516 Pleasant St, Winthrop MA 02152
Winthrop, MA 02152
$1,600,000
$1,499,000
Est. $8,826/month
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, (all outside the flood-zone by the way!!) 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. The 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.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!
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Recently Sold Nearby
Property History
Market Insights
1
Price Changes
6.3%
Price Range
Property Timeline
Price Reduced
Jul 22, 2026
$1,499,000
$101,000
(-6.31%)
From $1,600,000 to $1,499,000 (-6.3%)
Listed for Sale
Jun 24, 2026
$1,600,000
Original listing
Agent: Amanda George
Office: Lamacchia Realty, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/22/2026 | ↓ Price Reduced | $1,499,000 | $101,000 | - | From $1,600,000 to $1,499,000 (-6.3%) |
| 06/24/2026 | 🏠 Listed for Sale | $1,600,000 | - | - | Original listing |
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
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
Investment Metrics
Units
3
Unit 1 Rent
— · N
Unit 2 Rent
— · N
Unit 3 Rent
— · N
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
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
Property Is Zoned And Taxed As A 2 Unit Per City Records, But References Occupancy As 3- Buyer To Perform Due Diligence. Offers To Be Made With This In Mind. Home Sits Outside The Flood Zone.
Exclusions
Sellers Personal Property.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
gray
Sq Ft Source
Public Record
Documents
None
County
Suffolk
Total market time (incl. prior listings)
32 days
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
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,889 sq ft above grade
Display Options
Outdoor Areas
PoolIn Ground
Patio & porchEnclosed, Deck - Roof, Deck - Wood, Deck - Vinyl, Patio, Patio - Enclosed
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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
Nearby Schools
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
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
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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Property Tax
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Homeowners Insurance
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95% Interest
Year 15
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Location
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Neighborhood
516 Pleasant St, Winthrop MA 02152
Winthrop, MA 02152
Listing Information
Listing Agent
Amanda George
Listing Office
Lamacchia Realty, Inc.
Office Phone
781-917-0491
Agent MLS ID
CT007220
Office MLS ID
AN6936
Listing Data Updated
Jul 26, 2026 3:06 AM 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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