509 Pleasant St

Winthrop, MA 02152

$829,999
Price
3
Beds
2,000 Sq. Ft.
$415 / Sq. Ft.
2,000
Sq. Ft.
$415
per Sq. Ft.

Description

Welcome to 509 Pleasant, where coastal charm meets modern chic. This 3 bed/2 bath cottage style home is located in the ideal spot for both beach and city lovers. It features a smart system including Nest thermostat and Ring doorbell, a newer roof, recessed lighting, two fireplaces, a walk-in closet, in-built cabinets, a fully finished basement, a bonus room ideal for a playroom or gym, and an updated gorgeous wet bar and seating area! There is a large mudroom upon entry of the home, and ample room...Welcome to 509 Pleasant, where coastal charm meets modern chic. This 3 bed/2 bath cottage style home is located in the ideal spot for both beach and city lovers. It features a smart system including Nest thermostat and Ring doorbell, a newer roof, recessed lighting, two fireplaces, a walk-in closet, in-built cabinets, a fully finished basement, a bonus room ideal for a playroom or gym, and an updated gorgeous wet bar and seating area! There is a large mudroom upon entry of the home, and ample room for storage. The sizeable patio is ideal for additional parking or to entertain your friends and family this summer. Located across the street from a marina, around the corner from parks and restaurants, a 10-minute walk to the blue line, and easy highway access. Come see this gem and everything it has to offer!
  1. Listed by Hayley Buonopane • Conway - Swampscott

Property Details for 509 Pleasant Street

Town
Winthrop
MLS Area
Belle Isle
Area
MA-Winthrop-Belle Isle, MA-Winthrop
Architectural Style
Cottage, Bungalow
Style
Cottage, Bungalow
Garage Spaces
0
Parking Spaces
3.00
Parking Spaces Total
3
LISTING UPDATED: 07/09/2025 03:30 AM

Property Details for 509 Pleasant Street

StatusUnder Agreement
MLS #73378423
Days on Market47
Taxes$6,734 / year
HOA Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1930
CountySuffolk County

Location

Listing Courtesy of Conway - Swampscott, Hayley Buonopane
Add your commute

Building Information for 509 Pleasant Street

Stories-Year Built1930Building Size-Lot Size0.10 AC / 4,370 SF

Payment Calculator

$4,910 per month

30 year fixed, 6.845% Interest

Principal and Interest

$4,349

Property Taxes

$561

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 509 Pleasant Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Laundromat, Bike Path, Highway Access, House of Worship, Marina, Public School, T-Station
  • Living Area: 2000.0
  • Color: White/Tan
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: Yes
  • Year Built Details: Actual
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
  • Basement Features: Full, Finished
  • Num of Baths: 2.0
  • Num of Full Baths: 2
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 2.00
  • Bathrooms Total Integer: 2
  • FireplaceFeatures: Living Room
  • FireplaceYN: Yes
  • Fireplaces: 2
  • Flooring: Tile, Hardwood, Wood Laminate, Laminate, Flooring - Stone/Ceramic Tile
  • Interior Features: Bonus Room, Mud Room, Office, Wetbar
  • Interior Features: Wetbar
  • Laundry Features: Sink, In Basement
  • SpaYN: No
Exterior Features
  • Construction: Stone
  • Exterior Features: Patio - Enclosed
  • Exterior Features: Porch - Enclosed
  • Patio And Porch Features: Enclosed
  • Roof Material: Shingle
  • Waterfront Features: 0 to 1/10 Mile To Beach
  • Waterview Features: Marina
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Paved Drive, Off-Street, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off-Street, Paved Driveway
  • Parking Features: Off-Street, Paved Driveway
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Heating: Central, Fireplace
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Features: Walk-In Closet(s),Flooring - Hardwood,Window Seat
  • Primary Bedroom Level: Second Floor
Bedroom 2
  • Bedroom2 Features: Closet,Flooring - Hardwood
  • Bedroom2 Level: Second
Bedroom 3
  • Bedroom3 Features: Closet,Flooring - Hardwood
  • Bedroom3 Level: First
Bathroom 1
  • Bathroom1 Features: Bathroom - Full,Flooring - Stone/Ceramic Tile,Recessed Lighting
  • Bathroom1 Level: First
Bathroom 2
  • Bathroom2 Features: Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile
  • Bathroom2 Level: Basement
Dining Room
  • Dining Room Features: Flooring - Hardwood,Lighting - Sconce
  • Dining Room Level: First
Kitchen
  • Kitchen Features: Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Stainless Steel Appliances,Gas Stove
  • Kitchen Level: First
Living Room
  • Room Living Room Features: Beamed Ceilings,Flooring - Hardwood,Recessed Lighting
  • Room Living Room Level: First
Other Room 1
  • Room Office Features: Fireplace,Flooring - Laminate
  • Room Office Level: Basement
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Disclosures: Sold As Is. There is a cracked window in the bonus room. Patio photograph is virtually staged.
Tax Information
  • Listing Terms: Seller W/Participate
  • Tax ID: 1423317
  • Assessments: $652,500
  • Book: 69806
  • Tax Year: 2025
  • Zoning: res
Building / Association Information
Living Characteristics
  • Beds Total: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 2
  • Heat Zones: 2
Complex & Association Information
  • Adult Community: No

Property History for 509 Pleasant Street

DateEvent & SourcePriceAppreciation
Jul 7, 2025

Under Agreement

MLS PIN #73378423

—
Jun 22, 2025

Contingent

MLS PIN #73378423

—
May 21, 2025

Listed (Active)

MLS PIN #73378423

$829,999—
Jan 12, 2024

Sold

MLS PIN #73141606

$785,000—
Nov 20, 2023

Under Agreement

MLS PIN #73141606

—
Nov 20, 2023

Contingent

MLS PIN #73141606

—
Aug 9, 2023

Temporarily Withdrawn

MLS PIN #73141606

$820,000—
Jul 27, 2023

Listed (Active)

MLS PIN #73141606

$820,000—
Mar 20, 2006

Canceled

MLS PIN #70313099

$397,000—
Jan 10, 2006

Listed (Active)

MLS PIN #70313099

$397,000—
Feb 15, 2005

Sold (Public Record)

Public Record #153857310

$320,000—
Feb 14, 2005

Sold

MLS PIN #70095457

$320,000—
Jan 13, 2005

Under Agreement

MLS PIN #70095457

—
Jan 13, 2005

Contingent

MLS PIN #70095457

—
Sep 24, 2004

Listed (Active)

MLS PIN #70095457

$359,000—
DateEvent & SourcePrice
07/07/2025

Under Agreement

MLS PIN #73378423

—
06/22/2025

Contingent

MLS PIN #73378423

—
05/21/2025

Listed (Active)

MLS PIN #73378423

$829,999
01/12/2024

Sold

MLS PIN #73141606

$785,000
11/20/2023

Under Agreement

MLS PIN #73141606

—
11/20/2023

Contingent

MLS PIN #73141606

—
08/09/2023

Temporarily Withdrawn

MLS PIN #73141606

$820,000
07/27/2023

Listed (Active)

MLS PIN #73141606

$820,000
03/20/2006

Canceled

MLS PIN #70313099

$397,000
01/10/2006

Listed (Active)

MLS PIN #70313099

$397,000
02/15/2005

Sold (Public Record)

Public Record #153857310

$320,000
02/14/2005

Sold

MLS PIN #70095457

$320,000
01/13/2005

Under Agreement

MLS PIN #70095457

—
01/13/2005

Contingent

MLS PIN #70095457

—
09/24/2004

Listed (Active)

MLS PIN #70095457

$359,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 509 Pleasant Street

Taxable ValueLand$311,500Additions$341,000Total$652,500
Tax Record2025$6,734 ($561 / month)
Home Facts
Beds3Baths1Total Finished SqFt1,313 SqFtAbove Grade Finished SqFt1,313 SqFtStories2Lot Size4,370 SqFtStyleSingle Family ResidenceYear Built1930CountySUFFOLKAPNWINT M:047 L:095

Schools near 509 Pleasant Street

This home is within Winthrop School District.
Rating
School
Type
Grades
Distance
Public - PK to 2
Public - 3 to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Arthur T. Cummings Elementary School
Public3 to 5

Winthrop Middle School
Public6 to 8

Winthrop Sr High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Conway - Swampscott, Hayley Buonopane

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.