22 Upland Rd

4,062 Sq. Ft.
$308 / Sq. Ft.
4,062
Sq. Ft.
$308
per Sq. Ft.

Description

In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, two off street parking spaces, and a nicely landscaped backyard....In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, two off street parking spaces, and a nicely landscaped backyard. You'll enjoy beautiful ocean views and it's just steps to Halford Beach. Pride of ownership is evident throughout. Winthrop by the Sea is just six miles to Boston, has a variety of wonderful restaurants, walk/jog trails, access to the Blue Line and close to Logan Airport - 22 Upland Road is an outstanding opportunity to own a home and collect rental income in one smart investment,
  1. Listed by Mary Ann Cash • Charlesgate Realty Group, llc

Property Details for 22 Upland Road

Town
Winthrop
Area
MA-Winthrop
Garage Spaces
0
Parking Spaces
2.00
Parking Spaces Total
2
LISTING UPDATED: 02/01/2026 12:21 PM

Property Details for 22 Upland Road

StatusNew
MLS #73473241
Days on Market1
Taxes$9,583 / year
HOA Fees-
Compass TypeMulti Family
MLS TypeMulti-family / 3 Family
Year Built1900
CountySuffolk County

Location

Listing Courtesy of Charlesgate Realty Group, llc, Mary Ann Cash
Add your commute

Building Information for 22 Upland Road

Stories4Residences3Year Built1900Building Size-Lot Size0.09 AC / 3,894 SF

Payment Calculator

$6,891 per month

30 year fixed, 6.15% Interest

Principal and Interest

$6,092

Property Taxes

$799

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 22 Upland Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Park, Walk/Jog Trails, Golf Course, Laundromat, House of Worship, Marina, Public School, T-Station
  • Living Area: 4062.0
  • Color: Blue
  • SqFt with Basement: No
  • Total Units: 3
  • Waterfront: No
  • Water View: Yes
  • Year Built Details: Approximate,Renovated Since
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Oven, Dishwasher, Disposal, Range, Refrigerator, Microwave
  • Basement Features: Interior Access
  • Num of Baths: 4.0
  • Num of Full Baths: 3
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 3.50
  • Bathrooms Total Integer: 4
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Tile, Hardwood, Wood
  • Interior Features: Ceiling Fan(s), Bathroom With Tub & Shower, Living Room, Dining Room, Kitchen, Sunroom, Office/Den
  • Laundry Features: Washer Hookup, Dryer Hookup, Gas Dryer Hookup
  • SpaYN: No
Exterior Features
  • Construction: Frame
  • Exterior Features: Deck, Patio
  • Patio And Porch Features: Deck, Patio
  • Roof Material: Shingle
  • Waterfront Features: Ocean
  • Waterview Features: Ocean
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Paved Drive, Off-Street, Tandem, On Street Permit, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off-Street, Tandem, On Street Permit, Paved Driveway
  • Parking Features: Off-Street, Tandem, On Street Permit, Paved Driveway
Utilities
  • Electric: Circuit Breakers, Individually Metered
  • Heating: Baseboard, Hot Water, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, for Gas Oven, for Gas Dryer, Washer Hookup
  • Water: Public
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Disclosures: All information is as of the entry date and is subject to change. Buyer/Buyer's Agent to verify all information provided. Property is being sold in "as is" condition. Appliances are gifts. Unit 2 will be delivered vacant. Photos and floor plan are of Unit 1.
Tax Information
  • Tax ID: 1425125
  • Assessments: $860,300
  • Book: 60174
  • Tax Year: 2026
  • Zoning: Res.
Building / Association Information
Living Characteristics
  • Beds Total: 6
  • Total Living Levels: 4
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Levels: 4
  • Heat Units: 3
Income / Expenses
  • GOI: $73,800.00
  • NOI: $73,800.00
Complex & Association Information
  • Adult Community: No
Unit Information
Unit 1 Description
  • Floor U1: 1
  • Lease U1: N
  • Levels U1: 1
Unit 2 Description
  • Floor U2: 2
  • Lease U2: N
  • Levels U2: 1
Unit 3 Description
  • Floor U3: 2
  • Lease U3: N
  • Levels U3: 2
Rental Info
Rental Info
  • Total Actual Rent: $6,150.00

Property History for 22 Upland Road

DateEvent & SourcePriceAppreciation
Feb 1, 2026

Listed (Active)

MLS PIN #73473241

$1,250,000
DateEvent & SourcePrice
02/01/2026

Listed (Active)

MLS PIN #73473241

$1,250,000

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

Public Records for 22 Upland Road

Taxable ValueLand$327,000Additions$395,600Total$722,600
Tax Record2025$7,457 ($621 / month)
Home Facts
Baths3Total Finished SqFt4,062 SqFtAbove Grade Finished SqFt4,062 SqFtStories2Lot Size3,894 SqFtStyleTriplexYear Built1900CountySUFFOLKAPNWINT M:072 L:070

Schools near 22 Upland Road

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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22 Upland Road is a multi-family home for sale in Winthrop, MA 02152. This listing's school district is Winthrop School District. Nearby schools include William P. Gorman/Fort Banks Elementary School, Arthur T. Cummings Elementary School and Winthrop Middle School. 22 Upland Road is a 6-bed, 4-bath, 4,062 sqft multi-family home built in 1900.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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 Charlesgate Realty Group, llc, Mary Ann Cash

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.