Real Estate Investment Properties for Sale in Chesterfield, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
73 North Road Chesterfield, MA Pastoral setting on 5 acres wrapped in solitude and peace at this unique retreat less than...	2 beds \| 2 baths \| 1,531 sq.ft.	$465,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 4.47% Airbnb Rental Income: $4152 Traditional Rental Income: $2916 Airbnb ROI: 5.29% Traditional ROI: 4.47%
Investment Properties for Sale in Other Cities of Massachusetts
40 Traveler St #507 Boston , MA Welcome to Siena Condominium, where modern city living meets elevated comfort. This south-...	1 beds \| 1 baths \| 741 sq.ft.	$760,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.21% Airbnb Rental Income: $2039 Traditional Rental Income: $2633 Airbnb ROI: -1.38% Traditional ROI: 0.21%
699 Hyde Park Ave #6 Boston , MA Sunny and well-maintained 2-bedroom condo in a convenient Roslindale location near Forest ...	2 beds \| 1 baths \| 746 sq.ft.	$414,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.16% Airbnb Rental Income: $2148 Traditional Rental Income: $2121 Airbnb ROI: 0.82% Traditional ROI: 2.16%
180 Commonwealth Ave #7 Boston , MA 180 Commonwealth Ave #7, Boston, MA 02116 \| Condo/Coop	3 beds \| 2 baths \| 1,070 sq.ft.	$1,450,000	Airbnb cash on cash: 0.07% Traditional cash on cash: -0.7% Airbnb Rental Income: $5016 Traditional Rental Income: $2954 Airbnb ROI: 0.07% Traditional ROI: -0.7%
74 Appleton St #4 Boston , MA 74 Appleton St #4, Boston, MA 02116 \| Condo/Coop	2 beds \| 1 baths \| 1,315 sq.ft.	$1,890,000	Airbnb cash on cash: -1.25% Traditional cash on cash: -1% Airbnb Rental Income: $2817 Traditional Rental Income: $2598 Airbnb ROI: -1.25% Traditional ROI: -1%
35 Fay St #202 Boston , MA 35 Fay St #202, Boston, MA 02118 \| Condo/Coop	1 beds \| 1 baths \| 1,004 sq.ft.	$775,000	Airbnb cash on cash: -1.38% Traditional cash on cash: -0.5% Airbnb Rental Income: $2142 Traditional Rental Income: $2228 Airbnb ROI: -1.38% Traditional ROI: -0.5%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$8,450,000	Airbnb cash on cash: -2.06% Traditional cash on cash: -1.39% Airbnb Rental Income: $1903 Traditional Rental Income: $6608 Airbnb ROI: -2.06% Traditional ROI: -1.39%
319 Forest Hills St #2 Boston , MA 319 Forest Hills St #2, Boston, MA 02130 \| Condo/Coop	2 beds \| 2 baths \| 1,070 sq.ft.	$769,500	Airbnb cash on cash: 0.52% Traditional cash on cash: 1.89% Airbnb Rental Income: $3068 Traditional Rental Income: $3352 Airbnb ROI: 0.52% Traditional ROI: 1.89%
198 Byron St Boston , MA 198 Byron St, Boston, MA 02128 \| Single Family Residential	3 beds \| 1 baths \| 2,385 sq.ft.	$1,150,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.22% Airbnb Rental Income: $3055 Traditional Rental Income: $2708 Airbnb ROI: -0.11% Traditional ROI: 0.22%
13 Wellington St Boston , MA Beautiful townhouse on quiet, tree-lined street minutes from T, Prudential Center, Symphon...	4 beds \| 3 baths \| 3,110 sq.ft.	$3,590,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.38% Airbnb Rental Income: $2904 Traditional Rental Income: $4312 Airbnb ROI: -1.01% Traditional ROI: -0.38%
1 Franklin St #1205 Boston , MA Move in and see why Millennium Tower Boston is the evolution of luxury residential living!...	2 beds \| 2 baths \| 1,161 sq.ft.	$1,675,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 0.19% Airbnb Rental Income: $3119 Traditional Rental Income: $5552 Airbnb ROI: -1.83% Traditional ROI: 0.19%
14 Avondale St Boston , MA 14 Avondale St, Boston, MA 02124 \| Single Family Residential	4 beds \| 2 baths \| 1,768 sq.ft.	$639,900	Airbnb cash on cash: 2.3% Traditional cash on cash: 3.65% Airbnb Rental Income: $3575 Traditional Rental Income: $3600 Airbnb ROI: 2.3% Traditional ROI: 3.65%
588 S Orleans Road Orleans , MA Lush lawns and hydrangeas flanking a winding seashell driveway create a storybook entrance...	3 beds \| 3 baths \| 2,841 sq.ft.	$1,595,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.04% Airbnb Rental Income: $1623 Traditional Rental Income: $3944 Airbnb ROI: -0.84% Traditional ROI: 1.04%
43 S Highland Road Truro , MA Unique, architecturally designed contemporary cape home set on 1.54 private wooded acres a...	2 beds \| 1 baths \| 1,317 sq.ft.	$925,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $1545 Traditional Rental Income: $2441 Airbnb ROI: -0.43% Traditional ROI: 1.13%

Real Estate investment in Chesterfield, MA

There are 1 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $465,000 and the average price per square foot is $304. In June 2026, the average monthly cash on cash return in Chesterfield is 4.00%. The average monthly rental income in Chesterfield is $2,916.

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

There are 1 investment properties available for sale in Chesterfield.

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

The ROI for Short-Term is higher than the Long-Term in Chesterfield with average rental income of $4,152.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, MA

73 North Road

Chesterfield, MA

2 beds | 2 baths | 1,531 sq.ft.

$465,000

Airbnb cash on cash: 5.29%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $4152

Traditional Rental Income: $2916

Airbnb ROI: 5.29%

Traditional ROI: 4.47%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

1 beds | 1 baths | 741 sq.ft.

$760,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 0.21%

Airbnb Rental Income: $2039

Traditional Rental Income: $2633

Airbnb ROI: -1.38%

Traditional ROI: 0.21%

Boston , MA

2 beds | 1 baths | 746 sq.ft.

$414,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $2148

Traditional Rental Income: $2121

Airbnb ROI: 0.82%

Traditional ROI: 2.16%

Boston , MA

3 beds | 2 baths | 1,070 sq.ft.

$1,450,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: -0.7%

Airbnb Rental Income: $5016

Traditional Rental Income: $2954

Airbnb ROI: 0.07%

Traditional ROI: -0.7%

Boston , MA

2 beds | 1 baths | 1,315 sq.ft.

$1,890,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: -1%

Airbnb Rental Income: $2817

Traditional Rental Income: $2598

Airbnb ROI: -1.25%

Traditional ROI: -1%

Boston , MA

1 beds | 1 baths | 1,004 sq.ft.

$775,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: -0.5%

Airbnb Rental Income: $2142

Traditional Rental Income: $2228

Airbnb ROI: -1.38%

Traditional ROI: -0.5%

Boston , MA

4 beds | 5 baths | 5,194 sq.ft.

$8,450,000

Airbnb cash on cash: -2.06%

Traditional cash on cash: -1.39%

Airbnb Rental Income: $1903

Traditional Rental Income: $6608

Airbnb ROI: -2.06%

Traditional ROI: -1.39%

Boston , MA

2 beds | 2 baths | 1,070 sq.ft.

$769,500

Airbnb cash on cash: 0.52%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $3068

Traditional Rental Income: $3352

Airbnb ROI: 0.52%

Traditional ROI: 1.89%

Boston , MA

3 beds | 1 baths | 2,385 sq.ft.

$1,150,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 0.22%