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.71% Airbnb Rental Income: $2423 Traditional Rental Income: $2392 Airbnb ROI: 1.49% Traditional ROI: 2.71%
12 Barrington Place Great Barrington, MA Charming Renovated 1900 Colonial ''On The Hill'' A beautifully updated home blends histori...	4 beds \| 2 baths \| 2,105 sq.ft.	$799,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 3.19% Airbnb Rental Income: $2461 Traditional Rental Income: $4119 Airbnb ROI: 0.15% Traditional ROI: 3.19%
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: 0.13% Traditional cash on cash: 3% Airbnb Rental Income: $2423 Traditional Rental Income: $4096 Airbnb ROI: 0.13% 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: 1.13% Traditional cash on cash: 3.59% Airbnb Rental Income: $3954 Traditional Rental Income: $6057 Airbnb ROI: 1.13% Traditional ROI: 3.59%
81 Castle Hill Ave Great Barrington, MA With its excellent curb appeal, charm and location, this property delivers! The inviting e...	3 beds \| 3 baths \| 1,760 sq.ft.	$729,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.02% Airbnb Rental Income: $2423 Traditional Rental Income: $3569 Airbnb ROI: 0.47% Traditional ROI: 3.02%
6 Thrushwood Ln Great Barrington, MA MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Be...	5 beds \| 4 baths \| 4,200 sq.ft.	$1,395,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.54% Airbnb Rental Income: $3954 Traditional Rental Income: $6304 Airbnb ROI: 0.07% Traditional ROI: 2.54%
165 - D Maple Ave Great Barrington, MA Experience the ease of downtown living in this immaculate Maple Grove condominium. Positio...	3 beds \| 2 baths \| 1,771 sq.ft.	$779,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.6% Airbnb Rental Income: $2423 Traditional Rental Income: $3504 Airbnb ROI: 0.29% Traditional ROI: 2.6%
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.	$1,249,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.33% Airbnb Rental Income: $2461 Traditional Rental Income: $3662 Airbnb ROI: -0.22% Traditional ROI: 1.33%
115 Bridge St Great Barrington, MA BRIDGERTOWN CXV A great opportunity to own or invest in a 2-unit In-town property. 3 bedro...	4 beds \| 2 baths \| 2,112 sq.ft.	$439,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 6.63% Airbnb Rental Income: $2461 Traditional Rental Income: $3705 Airbnb ROI: 2.15% Traditional ROI: 6.63%
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.	$474,900	Airbnb cash on cash: 1.81% Traditional cash on cash: 5.44% Airbnb Rental Income: $2461 Traditional Rental Income: $3478 Airbnb ROI: 1.81% Traditional ROI: 5.44%
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: 2.99% Traditional cash on cash: 6.75% Airbnb Rental Income: $3954 Traditional Rental Income: $5384 Airbnb ROI: 2.99% Traditional ROI: 6.75%
783 Main St Great Barrington, MA Renovated, well-maintained, multi-use building perfect for a live-work situation in prime ...	4 beds \| 1 baths \| 3,000 sq.ft.	$649,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.73% Airbnb Rental Income: $2461 Traditional Rental Income: $3083 Airbnb ROI: 0.71% Traditional ROI: 2.73%
20 Sheffield Egremont Rd Great Barrington, MA This quintessential turn of the century antique home, built in 1909, is in immaculate cond...	4 beds \| 4 baths \| 3,240 sq.ft.	$1,395,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 2.73% Airbnb Rental Income: $2461 Traditional Rental Income: $5716 Airbnb ROI: -0.24% Traditional ROI: 2.73%
80 Taconic Ave #3 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: -0.41% Traditional cash on cash: 1.96% Airbnb Rental Income: $2080 Traditional Rental Income: $3082 Airbnb ROI: -0.41% Traditional ROI: 1.96%
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: -3.92% Traditional cash on cash: -0.19% Airbnb Rental Income: $883 Traditional Rental Income: $2109 Airbnb ROI: -3.92% Traditional ROI: -0.19%
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.	$595,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 4.04% Airbnb Rental Income: $2423 Traditional Rental Income: $3352 Airbnb ROI: 1.3% Traditional ROI: 4.04%
265 State Rd Great Barrington, MA This spacious estate-style home sits in a premier Great Barrington setting, offering ample...	4 beds \| 2 baths \| 1,980 sq.ft.	$585,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 4.28% Airbnb Rental Income: $2461 Traditional Rental Income: $3566 Airbnb ROI: 1.16% Traditional ROI: 4.28%
80 Taconic Ave #13 Great Barrington, MA Oakwood Condominium near the hospital. This 3 bedroom 2 bath has been recently up dated. E...	3 beds \| 2 baths \| 1,898 sq.ft.	$785,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.55% Airbnb Rental Income: $2423 Traditional Rental Income: $3414 Airbnb ROI: 0.38% Traditional ROI: 2.55%
43 Hart St Great Barrington, MA OPEN HOUSE FRIDAY 4/24 3:30-5:30PM. Nestled on a quiet setback lot in the desirable Housat...	2 beds \| 2 baths \| 1,970 sq.ft.	$460,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 4.9% Airbnb Rental Income: $2080 Traditional Rental Income: $3063 Airbnb ROI: 1.38% Traditional ROI: 4.9%
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: 3.97% Traditional cash on cash: 10.12% Airbnb Rental Income: $2080 Traditional Rental Income: $2967 Airbnb ROI: 3.97% Traditional ROI: 10.12%

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 $675,000 and the average price per square foot is $306. In May 2026, the average monthly cash on cash return in Great Barrington is 3.00%. The average monthly rental income in Great Barrington is $3,476.

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 $3,476.

Your search for investment property begins and ends here

Investment Property for Sale in Great Barrington, MA

497 S Main St

Great Barrington, MA

3 beds | 3 baths | 2,480 sq.ft.

$465,000

Airbnb cash on cash: 1.78%

Traditional cash on cash: 6.57%

Airbnb Rental Income: $2423

Traditional Rental Income: $3914

Airbnb ROI: 1.78%

Traditional ROI: 6.57%

6 Lake Ave

Great Barrington, MA

2 beds | 1 baths | 1,107 sq.ft.

$599,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2080

Traditional Rental Income: $2373

Airbnb ROI: 0.59%

Traditional ROI: 2.07%

119 Hollenbeck Ave

Great Barrington, MA

3 beds | 1 baths | 1,031 sq.ft.

$595,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $2423

Traditional Rental Income: $2196

Airbnb ROI: 1.32%

Traditional ROI: 1.97%

2 Walnut St

Great Barrington, MA

4 beds | 2 baths | 1,588 sq.ft.

$399,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 6.08%

Airbnb Rental Income: $2461

Traditional Rental Income: $3111

Airbnb ROI: 2.74%

Traditional ROI: 6.08%

9 Forest Row

Great Barrington, MA

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

$307,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $2080

Traditional Rental Income: $1728

Airbnb ROI: 2.74%

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: 1.64%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $3954

Traditional Rental Income: $5532

Airbnb ROI: 1.64%

Traditional ROI: 4.78%

153 State Rd

Great Barrington, MA

4 beds | 1 baths | 1,337 sq.ft.

$399,900

Airbnb cash on cash: 2.47%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $2461

Traditional Rental Income: $3097

Airbnb ROI: 2.47%

Traditional ROI: 5.77%

165 Maple Ave unit: D

Great Barrington, MA

3 beds | 2 baths | 1,771 sq.ft.

$779,000

Airbnb cash on cash: 0.37%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2423

Traditional Rental Income: $3473

Airbnb ROI: 0.37%