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modified
5+ Days Ago

Highlights

  • Modern amenities
  • City views
  • In-unit washer/dryer
  • Central air
  • Convenient proximity

Location

550 Pleasant St, Winthrop, MA 02152, USA|Downtown Winthrop

Property Overview

This property features modern amenities, city views, and in-unit washer/dryer, enhancing everyday convenience. Its advantageous location offers a vibrant social scene with numerous theaters, restaurants, and mixed-use spaces nearby, while also supporting a healthy lifestyle with parks and fitness facilities within reach. High-value per square foot and access to reliable public transit further contribute to its appeal for those working from home or seeking an urban environment.

This summary uses Zumper’s proprietary data. “Things you’ll love” and “Great for” are based on our internal analyses of market trends and renter insights.

Things you’ll love

  • More space
  • Dishwasher
  • Images Available

Great for

  • Wellness
  • Work-from-home
  • Eco living

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The price shown is for a 12-month lease. Fees may apply.
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$3,292–$4,117

The price shown is for a 12-month lease. Fees may apply.
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$3,210–$3,430

The price shown is for a 12-month lease. Fees may apply.
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West End • 1 Emerson Pl Apt 8n

1 Bed

$3,125–$3,760

The price shown is for a 12-month lease. Fees may apply.
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West End • 3 Longfellow Pl

1 Bed

$3,055–$4,250

The price shown is for a 12-month lease. Fees may apply.
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1 Bed

$3,386–$4,275

The price shown is for a 12-month lease. Fees may apply.
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Thompson Square - Bunker Hill • 250 1st Ave

1 Bed

$3,131–$5,922

The price shown is for a 12-month lease. Fees may apply.
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1 Bed

$2,535–$2,930

The price shown is for a 12-month lease. Fees may apply.

Rent trends in Downtown Winthrop

1-bedroom apartments at 550 Pleasant St cost about 18% more than the average rent price for 1-bedroom apartments in Winthrop Town.

Median rents as of Sep 6 2025.
Downtown Winthrop
Winthrop Town
A table of 1-bedroom apartment rental data trends in Winthrop Town
MonthMedian Rent
September 2023$2,236
October 2023$2,173
November 2023$2,056
December 2023$1,950
January 2024$2,062
February 2024$2,375
March 2024$2,282
April 2024$2,362
May 2024$2,283
June 2024$2,110
July 2024$2,053
August 2024$2,140
September 2024$2,162
October 2024$2,008
November 2024$1,995
December 2024$1,995
January 2025$2,148
February 2025$2,031
March 2025$2,195
April 2025$2,000
May 2025$2,160
June 2025$2,200
July 2025$2,166
August 2025$1,995
September 2025$2,000
A table of 1-bedroom apartment rental data trends in Downtown Winthrop
MonthMedian Rent
September 2023$2,100
October 2023$2,343
November 2023$2,175
December 2023$2,137
January 2024$2,375
February 2024$2,450
March 2024$2,387
April 2024$2,472
May 2024$2,463
June 2024$2,525
August 2025$2,500
September 2025$2,500

Rent history

The increase or decrease in monthly rent compared to the previous listing price.
Check out the past listing prices for monthly rent at 550 Pleasant St, Winthrop Town, MA.
Last month$2,950

Schools near 550 Pleasant St

Arthur T. Cummings Elementary School

40 hermon st

winthrop, MA, 2152

3-5Public
B-

William P. Gorman Fort Banks Elementary School

101 kennedy dr

winthrop, MA, 2152

PK, K-2Public
A-
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Internet available near 550 Pleasant St

Getting around Winthrop near 550 Pleasant St

Walking

5/10
Some shops and stores are within a few minutes.

Driving

10/10
Commuting is easy with multiple accessible routes and plenty of parking.

Cycling

5/10
More spots are within biking distance and some roads are cyclist-friendly.

Transit

5/10
Frequent public transit options are within walking distance.

Points of interest for 550 Pleasant St, Winthrop

Groceries

6/10
At least one supermarket within a 15-minute walk

Shopping

3/10
Some shops within walking distance

Cafes

6/10
Some cafés within a few minutes’ walk

Restaurants

5/10
Some restaurants within a few minutes’ walk

Primary schools

8/10
At least one elementary school within a 15-minute walk

High schools

6/10
At least one high school within a 15-minute walk

Parks

8/10
Very large amount of park space within a few minutes' walk

Nightlife

4/10
Some bars within walking distance

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