Real Estate Investment Properties for Sale in Chestnut Hill, MA

Looking for investment property in Chestnut Hill, MA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Chestnut Hill, Massachusetts at the moment.
Other Investment Properties for Sale in Massachusetts
1 Huntington Ave #903 Boston , MA 1 Huntington Ave #903, Boston, MA 02116 \| Condo/Coop	3 beds \| 2 baths \| 2,702 sq.ft.	$4,750,000	Airbnb cash on cash: -1.98% Traditional cash on cash: -2.5% Airbnb Rental Income: $6970 Traditional Rental Income: $3347 Airbnb ROI: -1.98% Traditional ROI: -2.5%
11 Robinwood Ave Boston , MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,399,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 0.27% Airbnb Rental Income: $991 Traditional Rental Income: $4593 Airbnb ROI: -1.5% Traditional ROI: 0.27%
86 Savin Hill Ave #3 Boston , MA 86 Savin Hill Ave #3, Boston, MA 02125 \| Condo/Coop	2 beds \| 1 baths \| 598 sq.ft.	$395,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.45% Airbnb Rental Income: $2545 Traditional Rental Income: $2034 Airbnb ROI: 2.17% Traditional ROI: 2.45%
121 Portland St #505 Boston , MA 121 Portland St #505, Boston, MA 02114 \| Condo/Coop	1 beds \| 1 baths \| 481 sq.ft.	$575,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 0.77% Airbnb Rental Income: $4476 Traditional Rental Income: $2212 Airbnb ROI: 3.25% Traditional ROI: 0.77%
112 Roslindale Ave #2 Boston , MA 112 Roslindale Ave #2, Boston, MA 02131 \| Condo/Coop	3 beds \| 2 baths \| 1,183 sq.ft.	$629,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.53% Airbnb Rental Income: $3272 Traditional Rental Income: $3187 Airbnb ROI: 1.42% Traditional ROI: 2.53%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$9,450,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -1.48% Airbnb Rental Income: $6280 Traditional Rental Income: $6608 Airbnb ROI: -1.66% Traditional ROI: -1.48%
78 Hutchings St #1 Boston , MA 78 Hutchings St #1, Boston, MA 02121 \| Condo/Coop	3 beds \| 2 baths \| 1,837 sq.ft.	$639,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.87% Airbnb Rental Income: $3221 Traditional Rental Income: $3338 Airbnb ROI: 1.45% Traditional ROI: 2.87%
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: 1.21% Traditional cash on cash: 0.22% Airbnb Rental Income: $4746 Traditional Rental Income: $2708 Airbnb ROI: 1.21% Traditional ROI: 0.22%
188 Gladstone St #1 Boston , MA 188 Gladstone St #1, Boston, MA 02128 \| Condo/Coop	2 beds \| 2 baths \| 1,220 sq.ft.	$589,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 2.09% Airbnb Rental Income: $5523 Traditional Rental Income: $2852 Airbnb ROI: 4.93% Traditional ROI: 2.09%
280 Beacon St #1 Boston , MA 280 Beacon St #1, Boston, MA 02116 \| Condo/Coop	1 beds \| 1 baths \| 685 sq.ft.	$699,000	Airbnb cash on cash: 2.22% Traditional cash on cash: -0.33% Airbnb Rental Income: $4611 Traditional Rental Income: $1986 Airbnb ROI: 2.22% Traditional ROI: -0.33%
2 Larose Pl #13 Boston , MA 2 Larose Pl #13, Boston, MA 02135 \| Condo/Coop	2 beds \| 1 baths \| 735 sq.ft.	$529,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 0.91% Airbnb Rental Income: $3341 Traditional Rental Income: $2121 Airbnb ROI: 1.87% Traditional ROI: 0.91%
75 Burbank St #501 Boston , MA 75 Burbank St #501, Boston, MA 02115 \| Condo/Coop	1 beds \| 1 baths \| 425 sq.ft.	$518,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 0.62% Airbnb Rental Income: $4291 Traditional Rental Income: $1833 Airbnb ROI: 3.83% Traditional ROI: 0.62%
261 Commonwealth Ave #5 Boston , MA 261 Commonwealth Ave #5, Boston, MA 02116 \| Townhouse	1 beds \| 1 baths \| 1,155 sq.ft.	$1,349,000	Airbnb cash on cash: -0.38% Traditional cash on cash: -1.61% Airbnb Rental Income: $4611 Traditional Rental Income: $2106 Airbnb ROI: -0.38% Traditional ROI: -1.61%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| N/A baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 0.17% Airbnb Rental Income: $5959 Traditional Rental Income: $3577 Airbnb ROI: 0.76% Traditional ROI: 0.17%
496 Shore Road unit: 21 #21 Truro , MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,299,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 0.78% Airbnb Rental Income: $4038 Traditional Rental Income: $3609 Airbnb ROI: 0.42% Traditional ROI: 0.78%

Chestnut-hill, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 0 investment properties available for sale in Chestnut-hill.

In 2025, the best neighborhood to buy investment property is Chestnut Hill.

The ROI for Short-Term is higher than the Long-Term in Chestnut-hill with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chestnut Hill, MA

Other Investment Properties for Sale in Massachusetts

Boston , MA

3 beds | 2 baths | 2,702 sq.ft.

$4,750,000

Airbnb cash on cash: -1.98%

Traditional cash on cash: -2.5%

Airbnb Rental Income: $6970

Traditional Rental Income: $3347

Airbnb ROI: -1.98%

Traditional ROI: -2.5%

Boston , MA

5 beds | 4 baths | 3,390 sq.ft.

$2,399,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $991

Traditional Rental Income: $4593

Airbnb ROI: -1.5%

Traditional ROI: 0.27%

Boston , MA

2 beds | 1 baths | 598 sq.ft.

$395,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $2545

Traditional Rental Income: $2034

Airbnb ROI: 2.17%

Traditional ROI: 2.45%

Boston , MA

1 beds | 1 baths | 481 sq.ft.

$575,000

Airbnb cash on cash: 3.25%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $4476

Traditional Rental Income: $2212

Airbnb ROI: 3.25%

Traditional ROI: 0.77%

Boston , MA

3 beds | 2 baths | 1,183 sq.ft.

$629,000

Airbnb cash on cash: 1.42%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $3272

Traditional Rental Income: $3187

Airbnb ROI: 1.42%

Traditional ROI: 2.53%

Boston , MA

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

$9,450,000

Airbnb cash on cash: -1.66%

Traditional cash on cash: -1.48%

Airbnb Rental Income: $6280

Traditional Rental Income: $6608

Airbnb ROI: -1.66%

Traditional ROI: -1.48%

Boston , MA

3 beds | 2 baths | 1,837 sq.ft.

$639,000

Airbnb cash on cash: 1.45%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $3221

Traditional Rental Income: $3338

Airbnb ROI: 1.45%

Traditional ROI: 2.87%

Boston , MA

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

$1,150,000

Airbnb cash on cash: 1.21%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $4746

Traditional Rental Income: $2708

Airbnb ROI: 1.21%

Traditional ROI: 0.22%

Boston , MA

2 beds | 2 baths | 1,220 sq.ft.

$589,000

Airbnb cash on cash: 4.93%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $5523