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
63 James St Greenfield, MA Perched above a tree-lined street just a short walk to downtown, this flexible home on a d...	4 beds \| 2 baths \| 2,142 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.42% Airbnb Rental Income: $null Traditional Rental Income: $3433 Airbnb ROI: N/A Traditional ROI: 6.42%
12 Leonard St Greenfield, MA 12 Leonard St, Greenfield, MA 01301 \| Multi Family	4 beds \| 3 baths \| 2,440 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.22% Airbnb Rental Income: $null Traditional Rental Income: $3836 Airbnb ROI: N/A Traditional ROI: 10.22%
336 Plain Rd Greenfield, MA 336 Plain Rd, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 2 baths \| 1,954 sq.ft.	$435,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 4.82% Airbnb Rental Income: $2336 Traditional Rental Income: $2961 Airbnb ROI: 1.87% Traditional ROI: 4.82%
130 Laurel St Greenfield, MA 130 Laurel St, Greenfield, MA 01301 \| Single Family Residential	1 beds \| 1 baths \| 1,050 sq.ft.	$275,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.65% Airbnb Rental Income: $1606 Traditional Rental Income: $1615 Airbnb ROI: 1.86% Traditional ROI: 3.65%
696 Bernardston Rd Greenfield, MA 696 Bernardston Rd, Greenfield, MA 01301 \| Single Family Residential	3 beds \| 2 baths \| 2,184 sq.ft.	$499,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.96% Airbnb Rental Income: $2336 Traditional Rental Income: $2977 Airbnb ROI: 1.35% Traditional ROI: 3.96%
58A Laurel St #58A Greenfield, MA 58A Laurel St #58A, Greenfield, MA 01301 \| Condo/Coop	3 beds \| 2 baths \| 1,336 sq.ft.	$289,900	Airbnb cash on cash: 2.42% Traditional cash on cash: 6.02% Airbnb Rental Income: $2336 Traditional Rental Income: $2743 Airbnb ROI: 2.42% Traditional ROI: 6.02%
335 Federal St Greenfield, MA 335 Federal St, Greenfield, MA 01301 \| Multi Family	5 beds \| 2 baths \| 2,448 sq.ft.	$299,999	Airbnb cash on cash: 3.68% Traditional cash on cash: 8.91% Airbnb Rental Income: $2336 Traditional Rental Income: $3234 Airbnb ROI: 3.68% Traditional ROI: 8.91%
36 West St Greenfield, MA 36 West St, Greenfield, MA 01301 \| Multi Family	6 beds \| 2 baths \| 1,858 sq.ft.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.29% Airbnb Rental Income: $null Traditional Rental Income: $3262 Airbnb ROI: N/A Traditional ROI: 7.29%
311 Chapman St Greenfield, MA 311 Chapman St, Greenfield, MA 01301 \| Multi Family	3 beds \| 2 baths \| 1,334 sq.ft.	$210,000	Airbnb cash on cash: 6.15% Traditional cash on cash: 11.03% Airbnb Rental Income: $2336 Traditional Rental Income: $2730 Airbnb ROI: 6.15% Traditional ROI: 11.03%
163 S Shelburne Rd Greenfield, MA 163 S Shelburne Rd, Greenfield, MA 01301 \| Single Family Residential	4 beds \| 3 baths \| 3,228 sq.ft.	$568,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $4315 Airbnb ROI: N/A Traditional ROI: 5.74%
46 Colrain St Greenfield, MA 46 Colrain St, Greenfield, MA 01301 \| Single Family Residential	2 beds \| 2 baths \| 1,313 sq.ft.	$189,900	Airbnb cash on cash: 7.19% Traditional cash on cash: 11.02% Airbnb Rental Income: $2374 Traditional Rental Income: $2482 Airbnb ROI: 7.19% Traditional ROI: 11.02%
116-120 Elm St Greenfield, MA 116-120 Elm St, Greenfield, MA 01301 \| Multi Family	7 beds \| 4 baths \| 3,205 sq.ft.	$465,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 9.34% Airbnb Rental Income: $2374 Traditional Rental Income: $5122 Airbnb ROI: 1.68% Traditional ROI: 9.34%
111-113 Deerfield St Greenfield, MA 111-113 Deerfield St, Greenfield, MA 01301 \| Multi Family	7 beds \| 2 baths \| 2,648 sq.ft.	$324,900	Airbnb cash on cash: 3.34% Traditional cash on cash: 8% Airbnb Rental Income: $2374 Traditional Rental Income: $3214 Airbnb ROI: 3.34% Traditional ROI: 8%
11-13 Colrain St Greenfield, MA 11-13 Colrain St, Greenfield, MA 01301 \| Multi Family	7 beds \| 4 baths \| 2,622 sq.ft.	$595,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.64% Airbnb Rental Income: $2374 Traditional Rental Income: $4461 Airbnb ROI: 0.83% Traditional ROI: 5.64%
23 Robbins Rd Greenfield, MA 23 Robbins Rd, Greenfield, MA 01301 \| Single Family Residential	1 beds \| 1 baths \| N/A	$250,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 3.46% Airbnb Rental Income: $1606 Traditional Rental Income: $1433 Airbnb ROI: 2.26% Traditional ROI: 3.46%
414 Mohawk Trl Greenfield, MA 414 Mohawk Trl, Greenfield, MA 01301 \| Other	N/A beds \| N/A baths \| N/A	$199,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.96% Airbnb Rental Income: $953 Traditional Rental Income: $1259 Airbnb ROI: 0.5% Traditional ROI: 3.96%
6 Pickett Ln Greenfield, MA 6 Pickett Ln, Greenfield, MA 01301 \| Other	N/A beds \| N/A baths \| N/A	$120,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 7.82% Airbnb Rental Income: $953 Traditional Rental Income: $1254 Airbnb ROI: 2.22% Traditional ROI: 7.82%
372 Federal St Greenfield, MA 372 Federal St, Greenfield, MA 01301 \| Single Family Residential	4 beds \| 2 baths \| 2,613 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.39% Airbnb Rental Income: $null Traditional Rental Income: $3293 Airbnb ROI: N/A Traditional ROI: 11.39%
34 Brookside Ave Greenfield, MA 34 Brookside Ave, Greenfield, MA 01301 \| Single Family Residential	5 beds \| 2 baths \| 1,600 sq.ft.	$349,987	Airbnb cash on cash: N/A Traditional cash on cash: 7.64% Airbnb Rental Income: $null Traditional Rental Income: $3335 Airbnb ROI: N/A Traditional ROI: 7.64%

Real Estate investment in Greenfield, MA

There are 19 properties for sale in the city of Greenfield . The median list price in Greenfield is $300,950 and the average price per square foot is $146. In February 2026, the average monthly cash on cash return in Greenfield is 8.00%. The average monthly rental income in Greenfield is $3,053.

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 Long-Term is higher than the Short-Term in Greenfield with average rental income of $3,053.

Your search for investment property begins and ends here

Investment Property for Sale in Greenfield, MA

63 James St

Greenfield, MA

4 beds | 2 baths | 2,142 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.42%

Airbnb Rental Income: $null

Traditional Rental Income: $3433

Airbnb ROI: N/A

Traditional ROI: 6.42%

12 Leonard St

Greenfield, MA

4 beds | 3 baths | 2,440 sq.ft.

$319,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.22%

Airbnb Rental Income: $null

Traditional Rental Income: $3836

Airbnb ROI: N/A

Traditional ROI: 10.22%

336 Plain Rd

Greenfield, MA

3 beds | 2 baths | 1,954 sq.ft.

$435,000

Airbnb cash on cash: 1.87%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $2336

Traditional Rental Income: $2961

Airbnb ROI: 1.87%

Traditional ROI: 4.82%

130 Laurel St

Greenfield, MA

1 beds | 1 baths | 1,050 sq.ft.

$275,000

Airbnb cash on cash: 1.86%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $1606

Traditional Rental Income: $1615

Airbnb ROI: 1.86%

Traditional ROI: 3.65%

696 Bernardston Rd

Greenfield, MA

3 beds | 2 baths | 2,184 sq.ft.

$499,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $2336

Traditional Rental Income: $2977

Airbnb ROI: 1.35%

Traditional ROI: 3.96%

58A Laurel St #58A

Greenfield, MA

3 beds | 2 baths | 1,336 sq.ft.

$289,900

Airbnb cash on cash: 2.42%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $2336

Traditional Rental Income: $2743

Airbnb ROI: 2.42%

Traditional ROI: 6.02%

335 Federal St

Greenfield, MA

5 beds | 2 baths | 2,448 sq.ft.

$299,999

Airbnb cash on cash: 3.68%

Traditional cash on cash: 8.91%

Airbnb Rental Income: $2336

Traditional Rental Income: $3234

Airbnb ROI: 3.68%

Traditional ROI: 8.91%

36 West St

Greenfield, MA

6 beds | 2 baths | 1,858 sq.ft.

$355,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.29%

Airbnb Rental Income: $null

Traditional Rental Income: $3262

Airbnb ROI: N/A