Real Estate Investment Properties for Sale in Brookline, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3 Glenoe Rd Brookline, MA Nearly $700k below assessed value, this 4855 sq ft colonial in one of Brookline's most sou...	4 beds \| 4 baths \| 4,855 sq.ft.	$2,195,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 1.06% Airbnb Rental Income: $5876 Traditional Rental Income: $6904 Airbnb ROI: -0.02% Traditional ROI: 1.06%
20 Chapel St #B811 Brookline, MA 20 Chapel St #B811, Brookline, MA 02446 \| Condo/Coop	4 beds \| 4 baths \| 2,463 sq.ft.	$2,500,000	Airbnb cash on cash: -2.36% Traditional cash on cash: -1.41% Airbnb Rental Income: $4022 Traditional Rental Income: $5363 Airbnb ROI: -2.36% Traditional ROI: -1.41%
239 Kelton St #41 Brookline, MA 239 Kelton St #41, Brookline, MA 02134 \| Condo/Coop	2 beds \| 1 baths \| 690 sq.ft.	$465,000	Airbnb cash on cash: 7.86% Traditional cash on cash: 1.41% Airbnb Rental Income: $6268 Traditional Rental Income: $2224 Airbnb ROI: 7.86% Traditional ROI: 1.41%
116 Thorndike St #1 Brookline, MA 116 Thorndike St #1, Brookline, MA 02446 \| Condo/Coop	4 beds \| 3 baths \| 2,663 sq.ft.	$2,500,000	Airbnb cash on cash: 0.35% Traditional cash on cash: -0.44% Airbnb Rental Income: $7900 Traditional Rental Income: $4572 Airbnb ROI: 0.35% Traditional ROI: -0.44%
75 Goddard Ave Brookline, MA 75 Goddard Ave, Boston, MA 02445 \| Single Family Residential	7 beds \| 7 baths \| 6,000 sq.ft.	$6,800,000	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.89% Airbnb Rental Income: $8327 Traditional Rental Income: $8475 Airbnb ROI: -1.17% Traditional ROI: -0.89%
79 Goddard Ave Brookline, MA 79 Goddard Ave, Boston, MA 02445 \| Other	N/A beds \| N/A baths \| N/A	$3,150,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -1.7% Airbnb Rental Income: $4112 Traditional Rental Income: $1618 Airbnb ROI: -1.15% Traditional ROI: -1.7%
1161 Commonwealth Ave #8 Brookline, MA 1161 Commonwealth Ave #8, Brookline, MA 02134 \| Condo/Coop	2 beds \| 1 baths \| 936 sq.ft.	$549,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 0.34% Airbnb Rental Income: $6268 Traditional Rental Income: $2275 Airbnb ROI: 5.72% Traditional ROI: 0.34%
147 Kelton #305 Brookline, MA 147 Kelton #305, Brookline, MA 02134 \| Condo/Coop	2 beds \| 2 baths \| 974 sq.ft.	$649,999	Airbnb cash on cash: 5.11% Traditional cash on cash: 1.41% Airbnb Rental Income: $6268 Traditional Rental Income: $2788 Airbnb ROI: 5.11% Traditional ROI: 1.41%
1778 Beacon St unit: 302 Brookline, MA A one of one in Brookline - immerse yourself in this sun-filled penthouse that seamlessly ...	2 beds \| 1 baths \| 1,157 sq.ft.	$1,049,000	Airbnb cash on cash: -1.5% Traditional cash on cash: -0.51% Airbnb Rental Income: $1986 Traditional Rental Income: $2423 Airbnb ROI: -1.5% Traditional ROI: -0.51%
33 Pond Ave #919 Brookline, MA 33 Pond Ave #919, Brookline, MA 02445 \| Condo/Coop	2 beds \| 2 baths \| 1,270 sq.ft.	$849,000	Airbnb cash on cash: -1.82% Traditional cash on cash: -0.4% Airbnb Rental Income: $2434 Traditional Rental Income: $2961 Airbnb ROI: -1.82% Traditional ROI: -0.4%
20 Chapel St #A 303 Brookline, MA 20 Chapel St #A 303, Brookline, MA 02446 \| Condo/Coop	1 beds \| 1 baths \| 795 sq.ft.	$725,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.57% Airbnb Rental Income: $2322 Traditional Rental Income: $2059 Airbnb ROI: -1.03% Traditional ROI: -0.57%
77 Pond Ave #401 Brookline, MA 77 Pond Ave #401, Brookline, MA 02445 \| Condo/Coop	3 beds \| 2 baths \| 1,565 sq.ft.	$1,125,000	Airbnb cash on cash: 0.86% Traditional cash on cash: -0.72% Airbnb Rental Income: $6267 Traditional Rental Income: $3374 Airbnb ROI: 0.86% Traditional ROI: -0.72%
45 Bartlett Cres #105 Brookline, MA 45 Bartlett Cres #105, Brookline, MA 02446 \| Condo/Coop	2 beds \| 2 baths \| 899 sq.ft.	$1,099,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 0.29% Airbnb Rental Income: $6268 Traditional Rental Income: $3227 Airbnb ROI: 2.06% Traditional ROI: 0.29%
45 Bartlett Cres #203 Brookline, MA 45 Bartlett Cres #203, Brookline, MA 02446 \| Condo/Coop	2 beds \| 2 baths \| 973 sq.ft.	$1,199,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.02% Airbnb Rental Income: $6268 Traditional Rental Income: $3201 Airbnb ROI: 1.66% Traditional ROI: 0.02%
36 Gordon St Brookline, MA 36 Gordon St, Brookline, MA 02134 \| Multi Family	8 beds \| 3 baths \| 3,246 sq.ft.	$1,799,999	Airbnb cash on cash: 0.73% Traditional cash on cash: 0.36% Airbnb Rental Income: $6268 Traditional Rental Income: $4404 Airbnb ROI: 0.73% Traditional ROI: 0.36%
1002 Beacon St Brookline, MA 1002 Beacon St, Brookline, MA 02446 \| Multi Family	3 beds \| 4 baths \| 8,325 sq.ft.	$5,990,000	Airbnb cash on cash: -1.93% Traditional cash on cash: -1.33% Airbnb Rental Income: $2322 Traditional Rental Income: $5076 Airbnb ROI: -1.93% Traditional ROI: -1.33%
122 Day St #3 Brookline, MA 122 Day St #3, Brookline, MA 02130 \| Condo/Coop	3 beds \| 1 baths \| 1,026 sq.ft.	$645,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 1.42% Airbnb Rental Income: $6267 Traditional Rental Income: $2599 Airbnb ROI: 5.47% Traditional ROI: 1.42%
45 Gordon St #4 Brookline, MA 45 Gordon St #4, Brookline, MA 02134 \| Condo/Coop	2 beds \| 1 baths \| 675 sq.ft.	$489,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 1.43% Airbnb Rental Income: $6268 Traditional Rental Income: $2151 Airbnb ROI: 7.73% Traditional ROI: 1.43%
36 Osborne Rd Brookline, MA 36 Osborne Rd, Brookline, MA 02446 \| Single Family Residential	4 beds \| 4 baths \| 4,069 sq.ft.	$3,450,000	Airbnb cash on cash: -0.25% Traditional cash on cash: -0.45% Airbnb Rental Income: $7900 Traditional Rental Income: $5776 Airbnb ROI: -0.25% Traditional ROI: -0.45%
36 Osborne Rd #1 Brookline, MA 36 Osborne Rd #1, Brookline, MA 02446 \| Townhouse	4 beds \| 4 baths \| 4,069 sq.ft.	$3,450,000	Airbnb cash on cash: -0.25% Traditional cash on cash: -0.43% Airbnb Rental Income: $7900 Traditional Rental Income: $5838 Airbnb ROI: -0.25% Traditional ROI: -0.43%
77 Pond Ave #1009 Brookline, MA 77 Pond Ave #1009, Brookline, MA 02445 \| Condo/Coop	1 beds \| 1 baths \| 860 sq.ft.	$566,000	Airbnb cash on cash: 2.39% Traditional cash on cash: -0.1% Airbnb Rental Income: $4351 Traditional Rental Income: $2118 Airbnb ROI: 2.39% Traditional ROI: -0.1%
1495 Beacon St unit: G Brookline, MA Prime Coolidge Corner location with parking just outside and in-unit laundry! Don't miss t...	2 beds \| 1 baths \| 962 sq.ft.	$699,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.59% Airbnb Rental Income: $1896 Traditional Rental Income: $2301 Airbnb ROI: -0.81% Traditional ROI: 0.59%
33 Pond Ave #1106 Brookline, MA 33 Pond Ave #1106, Brookline, MA 02445 \| Condo/Coop	1 beds \| 1 baths \| 870 sq.ft.	$549,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.21% Airbnb Rental Income: $2354 Traditional Rental Income: $2118 Airbnb ROI: -0.88% Traditional ROI: -0.21%
401 Clinton Rd Brookline, MA 401 Clinton Rd, Brookline, MA 02445 \| Single Family Residential	5 beds \| 3 baths \| 3,463 sq.ft.	$2,575,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -0.25% Airbnb Rental Income: $3245 Traditional Rental Income: $4798 Airbnb ROI: -1.21% Traditional ROI: -0.25%
1263 Commonwealth Ave #4 Brookline, MA 1263 Commonwealth Ave #4, Brookline, MA 02134 \| Condo/Coop	2 beds \| 1 baths \| 968 sq.ft.	$575,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 1.01% Airbnb Rental Income: $6268 Traditional Rental Income: $2305 Airbnb ROI: 6.09% Traditional ROI: 1.01%
60 W Glen Rd #101 Brookline, MA 60 W Glen Rd #101, Brookline, MA 02445 \| Condo/Coop	2 beds \| 1 baths \| 740 sq.ft.	$809,000	Airbnb cash on cash: 2.67% Traditional cash on cash: -0.82% Airbnb Rental Income: $6066 Traditional Rental Income: $2239 Airbnb ROI: 2.67% Traditional ROI: -0.82%
77 Pond Ave #805 Brookline, MA 77 Pond Ave #805, Brookline, MA 02445 \| Condo/Coop	2 beds \| 2 baths \| 1,265 sq.ft.	$789,000	Airbnb cash on cash: 2.34% Traditional cash on cash: -0.23% Airbnb Rental Income: $6066 Traditional Rental Income: $2981 Airbnb ROI: 2.34% Traditional ROI: -0.23%
11 Mark #2 Brookline, MA 11 Mark #2, Brookline, MA 02130 \| Condo/Coop	2 beds \| 1 baths \| 830 sq.ft.	$586,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 1.19% Airbnb Rental Income: $6066 Traditional Rental Income: $2294 Airbnb ROI: 5.89% Traditional ROI: 1.19%
85 Brainerd #302 Brookline, MA 85 Brainerd #302, Brookline, MA 02134 \| Condo/Coop	2 beds \| 2 baths \| 1,020 sq.ft.	$850,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 0.47% Airbnb Rental Income: $6268 Traditional Rental Income: $2855 Airbnb ROI: 3.22% Traditional ROI: 0.47%
18 Glenville Ave #3A Brookline, MA 18 Glenville Ave #3A, Brookline, MA 02134 \| Condo/Coop	1 beds \| 1 baths \| 495 sq.ft.	$374,900	Airbnb cash on cash: 6.05% Traditional cash on cash: 1.42% Airbnb Rental Income: $4397 Traditional Rental Income: $1848 Airbnb ROI: 6.05% Traditional ROI: 1.42%
1874 Beacon St #4 Brookline, MA 1874 Beacon St #4, Brookline, MA 02445 \| Condo/Coop	2 beds \| 1 baths \| 955 sq.ft.	$725,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.58% Airbnb Rental Income: $1986 Traditional Rental Income: $2339 Airbnb ROI: -0.71% Traditional ROI: 0.58%
44 Washington St #915 Brookline, MA 44 Washington St #915, Brookline, MA 02445 \| Condo/Coop	N/A beds \| 1 baths \| 500 sq.ft.	$395,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.5% Airbnb Rental Income: $1978 Traditional Rental Income: $1737 Airbnb ROI: -0.25% Traditional ROI: 0.5%
239 Kelton St #11 Brookline, MA 239 Kelton St #11, Brookline, MA 02134 \| Condo/Coop	2 beds \| 1 baths \| 690 sq.ft.	$465,000	Airbnb cash on cash: 8.11% Traditional cash on cash: 1.5% Airbnb Rental Income: $6268 Traditional Rental Income: $2158 Airbnb ROI: 8.11% Traditional ROI: 1.5%
44 Washington St #508 Brookline, MA 44 Washington St #508, Brookline, MA 02445 \| Condo/Coop	N/A beds \| 1 baths \| 500 sq.ft.	$419,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 0.58% Airbnb Rental Income: $1978 Traditional Rental Income: $1737 Airbnb ROI: -0.13% Traditional ROI: 0.58%

Real Estate investment in Brookline, MA

There are 49 properties for sale in the city of Brookline . The median list price in Brookline is $755,000 and the average price per square foot is $354. In April 2026, the average monthly cash on cash return in Brookline is 1.00%. The average monthly rental income in Brookline is $2,433.

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

There are 49 investment properties available for sale in Brookline.

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

The ROI for Short-Term is higher than the Long-Term in Brookline with average rental income of $4,397.

Your search for investment property begins and ends here

Investment Property for Sale in Brookline, MA

3 Glenoe Rd

Brookline, MA

4 beds | 4 baths | 4,855 sq.ft.

$2,195,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $5876

Traditional Rental Income: $6904

Airbnb ROI: -0.02%

Traditional ROI: 1.06%

20 Chapel St #B811

Brookline, MA

4 beds | 4 baths | 2,463 sq.ft.

$2,500,000

Airbnb cash on cash: -2.36%

Traditional cash on cash: -1.41%

Airbnb Rental Income: $4022

Traditional Rental Income: $5363

Airbnb ROI: -2.36%

Traditional ROI: -1.41%

239 Kelton St #41

Brookline, MA

2 beds | 1 baths | 690 sq.ft.

$465,000

Airbnb cash on cash: 7.86%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $6268

Traditional Rental Income: $2224

Airbnb ROI: 7.86%

Traditional ROI: 1.41%

116 Thorndike St #1

Brookline, MA

4 beds | 3 baths | 2,663 sq.ft.

$2,500,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: -0.44%

Airbnb Rental Income: $7900

Traditional Rental Income: $4572

Airbnb ROI: 0.35%

Traditional ROI: -0.44%

75 Goddard Ave

Brookline, MA

7 beds | 7 baths | 6,000 sq.ft.

$6,800,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $8327

Traditional Rental Income: $8475

Airbnb ROI: -1.17%

Traditional ROI: -0.89%

79 Goddard Ave

Brookline, MA

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

$3,150,000

Airbnb cash on cash: -1.15%

Traditional cash on cash: -1.7%

Airbnb Rental Income: $4112

Traditional Rental Income: $1618

Airbnb ROI: -1.15%

Traditional ROI: -1.7%

1161 Commonwealth Ave #8

Brookline, MA

2 beds | 1 baths | 936 sq.ft.

$549,000

Airbnb cash on cash: 5.72%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $6268

Traditional Rental Income: $2275

Airbnb ROI: 5.72%

Traditional ROI: 0.34%

147 Kelton #305

Brookline, MA

2 beds | 2 baths | 974 sq.ft.

$649,999

Airbnb cash on cash: 5.11%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $6268

Traditional Rental Income: $2788

Airbnb ROI: 5.11%