SOLD SEP 11, 2026

Sold on sep 2026

$1,325,000

•

2,475

sq ft

89R Upland, Winthrop, MA 02152

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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

$535Price/Sq.Ft.

3 spacesParking

Listed by David Cody • Orchard Park Realty

Listed by • Orchard Park Realty

Bought with Gayle Winters & Co. Team • Compass

Redfin checked: 3 minutes ago

•Source:MLS PIN #73534719

Redfin Estimate

$1,342,595

$18K since sold in September 2026$19K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 56.3% higher than the average sale price ($859K) of 6 comparable homes.

SOLD SEP 11, 2026
$877,700
A
3 beds2.5 baths2,451 sq ft
211 Grovers Ave, Winthrop, MA 02152
SOLD JUL 30, 2026
$835,000
B
4 beds2.5 baths2,447 sq ft
143 Morton St, Winthrop, MA 02152
SOLD MAR 13, 2026
$815,000
C
4 beds2 baths2,317 sq ft
45 Read St, Winthrop, MA 02152
SOLD AUG 17, 2026
$900,000
D
4 beds3 baths2,424 sq ft
109 Eustis St, Revere, MA 02151
SOLD OCT 5, 2026
$750,000
E
4 beds2 baths1,755 sq ft
118 Sunnyside Ave, Winthrop, MA 02152
SOLD FEB 4, 2026
$975,000
F
3 beds2 baths2,820 sq ft
5 Quincy Ave, Winthrop, MA 02152

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Market trends in 02152, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.8%

+0.1% MoM

Median sale price

$629K

$6K MoM

Avg. days on market

23d

3 days MoM

Recently sold homes

5 MoM

New listings for sale

FOR SALE BY OWNER
$519,000
3 beds1 bath1,374 sq ft
23 Trident Ave, Winthrop, MA 02152
OPEN OCT 12, 11AM TO 12:30PM
$665,000
3 beds1.5 baths1,413 sq ft
14 Irwin St, Winthrop, MA 02152
$1,250,000
6 beds3 baths3,420 sq ft
23-25 Fremont St, Winthrop, MA 02152
$449,900
1 bed1 bath623 sq ft
130 Shirley St #8, Winthrop, MA 02152
$599,900
1 bed1 bath1,005 sq ft
1 Seal Harbor Rd #601, Winthrop, MA 02152
$599,900
5 beds2.5 baths2,200 sq ft
91 Fremont St, Winthrop, MA 02152
LISTED BY REDFIN
$799,900
5 beds2.5 baths2,437 sq ft
43 Dolphin Ave, Winthrop, MA 02152
$491,900
1 bed1 bath691 sq ft
10 Somerset #205, Winthrop, MA 02152
3D WALKTHROUGH
$529,900
3 beds1 bath1,788 sq ft
283 Revere St #2, Winthrop, MA 02152
$1,095,000
4 beds2.5 baths2,910 sq ft
61 Read St, Winthrop, MA 02152
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Rental estimate

Est. $2,907 per month, based on comparable rentals

Sale and tax history for 89R Upland

Sale History
Tax History

Date

Event

Price

MLS PIN #73534719

Sep 11, 2026

Sold

$1,325,000

$535/sq ft

Sep 3, 2026

Pending

—

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

—

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.

Property details

Parking

Parking Information
Has Open Parking
Open Parking Spaces: 3
Parking Spaces: 3
Parking Features: Off Street, Stone/Gravel, Paved

Interior

Virtural Tour Information
Virtual Tour 1 (External Link)

Master Bedroom Information
Level: Third
Features: Walk-In Closet(s),Balcony - Exterior,Recessed Lighting,Flooring - Engineered Hardwood

Bedroom #2 Information
Level: Second
Features: Closet,Recessed Lighting,Flooring - Engineered Hardwood

Bedroom #3 Information
Level: Second
Features: Closet,Recessed Lighting,Flooring - Engineered Hardwood

Bedroom #4 Information
Level: Second
Features: Closet,Recessed Lighting,Flooring - Engineered Hardwood

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile

Bathroom #3 Information
Level: Third
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile,Recessed Lighting

Living Room Information
Level: First
Features: Flooring - Stone/Ceramic Tile,Exterior Access,Open Floorplan,Recessed Lighting

Dining Room Information
Level: First
Features: Flooring - Stone/Ceramic Tile,Open Floorplan,Recessed Lighting

Kitchen Information
Level: First
Features: Kitchen Island,Exterior Access,Open Floorplan,Recessed Lighting,Stainless Steel Appliances,Lighting - Pendant

Basement Information
Basement: Full, Walk-Out Access, Interior Entry, Unfinished

Laundry Information
Laundry Features: Second Floor

Appliances
Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Wine Refrigerator

Interior Features
# of Rooms (Total): 8
Flooring: Tile, Engineered Hardwood

Exterior

Building Information
Building Area (Total): 2,475
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Renovated Since,Finished, Never Occupied

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck - Composite
Exterior Features: Deck - Composite, Balcony

Property Information
PropertySubType: Single Family Residence
Above Grade Finished Area: 2475
Has Waterview
ADU: N

Lot Information
Lot Size (Acres): 0.2
Lot Features: Easements, Sloped
ViewYN: Has View
View: Scenic View(s)

Financial

Tax Information
Tax Annual Amount: $10,259
Tax Year: 2026

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Central
Cooling: Central Air

Location

Location Information
Directions: Quincy Ave to Upland Rd. GPS
UnparsedAddress: 89R Upland, Winthrop MA 02152

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Bike Path, Marina

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 964
Stories: 2.0
Lot Size: 8,712 square feet
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Suffolk County
APN: 1425579

Home facts updated by county records on Jul 25, 2025

Other

Miscellaneous Information
Heat Zones: 2

Listing Information
StandardStatus: Closed

Around this home

Schools

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

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

This home ranks in the top 3% for direct sun exposure in Winthrop. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.2 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.28M – $1.54M

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New listings for sale in 02152

FOR SALE BY OWNER

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14 Irwin St, Winthrop, MA 02152

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LISTED BY REDFIN3D WALKTHROUGH

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Home values near 89R Upland

Data from public records.

Address	Redfin Estimate
80 Upland Road, Winthrop, MA 3 Beds \| 2.5 Baths \| 2102 Sq. Ft.	$837,234
96 Upland Road, Winthrop, MA 2 Beds \| 2 Baths \| 1021 Sq. Ft.	$729,174

Address	Redfin Estimate
86-92 Upland Road, Winthrop, MA 5 Beds \| 3 Baths \| 2876 Sq. Ft.	$973,227
98 Upland Road, Winthrop, MA 2 Beds \| 1 Baths \| 690 Sq. Ft.	$468,133

Address	Redfin Estimate
94 Upland Road, Winthrop, MA 3 Beds \| 2.5 Baths \| 1494 Sq. Ft.	$765,581
100 Upland Road, Winthrop, MA 3 Beds \| 1 Baths \| 1424 Sq. Ft.	$708,368

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Market trends in 02152, MA

Homeowner tools

Sale and tax history for 89R Upland

Public record

Property details

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02152

Home values near 89R Upland

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