Real Estate Investment Properties for Sale in Winthrop, MA
Looking for investment property in Winthrop, MA with high ROI ?
Explore a variety of short-term homes & houses in Winthrop, MA. Invest wisely with VRBO & Winthrop, 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 Winthrop, MA
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1203 Bennington StWinthrop, MA1203 Bennington St, Winthrop, MA 02128 | Single Family Residential |
5 beds | 3 baths | 1,568 sq.ft. |
$793,721 |
Airbnb cash on cash: 1.21%
|
20 Nancia StWinthrop, MA20 Nancia St, Winthrop, MA 02128 | Single Family Residential |
3 beds | 1 baths | 1,188 sq.ft. |
$1,500,000 |
Airbnb cash on cash: -0.88%
|
600 Shirley Street #3Winthrop, MAâThe Cove at 600â was converted in 2022 and is located on the site of the historic Cry... |
2 beds | 2 baths | 773 sq.ft. |
$549,900 |
Airbnb cash on cash: 1.41%
|
426 Winthrop StWinthrop, MAWelcome home to this open concept colonial home in sought after Winthrop! The home offers... |
5 beds | 3 baths | 2,394 sq.ft. |
$749,900 |
Airbnb cash on cash: 1.71%
|
16 Pebble AveWinthrop, MALocated just a couple hundred yards from the water, this two-bedroom, one bathroom propert... |
2 beds | 1 baths | 866 sq.ft. |
$399,950 |
Airbnb cash on cash: 2.49%
|
Real Estate investment in Winthrop, MA
There are 5 properties for sale in the city of Winthrop . The median list price in Winthrop is $749,900 and the average price per square foot is $552. In December 2025, the average monthly cash on cash return in Winthrop is 3.00%. The average monthly rental income in Winthrop is $3,672.