For sale

Price cut: $101K (7/22)

$1,499,000

516 Pleasant St, Winthrop, MA 02152

5beds

2,889sqft

$9,079/mo

Get pre-qualified

Multi Family

Built in 1900

-- sqft lot

$1,450,100 Zestimate^®

$519/sqft

$-- HOA

What's special

In-ground poolRoof deckSunroom with gas stovePrivate boat launchDirect water accessWest-facing harbor views

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!

55 days

1,666

83

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 3
Full bathrooms: 3

Features

Flooring: Wood, Tile, Varies
Basement: Full,Interior Entry,Unfinished
Number of fireplaces: 1

Interior area

Total structure area: 2,889
Total interior livable area: 2,889 sqft
Finished area above ground: 2,889

Video & virtual tour

View virtual tour

Property

Parking

Total spaces: 4
Parking features: Off Street, Driveway
Uncovered spaces: 4

Features

Patio & porch: Enclosed, Deck - Roof, Deck - Wood, Deck - Vinyl, Patio, Patio - Enclosed
Exterior features: Rain Gutters, Professional Landscaping, Sprinkler System
Pool features: In Ground
Fencing: Fenced/Enclosed,Fenced
Has view: Yes
View description: City View(s), City, Water, Harbor
Has water view: Yes
Water view: Harbor,Water
Waterfront features: Waterfront, Harbor, Harbor, Ocean, Direct Access, Frontage, 0 to 1/10 Mile To Beach

Lot

Size: 8,550 Square Feet

Details

Parcel number: M:0047 B:0008 L:0000,1423226
Zoning: rh6

Construction

Type & style

Home type: MultiFamily
Property subtype: Multi Family

Materials

Frame
Foundation: Other
Roof: Shingle

Condition

Year built: 1900

Utilities & green energy

Electric: 200+ Amp Service
Sewer: Public Sewer
Water: Public
Utilities for property: for Gas Range

Community & HOA

Community

Features: Shopping, Pool, Park, Walk/Jog Trails, Conservation Area, Highway Access, House of Worship, Marina, Public School

Location

Region: Winthrop

Financial & listing details

Price per square foot: $519/sqft
Tax assessed value: $1,127,000
Annual tax amount: $12,555
Date on market: 6/24/2026
Exclusions: Sellers Personal Property.
Total actual rent: 0

Estimated market value

$1,450,100

$1.38M - $1.52M

$3,146/mo

Price history

Date	Event	Price
7/22/2026	Price change	$1,499,000-6.3%$519/sqft
Source: MLS PIN #73541145 Report a problem
6/24/2026	Listed for sale	$1,600,000+672.9%$554/sqft
Source: MLS PIN #73541145 Report a problem
9/30/1993	Sold	$207,000$72/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$11,096 +14%	$1,075,200 +15.1%
2024	$9,730 -4.2%	$933,800 -1.6%
2023	$10,158 +5.4%	$949,300 +15.9%
2022	$9,634 -1.6%	$819,200 +6.1%
2021	$9,788 +9.6%	$771,900 +9.1%
2020	$8,930 +3.9%	$707,600 +8.5%
2019	$8,597 -2.6%	$652,300 +4.6%
2018	$8,829 +1.2%	$623,500 +3%
2017	$8,721 +2.9%	$605,200 +9.8%
2016	$8,472 +13.5%	$551,200 +5.9%
2015	$7,467 +8.4%	$520,700 +12.7%
2013	$6,888 +1.4%	$462,000 -1.5%
2012	$6,794 +6.8%	$468,900 +1.8%
2011	$6,359 -0.3%	$460,800 -8.2%
2010	$6,377 +18%	$502,100 -7.4%
2009	$5,404 +3.3%	$542,000 -3.6%
2008	$5,229 +1.9%	$562,300 -3.3%
2007	$5,131 +8%	$581,700 +5.8%
2006	$4,749 +2.8%	$549,600 +7.3%
2005	$4,621 +0.9%	$512,300 +17%
2004	$4,578 +2.1%	$437,700
2003	$4,486 +6.6%	$437,700 +64.4%
2002	$4,208 +28.2%	$266,300
2000	$3,283	$266,300