Real Estate Investment Properties for Sale in Lenox, MA

Looking for investment property in Lenox, MA with high ROI ?

Explore a variety of short-term homes & houses in Lenox, MA. Invest wisely with VRBO & Lenox, 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 Lenox, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7 Rolling Hill #7-1 Lenox, MA Think spring in the Berkshires and enjoy condo living in Lenox at Rolling Hills. Spacious ...	2 beds \| 3 baths \| 1,552 sq.ft.	$324,500	Airbnb cash on cash: 0.1% Traditional cash on cash: 7.98% Airbnb Rental Income: $1080 Traditional Rental Income: $3116 Airbnb ROI: 0.1% Traditional ROI: 7.98%
130 E Dugway Rd Lenox, MA Two beautifully landscaped acres with perennial gardens blooming throughout the season. An...	4 beds \| 4 baths \| 3,805 sq.ft.	$1,590,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 2.13% Airbnb Rental Income: $1743 Traditional Rental Income: $5584 Airbnb ROI: -0.79% Traditional ROI: 2.13%
74 Holmes Rd Lenox, MA Charming Cape in Lenox! Spacious eat in kitchen with access to a screened porch and large ...	3 beds \| 1 baths \| 1,140 sq.ft.	$279,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 7.38% Airbnb Rental Income: $923 Traditional Rental Income: $2568 Airbnb ROI: -0.18% Traditional ROI: 7.38%
7 Rolling Hills #7-8 Lenox, MA This attractive multi level townhome has been renovated and ready for a new owner to enjoy...	2 beds \| 3 baths \| 1,730 sq.ft.	$393,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 6.9% Airbnb Rental Income: $1080 Traditional Rental Income: $3273 Airbnb ROI: -0.05% Traditional ROI: 6.9%
18 Highcrest Rd Lenox, MA Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots...	4 beds \| 5 baths \| 2,691 sq.ft.	$1,279,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 3.02% Airbnb Rental Income: $1743 Traditional Rental Income: $5526 Airbnb ROI: -0.57% Traditional ROI: 3.02%
63 Sherwood Dr Lenox, MA Don't miss this Lenox beauty! Tucked away on a quiet street and abutting preserved land, t...	3 beds \| 3 baths \| 2,680 sq.ft.	$847,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 3.1% Airbnb Rental Income: $923 Traditional Rental Income: $3977 Airbnb ROI: -1.2% Traditional ROI: 3.1%
3 Rolling #2 Lenox, MA Beautifully maintained 2 bedroom, 2 bath condo, both bedrooms/ baths on main level with co...	2 beds \| 2 baths \| 1,624 sq.ft.	$299,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 8.59% Airbnb Rental Income: $1080 Traditional Rental Income: $3042 Airbnb ROI: 0.31% Traditional ROI: 8.59%
54 Dunmore Ct Lenox, MA Discover comfortable & gracious living in this impeccably renovated home in Lenox. 4 BRs &...	4 beds \| 4 baths \| 4,043 sq.ft.	$1,295,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.98% Airbnb Rental Income: $1743 Traditional Rental Income: $5647 Airbnb ROI: -0.66% Traditional ROI: 2.98%
137 Housatonic St Lenox, MA Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious livi...	3 beds \| 2 baths \| 3,038 sq.ft.	$425,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 5.18% Airbnb Rental Income: $923 Traditional Rental Income: $2870 Airbnb ROI: -0.57% Traditional ROI: 5.18%

Real Estate investment in Lenox, MA

There are 9 properties for sale in the city of Lenox . The median list price in Lenox is $437,000 and the average price per square foot is $140. In May 2026, the average monthly cash on cash return in Lenox is 3.00%. The average monthly rental income in Lenox is $3,142.

Lenox, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 9 investment properties available for sale in Lenox.

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

The ROI for Long-Term is higher than the Short-Term in Lenox with average rental income of $3,142.

Your search for investment property begins and ends here

Investment Property for Sale in Lenox, MA

7 Rolling Hill #7-1

Lenox, MA

2 beds | 3 baths | 1,552 sq.ft.

$324,500

Airbnb cash on cash: 0.1%

Traditional cash on cash: 7.98%

Airbnb Rental Income: $1080

Traditional Rental Income: $3116

Airbnb ROI: 0.1%

Traditional ROI: 7.98%

130 E Dugway Rd

Lenox, MA

4 beds | 4 baths | 3,805 sq.ft.

$1,590,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $1743

Traditional Rental Income: $5584

Airbnb ROI: -0.79%

Traditional ROI: 2.13%

74 Holmes Rd

Lenox, MA

3 beds | 1 baths | 1,140 sq.ft.

$279,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 7.38%

Airbnb Rental Income: $923

Traditional Rental Income: $2568

Airbnb ROI: -0.18%

Traditional ROI: 7.38%

7 Rolling Hills #7-8

Lenox, MA

2 beds | 3 baths | 1,730 sq.ft.

$393,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $1080

Traditional Rental Income: $3273

Airbnb ROI: -0.05%

Traditional ROI: 6.9%

18 Highcrest Rd

Lenox, MA

4 beds | 5 baths | 2,691 sq.ft.

$1,279,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $1743

Traditional Rental Income: $5526

Airbnb ROI: -0.57%

Traditional ROI: 3.02%

63 Sherwood Dr

Lenox, MA

3 beds | 3 baths | 2,680 sq.ft.

$847,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $923

Traditional Rental Income: $3977

Airbnb ROI: -1.2%

Traditional ROI: 3.1%

3 Rolling #2

Lenox, MA

2 beds | 2 baths | 1,624 sq.ft.

$299,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 8.59%

Airbnb Rental Income: $1080

Traditional Rental Income: $3042

Airbnb ROI: 0.31%

Traditional ROI: 8.59%

54 Dunmore Ct

Lenox, MA

4 beds | 4 baths | 4,043 sq.ft.

$1,295,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $1743

Traditional Rental Income: $5647

Airbnb ROI: -0.66%