Homes for Sale in Winthrop

Coastal peninsula with beaches, harbor views, and a small-town feel.

Winthrop is a coastal peninsula town north of Boston with beaches, harbor views, and a small-town residential character. The housing market includes single-family homes, condominiums, and multi-family properties. Buyers are drawn to the combination of ocean access, quiet streets, and convenient ferry or bus connections to the city.

Beach and harbor proximity are meaningful premiums. Flood considerations apply near the water, and insurance costs should be reviewed carefully. Parking and outdoor space are more available than in denser areas. Newer construction is limited, so the condition of existing homes is an important factor.

$965,000

Condo

2 bd · 2.1 ba · 1,978 sqft · Active

1001 Shirley St #1, Winthrop

$549,900

Condo

2 bd · 1 ba · 782 sqft · Active

130 Shirley Street #220, Winthrop

$999,888

Multi FamilyWaterfront

2,635 sqft · Active

66 Sunnyside Ave, Winthrop

$2,250,000

Multi FamilyMBTA

10,000 sqft · Active

63-69 Putnam St, Winthrop

$1,049,900

Multi Family

2,949 sqft · Active

32 Irwin St, Winthrop

$699,900

Condo

2 bd · 2 ba · 1,113 sqft · Active

130 Shirley Street #250, Winthrop

$519,000

Condo

3 bd · 1 ba · 1,374 sqft · Active

23 Trident #1, Winthrop

$549,995

Condo

2 bd · 1 ba · 1,614 sqft · Active

54 Trident Ave #54, Winthrop

$519,000

CondoMBTA

3 bd · 2 ba · 1,256 sqft · Active

173-175 Shirley St #6, Winthrop

$740,000

Multi FamilyMBTA

2,000 sqft · Active

120 Hermon St, Winthrop

$525,000

Condo

3 bd · 1 ba · 1,270 sqft · Active

111 Locust St #2, Winthrop

$849,000

CondoWaterfront

3 bd · 2 ba · 1,770 sqft · Active

25 Locust St #2, Winthrop

Price	Beds	Baths	Sq Ft	Address	Status
$965,000	2	2.1	1,978	1001 Shirley St #1, Winthrop	Active
$549,900	2	1	782	130 Shirley Street #220, Winthrop	Active
$999,888			2,635	66 Sunnyside Ave, Winthrop	Active
$2,250,000			10,000	63-69 Putnam St, Winthrop	Active
$1,049,900			2,949	32 Irwin St, Winthrop	Active
$699,900	2	2	1,113	130 Shirley Street #250, Winthrop	Active
$519,000	3	1	1,374	23 Trident #1, Winthrop	Active
$549,995	2	1	1,614	54 Trident Ave #54, Winthrop	Active
$519,000	3	2	1,256	173-175 Shirley St #6, Winthrop	Active
$740,000			2,000	120 Hermon St, Winthrop	Active
$525,000	3	1	1,270	111 Locust St #2, Winthrop	Active
$849,000	3	2	1,770	25 Locust St #2, Winthrop	Active

Overview

Winthrop Profile	Snapshot
Primary Vibe	Quiet coastal town with beaches, ocean views, and a residential peninsula character. Popular with buyers seeking water access and a lower-key setting.
Housing Prices	Prices vary by proximity to the water. Beachfront and view properties command premiums. Multi-family homes offer additional options.
Commute to Boston	Ferry and bus provide access. Driving is common. Parking and outdoor space are readily available.
Schools	Served by Winthrop Public Schools. Confirm assignments with the district.
Market	Demand supported by coastal location. Updated homes near the beach or with views attract interest.
Housing Styles	Single-family homes, condominiums, and multi-family properties. Outdoor space is common.

Neighborhoods

Neighborhood / Area	Vibe / Character	Primary Property Type / Approx. Price	Market Note
Beachfront Areas	Coastal & Scenic	Homes & Condos Premiums for views.	Ocean access. Confirm flood considerations.
Harbor Edge	Residential & Water-Oriented	Homes Prices depend on condition.	Harbor views. Quieter setting.
Inland Residential Streets	Neighborhood & Quiet	Single-Family & Multi-Family More approachable pricing.	Settled character. Review systems.