For sale

$947,900

Est. $6,146/mo —

•

2,650

sq ft

217 Pleasant St, Winthrop, MA 02152

About this home

At this attractive new price, this is more than just a home, it’s a chance to embrace the coastal lifestyle that makes Winthrop so special! Just moments from the beach, this beautifully updated 6-bedroom Colonial offers the rare combination of timeless character, modern comfort, and a lot of room for everyone. Featuring over 2,600 square feet of living space (plus additional 600+ sq ft in finished basement) gleaming hardwood floors, fireplaces, a partially finished lower level, and a very welcoming front porch, every space invites you to relax, gather, and create lasting memories. Extensive upgrades, including updated electrical, plumbing, heating, central A/C and very efficient mini spit system. Outside, enjoy a good sized, fenced backyard, large 2-car detached garage, and plenty of off-street parking. At this price, opportunities like this are hard to find in this section of Winthrop! Come experience the charm, space, and value for yourself! Very easy to view! Book your appointment now before it is too late!

Single-familyProperty Type

1896Year Built

6,210 sq ftLot Size

$358Price/Sq.Ft.

2 garage spacesParking

Listed by Louis Bonavita • Benton Real Estate Company

Listed by • Benton Real Estate Company

Listing updated: Oct 11, 2026 at 03:11am

Redfin checked: a few seconds ago

•Source:MLS PIN #73567723

Payment calculator

$6,146 per month

Principal and interest$5,238

Property taxes

$750

HOA dues

Home insurance

$158

Utilities

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This home is unavailable to tour on this day.

Next available date: Monday, October 26

Open houses

No upcoming open houses.

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Around this home

Schools

K - 12
Preschool & daycare

Arthur T. Cummings Elementary School

Public 3-5 • Assigned • 0.3mi

5/10

Winthrop Middle School

Public 6-8 • Assigned • 0.7mi

8/10

Winthrop Senior High School

Public 9-12 • Assigned • 0.7mi

5/10

Provided by GreatSchools

About Downtown

Winthrop

Downtown Winthrop, located between Winthrop Beach and Belle Isle Marsh Reservation, is a coastal and walkable Winthrop neighborhood with a compact main street and harbor breezes. The neighborhood’s character concentrates around the Winthrop Center area along Shirley Street, where small storefronts, cafés, and everyday services line the sidewalks. Early-20th-century wood-frame homes and tidy multifamily buildings sit behind the commercial strip, giving the streets a classic seaside-town rhythm. Winthrop Center Café, Blackstrap BBQ, and the Winthrop Public Library act as familiar community anchors. Short blocks lead toward the shoreline, while inland edges meet marsh views and open sky. Side streets stay calm, with pocket parks and civic buildings shaping daily routines.

Provided by Walk Score and Local Logic

Offer insights

217 Pleasant St · $947,900

Strong offer

$947K and above

75% chance or better to win

Why $947K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 31 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Fireplace in the living room
Partially finished basement
Two fireplaces

Bedrooms
Five bedrooms on the second and third floors

Bathrooms
Two full bathrooms and one half bathroom

Kitchen
Remodeled kitchen with upgraded countertops, stainless steel appliances, and wood flooring
Gas range, dishwasher, disposal, microwave, and refrigerator

Laundry & utility
Washer and dryer included
Washer hookup and electric dryer hookup

Flooring
Wood, tile, and engineered hardwood flooring

Heating & cooling
Forced-air, natural gas, and other heating
Central air and other cooling

Sale and tax history for 217 Pleasant St

Sale History
Tax History

Date

Event

Price

MLS PIN #73567723

Oct 7, 2026

Price Changed

$947,900

$358/sq ft

Sep 29, 2026

Price Changed

$949,900

$358/sq ft

Sep 11, 2026

Price Changed

$979,900

$370/sq ft

Aug 25, 2026

Listed

$998,900

$377/sq ft

MLS PIN #72728112

Nov 13, 2020

Sold

$697,500

$263/sq ft

Sep 28, 2020

Contingent

—

Sep 17, 2020

Listed

$689,000

$260/sq ft

+22

For the first time in many years this Whittemore built home which is full of love, memories and an abundance of charm is being offered to you.This well maintained home still has originals such as natural woodwork,built-ins and a pocket door between LR/DR to name a few of the things that bring out the true beauty of this home. To anyone with a desire for craftsmanship and detail this home is sure to please and will not disappoint. The large living room with a fireplace and the dining room with built-ins make a great space for family time. Public record shows 4 BR however with 2 additional on the 3rd level and all with closets this could be considered 6 BR. Every room is great size.The front porch which comes with custom made screens is another great place to sit back and relax with a good book and your favorite beverage.The driveway leads to your 2 car garage and plenty of off st parking which is a bonus in this town. Massport windows and newer roof. Must see to appreciate !!

Year

Property tax

Land + Additions

Assessment*

2023

$7,287 (+4.1%)

$284,100 + $396,900

$681,000

2022

$6,998 (+18.9%)

$253,500 + $341,600

$595,100

2021

$5,886 (+0.5%)

$226,400 + $237,800

$464,200

2020

$5,858 (+2.1%)

$226,400 + $237,800

$464,200

2019

$5,735 (+2.7%)

$208,600 + $226,500

$435,100

2018

$5,583 (+7.3%)

$179,100 + $215,200

$394,300

2017

$5,201 (+1.9%)

$161,900 + $199,000

$360,900

2016

$5,103 (+12.1%)

$137,900 + $194,100

$332,000

2014

$4,554 (+4.5%)

$119,200 + $173,100

$292,300

2013

$4,358 (+2.9%)

$119,200 + $173,100

$292,300

2012

$4,235 (+2.2%)

$119,200 + $173,100

$292,300

2011

$4,143 (+3.5%)

$132,400 + $167,800

$300,200

2010

$4,001 (+14.8%)

$147,200 + $167,800

$315,000

2009

$3,485

$175,700 + $173,800

$349,500

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

6,098 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

2,267

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,267

Year built

1896

Style

Single Family Residential

County

Suffolk County

APN

1421640

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 95° expected this year, 15 days in 30 years

6/10 Wind Factor

67% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winthrop, MA • 02152

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

89/ 100

Very good sunlight

Sunscore

This home ranks in the top 26% for direct sun exposure in Winthrop. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.5 hrs

5.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 217 Pleasant St

$924,267

$24K under list price of $948K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $620K to $1.2M.

SOLD SEP 2, 2026
$960,000 Last sold price
5 beds2 baths2,123 sq ft
57 Loring Rd, Winthrop, MA 02152
$94/sq ft
smaller lot
21 years newer
SOLD AUG 18, 2026
$1,180,000 Last sold price
3 beds2 baths2,214 sq ft
32 Faun Bar Ave, Winthrop, MA 02152
$175/sq ft
smaller lot
92 years newer
SOLD MAR 13, 2026
$815,000 Last sold price
4 beds2 baths2,317 sq ft
45 Read St, Winthrop, MA 02152
$6/sq ft
larger lot
24 years newer
SOLD SEP 11, 2026
$877,700 Last sold price
3 beds2.5 baths2,451 sq ft
211 Grovers Ave, Winthrop, MA 02152
smaller lot
50 years newer
no basement
SOLD JUN 15, 2026
$620,000 Last sold price
4 beds2 baths2,456 sq ft
33 Dolphin Ave, Winthrop, MA 02152
$106/sq ft
smaller lot
6 years older
SOLD OCT 16, 2026
$770,000 Last sold price
4 beds4 baths2,910 sq ft
26 George St, Winthrop, MA 02152
$93/sq ft
smaller lot
34 years newer

Rental earnings

Est. $3,739 per month, based on comparable rentals

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(617) 764-9118

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173-175 Shirley St #6, Winthrop, MA 02152

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23 Sagamore, Winthrop, MA 02152

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316 Bowdoin St, Winthrop, MA 02152

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Details provided by MLS PIN and may not match the public record. Learn more.

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