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
321 Hammond Pond Parkway #103 Brookline, MA Sunny and luxury 2 beds & 2 baths condo built in 2012 with open floor plan. Fabulous chef'...	2 beds \| 2 baths \| 1,350 sq.ft.	$1,099,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.29% Airbnb Rental Income: $3273 Traditional Rental Income: $3089 Airbnb ROI: -0.25% Traditional ROI: 0.29%
52 Babcock Street #6 Brookline, MA Coolidge Corner Oasis!Move right into this sun-filled penthouse condo in the heart of Cool...	2 beds \| 1 baths \| 1,024 sq.ft.	$899,500	Airbnb cash on cash: 3.7% Traditional cash on cash: -0.14% Airbnb Rental Income: $6868 Traditional Rental Income: $2317 Airbnb ROI: 3.7% Traditional ROI: -0.14%
69 Walnut St 6 Brookline, MA Escape to quiet luxury in this corner residence at Walnut Crossing, Brookline's premier ne...	2 beds \| 2 baths \| 983 sq.ft.	$1,339,999	Airbnb cash on cash: 1.91% Traditional cash on cash: 0.32% Airbnb Rental Income: $6515 Traditional Rental Income: $3255 Airbnb ROI: 1.91% Traditional ROI: 0.32%
197 Winchester St #197 Brookline, MA This stunning, professionally designed 4-bedroom, 3.5-bathroom condo in Brooklineâs soug...	4 beds \| 4 baths \| 3,261 sq.ft.	$3,595,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 0.4% Airbnb Rental Income: $7900 Traditional Rental Income: $6192 Airbnb ROI: 0.46% Traditional ROI: 0.4%
33 Pond Ave PH1207 Brookline, MA This Brook House pond facing spectacular 2BR,2.5 bathroom penthouse residence with 2 garag...	2 beds \| 3 baths \| 1,800 sq.ft.	$899,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.78% Airbnb Rental Income: $2434 Traditional Rental Income: $3445 Airbnb ROI: -0.14% Traditional ROI: 1.78%
19 Winchester Street #102 Brookline, MA Welcome to 19 Winchester Street, Unit 102. This 1 bedroom home in the heart of Coolidge Co...	1 beds \| 1 baths \| 613 sq.ft.	$579,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.12% Airbnb Rental Income: $2423 Traditional Rental Income: $1982 Airbnb ROI: -0.16% Traditional ROI: 0.12%
63 Babcock St #B1 Brookline, MA Welcome to this sunlit and spacious 2BR condo ideally located in the heart of Coolidge Cor...	2 beds \| 1 baths \| 1,073 sq.ft.	$829,500	Airbnb cash on cash: 4.24% Traditional cash on cash: 0.15% Airbnb Rental Income: $6868 Traditional Rental Income: $2368 Airbnb ROI: 4.24% Traditional ROI: 0.15%
121 Centre St #PH3 Brookline, MA Step into this sunny and spacious top-floor, end-unit condo in a popular 2003 elevator bui...	2 beds \| 2 baths \| 1,056 sq.ft.	$1,043,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 0.08% Airbnb Rental Income: $6268 Traditional Rental Income: $2830 Airbnb ROI: 2.36% Traditional ROI: 0.08%

Real Estate investment in Brookline, MA

There are 9 properties for sale in the city of Brookline . The median list price in Brookline is $971,450 and the average price per square foot is $635. In September 2025, the average monthly cash on cash return in Brookline is N/A%. The average monthly rental income in Brookline is $3,089.

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

There are 9 investment properties available for sale in Brookline.

In 2025, the best neighborhood to buy investment property is Emerson Garden.

The ROI for Long-Term is higher than the Short-Term in Brookline with average rental income of $3,089.

Your search for investment property begins and ends here

Investment Property for Sale in Brookline, MA

321 Hammond Pond Parkway #103

Brookline, MA

2 beds | 2 baths | 1,350 sq.ft.

$1,099,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $3273

Traditional Rental Income: $3089

Airbnb ROI: -0.25%

Traditional ROI: 0.29%

52 Babcock Street #6

Brookline, MA

2 beds | 1 baths | 1,024 sq.ft.

$899,500

Airbnb cash on cash: 3.7%

Traditional cash on cash: -0.14%

Airbnb Rental Income: $6868

Traditional Rental Income: $2317

Airbnb ROI: 3.7%

Traditional ROI: -0.14%

69 Walnut St 6

Brookline, MA

2 beds | 2 baths | 983 sq.ft.

$1,339,999

Airbnb cash on cash: 1.91%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $6515

Traditional Rental Income: $3255

Airbnb ROI: 1.91%

Traditional ROI: 0.32%

197 Winchester St #197

Brookline, MA

4 beds | 4 baths | 3,261 sq.ft.

$3,595,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $7900

Traditional Rental Income: $6192

Airbnb ROI: 0.46%

Traditional ROI: 0.4%

33 Pond Ave PH1207

Brookline, MA

2 beds | 3 baths | 1,800 sq.ft.

$899,900

Airbnb cash on cash: -0.14%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $2434

Traditional Rental Income: $3445

Airbnb ROI: -0.14%

Traditional ROI: 1.78%

19 Winchester Street #102

Brookline, MA

1 beds | 1 baths | 613 sq.ft.

$579,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2423

Traditional Rental Income: $1982

Airbnb ROI: -0.16%

Traditional ROI: 0.12%

63 Babcock St #B1

Brookline, MA

2 beds | 1 baths | 1,073 sq.ft.

$829,500

Airbnb cash on cash: 4.24%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $6868

Traditional Rental Income: $2368

Airbnb ROI: 4.24%

Traditional ROI: 0.15%

121 Centre St #PH3

Brookline, MA

2 beds | 2 baths | 1,056 sq.ft.

$1,043,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 0.08%

Airbnb Rental Income: $6268

Traditional Rental Income: $2830

Airbnb ROI: 2.36%