For sale

$1,399,000

Est. $8,047/mo —

•

2,475

sq ft

89R Upland, Winthrop, MA 02152

About this home

Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive improvements throughout. The open-concept layout is filled with natural light and showcases a beautifully appointed kitchen with custom cabinetry, quartz countertops, stainless steel appliances, a beverage refrigerator, and a large center island. Occupying the entire third level, the private primary suite offers breathtaking water views, a private balcony, a walk-in closet, and a spa-inspired bath. A rare opportunity to own a thoughtfully reimagined coastal home where panoramic water views, abundant natural light, and extensive recent reconstruction come together in one exceptional setting.

Single-familyProperty Type

1930Year Built

8,628 sq ftLot Size

$565Price/Sq.Ft.

3 spacesParking

Listed by David Cody • Orchard Park Realty

Listed by • Orchard Park Realty

Listing updated: Aug 10, 2026 at 03:11am

Redfin checked: a minute ago

•Source:MLS PIN #73534719

Payment calculator

$8,047 per month

Principal and interest$6,982

Property taxes

$855

HOA dues

Home insurance

$210

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN WED, 4PM TO 5:30PM
$899,900
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52 Burpee Rd, Swampscott, MA 01907
OPEN THU, 4PM TO 5:30PM
$1,650,000
2 beds2 baths2,153 sq ft
131 Nichols Rd, Cohasset, MA 02025
OPEN THU, 4PM TO 5:30PM
$1,650,000
2 beds2 baths2,153 sq ft
131 Nichols Rd #6, Cohasset, MA 02025
OPEN THU, 4:30PM TO 6PM
$899,000
3 beds2.5 baths2,240 sq ft
123 Eastman Ave, Swampscott, MA 01907
OPEN THU, 5PM TO 6:30PM3D WALKTHROUGH
$775,000
5 beds2.5 baths1,797 sq ft
20 Paragon, West Roxbury, MA 02132
OPEN THU, 6PM TO 8PM
$999,900
6 beds3 baths4,025 sq ft
15 Mclellan St, Dorchester, MA 02121
OPEN FRI, 2:30PM TO 4PM
$1,249,000
7 beds4 baths4,306 sq ft
34 Avon Way, Quincy, MA 02169
OPEN SAT, 11AM TO 1PM
$999,900
3 beds2.5 baths2,000 sq ft
8 Willowdale Dr, Lynnfield, MA 01940
OPEN SAT, 11AM TO 12:30PM
$650,000
2 beds2 baths1,098 sq ft
18 Kittredge St #1, Roslindale, MA 02131
OPEN SAT, 12PM TO 1:30PM
$1,899,000
4 beds4.5 baths4,874 sq ft
10 Whitehead Ave, Hull, MA 02045

Around this home

Schools

K - 12
Preschool & daycare

William P. Gorman/Fort Banks Elementary School

Public PreK-2 • Assigned • 0.3mi

Winthrop Middle School

Public 6-8 • Assigned • 0.7mi

8/10

Winthrop Senior High School

Public 9-12 • Assigned • 0.6mi

5/10

Provided by GreatSchools

About Whinthrop

Highlands

Whinthrop Highlands, located between Winthrop Beach and Deer Island, is a coastal and residential Winthrop neighborhood with ocean-facing streets and bluff-top views. The neighborhood’s character concentrates around the Winthrop Shore Drive and Revere Street corridor, where corner markets, takeout counters, and shoreline foot traffic set a steady, salt-air rhythm. Triple-deckers and compact cottages mix with newer condos, many oriented toward the water. Short blocks lead to pocket parks and long stretches of sand, with planes tracing the sky from nearby Logan. Community touchstones include Belle Isle Seafood, Winthrop Arms Hotel, and the Winthrop Ferry Terminal.

Provided by Walk Score and Local Logic

Offer insights

89R Upland · $1,399,000

Strong offer

$1.39M and above

75% chance or better to win

Why $1.39M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 21 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Interior features
Open floorplan
Recessed lighting
Exterior access from living areas
Kitchen island
Pendant lighting
Full unfinished basement with walk-out access and interior entry
Total of 8 rooms

Bedrooms
Primary bedroom on third floor with walk-in closet and exterior balcony
Three additional bedrooms on second floor, each with closet and recessed lighting

Bathrooms
Two full bathrooms (one on second floor, one on third floor) with tile flooring; the third-floor bath includes recessed lighting
One half bathroom on first floor with tile flooring

Kitchen
Stainless steel appliances
Range
Dishwasher
Refrigerator
Wine refrigerator
Kitchen island
Kitchen has exterior access

Laundry & utility
Laundry located on second floor
Gas water heater

Flooring
Engineered hardwood
Tile (stone/ceramic)

Heating & cooling
Central heating
Central air conditioning

Sale and tax history for 89R Upland

Sale History
Tax History

Date

Event

Price

MLS PIN #73534719

Aug 6, 2026

Price Changed

$1,399,000

$565/sq ft

Jun 27, 2026

Price Changed

$1,480,000

$598/sq ft

Jun 11, 2026

Listed

$1,525,000

$616/sq ft

MLS PIN #73138011

Oct 27, 2023

Sold

$750,000

$303/sq ft

Sep 16, 2023

Contingent

—

Aug 22, 2023

Price Changed

$779,000

$315/sq ft

Jul 31, 2023

Price Changed

$799,000

$323/sq ft

Jul 19, 2023

Listed

$839,000

$339/sq ft

+37

Price Reduced!!!! Experience tranquil serenity with this charming waterfront cottage nestled in Highland’s neighborhood in Winthrop. Step into a warm ambiance on the first floor, featuring charming wood floors, beamed ceilings, and a cozy gas fireplace. Walls of windows provide breathtaking panoramas of the seascape, infusing every room, including the bright, eat-in kitchen, with uplifting natural light. Wake up to mesmerizing sunrises in the master bedroom and wind down with stunning sunsets from your porch. The potential for expansion allows for a transformation of the attic into a spacious master suite, and the first floor can be remodeled for an extra wow factor. This home offers the convenience of off-street parking for 3 cars.

MLS PIN #72810741

May 12, 2022

Sold

$760,000

$307/sq ft

Mar 16, 2022

Contingent

—

Mar 10, 2022

Relisted

—

Mar 4, 2022

Contingent

—

Jan 3, 2022

Relisted

—

Dec 1, 2021

Listing Removed

—

Nov 3, 2021

Price Changed

$799,900

$323/sq ft

Sep 29, 2021

Price Changed

$839,900

$339/sq ft

Aug 12, 2021

Price Changed

$889,900

$360/sq ft

Jul 16, 2021

Price Changed

$899,900

$364/sq ft

Jun 10, 2021

Price Changed

$950,000

$384/sq ft

Apr 7, 2021

Listed

$999,900

$404/sq ft

+31

OPPORTUNITY KNOCKS IN 2022, FOR THAT WATERFRONT HOME.........A HIDDEN ESCAPE, DIRECT OCEANFRONT, IN WINTHROP BY THE SEA, JUST MINUTES TO BOSTON! This unique property offers over 8,000 Sq. Ft. of land with a pretty country setting leading to a sweet vacation-style home set high on a hill overlooking the ocean. The first level has lots of large window to capture those amazing views from every room, literally walls of windows! Enter into a bright, eat in kitchen to one side and on the other, an open dining room/living room with wood floors, beam ceilings and a gas fireplace for cozy gatherings and personal enjoyment. There is plenty of off street parking (3 cars) and easy access to Boston by car, ferry and close to the T. Enjoy the incredible sunrises while having your morning coffee and live every day as if you are on vacation. ***NO FLOOD INSURANCE NEEDED***

Public Records

Jul 31, 1991

Sold

$156,000

$63/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$7,825 (+1.4%)

$533,700 + $197,600

$731,300

2022

$7,717 (+1.4%)

$479,200 + $177,000

$656,200

2021

$7,608 (+0.5%)

$427,900 + $172,100

$600,000

2020

$7,572 (+2.9%)

$427,900 + $172,100

$600,000

2019

$7,357 (+5.1%)

$394,300 + $163,900

$558,200

2018

$6,998 (+11.1%)

$338,500 + $155,700

$494,200

2017

$6,300 (+5.8%)

$294,000 + $143,200

$437,200

2016

$5,956 (+18.2%)

$247,800 + $139,700

$387,500

2014

$5,037 (+4.5%)

$198,800 + $124,500

$323,300

2013

$4,820 (+2.9%)

$198,800 + $124,500

$323,300

2012

$4,685 (−2.2%)

$198,800 + $124,500

$323,300

2011

$4,791 (+1.7%)

$234,400 + $112,800

$347,200

2010

$4,713 (+14.6%)

$258,300 + $112,800

$371,100

2009

$4,114

$284,900 + $127,700

$412,600

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

8,712 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

964

Unfinished Sq. Ft.

—

Total Sq. Ft.

964

Year built

1930

Style

Single Family Residential

County

Suffolk County

APN

1425579

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 25, 2025.

May 9, 2025 • Active

Electrical

Perform a full electrical rewiring of a single-family home and upgrade the electrical service.

Electrical

Mar 16, 2025 • Final

Building permit - residential

Perform selective renovations throughout the building and construct an addition according to the provided plans.

Addition

Remodel

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

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

5/10 Heat Factor

6 days above 95° expected this year, 12 days in 30 years

6/10 Wind Factor

68% 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

93/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.2 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 89R Upland

$1,299,557

$99K under list price of $1.40M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $835K to $994K.

SOLD NOV 17, 2025
$960,000 Last sold price
3 beds2.5 baths2,441 sq ft
69 Leverett Ave, Revere, MA 02151
$172/sq ft
smaller lot
65 years newer
SOLD JUL 21, 2026
$950,000 Last sold price
7 beds2 baths2,728 sq ft
1748 N Shore Rd, Revere, MA 02151
$217/sq ft
smaller lot
10 years older
SOLD JUL 30, 2026
$835,000 Last sold price
4 beds2.5 baths2,447 sq ft
143 Morton St, Winthrop, MA 02152
$224/sq ft
smaller lot
24 years newer
SOLD MAR 6, 2026
$884,000 Last sold price
5 beds2.5 baths2,397 sq ft
2 Deane Ave, Winthrop, MA 02152
$196/sq ft
smaller lot
30 years older
SOLD JUL 30, 2026
$994,000 Last sold price
5 beds3 baths2,564 sq ft
156 Locust St, Winthrop, MA 02152
$177/sq ft
smaller lot
60 years older
SOLD OCT 3, 2025
$875,000 Last sold price
3 beds2.5 baths1,800 sq ft
3 Agneous Ave, Revere, MA 02151
$79/sq ft
smaller lot
95 years newer

Rental earnings

Est. $2,846 per month, based on comparable rentals

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Listing provided by Zillow

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New listings for sale in 02152

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

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