Real Estate Investment Properties for Sale in Greenfield, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
71 Washington St Greenfield, MA Alert! The reserve price is being revealed on this property so you will know the bid to b...	2 beds \| 1 baths \| 887 sq.ft.	$235,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 5.12% Airbnb Rental Income: $1411 Traditional Rental Income: $1691 Airbnb ROI: 1.95% Traditional ROI: 5.12%
73 Washington St Greenfield, MA 73 Washington St, Greenfield, MA 01301 \| Single Family Residential	2 beds \| 1 baths \| 843 sq.ft.	$139,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 9.77% Airbnb Rental Income: $1411 Traditional Rental Income: $1700 Airbnb ROI: 4.46% Traditional ROI: 9.77%
8 Water St Greenfield, MA 8 Water, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 2 baths \| 1,409 sq.ft.	$265,900	Airbnb cash on cash: 3.71% Traditional cash on cash: 8.78% Airbnb Rental Income: $2124 Traditional Rental Income: $2852 Airbnb ROI: 3.71% Traditional ROI: 8.78%
37 Cleveland St Greenfield, MA 37 Cleveland St, Greenfield, MA 01301 \| Multi Family	2 beds \| 2 baths \| 1,668 sq.ft.	$274,500	Airbnb cash on cash: 3.54% Traditional cash on cash: 7.74% Airbnb Rental Income: $2124 Traditional Rental Income: $2670 Airbnb ROI: 3.54% Traditional ROI: 7.74%
173-175 Conway Greenfield, MA 173-175 Conway, Greenfield, MA 01301 \| Multi Family	6 beds \| 4 baths \| 2,850 sq.ft.	$475,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 7.96% Airbnb Rental Income: $2124 Traditional Rental Income: $4619 Airbnb ROI: 1.13% Traditional ROI: 7.96%
2 Water St Greenfield, MA 2 Water St, Greenfield, MA 01301 \| Multi Family	5 beds \| 2 baths \| 1,826 sq.ft.	$250,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 11.29% Airbnb Rental Income: $2124 Traditional Rental Income: $3281 Airbnb ROI: 4.09% Traditional ROI: 11.29%
85 Verde Dr Greenfield, MA 85 Verde Dr, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 2 baths \| 2,625 sq.ft.	$825,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.09% Airbnb Rental Income: $2124 Traditional Rental Income: $3408 Airbnb ROI: -0.29% Traditional ROI: 2.09%
20 Dunnell Rd Greenfield, MA Tucked along a quiet street, this storybook Greenfield home invites you in with timeless c...	2 beds \| 2 baths \| 1,370 sq.ft.	$365,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 5.69% Airbnb Rental Income: $1411 Traditional Rental Income: $2820 Airbnb ROI: 0.34% Traditional ROI: 5.69%
13 River St Greenfield, MA 13 River St, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 2 baths \| 2,350 sq.ft.	$289,900	Airbnb cash on cash: 3.23% Traditional cash on cash: 8.55% Airbnb Rental Income: $2124 Traditional Rental Income: $3032 Airbnb ROI: 3.23% Traditional ROI: 8.55%
306 Country Side Rd #306 Greenfield, MA 306 Country Side Rd #306, Greenfield, MA 01301 \| Condo/Coop	2 beds \| 2 baths \| 1,606 sq.ft.	$425,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 3.28% Airbnb Rental Income: $1411 Traditional Rental Income: $2729 Airbnb ROI: -1.09% Traditional ROI: 3.28%
159 Chapman St Greenfield, MA 159 Chapman St, Greenfield, MA 01301 \| Single Family Residential	4 beds \| 2 baths \| 2,024 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.07% Airbnb Rental Income: $null Traditional Rental Income: $3362 Airbnb ROI: N/A Traditional ROI: 7.07%

Real Estate investment in Greenfield, MA

There are 15 properties for sale in the city of Greenfield . The median list price in Greenfield is $296,000 and the average price per square foot is $149. In May 2026, the average monthly cash on cash return in Greenfield is 8.00%. The average monthly rental income in Greenfield is $2,775.

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

There are 15 investment properties available for sale in Greenfield.

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

The ROI for Long-Term is higher than the Short-Term in Greenfield with average rental income of $2,775.

Your search for investment property begins and ends here

Investment Property for Sale in Greenfield, MA

71 Washington St

Greenfield, MA

2 beds | 1 baths | 887 sq.ft.

$235,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1411

Traditional Rental Income: $1691

Airbnb ROI: 1.95%

Traditional ROI: 5.12%

73 Washington St

Greenfield, MA

2 beds | 1 baths | 843 sq.ft.

$139,900

Airbnb cash on cash: 4.46%

Traditional cash on cash: 9.77%

Airbnb Rental Income: $1411

Traditional Rental Income: $1700

Airbnb ROI: 4.46%

Traditional ROI: 9.77%

8 Water St

Greenfield, MA

3 beds | 2 baths | 1,409 sq.ft.

$265,900

Airbnb cash on cash: 3.71%

Traditional cash on cash: 8.78%

Airbnb Rental Income: $2124

Traditional Rental Income: $2852

Airbnb ROI: 3.71%

Traditional ROI: 8.78%

37 Cleveland St

Greenfield, MA

2 beds | 2 baths | 1,668 sq.ft.

$274,500

Airbnb cash on cash: 3.54%

Traditional cash on cash: 7.74%

Airbnb Rental Income: $2124

Traditional Rental Income: $2670

Airbnb ROI: 3.54%

Traditional ROI: 7.74%

173-175 Conway

Greenfield, MA

6 beds | 4 baths | 2,850 sq.ft.

$475,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 7.96%

Airbnb Rental Income: $2124

Traditional Rental Income: $4619

Airbnb ROI: 1.13%

Traditional ROI: 7.96%

2 Water St

Greenfield, MA

5 beds | 2 baths | 1,826 sq.ft.

$250,000

Airbnb cash on cash: 4.09%

Traditional cash on cash: 11.29%

Airbnb Rental Income: $2124

Traditional Rental Income: $3281

Airbnb ROI: 4.09%

Traditional ROI: 11.29%

85 Verde Dr

Greenfield, MA

3 beds | 2 baths | 2,625 sq.ft.

$825,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $2124

Traditional Rental Income: $3408

Airbnb ROI: -0.29%

Traditional ROI: 2.09%

20 Dunnell Rd

Greenfield, MA

2 beds | 2 baths | 1,370 sq.ft.

$365,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1411

Traditional Rental Income: $2820

Airbnb ROI: 0.34%