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516 Pleasant St, Winthrop MA 02152

Winthrop, MA 02152
$1,600,000
Est. $9,337/month
5
Beds
3
Baths
2,889
Sq Ft
$554
Price/Sq Ft
0.20
Acres
1900
Year Built
11 hours 39 minutes
Time on Market
Active Listed Jun 24, 2026 • MLS# 73541145 Copied!

About this home

Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. 3 units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture. Many updates include replacement windows, mass-save insulation, professional landscaping and irrigation, mini-splits, replacement chimney liner, hunter-douglas shades, front porch replacement, and more. Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

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Property Overview

Property Type
Multi Family
Listing Type
For Sale
Year Built
1900
Bedrooms
5
Full Bathrooms
3
Living Area
2,889 sq ft
Total Rooms
13
Stories
3
Levels
3

Facts & Features

Home Facts

Type Residential Income
Style Multi Family
Year Built 1900
Living Area 2,889 sq ft
Lot Size 0.20 acres
Bedrooms 5
Full Baths 3
Total Rooms 13

Interior

Heating None
Cooling None
Flooring Wood, Tile, Varies
Appliances None
Fireplace None
Fireplaces 1
Basement Full, Interior Entry, Unfinished
Laundry None
Features None

Exterior

Construction Frame
Architecture None
Roof Shingle
Features Rain Gutters, Professional Landscaping, Sprinkler System
Pool In Ground
Spa None
Fencing Fenced/enclosed, Fenced
Patio/Porch Enclosed, Deck - Roof, Deck - Wood, Deck - Vinyl, Patio, Patio - Enclosed

Parking

Features Off Street, Driveway
Total Spaces 4

Utilities

Electric 200+ Amp Service
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range

Financial

Annual Tax $12,555
Assessed Value $1,127,000

Interior Features

Flooring: Wood, Tile, Varies
Appliances:
Interior Features:
Windows:
Basement: Full, Interior Entry, Unfinished
Laundry:
Security:

Construction & Materials

Year Built: 1900
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Other
Stories: 3

Heating, Cooling & Utilities

Heating:
Heating Zones: 3
Cooling:
Cooling Zones: 3
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Rain Gutters, Professional Landscaping, Sprinkler System
Patio & Porch: Enclosed, Deck - Roof, Deck - Wood, Deck - Vinyl, Patio, Patio - Enclosed
Fencing: Fenced/Enclosed, Fenced
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Total Parking Spaces: 4
Parking Features: Off Street, Driveway

Special Features

Fireplaces: 1
Fireplace Type:
Waterfront: Yes
Waterfront Type: Waterfront, Harbor, Harbor, Ocean, Direct Access, Frontage, 0 to 1/10 Mile To Beach
View: Yes
View Type: City View(s), City
Community Amenities: Shopping, Pool, Park, Walk/Jog Trails, Conservation Area, Highway Access, House of Worship, Marina, Public School

Location

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Neighborhood

516 Pleasant St, Winthrop MA 02152

Winthrop, MA 02152

Walkability

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Nearby Schools

E

Elementary Schools

3 schools
B-
Arthur T. Cummings Elementary School
0.4 mi | #453 of 824 | Score: 46.0
Improved 101 spots from last year
-12.2 below state avg
467 students Less Diverse
Rising School Strong Attendance
Grades 03-05
William P. Gorman/Fort Banks Elementary School
0.7 mi
487 students Less Diverse
Grades PK-02
F
Guild Elementary School
0.9 mi | #789 of 824 | Score: 29.4
Dropped 218 spots from last year
-28.8 below state avg
259 students Less Diverse
Grades PK-06
M

Middle Schools

3 schools
B+
Winthrop Middle School
0.7 mi | #119 of 352 | Score: 47.4
Dropped 26 spots from last year
-10.8 below state avg
439 students Less Diverse
Grades 06-08
C
Garfield Middle School
1.6 mi | #264 of 352 | Score: 35.1
Dropped 12 spots from last year
-23.1 below state avg
542 students Moderate
Grades 06-08
D
Clark Avenue School
2.3 mi | #329 of 352 | Score: 28.3
Improved 32 spots from last year
-29.9 below state avg
673 students Less Diverse
Rising School
Grades 05-08
H

High Schools

3 schools
C+
Winthrop High School
0.7 mi | #241 of 346 | Score: 47.2
Dropped 112 spots from last year
-11 below state avg
568 students Less Diverse
18 sports • 1,118 athletes
College Ready Curriculum Strong Athletics
Grades 09-12
D
CityLab Innovation High School
1.0 mi | #327 of 346 | Score: 28.4
Improved 14 spots from last year
-29.8 below state avg
117 students Moderate
College Ready Curriculum
Grades 09-12
East Boston High
2.2 mi
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Monthly Payment Calculator

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Loan Amount
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After down payment
Total Interest
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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,046
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Property Timeline

🏠
Listed for Sale
Jun 24, 2026
$1,600,000
Original listing
Agent: Amanda George Office: Lamacchia Realty, Inc.

Price & Status History

Date Event Price Change
Jun 24, 2026 New Listing Added $1,600,000

Market Statistics

Time on Market
11 hours 39 minutes
Price per Sq Ft
$554

Tax History

Year Taxes Assessment
2026 $12,555 $1,127,000

Financial Details

Annual Property Tax
$12,555
Tax Year 2026
Assessed Value
$1,127,000

Listing Information

Listing Agent Amanda George
Listing Office Lamacchia Realty, Inc.
Agent MLS ID CT007220
Office MLS ID AN6936
Listing Data Updated Jun 24, 2026 3:49 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Market Analytics for Winthrop, MA

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