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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
321 Hammond Pond Parkway #103Brookline, MASunny 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: 1.33%
|
69 Walnut St 6Brookline, MAEscape 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%
|
199 Winchester St #199Brookline, MA199 Winchester Street is a multigenerational home featuring 4-bedrooms, 3.5-bathrooms, den... |
4 beds | 4 baths | 2,696 sq.ft. |
$2,965,000 |
Airbnb cash on cash: 0.86%
|
197 Winchester St #197Brookline, MAThis stunning, professionally designed 4-bedroom, 3.5-bathroom condo in Brooklineâs soug... |
4 beds | 4 baths | 3,261 sq.ft. |
$3,795,000 |
Airbnb cash on cash: 0.39%
|
33 Pond Ave PH1207Brookline, MAThis 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: 3.22%
|
19 Winchester Street #102Brookline, MAWelcome to 19 Winchester Street, Unit 102. This 1 bedroom home in the heart of Coolidge Co... |
1 beds | 1 baths | 613 sq.ft. |
$599,000 |
Airbnb cash on cash: 2.17%
|
197-199 Winchester StBrookline, MANew Renovation Plus Addition Two Family with exceptional rental potential. This one-of-a-k... |
8 beds | 8 baths | 5,957 sq.ft. |
$6,600,000 |
Airbnb cash on cash: 0.03%
|
10 Bradford Ter #5Brookline, MAA welcoming gated front entrance leads to this highly sought-after brick courtyard buildin... |
3 beds | 2 baths | 1,365 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 1.41%
|
63 Babcock St #B1Brookline, MAWelcome 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%
|
333 Clark RoadBrookline, MAWelcome to 333 Clark Road, a beautiful Colonial home situated in one of the most sought-af... |
5 beds | 4 baths | 3,100 sq.ft. |
$2,925,000 |
Airbnb cash on cash: 1.41%
|
22 Chestnut Place #608Brookline, MAWelcome to Sargent Estates Manor! This spacious one-bedroom plus den condo includes a deed... |
1 beds | 2 baths | 774 sq.ft. |
$569,888 |
Airbnb cash on cash: 4.26%
|
Real Estate investment in Brookline, MA
There are 11 properties for sale in the city of Brookline . The median list price in Brookline is $1,174,500 and the average price per square foot is $587. In July 2025, the average monthly cash on cash return in Brookline is N/A%. The average monthly rental income in Brookline is $3,142.