This beautifully maintained two-family home offers the perfect blend of meticulous care, charm and city convenience. Just minutes from downtown Boston and Logan Airport, enjoy easy commuting paired with the tranquility of a vibrant beachside community. Nearly 4,000 sq. ft. of living space features hardwood floors, a custom kitchen with island, gas fireplace, and a flexible floor plan with home office or first-floor bedroom. Upstairs offers two bedrooms, laundry, and a finished walk-up attic —ideal as a private suite or playroom. The lower-level unit includes a separate entrance, kitchenette, bedroom, bath and private laundry—perfect for in-law, au pair, or guests. Outside, enjoy a private fenced yard with hardscaping, raised garden beds, and a large shed. Updated systems, newer roof, siding, and windows ensure low-maintenance living. Walk to the beach, harbor, and local cafés—lifestyle, location, and value in one of Greater Boston’s most desirable coastal towns!
Listed by Danielle McCarthy
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Berkshire Hathaway HomeServices Commonwealth Real Estate
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774-245-9356
Last updated October 13, 2025
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Source: MLSPin #73441633
Listing Facts
TypeSingle-family
NeighborhoodDowntown Winthrop
Bedrooms5
Bathrooms3
Days on Prevu12
Taxes$7,072/year
Size3,776 sqft
Price per sqft$238
Amenities
Dishwasher
Private Outdoor Space
Washer/Dryer
Parking
Location
Mortgage Calculator
Listing History
10/09/2025
Listed by Berkshire Hathaway HomeServices Commonwealth Real Estate
$900,000
Property Details for 339 Winthrop St
Association
Amenities
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Laundromat, Highway Access, House Of Worship, Marina, Public School, T-Station
Exterior
Construction
Roof: Shingle
Window Features: Insulated Windows
Year Built: 1910
Year Built Details: Actual
Architectural Style: Colonial
Construction Materials: Frame
Exterior Features: Porch - Enclosed, Deck - Composite, Patio, Rain Gutters, Storage, Professional Landscaping, Fenced Yard, Garden, Stone Wall
Exclusions: Paver Stones Along Side Of Shed; 2nd And Third Floor Curtains
Parking
Parking
Open Parking: Yes
Parking Features: Off Street, Driveway
Parking Total: 2
Utilities
Equipment
Cooling: Ductless
Has Cooling: Yes
Electric: 220 Volts, Circuit Breakers
Heating: Baseboard, Hot Water, Natural Gas, Electric, Ductless
Has Heating: Yes
Laundry Features: Electric Dryer Hookup, Washer Hookup, Second Floor
Sewer: Public Sewer
Utilities: For Gas Range, For Electric Dryer, Washer Hookup
Water Source: Public
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