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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: N/A Traditional cash on cash: 7.74% Airbnb Rental Income: $null Traditional Rental Income: $2670 Airbnb ROI: N/A Traditional ROI: 7.74%
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: N/A Traditional cash on cash: 11.29% Airbnb Rental Income: $null Traditional Rental Income: $3281 Airbnb ROI: N/A Traditional ROI: 11.29%
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: 4.55% Traditional cash on cash: 8.55% Airbnb Rental Income: $2555 Traditional Rental Income: $3032 Airbnb ROI: 4.55% 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 \| 1,705 sq.ft.	$415,000	Airbnb cash on cash: -2.52% Traditional cash on cash: 3.42% Airbnb Rental Income: $732 Traditional Rental Income: $2729 Airbnb ROI: -2.52% Traditional ROI: 3.42%
30 Mohawk Trl Greenfield, MA 30 Mohawk Trl, Greenfield, MA 01301 \| Multi Family	3 beds \| 3 baths \| 1,617 sq.ft.	$350,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 7.63% Airbnb Rental Income: $732 Traditional Rental Income: $3332 Airbnb ROI: -1.22% Traditional ROI: 7.63%
104 Silver St Greenfield, MA 104 Silver St, Greenfield, MA 01301 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.06% Airbnb Rental Income: $null Traditional Rental Income: $1383 Airbnb ROI: N/A Traditional ROI: 11.06%
20 Myers Farm Ln #20 Greenfield, MA 20 Myers Farm Ln #20, Greenfield, MA 01301 \| Condo/Coop	1 beds \| 2 baths \| 1,255 sq.ft.	$299,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 3.36% Airbnb Rental Income: $1739 Traditional Rental Income: $2453 Airbnb ROI: -0.87% Traditional ROI: 3.36%
167 South Shelburne Rd Greenfield, MA 167 South Shelburne Rd, Greenfield, MA 01301 \| Single Family Residential	4 beds \| 4 baths \| 3,737 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.37% Airbnb Rental Income: $null Traditional Rental Income: $5465 Airbnb ROI: N/A Traditional ROI: 7.37%
198 Leyden Rd Greenfield, MA 198 Leyden Rd, Greenfield, MA 01301 \| Single Family Residential	5 beds \| 2 baths \| 2,612 sq.ft.	$545,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $3497 Airbnb ROI: N/A Traditional ROI: 4.46%
36 Green River Rd Greenfield, MA 36 Green River Rd, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 1 baths \| 1,257 sq.ft.	$450,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 3.38% Airbnb Rental Income: $2555 Traditional Rental Income: $2452 Airbnb ROI: 2.17% Traditional ROI: 3.38%
12 Barton Hts Greenfield, MA 12 Barton Hts, Greenfield, MA 01301 \| Single Family Residential	2 beds \| 1 baths \| 911 sq.ft.	$269,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 5% Airbnb Rental Income: $732 Traditional Rental Income: $1931 Airbnb ROI: -0.93% Traditional ROI: 5%
40 Newell Pond Rd Greenfield, MA 40 Newell Pond Rd, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 1 baths \| 1,220 sq.ft.	$369,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.5% Airbnb Rental Income: $2555 Traditional Rental Income: $2418 Airbnb ROI: 3.12% Traditional ROI: 4.5%
68 Hastings St Greenfield, MA 68 Hastings St, Greenfield, MA 01301 \| Single Family Residential	4 beds \| 2 baths \| 1,862 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.38% Airbnb Rental Income: $null Traditional Rental Income: $3596 Airbnb ROI: N/A Traditional ROI: 7.38%
22 Union St Greenfield, MA 22 Union St, Greenfield, MA 01301 \| Multi Family	6 beds \| 2 baths \| 3,076 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $3486 Airbnb ROI: N/A Traditional ROI: 8.1%
52 Prospect St #A Greenfield, MA 52 Prospect St #A, Greenfield, MA 01376 \| Townhouse	2 beds \| 1 baths \| 823 sq.ft.	$209,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 5.84% Airbnb Rental Income: $732 Traditional Rental Income: $1910 Airbnb ROI: -1.68% Traditional ROI: 5.84%

Real Estate investment in Greenfield, MA

There are 19 properties for sale in the city of Greenfield . The median list price in Greenfield is $332,328 and the average price per square foot is $166. In June 2026, the average monthly cash on cash return in Greenfield is 7.00%. The average monthly rental income in Greenfield is $2,729.

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

There are 19 investment properties available for sale in Greenfield.

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

The ROI for Short-Term is higher than the Long-Term in Greenfield with average rental income of $2,555.

Your search for investment property begins and ends here

Investment Property for Sale in Greenfield, MA

37 Cleveland St

Greenfield, MA

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

$274,500

Airbnb cash on cash: N/A

Traditional cash on cash: 7.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2670

Airbnb ROI: N/A

Traditional ROI: 7.74%

2 Water St

Greenfield, MA

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

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.29%

Airbnb Rental Income: $null

Traditional Rental Income: $3281

Airbnb ROI: N/A

Traditional ROI: 11.29%

13 River St

Greenfield, MA

3 beds | 2 baths | 2,350 sq.ft.

$289,900

Airbnb cash on cash: 4.55%

Traditional cash on cash: 8.55%

Airbnb Rental Income: $2555

Traditional Rental Income: $3032

Airbnb ROI: 4.55%

Traditional ROI: 8.55%

306 Country Side Rd #306

Greenfield, MA

2 beds | 2 baths | 1,705 sq.ft.

$415,000

Airbnb cash on cash: -2.52%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $732

Traditional Rental Income: $2729

Airbnb ROI: -2.52%

Traditional ROI: 3.42%

30 Mohawk Trl

Greenfield, MA

3 beds | 3 baths | 1,617 sq.ft.

$350,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: 7.63%

Airbnb Rental Income: $732

Traditional Rental Income: $3332

Airbnb ROI: -1.22%

Traditional ROI: 7.63%

104 Silver St

Greenfield, MA

N/A beds | N/A baths | N/A

$100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.06%

Airbnb Rental Income: $null

Traditional Rental Income: $1383

Airbnb ROI: N/A

Traditional ROI: 11.06%

20 Myers Farm Ln #20

Greenfield, MA

1 beds | 2 baths | 1,255 sq.ft.

$299,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1739

Traditional Rental Income: $2453

Airbnb ROI: -0.87%

Traditional ROI: 3.36%

167 South Shelburne Rd

Greenfield, MA

4 beds | 4 baths | 3,737 sq.ft.

$599,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.37%

Airbnb Rental Income: $null

Traditional Rental Income: $5465

Airbnb ROI: N/A