Virginia Todd
Leading Edge Real Estate
(857) 323-6892
50 Total Sales
1 in Winthrop Highlands
$679,000 Price
22 Upland Rd Winthrop, MA 02152
Winthrop Highlands NeighborhoodEstimated Value: $1,150,000 - $1,201,000
6
Beds
3.5
Baths
4,062
Sq Ft
$289/Sq Ft
Est. Value
Highlights
- Marina
- Ocean View
- Waterfront
- William P. Gorman/Fort Banks Elementary School Rated A-
- Property is near a beach
- 1-minute walk to Rocky Beach
About This Home
As of April 2026In 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, one off street parking space, 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,
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Property Details
Home Type
- Multi-Family
Est. Annual Taxes
- $9,583
Year Built
- Built in 1900
Lot Details
- 3,894 Sq Ft Lot
- Waterfront
Home Design
- Frame Construction
- Shingle Roof
- Concrete Perimeter Foundation
Interior Spaces
- 4,062 Sq Ft Home
- Property has 1 Level
- Ceiling Fan
- Living Room
- Dining Room
- Home Office
- Sun or Florida Room
- Ocean Views
Kitchen
- Oven
- Range
- Microwave
- Dishwasher
- Disposal
Flooring
- Wood
- Tile
Bedrooms and Bathrooms
- 6 Bedrooms
- Bathtub with Shower
Laundry
- Dryer
- Washer
Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
- Sump Pump
Parking
- 2 Car Parking Spaces
- Driveway
- Paved Parking
- On-Street Parking
- 2 Open Parking Spaces
- Off-Street Parking
Outdoor Features
- Property is near a beach
- Balcony
- Deck
- Patio
Location
- Property is near golf course, public transit, and schools
Utilities
- Window Unit Cooling System
- Heating System Uses Natural Gas
- Baseboard Heating
- Hot Water Heating System
- Separate Meters
Listing and Financial Details
- Total Actual Rent $6,150
- Rent includes unit 1(water), unit 2(water), unit 3(water)
- Assessor Parcel Number 1425125
Community Details
Recreation
- Marina
- Park
- Jogging Path
Additional Features
- 3 Units
- Coin Laundry
- Net Operating Income $73,800
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Feb 1, 2026
Closed on
Apr 15, 2026
Sold by
Bought by
Seller's Agent
Mary Ann Cash
Charlesgate Realty Group, llc
Buyer's Agent
Riode Jean Felix
Compass
List Price
$1,250,000
Sold Price
$1,175,000
Premium/Discount to List
-$75,000
-6%
Views
27
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$237
Avg. Annual Appreciation
0.06%
Purchase Details
Listed on
Feb 1, 2026
Closed on
Mar 25, 2026
Sold by
Bought by
Seller's Agent
Mary Ann Cash
Charlesgate Realty Group, llc
Buyer's Agent
Riode Jean Felix
Compass
List Price
$1,250,000
Sold Price
$1,175,000
Premium/Discount to List
-$75,000
-6%
Views
27
Purchase Details
Closed on
Sep 17, 2018
Sold by
Bought by
Purchase Details
Closed on
Mar 31, 1988
Sold by
Bought by
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Winthrop Highlands, MA
-
Virginia Todd
-
Lisa Licata-Schepici
Lisa Licata-Schepici
Responds QuicklyL.L.S. Realty LLC
(351) 666-4792
59 Total Sales
1 in Winthrop Highlands
$490,000 Price
-
Nicole Bettano
Nicole Bettano
Real Broker MA, LLC
(781) 755-3931
69 Total Sales
6 in Winthrop Highlands
$510K - $1M Price Range
-
The Young Group
The Young Group
Leopold & McMasters Realty
(339) 333-8140
74 Total Sales
1 in Winthrop Highlands
$435,000 Price
-
Alexa McCormick
Alexa McCormick
Responds QuicklyLyv Realty
(508) 281-2432
33 Total Sales
1 in Winthrop Highlands
$850,000 Price
-
Alex Walsh
Alex Walsh
Responds QuicklyAccess
(339) 218-6016
533 Total Sales
2 in Winthrop Highlands
$390K - $538K Price Range
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $1,175,000 | -- | ||
| -- | -- | ||
| -- | -- | ||
| $263,000 | -- |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/15/2026 04/15/26 | Sold | $1,175,000 | -6.0% | $289 / Sq Ft |
| 03/06/2026 03/06/26 | Pending | -- | -- | -- |
| 02/01/2026 02/01/26 | For Sale | $1,250,000 | -- | $308 / Sq Ft |
Source: MLS Property Information Network (MLS PIN)
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $7,457 | $722,600 | $327,000 | $395,600 |
| 2024 | $7,369 | $707,200 | $314,300 | $392,900 |
| 2023 | $7,572 | $707,700 | $287,700 | $420,000 |
| 2022 | $7,962 | $677,000 | $257,000 | $420,000 |
| 2021 | $7,791 | $614,400 | $229,400 | $385,000 |
| 2020 | $7,108 | $563,200 | $229,400 | $333,800 |
| 2019 | $6,830 | $518,200 | $211,400 | $306,800 |
| 2018 | $6,725 | $474,900 | $181,500 | $293,400 |
| 2017 | $6,235 | $432,700 | $160,900 | $271,800 |
| 2016 | $5,890 | $383,200 | $139,900 | $243,300 |
| 2015 | $5,145 | $358,800 | $135,800 | $223,000 |
| 2014 | $5,363 | $344,200 | $126,300 | $217,900 |
Source: Public Records
Agents Affiliated with this Home
-
Mary Ann Cash
M
Seller's Agent in 2026
Mary Ann Cash
Charlesgate Realty Group, llc
(617) 846-1234
4 in this area
43 Total Sales
-
Riode Jean Felix
Buyer's Agent in 2026
Riode Jean Felix
Compass
(617) 939-7327
1 in this area
33 Total Sales
Map
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73473241
APN: WINT-000072-000000-000070
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. 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. 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.
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