Real Estate Investment Properties for Sale in Ashland, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
102 Captain Eames Cir unit: 102 #102 Ashland, MA Located in the desirable Starlight Village, this 2-bedroom tri-level townhouse awaits you....	2 beds \| 2 baths \| 1,967 sq.ft.	$519,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.66% Airbnb Rental Income: $2977 Traditional Rental Income: $3441 Airbnb ROI: 1.29% Traditional ROI: 3.66%
373 Eliot St Ashland, MA Three bedroom, one bathroom Ranch! Needs much work! SOLD AS-IS! Seller makes no representa...	3 beds \| 1 baths \| 1,296 sq.ft.	$345,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 5.36% Airbnb Rental Income: $2506 Traditional Rental Income: $2636 Airbnb ROI: 3.09% Traditional ROI: 5.36%
Investment Properties for Sale in Other Cities of Massachusetts
11 Robinwood Ave Boston , MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $4593 Airbnb ROI: N/A Traditional ROI: 0.27%
496 Shore Road unit: 21 #21 Truro , MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,299,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.78% Airbnb Rental Income: $2850 Traditional Rental Income: $3609 Airbnb ROI: -0.4% Traditional ROI: 0.78%
73 Joshua Jethro Road Chatham , MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,520,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.11% Airbnb Rental Income: $2063 Traditional Rental Income: $3418 Airbnb ROI: -0.23% Traditional ROI: 1.11%
27 Quaker Lane Harwich , MA This Harwich home is set in the perfect location! Ideally situated near popular restaurant...	2 beds \| 1 baths \| 1,019 sq.ft.	$549,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 2.88% Airbnb Rental Income: $2729 Traditional Rental Income: $2298 Airbnb ROI: 2.46% Traditional ROI: 2.88%
14 Colonial Road Webster , MA 14 Colonial Drive in Webster is a must see! Located in a sought-after Webster Lake neighbo...	3 beds \| 2 baths \| 1,248 sq.ft.	$399,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 5.76% Airbnb Rental Income: $2687 Traditional Rental Income: $2938 Airbnb ROI: 3.39% Traditional ROI: 5.76%
118 Driftwood Lane South Yarmouth , MA Cape Cod Luxury Waterfront Living on Follins Pond~Bass River! Imagine waking up to blue sk...	4 beds \| 4 baths \| 3,978 sq.ft.	$3,374,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.71% Airbnb Rental Income: $2197 Traditional Rental Income: $7060 Airbnb ROI: -1.02% Traditional ROI: 0.71%
200 Cove Way unit: 614 #614 Quincy , MA Are you an outdoors type that enjoys sailing, swimming, tennis or do you like dining out, ...	2 beds \| 2 baths \| 1,051 sq.ft.	$415,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.25% Airbnb Rental Income: $1458 Traditional Rental Income: $2449 Airbnb ROI: -1.41% Traditional ROI: 2.25%
35 Bayshore Drive Mashpee , MA Set along the marshfront with views of Hamblin Pond, this beautiful home offers a peaceful...	4 beds \| 4 baths \| 3,236 sq.ft.	$1,395,500	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.63% Airbnb Rental Income: $5855 Traditional Rental Income: $5443 Airbnb ROI: 2.05% Traditional ROI: 2.63%
2 Prince St Beverly , MA This renovated coastal residence offers a refined yet relaxed lifestyle in one of Beverlyâ...	4 beds \| 3 baths \| 3,329 sq.ft.	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.05% Airbnb Rental Income: $null Traditional Rental Income: $4518 Airbnb ROI: N/A Traditional ROI: 1.05%
93 Chapman Place unit: 93 #93 LEOMINSTER , MA Welcome home to this beautifully maintained townhouse in the desirable Chapman Place commu...	2 beds \| 2 baths \| 1,384 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $3017 Airbnb ROI: N/A Traditional ROI: 5.01%
60 Ashumet Avenue Mashpee , MA Welcome to 60 Ashumet Ave, a beautifully updated home in an association neighborhood with ...	3 beds \| 2 baths \| 1,228 sq.ft.	$515,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 4.22% Airbnb Rental Income: $3738 Traditional Rental Income: $2854 Airbnb ROI: 4.37% Traditional ROI: 4.22%
242 Eastwood Dr Westfield , MA Westfield - Contractors, horse enthusiasts and car buffs rejoice. This incredible opportun...	4 beds \| 3 baths \| 4,814 sq.ft.	$950,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.63% Airbnb Rental Income: $2859 Traditional Rental Income: $4415 Airbnb ROI: 0.11% Traditional ROI: 2.63%
10 Rockledge Drive North Falmouth , MA Welcome to this inviting 3-bed, 2.5-bath home that combines comfort, charm, and an excepti...	3 beds \| 2 baths \| 2,583 sq.ft.	$985,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.26% Airbnb Rental Income: $2001 Traditional Rental Income: $3600 Airbnb ROI: -0.06% Traditional ROI: 2.26%
116 Oak Lane unit: 12 #12 Brockton , MA Ready for a quick close and all reasonable offers considered. Located in the desirable Wes...	1 beds \| 1 baths \| 755 sq.ft.	$220,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 4.9% Airbnb Rental Income: $1345 Traditional Rental Income: $2027 Airbnb ROI: -0.36% Traditional ROI: 4.9%
497 South 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: 4.04% Traditional cash on cash: 6.75% Airbnb Rental Income: $3505 Traditional Rental Income: $3914 Airbnb ROI: 4.04% Traditional ROI: 6.75%

Real Estate investment in Ashland, MA

There are 2 properties for sale in the city of Ashland . The median list price in Ashland is $575,000 and the average price per square foot is $311. In January 2026, the average monthly cash on cash return in Ashland is 5.00%. The average monthly rental income in Ashland is $3,039.

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

There are 2 investment properties available for sale in Ashland.

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

The ROI for Long-Term is higher than the Short-Term in Ashland with average rental income of $3,039.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, MA

102 Captain Eames Cir unit: 102 #102

Ashland, MA

2 beds | 2 baths | 1,967 sq.ft.

$519,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $2977

Traditional Rental Income: $3441

Airbnb ROI: 1.29%

Traditional ROI: 3.66%

373 Eliot St

Ashland, MA

3 beds | 1 baths | 1,296 sq.ft.

$345,000

Airbnb cash on cash: 3.09%

Traditional cash on cash: 5.36%

Airbnb Rental Income: $2506

Traditional Rental Income: $2636

Airbnb ROI: 3.09%

Traditional ROI: 5.36%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

5 beds | 4 baths | 3,390 sq.ft.

$2,399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $4593

Airbnb ROI: N/A

Traditional ROI: 0.27%

Truro , MA

3 beds | 2 baths | 2,018 sq.ft.

$1,299,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $2850

Traditional Rental Income: $3609

Airbnb ROI: -0.4%

Traditional ROI: 0.78%

Chatham , MA

3 beds | 2 baths | 2,307 sq.ft.

$1,520,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $2063

Traditional Rental Income: $3418

Airbnb ROI: -0.23%

Traditional ROI: 1.11%

Harwich , MA

2 beds | 1 baths | 1,019 sq.ft.

$549,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $2729

Traditional Rental Income: $2298

Airbnb ROI: 2.46%

Traditional ROI: 2.88%

Webster , MA

3 beds | 2 baths | 1,248 sq.ft.

$399,900

Airbnb cash on cash: 3.39%

Traditional cash on cash: 5.76%

Airbnb Rental Income: $2687

Traditional Rental Income: $2938

Airbnb ROI: 3.39%

Traditional ROI: 5.76%

South Yarmouth , MA

4 beds | 4 baths | 3,978 sq.ft.

$3,374,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $2197

Traditional Rental Income: $7060

Airbnb ROI: -1.02%

Traditional ROI: 0.71%

Quincy , MA

2 beds | 2 baths | 1,051 sq.ft.

$415,000

Airbnb cash on cash: -1.41%