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 |
|---|---|---|---|
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: -0.81%
|
3 Walley StWinthrop, MA3 Walley St, Winthrop, MA 02128 | Multi Family |
4 beds | 2 baths | 2,556 sq.ft. |
$1,100,000 |
Airbnb cash on cash: N/A
|
28 Swan Ave #1Winthrop, MA28 Swan Ave #1, Winthrop, MA 02128 | Condo/Coop |
2 beds | 2 baths | 1,009 sq.ft. |
$649,900 |
Airbnb cash on cash: -0.69%
|
30 Swan Ave Ph 1Winthrop, MA30 Swan Ave Ph 1, Winthrop, MA 02128 | Condo/Coop |
3 beds | 2 baths | 1,236 sq.ft. |
$749,900 |
Airbnb cash on cash: -0.22%
|
95 Shirley St #3Winthrop, MAPRIVATE DECK, PRIVATE LAUNDRY & GARAGE are bonuses with this stunning top floor 2 bdrm con... |
2 beds | 1 baths | 1,100 sq.ft. |
$469,000 |
Airbnb cash on cash: 0.47%
|
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: N/A
|
100 Sargent StWinthrop, MAThis 5278 square foot single family home has 7 bedrooms and 5.5 bathrooms. This home is lo... |
6 beds | 5 baths | 5,278 sq.ft. |
$1,450,000 |
Airbnb cash on cash: N/A
|
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: -1.17%
|
47 Bellevue AveWinthrop, MA47 Bellevue Ave, Winthrop, MA 02152 | Multi Family |
6 beds | 3 baths | 3,400 sq.ft. |
$1,180,000 |
Airbnb cash on cash: -1.04%
|
10 Beach Rd #1Winthrop, MA10 Beach Rd #1, Winthrop, MA 02152 | Condo/Coop |
3 beds | 1 baths | 1,377 sq.ft. |
$569,000 |
Airbnb cash on cash: -0.17%
|
66 Plummer Ave #3Winthrop, MA66 Plummer Ave #3, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 955 sq.ft. |
$419,000 |
Airbnb cash on cash: -0.81%
|
1 Seal Hbr #210Winthrop, MA1 Seal Hbr #210, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 947 sq.ft. |
$499,900 |
Airbnb cash on cash: -1.92%
|
10 Somerset #207Winthrop, MA10 Somerset #207, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 898 sq.ft. |
$569,000 |
Airbnb cash on cash: -0.77%
|
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: -1.55%
|
51 Harbor View Ave #1Winthrop, MA51 Harbor View Ave #1, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 1,213 sq.ft. |
$639,000 |
Airbnb cash on cash: -0.43%
|
47 Highland AveWinthrop, MA47 Highland Ave, Winthrop, MA 02152 | Single Family Residential |
3 beds | 1 baths | 1,728 sq.ft. |
$650,000 |
Airbnb cash on cash: 0.59%
|
43 Sagamore Ave #1Winthrop, MA43 Sagamore Ave #1, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 769 sq.ft. |
$519,000 |
Airbnb cash on cash: 0.32%
|
26 Forrest #1Winthrop, MA26 Forrest #1, Winthrop, MA 02152 | Condo/Coop |
3 beds | 1 baths | 1,325 sq.ft. |
$515,000 |
Airbnb cash on cash: 0.67%
|
54 Wilshire StWinthrop, MA54 Wilshire St, Winthrop, MA 02152 | Other |
N/A beds | N/A baths | N/A |
$549,000 |
Airbnb cash on cash: 0.96%
|
63-69 Putnam StWinthrop, MA63-69 Putnam St, Winthrop, MA 02152 | Other |
N/A beds | N/A baths | N/A |
$2,460,000 |
Airbnb cash on cash: -1.51%
|
10 Somerset #402Winthrop, MA10 Somerset #402, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 1,024 sq.ft. |
$699,000 |
Airbnb cash on cash: -2.1%
|
300 Governors Dr #21Winthrop, MA300 Governors Dr #21, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 723 sq.ft. |
$365,000 |
Airbnb cash on cash: -0.1%
|
5 Oceanview StWinthrop, MA5 Oceanview St, Winthrop, MA 02152 | Single Family Residential |
3 beds | 2 baths | 1,500 sq.ft. |
$829,000 |
Airbnb cash on cash: -0.02%
|
24 Fairview StWinthrop, MA24 Fairview St, Winthrop, MA 02152 | Single Family Residential |
4 beds | 1 baths | 2,916 sq.ft. |
$1,300,000 |
Airbnb cash on cash: -1.15%
|
140 Shirley St #210Winthrop, MA140 Shirley St #210, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 874 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.32%
|
140 Shirley St #330Winthrop, MA140 Shirley St #330, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 623 sq.ft. |
$499,900 |
Airbnb cash on cash: -0.95%
|
229 Washington Ave #3AWinthrop, MAEnjoy coastal living in this charming waterfront condominium in Winthrop, offering the per... |
1 beds | 1 baths | 350 sq.ft. |
$235,000 |
Airbnb cash on cash: 0.84%
|
35 Somerset Ave #3Winthrop, MA35 Somerset Ave #3, Winthrop, MA 02152 | Condo/Coop |
2 beds | 2 baths | 969 sq.ft. |
$559,900 |
Airbnb cash on cash: -0.08%
|
28 Irwin StWinthrop, MA28 Irwin St, Winthrop, MA 02152 | Single Family Residential |
4 beds | 1 baths | 1,421 sq.ft. |
$499,900 |
Airbnb cash on cash: 0.55%
|
15 Wave Way AveWinthrop, MA15 Wave Way Ave, Winthrop, MA 02152 | Single Family Residential |
3 beds | 1 baths | 1,588 sq.ft. |
$765,000 |
Airbnb cash on cash: 0.17%
|
21 Sewall AveWinthrop, MA21 Sewall Ave, Winthrop, MA 02152 | Single Family Residential |
3 beds | 2 baths | 2,200 sq.ft. |
$1,100,000 |
Airbnb cash on cash: -0.56%
|
8 Siren StWinthrop, MA8 Siren St, Winthrop, MA 02152 | Single Family Residential |
3 beds | 2 baths | 1,728 sq.ft. |
$739,000 |
Airbnb cash on cash: 0.25%
|
308 BowdoinWinthrop, MA308 Bowdoin, Winthrop, MA 02152 | Multi Family |
7 beds | 3 baths | 3,628 sq.ft. |
$999,900 |
Airbnb cash on cash: -0.39%
|
118 Sunnyside AveWinthrop, MA118 Sunnyside Ave, Winthrop, MA 02152 | Single Family Residential |
4 beds | 2 baths | 1,755 sq.ft. |
$1,100,000 |
Airbnb cash on cash: -0.96%
|
51 Undine AveWinthrop, MA51 Undine Ave, Winthrop, MA 02152 | Single Family Residential |
3 beds | 1 baths | 1,250 sq.ft. |
$700,000 |
Airbnb cash on cash: 0.39%
|
22 Adams StWinthrop, MA22 Adams St, Winthrop, MA 02152 | Multi Family |
7 beds | 3 baths | 3,989 sq.ft. |
$1,299,000 |
Airbnb cash on cash: -0.81%
|
1000 Governors Dr #4Winthrop, MA1000 Governors Dr #4, Winthrop, MA 02152 | Condo/Coop |
2 beds | 1 baths | 977 sq.ft. |
$379,000 |
Airbnb cash on cash: -0.04%
|
1 Seal Hbr Ph 16Winthrop, MA1 Seal Hbr Ph 16, Winthrop, MA 02152 | Condo/Coop |
2 beds | 2 baths | 1,417 sq.ft. |
$799,999 |
Airbnb cash on cash: -2.02%
|
26 Shirley St #BWinthrop, MA26 Shirley St #B, Winthrop, MA 02152 | Condo/Coop |
4 beds | 2 baths | 1,833 sq.ft. |
$774,995 |
Airbnb cash on cash: -0.43%
|
10 Somerset #309Winthrop, MA10 Somerset #309, Winthrop, MA 02152 | Condo/Coop |
1 beds | 1 baths | 729 sq.ft. |
$519,900 |
Airbnb cash on cash: -1.34%
|
Real Estate investment in Winthrop, MA
There are 50 properties for sale in the city of Winthrop . The median list price in Winthrop is $657,500 and the average price per square foot is $407. In May 2026, the average monthly cash on cash return in Winthrop is 2.00%. The average monthly rental income in Winthrop is $2,887.