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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
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Property management
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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- Images Available
Great for
Wellness
Work-from-home
Eco living
Amenities for 550 Pleasant St, Downtown Winthrop
Features
| Air Conditioning | Forced Air |
| Freezer | Hardwood Floor |
| Washer/Dryer Hookups | Water |
Appliances
| Dishwasher | Garbage Disposal |
| In-Unit Laundry | Microwave |
| Range/Oven | Refrigerator |
Tech
| Alarm System | Cable Ready |
| Wired For Internet |
Community
| Controlled Building | Intercom |
| Onsite Laundry | Security Cameras |
Grounds
| Assigned Parking | Garage Parking |
| Off-Street Parking |
Neighborhood
| Near Parks |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
Parking Policy
Assigned Parking
Building details
Property details
| Lease terms | 12+ months |
|---|
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About 550 Pleasant St
Property Id: 2071065 Welcome to your dream condo in the heart of Winthrop! This stunning, spacious 1 bed, 1 bath apartment features modern amenities including in-unit washer/dryer, dishwasher, microwave, and security features. Enjoy sunsets with water and city views, central air, 2 deeded parking spaces. Convenient proximity to beaches, parks, public transportation (MBTA blue line) and Boston. Don't miss out on this gem! Rent: $2950/month, Available 10/1/25
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 550 Pleasant St compares to other nearby properties.
Positives
- More space
- The 1-bedroom is 317 sqft larger than other listings nearby
- Images Available
- There are at least 10 photos of this address
Considerations
- Greater distance from high schools
- The nearest high school is farther than 1 mile away
- Greater distance from middle schools
- The nearest middle school is farther than 1 mile away
Address details
| Neighborhood | Downtown Winthrop |
|---|---|
| Zip code | 02152 |
| Type | Condo for rent |
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Available rentals nearby
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The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.
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The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.
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The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.
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Our team has verified this companyChinatown - Leather District • 660 Washington St
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The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.
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Our team has verified this companyEast Cambridge • 2 Leighton St
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$3,310–$3,390
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.
Avalon North Station
Our team has verified this companyDowntown Boston • 1 Nashua St
1 Bed
N/A
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Residences @ Malden Station
Our team has verified this companyMalden Center • 138 Pleasant St
1 Bed
$2,552–$2,580
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Harborview at the Navy Yard
Our team has verified this companyThompson Square - Bunker Hill • 250 1st Ave
1 Bed
$3,201–$3,764
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Harbor Point
Our team has verified this companyColumbia Point • 24 Oyster Bay Rd
1 Bed
$2,145–$3,097
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Chapman House
Our team has verified this companyEagle Hill • 61 Eutaw St
1 Bed
$2,650
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Avenir
Our team has verified this companyDowntown Boston • 101 Canal St
1 Bed
$3,385–$4,255
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.660 Washington
Our team has verified this companyChinatown - Leather District • 660 Washington St
1 Bed
$3,383–$4,258
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.AVA North Point
Our team has verified this companyEast Cambridge • 2 Leighton St
1 Bed
$3,310–$3,390
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Avalon North Station
Our team has verified this companyDowntown Boston • 1 Nashua St
1 Bed
N/A
The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.Rent trends in Downtown Winthrop
1-bedroom apartments at 550 Pleasant St cost about 21% more than the average rent price for 1-bedroom apartments in Winthrop Town.
Median rents as of Mar 28 2026.
Downtown Winthrop
Winthrop Town
| Month | Median Rent |
|---|---|
| April 2024 | $2,342 |
| 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 | $1,976 |
| October 2025 | $1,878 |
| November 2025 | $1,892 |
| December 2025 | $2,325 |
| January 2026 | $2,300 |
| February 2026 | $2,285 |
| March 2026 | $2,368 |
| Month | Median Rent |
|---|---|
| April 2024 | $2,462 |
| May 2024 | $2,463 |
| June 2024 | $2,525 |
| August 2025 | $2,500 |
| September 2025 | $2,500 |
| December 2025 | $2,400 |
| January 2026 | $2,400 |
| February 2026 | $2,400 |
| March 2026 | $2,419 |
Rent history
The increase or decrease in monthly rent compared to the previous listing price.| 8 months ago | $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-
Capic Head Start
67 crescent ave
chelsea, MA, 2150
PKPublic
Webster Extension
548 broadway
everett, MA, 2149
PKPublic
Webster School
30 dartmouth st
everett, MA, 2149
PK, K-5Public
B-
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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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