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 | 2 baths | 1,188 sq.ft. |
$1,300,000 |
Airbnb cash on cash: -0.67%
|
3 Walley StWinthrop, MA3 Walley St, Winthrop, MA 02128 | Multi Family |
4 beds | 2 baths | 2,556 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 0.15%
|
426 Winthrop StWinthrop, MAWelcome home to this open concept colonial home in sought after Winthrop! The home offers ... |
5 beds | 2 baths | 2,394 sq.ft. |
$749,900 |
Airbnb cash on cash: 1.71%
|
960 Shirley StWinthrop, MA960 Shirley St, Winthrop, MA 02152 | Single Family Residential |
3 beds | 1 baths | 1,764 sq.ft. |
$705,000 |
Airbnb cash on cash: 0.63%
|
129 StrandwayWinthrop, MA129 Strandway, Winthrop, MA 02152 | Single Family Residential |
4 beds | 3 baths | 2,640 sq.ft. |
$1,324,900 |
Airbnb cash on cash: -0.15%
|
600 Shirley Street unit: 3Winthrop, MA"The Cove at 600" was converted in 2022 and is located on the site of the historic Crystal... |
2 beds | 2 baths | 773 sq.ft. |
$549,900 |
Airbnb cash on cash: 0.04%
|
56 Main StWinthrop, MA56 Main St, Winthrop, MA 02152 | Multi Family |
4 beds | 2 baths | 2,103 sq.ft. |
$799,900 |
Airbnb cash on cash: 0.11%
|
47 Bellevue AveWinthrop, MA47 Bellevue Ave, Winthrop, MA 02152 | Multi Family |
6 beds | 3 baths | 3,400 sq.ft. |
$1,280,000 |
Airbnb cash on cash: -0.76%
|
600 Shirley St #1Winthrop, MA600 Shirley St #1, Winthrop, MA 02152 | Condo/Coop |
1 beds | 2 baths | 604 sq.ft. |
$410,000 |
Airbnb cash on cash: -0.37%
|
50-52 Wilshire StWinthrop, MA50-52 Wilshire St, Winthrop, MA 02152 | Multi Family |
6 beds | 2 baths | 2,212 sq.ft. |
$990,000 |
Airbnb cash on cash: -0.8%
|
10 Somerset #401Winthrop, MA10 Somerset #401, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 684 sq.ft. |
$530,784 |
Airbnb cash on cash: -0.43%
|
1001 Shirley #5Winthrop, MA1001 Shirley #5, Winthrop, MA 02152 | Townhouse |
2 beds | 2 baths | 1,785 sq.ft. |
$1,050,000 |
Airbnb cash on cash: -0.99%
|
600 Shirley #4Winthrop, MA600 Shirley #4, Winthrop, MA 02152 | Condo/Coop |
1 beds | 2 baths | 585 sq.ft. |
$389,900 |
Airbnb cash on cash: -0.27%
|
86N Undine AveWinthrop, MA86N Undine Ave, Winthrop, MA 02152 | Single Family Residential |
3 beds | 2 baths | 2,250 sq.ft. |
$1,350,000 |
Airbnb cash on cash: -0.73%
|
10 Somerset #304SWinthrop, MA10 Somerset #304S, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 546 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.43%
|
550 Pleasant St #506Winthrop, MA550 Pleasant St #506, Winthrop, MA 02152 | Condo/Coop |
2 beds | 2 baths | 1,975 sq.ft. |
$1,030,000 |
Airbnb cash on cash: -1.89%
|
1001 Shirley #3Winthrop, MA1001 Shirley #3, Winthrop, MA 02152 | Townhouse |
2 beds | 2 baths | 1,551 sq.ft. |
$939,900 |
Airbnb cash on cash: -0.78%
|
1001 Shirley #1Winthrop, MA1001 Shirley #1, Winthrop, MA 02152 | Townhouse |
2 beds | 2 baths | 1,978 sq.ft. |
$1,125,000 |
Airbnb cash on cash: -1.1%
|
800 Governors Dr #6Winthrop, MA800 Governors Dr #6, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 772 sq.ft. |
$340,000 |
Airbnb cash on cash: 1.61%
|
1 Seal Hbr #210Winthrop, MA1 Seal Hbr #210, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 947 sq.ft. |
$519,000 |
Airbnb cash on cash: -1.02%
|
1 Seal Harbor Rd #701Winthrop, MA1 Seal Harbor Rd #701, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 1,005 sq.ft. |
$549,000 |
Airbnb cash on cash: -1.43%
|
140 Shirley St #310Winthrop, MA140 Shirley St #310, Winthrop, MA 02152 | Condo/Coop |
2 beds | 2 baths | 1,113 sq.ft. |
$749,900 |
Airbnb cash on cash: -0.29%
|
279-283 Shirley St #2Winthrop, MA279-283 Shirley St #2, Winthrop, MA 02152 | Condo/Coop |
3 beds | 1 baths | 1,105 sq.ft. |
$529,000 |
Airbnb cash on cash: 1.06%
|
140 Shirley St #201Winthrop, MA140 Shirley St #201, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 874 sq.ft. |
$624,900 |
Airbnb cash on cash: 0.29%
|
10 Somerset #207Winthrop, MA10 Somerset #207, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 898 sq.ft. |
$569,000 |
Airbnb cash on cash: 0.24%
|
10 Somerset #308Winthrop, MA10 Somerset #308, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 774 sq.ft. |
$559,000 |
Airbnb cash on cash: -0.6%
|
142 Washington AveWinthrop, MA142 Washington Ave, Winthrop, MA 02152 | Single Family Residential |
6 beds | 3 baths | 4,754 sq.ft. |
$1,599,999 |
Airbnb cash on cash: -0.51%
|
51 Harbor View Ave #2Winthrop, MA51 Harbor View Ave #2, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 1,250 sq.ft. |
$675,000 |
Airbnb cash on cash: 0.08%
|
3 Seal Hbr #344Winthrop, MA3 Seal Hbr #344, Winthrop, MA 02152 | Condo/Coop |
2 beds | 2 baths | 1,302 sq.ft. |
$649,000 |
Airbnb cash on cash: -0.89%
|
51 Harbor View Ave #1Winthrop, MA51 Harbor View Ave #1, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 1,220 sq.ft. |
$650,000 |
Airbnb cash on cash: 0.19%
|
130 Shirley St #202Winthrop, MA130 Shirley St #202, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 782 sq.ft. |
$549,900 |
Airbnb cash on cash: 0.63%
|
247 Washington Ave #10Winthrop, MA247 Washington Ave #10, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 702 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.25%
|
19 Moore StWinthrop, MA19 Moore St, Winthrop, MA 02152 | Multi Family |
5 beds | 2 baths | 2,212 sq.ft. |
$829,974 |
Airbnb cash on cash: N/A
|
10 Somerset #405Winthrop, MA10 Somerset #405, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 683 sq.ft. |
$512,250 |
Airbnb cash on cash: -0.37%
|
Real Estate investment in Winthrop, MA
There are 38 properties for sale in the city of Winthrop . The median list price in Winthrop is $687,500 and the average price per square foot is $456. In March 2026, the average monthly cash on cash return in Winthrop is 1.00%. The average monthly rental income in Winthrop is $2,981.