22 Upland Rd, Winthrop, MA 02152
Property image
Property image
SOLD
APR 15, 2026

$1,175,500

Trulia Estimate
  • 6 Beds
  • 3.5 Baths
  • 4,062 sqft

22 Upland Rd, Winthrop, MA 02152

Est. Refi. Payment $6,675/mo*
Refinance Your Home
Currently Off Market - Sold Apr 15, 2026 for $1,175,000 (6% below list price)

Home Value

Trulia Estimate
$1.18M
Since last month
$0 (0%)
Since last year
Increased$238K (+25.4%)
Since last sale
$500 (0%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +106% in the last 10 years
MonthEstimated value
2026
August 2026$1.18M
August 2026$1.17M
July 2026$1.18M
June 2026$1.18M
May 2026$1.18M
April 2026$1.18M
March 2026$1.2M
February 2026$1.22M
January 2026$908K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
144 Quincy Ave, Winthrop, MA
0.05
Multi-Family Home
$1,600,000
03/12/26
5
4
3,866
419 Revere St, Winthrop, MA
0.16
Multi-Family Home
$1,331,000
05/28/26
8
4
4,260
117 Revere St, Winthrop, MA
0.37
Multi-Family Home
$1,280,000
07/24/26
9
3
3,621
212-214 Bradstreet Ave, Revere, MA
0.60
Multi-Family Home
$970,000
11/25/25
6
3.5
3,205
89-91 Sagamore Ave, Winthrop, MA
0.34
Multi-Family Home
$830,000
11/14/25
4
2.5
2,000
50-52 Wilshire St, Winthrop, MA
0.52
Multi-Family Home
$990,000
04/16/26
6
2
2,212
24 Trident Ave, Winthrop, MA
0.72
Multi-Family Home
$1,141,500
06/12/26
10
3
3,978
37 Trident Ave, Winthrop, MA
0.74
Multi-Family Home
$1,260,000
03/31/26
8
3
3,708

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
53 Upland Rd, Winthrop, MA 02152
0.05
$999,800
3
2.5
1,516
Off Market
144 Quincy Ave, Winthrop, MA 02152
0.05
$1,600,000
5
4
3,866
Recently Sold
2 Deane Ave, Winthrop, MA 02152
0.07
$884,000
5
2.5
2,397
Recently Sold
92 Quincy Ave, Winthrop, MA 02152
0.07
$1,061,900
4
2.5
2,497
Off Market
89-89 Upland Rd #R, Winthrop, MA 02152
0.11
-
3
1
1,194
Off Market
44 Cliff Ave #3, Winthrop, MA 02152
0.10
$679,900
3
2
1,849
Off Market
293 Revere St #2, Winthrop, MA 02152
0.09
$500,000
4
1
2,037
Recently Sold
283 Revere St #2, Winthrop, MA 02152
0.11
$549,000
3
1
1,788
For Sale
5 Quincy Ave, Winthrop, MA 02152
0.13
$975,000
3
2
2,820
Recently Sold
286 Revere St #286, Winthrop, MA 02152
0.12
$535,000
3
2
1,378
Recently Sold
68-70 Floyd St, Winthrop, MA 02152
0.14
-
4
3.5
3,432
Off Market

Local Information

  • Map ViewExplore the area around 22 Upland Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1900
4,062 sqft
$289/sqft
2 Open Spaces

About this House

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, 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,
22 Upland Rd, Winthrop, MA 02152 is a 6 bedroom, 4 bathroom, 4,062 sqft multi-family built in 1900. It last sold for $1,175,000 on Apr 15, 2026 (6% below the $1,250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,175,500, with a rent estimate of $3,880/month.
Last check for updates: about 18 hours ago
Listed by Mary Ann Cash, (617) 846-1234
Charlesgate Realty Group, llc, (617) 587-0100
Bought with: Riode Jean Felix, (617) 939-7327, Compass, (617) 206-3333
Source: MLS PIN, MLS#73473241

Home Details for 22 Upland Rd

Interior Features

Interior Details
Basement: Full,Interior Entry,Sump Pump,ConcreteNumber of Rooms: 17
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4062 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, for Electric Dryer, Washer HookupAppliances: Oven, Dishwasher, Disposal, Range, Refrigerator, Microwave, Washer, DryerDishwasherDisposalDryerLaundry: Washer Hookup,Dryer Hookup,Gas Dryer Hookup,Electric Dryer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Natural GasHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers, Common, Individually Metered
Windows, Doors, Floors & Walls
Flooring: Tile, Hardwood
Levels, Entrance, & Accessibility
Number of Stories: 4Floors: Tile, Hardwood
View
Has a ViewView: Water, Ocean

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, PatioExterior: Balcony/DeckFoundation: Concrete Perimeter
Parking & Garage
Open Parking Spaces: 2No GarageHas Open ParkingParking Spaces: 2Parking: Paved Drive,Off Street,On Street,Paved
Frontage
Waterfront: Ocean, 0 to 1/10 Mile To BeachNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4062

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: 3 Family
Building
Construction Materials: FrameDoes Not Include Home Warranty
Property Information
Parcel Number: 1425125

Price & Status

Price
List Price: $1,250,000Price Per Sqft: $289/sqft
Status Change & Dates
Off Market Date: Thu Mar 19 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winthrop

Building

Building Area
Building Area: 4062 Square Feet

Community

Community Features: Public Transportation, Park, Walk/Jog Trails, Golf, Laundromat, House of Worship, Marina, Public School, T-StationNot Senior Community

Lot Information

Lot Area: 3894 sqft

Offer

Contingencies: Pending P&S

Rental Terms, Policies & Fees

Rent Includes: Unit 1(Water), Unit 2(Water), Unit 3(Water)

Miscellaneous

BasementMls Number: 73473241Water ViewWater View: Ocean, WaterAbove Grade Unfinished Area: 4062

Additional Information

Public TransportationParkWalk/Jog TrailsGolfLaundromatHouse of WorshipMarinaPublic SchoolT-Station

Price and Tax history

DateEventPrice
Apr 15, 2026
Source: MLS PIN #73473241
Sold
$1,175,000
Mar 6, 2026
Source: MLS PIN #73473241
Contingent
$1,250,000
Feb 1, 2026
Source: MLS PIN #73473241
Listed For Sale
$1,250,000
Mar 31, 1988
Source: N/A
Sold
$263,000

Market trends in Winthrop

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
74

Around this home

What Locals Say about Winthrop

At least 174 Trulia users voted on each feature.

  • 94 % Say there are sidewalks

  • 92 % Say it's dog friendly

  • 84 % Say it's walkable to restaurants

  • 84 % Say parking is easy

  • 83 % Say people would walk alone at night

  • 80 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 72 % Say yards are well-kept

  • 67 % Say it's walkable to grocery stores

  • 66 % Say they plan to stay for at least 5 years

  • 65 % Say kids play outside

  • 64 % Say it's quiet

  • 62 % Say car is needed

  • 60 % Say neighbors are friendly

  • 45 % Say there's wildlife

  • 42 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Yv9h5vmcvm
    "Great neighborhood community, with alot of outdoor space. No school bus route but everything is relatively close and walkable. Easy access to public transportation. The community is welcoming and supportive."
    0
    Flag
  • Trulia User
    "Reliable bus to the nearby T station makes the commute manageable and coffee shops add to the experience."
    0
    Flag
  • Job4cwsouthworth
    "Great area! Its mostly quiet and you have access to all Boston has to offer. There are frequent local events outside in the summer and a lot of clubs and thing to do indoors in winter. The city center is small but it has the essentials and some nice cafes. The BBQ place does a great brunch! Plus you have ocean access! The ocean micro-climate in Winthrop means warmer winters and cooler in the summers. Nothing in life is perfect, but Winthrop comes close! "
    0
    Flag
  • Trulia User
    "You can park at orient heights for 6 bucks or one of the other lots along the blue line. The commute in is easy. Easy like Sunday morning."
    0
    Flag
  • Trulia User
    "Coughlin Park is a great place to meet up with other dogs! usually after work lots of people bring their dogs there and let them play! always good to be around other dog lovers !"
    0
    Flag
  • Trulia User
    "Winthrop is close to downtown Boston, the beach, Logan Airport and the MBTA (both bus and train lines)."
    0
    Flag
  • Trulia User
    "Winthrop is near the beach, near Boston, near the Airport, near highways and has access to public transportation. City life without the city!"
    0
    Flag
  • Alexander21mp
    "Not good, this lovely city should have a better transportation. Also, traffic can be very ugly during morning and evening."
    6
    Flag
  • Joey C.
    "Lots of small town events. Craft fairs, holiday gift shows The Horribles Parade and Firewomen. Halloween haunt and holiday tree lighting in town center."
    3
    Flag
  • Mikeborghe
    "Great neighborhood!! On the ocean and next to the city. But most importantly very safe! Friendly environment. "
    1
    Flag
  • Andrea L. G.
    "I lived here for 5 years and love it! Love walks to the beach and shops & restaurants in the center of town. "
    0
    Flag
  • Janelleallison90
    "Santa comes plus School fundraisers and sporting events. Winthrop market always supports kids in need. "
    1
    Flag
  • Jojowhite118
    "Commute would be better if we got a discount on the tolls. I go though Chelsea, Everett, Charlestown to get to work at TD Garden. I come home the same way which is so out of my way. To pay the Tolls it’s like another big bill on my hands. I love living in Winthrop but I’ll probably move out because of the toll’s. "
    5
    Flag
  • Kbiti01
    "I live here it is a great town with lots of little shops and really nice people. It is very close to walking distance of the beach. "
    0
    Flag
  • Pinzonaleja
    "I love Winthrop, is a safe and beautiful environment and is close to the sea also has public transportation (bus) every 15 min "
    0
    Flag
  • Chris
    "I've lived in Winthrop 10byears. I have a six year old son and I am going to raise him here. This is a great town. I have lived all over and Winthrop is excellent. Small town feel next to big city and all that has to offer. Culture, safe, great schools and the beach! "
    9
    Flag
  • Katlyn J.
    "It’s a great town to live in awesome schools and teachers. People around here are pretty nice. Foods amazing around here lots of restaurants and we have beaches as well"
    4
    Flag
  • Nicole P. .
    "Quick walk to the 712 bus which takes you to Orient Heights on the blue line. About 35 mins door to door to downtown Boston."
    2
    Flag
  • Trulia User
    "Winthrop is a great suburban town located in close proximity to both Boston and Logan airport. It’s a safe family oriented community, offering many family oriented activities throughout the year. It’s great for outdoor living as well, being a costal community, there are many ways to enjoy the great outdoors in Winthrop. No matter what your into... walking, biking, water sports... whatever... Winthrop is nice place to call home...😎"
    2
    Flag
  • Pinzonaleja
    "Winthrop is not close to the T, but it has regular bus service to the orient heights station. At least every 15- 20 min there is a bus going to the station or departing to Winthrop. "
    2
    Flag
  • Tacm12000
    "Movies on the beach. Santa’s parade. Town hall meetings for residents. Nice police force. Very reactive. "
    0
    Flag
  • Elaine C.
    "Every festival makes our community like a family, but I Think the drama club of middle school, at the center the Blue light tree at Christmas even. "
    0
    Flag
  • Elaine C.
    "We moved to Winthrop 5 years ago and we like the hole family fall in love with the city. My kids grow so much here in all potencial areas, my son Plays football and Basketball for High school we are very happy here."
    0
    Flag
  • Trulia User
    "Great parks, nice playground, for toddlers and older kids, skate park, courts for basketball. Sporting goods store in the center for kids who play sports! Nice restaurants all throughout town! Safe neighborhood to walk around in! "
    0
    Flag
  • Alyssa S.
    "Plenty of buses that take you to the blue line at Orient Heights station...4 stops to Boston. You could also choose to drive to the station to park and take the train"
    1
    Flag
  • Odwyro
    "Skunks share the hill and dogs get sprayed regularly especially when let out in the yard at night I attended. Beach is seasonal for dogs."
    1
    Flag

LGBTQ Local Legal Protections

The property listing data and information 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 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 set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 22 Upland Rd

  • What is 22 Upland Rd estimated to be worth?
    Trulia's estimated value for 22 Upland Rd in Winthrop, MA is $1,175,500.
  • What is the price history for 22 Upland Rd?
    22 Upland Rd in Winthrop, MA last sold for $1,175,000 in April 2026.
  • Is Winthrop a buyer's or seller's market?
    Winthrop is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winthrop?
    Residents describe Winthrop, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See recently sold homes in Winthrop, MA.
  • Does 22 Upland Rd have air conditioning?
    Yes, 22 Upland Rd in Winthrop, MA has air conditioning.
  • Does 22 Upland Rd have laundry facilities?
    Yes, 22 Upland Rd in Winthrop, MA has in-unit laundry.

Explore by feature - Pet Friendly

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