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.

Grape Creek Investment Property for Sale in Great Barrington, MA

Search for Grape Creek Investment Property for Sale in Great Barrington, Massachusetts. Browse all of Mashvisor’s Grape Creek Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 30 Grape Creek Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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: 3.86% Traditional cash on cash: 6.57% Airbnb Rental Income: $3505 Traditional Rental Income: $3914 Airbnb ROI: 3.86% 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: 0.47% Traditional cash on cash: 1.2% Airbnb Rental Income: $2001 Traditional Rental Income: $1887 Airbnb ROI: 0.47% Traditional ROI: 1.2%
9 Forest Row Great Barrington, MA Immaculate ground level unit in the private country community of Forest Row., located just...	2 beds \| 1 baths \| 1,008 sq.ft.	$315,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 3.26% Airbnb Rental Income: $2001 Traditional Rental Income: $1728 Airbnb ROI: 2.42% Traditional ROI: 3.26%
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: 3.78% Traditional cash on cash: 4.78% Airbnb Rental Income: $5934 Traditional Rental Income: $5532 Airbnb ROI: 3.78% 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: 4.95% Traditional cash on cash: 5.77% Airbnb Rental Income: $3576 Traditional Rental Income: $3097 Airbnb ROI: 4.95% 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: 1.61% Traditional cash on cash: 2.63% Airbnb Rental Income: $3505 Traditional Rental Income: $3473 Airbnb ROI: 1.61% 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: 0.17% Traditional cash on cash: 1.8% Airbnb Rental Income: $2001 Traditional Rental Income: $3366 Airbnb ROI: 0.17% 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: 1.47% Traditional cash on cash: 3.7% Airbnb Rental Income: $5934 Traditional Rental Income: $7501 Airbnb ROI: 1.47% 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: 0.31% Traditional cash on cash: 1.68% Airbnb Rental Income: $3505 Traditional Rental Income: $4000 Airbnb ROI: 0.31% 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 \| 2 baths \| 2,631 sq.ft.	$935,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 3.53% Airbnb Rental Income: $3576 Traditional Rental Income: $4873 Airbnb ROI: 1.14% 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: -0.41% Traditional cash on cash: 2.17% Airbnb Rental Income: $2001 Traditional Rental Income: $3387 Airbnb ROI: -0.41% 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.	$600,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.91% Airbnb Rental Income: $3505 Traditional Rental Income: $3597 Airbnb ROI: 2.36% Traditional ROI: 3.91%
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: 3.44% Traditional cash on cash: 2.71% Airbnb Rental Income: $3505 Traditional Rental Income: $2392 Airbnb ROI: 3.44% 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: 1.4% Traditional cash on cash: 3.19% Airbnb Rental Income: $3576 Traditional Rental Income: $4119 Airbnb ROI: 1.4% 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.	$875,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.88% Airbnb Rental Income: $3505 Traditional Rental Income: $4096 Airbnb ROI: 1.21% Traditional ROI: 2.88%
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.	$1,290,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 3.59% Airbnb Rental Income: $5934 Traditional Rental Income: $6057 Airbnb ROI: 2.51% 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 \| 2 baths \| 1,760 sq.ft.	$729,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.02% Airbnb Rental Income: $3505 Traditional Rental Income: $3569 Airbnb ROI: 1.79% 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: 1.34% Traditional cash on cash: 2.54% Airbnb Rental Income: $5934 Traditional Rental Income: $6304 Airbnb ROI: 1.34% Traditional ROI: 2.54%
41 Pearl St unit: 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: 3.9% Traditional cash on cash: 6.22% Airbnb Rental Income: $3576 Traditional Rental Income: $3824 Airbnb ROI: 3.9% Traditional ROI: 6.22%
6 Blue Hill Rd Great Barrington, MA Set on a deep, level one-acre lot, this colonial offers a nice balance of space, privacy, ...	3 beds \| 2 baths \| 1,632 sq.ft.	$575,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.87% Airbnb Rental Income: $3505 Traditional Rental Income: $3249 Airbnb ROI: 2.9% Traditional ROI: 3.87%
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: 1.54% Traditional cash on cash: 2.6% Airbnb Rental Income: $3505 Traditional Rental Income: $3504 Airbnb ROI: 1.54% Traditional ROI: 2.6%
127 Monument Valley Rd Great Barrington, MA Beautifully renovated New England Farmhouse with thoughtful modern updates! The home retai...	3 beds \| 3 baths \| 1,860 sq.ft.	$1,249,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.33% Airbnb Rental Income: $3505 Traditional Rental Income: $3662 Airbnb ROI: 0.53% 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: 4.41% Traditional cash on cash: 6.63% Airbnb Rental Income: $3576 Traditional Rental Income: $3705 Airbnb ROI: 4.41% Traditional ROI: 6.63%
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: 5.71% Traditional cash on cash: 6.75% Airbnb Rental Income: $5934 Traditional Rental Income: $5384 Airbnb ROI: 5.71% 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: 2.25% Traditional cash on cash: 2.73% Airbnb Rental Income: $3576 Traditional Rental Income: $3083 Airbnb ROI: 2.25% 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: 0.48% Traditional cash on cash: 2.73% Airbnb Rental Income: $3576 Traditional Rental Income: $5716 Airbnb ROI: 0.48% Traditional ROI: 2.73%
80 Taconic Ave unit: 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: -0.51% Traditional cash on cash: 1.96% Airbnb Rental Income: $2001 Traditional Rental Income: $3082 Airbnb ROI: -0.51% Traditional ROI: 1.96%
148 Maple Ave unit: 12 Great Barrington, MA Nestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of ...	1 beds \| 1 baths \| 568 sq.ft.	$437,360	Airbnb cash on cash: -3.43% Traditional cash on cash: -0.17% Airbnb Rental Income: $1158 Traditional Rental Income: $2109 Airbnb ROI: -3.43% Traditional ROI: -0.17%
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.	$625,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 3.8% Airbnb Rental Income: $3505 Traditional Rental Income: $3352 Airbnb ROI: 2.74% Traditional ROI: 3.8%

Your search for investment property begins and ends here

Grape Creek 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: 3.86%

Traditional cash on cash: 6.57%

Airbnb Rental Income: $3505

Traditional Rental Income: $3914

Airbnb ROI: 3.86%

Traditional ROI: 6.57%

6 Lake Ave

Great Barrington, MA

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

$599,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $2001

Traditional Rental Income: $1887

Airbnb ROI: 0.47%

Traditional ROI: 1.2%

9 Forest Row

Great Barrington, MA

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

$315,000

Airbnb cash on cash: 2.42%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $2001

Traditional Rental Income: $1728

Airbnb ROI: 2.42%

Traditional ROI: 3.26%

Thrushwood Ln lot: 10

Great Barrington, MA

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

$829,000

Airbnb cash on cash: 3.78%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $5934

Traditional Rental Income: $5532

Airbnb ROI: 3.78%

Traditional ROI: 4.78%

153 State Rd

Great Barrington, MA

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

$399,900

Airbnb cash on cash: 4.95%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $3576

Traditional Rental Income: $3097

Airbnb ROI: 4.95%

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: 1.61%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $3505

Traditional Rental Income: $3473

Airbnb ROI: 1.61%

Traditional ROI: 2.63%

114 Brush Hill Rd

Great Barrington, MA

2 beds | 2 baths | 1,584 sq.ft.

$1,250,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $2001

Traditional Rental Income: $3366

Airbnb ROI: 0.17%

Traditional ROI: 1.8%

6-10 Manville St

Great Barrington, MA

16 beds | 10 baths | 8,870 sq.ft.

$1,330,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $5934

Traditional Rental Income: $7501

Airbnb ROI: 1.47%