Get Natick and Metrowest Listings and Market Information

Work with Robb Enterprises real estate to buy, sell, or lease property that is right for you

  • Properties
    • For Rent
    • For Sale
    • Vacation Rental
    • Commercial
  • Specialty Properties
    • Natick New Construction
    • Natick Waterfront
    • Apartments for Rent in Natick MA 01760
    • Section 8 Advertised Properties
  • Agents
  • Compare
  • Blog
  • Contact Us

Properties

  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
  • 338 Pleasant St, Winthrop, Massachusetts, 3 Bedrooms Bedrooms, 6 Rooms Rooms,2 BathroomsBathrooms,Residential Lease,For Rent,Pleasant St,73555451
Property Description

Welcome to one of Winthrop’s most sought-after neighborhoods—the desirable Maze! Beautifully renovated and thoughtfully designed with two levels of stylish living, this home offers the perfect blend of comfort and functionality. The sun-filled main level features an open-concept living and dining area enhanced with recessed lighting, crown molding, and an inviting atmosphere ideal for both everyday living and entertaining. The well-appointed kitchen showcases stainless steel appliances, custom shaker-style cabinetry, granite countertops, pendant lighting, and an expansive peninsula that serves as the heart of the home for gathering with family and friends. Two generously sized bedrooms and a beautifully updated full bath complete the main level. The finished lower level offers a spacious private bedroom suite with its own en-suite bath, making it ideal for guests, extended family, or a luxurious primary retreat. A dedicated laundry area adds everyday convenience. Outside, enjoy the patio perfect for grilling, outdoor dining, or relaxing, and off-street parking conveniently located just steps from the rear entrance. Central air conditioning keeps you comfortable throughout the summer, while efficient gas heat provides warmth during the colder months. Ideally located just minutes from Logan Airport, downtown Boston, and major highways north and south, this home also offers easy access to everything Winthrop has to offer—including beautiful beaches, waterfront dining, local shops, neighborhood cafés, a convenient local market, and the charm of this vibrant seaside community!

Features
Heating System:
Forced Air, Natural Gas
Pet Policy:
Yes W/ Restrictions
Appliances:
Disposal, Range, Dishwasher, Refrigerator, Washer, Dryer, Freezer
Exterior Unit Features:
Patio, Porch
Disclosure
Lead Paint:
No
Laundry Features:
In Unit, In Basement, Countertops - Stone/granite/solid, Recessed Lighting, Flooring - Laminate
Rent Fee Includes:
Water, Laundry Facilities, Parking , Extra Storage, Sewer, Gardener
Deposit Reqd:
Yes
Insurance Reqd:
Yes
Last Mon Reqd:
Yes
References Reqd:
Yes
First Mon Reqd:
Yes
Additional Information
Grade School:
Fort Banks/Atc
High School:
Winthrop
Middle School:
Winthrop
Parking Spaces:
2
Status:
Active
Price Per Sqft:
$2
Unit Building:
1
Orig Price:
$3,600
Sec Deposit:
$1,800
Date Available:
08/01/2026 00:00:00
Waterfront:
No
MlsStatus:
New
Address Map
City:
Winthrop
State:
MA
County:
Suffolk
Postal Code:
02152
Longitude:
W71° 0' 29.4''
Latitude:
N42° 22' 30.1''
  • Google Map

Residential Lease

338 Pleasant St, Winthrop, Massachusetts

3 Bedrooms
2 Total Bathrooms
1,629 Sqft
$3,600
Listing ID #73555451
Basic Details
Property Type :
Residential Lease
Listing Type :
For Rent
Price :
$3,600
Bedrooms :
3
Rooms :
6
Total Bathrooms :
2
Full Bathrooms :
2
Square Footage :
1,629 Sqft
Listing ID :
73555451
  • Share on Facebook
  • Share on Twitter
  • Share on Pinterest
  • PDF
  • Send to Friend
  • Request a Visit
Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

Similar Properties

Residential Lease

Residential Lease

111 Winthrop Shore Drive, Winthrop, Massachusetts

More
Residential Lease

Residential Lease

235 Washington Ave, Winthrop, Massachusetts

More
60 Hermon Street, Winthrop, Massachusetts, 1 Bedroom Bedrooms, 6 Rooms Rooms,1 BathroomBathrooms,Residential Lease,For Rent,Hermon Street,73555434

Residential Lease

60 Hermon Street, Winthrop, Massachusetts

More
Residential Lease

Residential Lease

876 Shirley St, Winthrop, Massachusetts

More
57 Eliot St, Revere, Massachusetts, 3 Bedrooms Bedrooms, 5 Rooms Rooms,1.5 BathroomsBathrooms,Residential Lease,For Rent,Eliot St,73555103

Residential Lease

57 Eliot St, Revere, Massachusetts

More
50 Pearl Avenue, Winthrop, Massachusetts, 1 Bedroom Bedrooms, 2 Rooms Rooms,1 BathroomBathrooms,Residential Lease,For Rent,Pearl Avenue,73553595

Residential Lease

50 Pearl Avenue, Winthrop, Massachusetts

More
249 Winthrop Shore Drive, Winthrop, Massachusetts, 2 Bedrooms Bedrooms, 4 Rooms Rooms,1 BathroomBathrooms,Residential Lease,For Rent,Winthrop Shore Drive,73552754

Residential Lease

249 Winthrop Shore Drive, Winthrop, Massachusetts

More
47 Prospect Ave, Winthrop, Massachusetts, 4 Bedrooms Bedrooms, 10 Rooms Rooms,2.5 BathroomsBathrooms,Residential Lease,For Rent,Prospect Ave,73551890

Residential Lease

47 Prospect Ave, Winthrop, Massachusetts

More
Realtyna

Copyright © 2026