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
12 Braeburn Lane #12 Ashland, MA Welcome to this sprawling free standing town home in Cookingham Greene that offers comfort...	2 beds \| 3 baths \| 2,067 sq.ft.	$750,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.89% Airbnb Rental Income: $2977 Traditional Rental Income: $3612 Airbnb ROI: 0% Traditional ROI: 1.89%
8 Pilgrim Road Ashland, MA Tucked away on a quiet cul-de-sac adjacent to Framingham Country Club, this stunning turn-...	4 beds \| 3 baths \| 2,670 sq.ft.	$1,159,999	Airbnb cash on cash: -1.42% Traditional cash on cash: 1.7% Airbnb Rental Income: $1171 Traditional Rental Income: $4150 Airbnb ROI: -1.42% Traditional ROI: 1.7%
17 Sewell St Ashland, MA Move right into The Good Life with this easy to maintain home! Built in 2005, this open-co...	3 beds \| 2 baths \| 2,191 sq.ft.	$650,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.06% Airbnb Rental Income: $2506 Traditional Rental Income: $3315 Airbnb ROI: 0.72% Traditional ROI: 3.06%
2 High Ridge Rd Ashland, MA Welcome to 2 High Ridgeâ a truly special home tucked away on a cul-de-sac abutting Town ...	4 beds \| 3 baths \| 3,768 sq.ft.	$1,250,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 1.72% Airbnb Rental Income: $1171 Traditional Rental Income: $4357 Airbnb ROI: -1.35% Traditional ROI: 1.72%
84 Meeting House Path #84 Ashland, MA WELCOME TO THIS DESIRABLE UNIT IN A QUIET NEIGHBORHOOD. WELL-MAINTAINED UNIT, WITH TWO BED...	2 beds \| 2 baths \| 1,316 sq.ft.	$489,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.13% Airbnb Rental Income: $2977 Traditional Rental Income: $2864 Airbnb ROI: 1.89% Traditional ROI: 3.13%
3 Johnson St Ashland, MA This well cared for, 3 bedroom 2 full bath home in Ashland is ready for new owners! Nestle...	3 beds \| 2 baths \| 1,700 sq.ft.	$579,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.8% Airbnb Rental Income: $2506 Traditional Rental Income: $3313 Airbnb ROI: 1.19% Traditional ROI: 3.8%
9 South Street Ashland, MA Welcome to this beautifully maintained center entrance colonial, perfect blend of classic ...	4 beds \| 3 baths \| 2,080 sq.ft.	$774,900	Airbnb cash on cash: -1.25% Traditional cash on cash: 3.09% Airbnb Rental Income: $1171 Traditional Rental Income: $3922 Airbnb ROI: -1.25% Traditional ROI: 3.09%
83 Spyglass Hill Drive #83 Ashland, MA Welcome to the good life at Spyglass Hill! Enjoy the unbeatable location just a short stro...	2 beds \| 3 baths \| 1,624 sq.ft.	$485,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.18% Airbnb Rental Income: $2977 Traditional Rental Income: $3345 Airbnb ROI: 1.86% Traditional ROI: 4.18%
102 Captain Eames Cir #102 Ashland, MA Located in the desirable Starlight Village, this 2-bedroom tri-level townhouse awaits you....	2 beds \| 3 baths \| 1,967 sq.ft.	$524,900	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.61% Airbnb Rental Income: $2977 Traditional Rental Income: $3441 Airbnb ROI: 1.27% Traditional ROI: 3.61%

Real Estate investment in Ashland, MA

There are 9 properties for sale in the city of Ashland . The median list price in Ashland is $650,000 and the average price per square foot is $302. In October 2025, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,441.

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

There are 9 investment properties available for sale in Ashland.

In 2025, 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 $3,441.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, MA

12 Braeburn Lane #12

Ashland, MA

2 beds | 3 baths | 2,067 sq.ft.

$750,000

Airbnb cash on cash: 0%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $2977

Traditional Rental Income: $3612

Airbnb ROI: 0%

Traditional ROI: 1.89%

8 Pilgrim Road

Ashland, MA

4 beds | 3 baths | 2,670 sq.ft.

$1,159,999

Airbnb cash on cash: -1.42%

Traditional cash on cash: 1.7%

Airbnb Rental Income: $1171

Traditional Rental Income: $4150

Airbnb ROI: -1.42%

Traditional ROI: 1.7%

17 Sewell St

Ashland, MA

3 beds | 2 baths | 2,191 sq.ft.

$650,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2506

Traditional Rental Income: $3315

Airbnb ROI: 0.72%

Traditional ROI: 3.06%

2 High Ridge Rd

Ashland, MA

4 beds | 3 baths | 3,768 sq.ft.

$1,250,000

Airbnb cash on cash: -1.35%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $1171

Traditional Rental Income: $4357

Airbnb ROI: -1.35%

Traditional ROI: 1.72%

84 Meeting House Path #84

Ashland, MA

2 beds | 2 baths | 1,316 sq.ft.

$489,900

Airbnb cash on cash: 1.89%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $2977

Traditional Rental Income: $2864

Airbnb ROI: 1.89%

Traditional ROI: 3.13%

3 Johnson St

Ashland, MA

3 beds | 2 baths | 1,700 sq.ft.

$579,900

Airbnb cash on cash: 1.19%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2506

Traditional Rental Income: $3313

Airbnb ROI: 1.19%

Traditional ROI: 3.8%

9 South Street

Ashland, MA

4 beds | 3 baths | 2,080 sq.ft.

$774,900

Airbnb cash on cash: -1.25%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $1171

Traditional Rental Income: $3922

Airbnb ROI: -1.25%

Traditional ROI: 3.09%

83 Spyglass Hill Drive #83

Ashland, MA

2 beds | 3 baths | 1,624 sq.ft.

$485,000

Airbnb cash on cash: 1.86%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2977

Traditional Rental Income: $3345

Airbnb ROI: 1.86%