2 Upland Rd, Winthrop, MA 02152
1029
1030
OFF MARKET

2 Upland Rd
Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,100 sqft

$849,700

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $4,823/mo*
Refinance Your Home

$849,700

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $4,823/mo*
Refinance Your Home
2 Beds
1 Bath
1,100 sqft

Local Information

  • Map ViewExplore the area around 2 Upland Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Living Area
1,100 sqft
Price/Sqft
$772

About this House

This multi-family home is located at 2 Upland Rd, Winthrop, MA. 2 Upland Rd is in Winthrop, MA and in ZIP code 02152. This property has 2 bedrooms, 1 bathroom and approximately 1,100 sqft of floor space.
2 Upland Rd, Winthrop, MA 02152 is a 2 bedroom, 1 bathroom, 1,100 sqft multi-family. More recently, it was listed as a rental in October 2023 with an asking price of $2,300 per month. That rental listing was removed on December 7, 2023. It is currently off market. The Trulia Estimate is $849,700, with a rent estimate of $2,747/month.

Home Details for 2 Upland Rd

Property Information

Property Type / Style
Property Type: Multi Family

Interior Features

Interior Details
Types of Rooms: Breakfast Nook, Office
Appliances & Utilities
DisposalDryer
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Parking & Garage
Parking: On Street

Community

Units in Building: 1

Price History for 2 Upland Rd

DatePriceEventSource
12/07/2023ListingRemovedZillow Rentals
11/28/2023$2,200PriceChange
Zillow Rentals
10/15/2023$2,250PriceChange
Zillow Rentals
10/12/2023$2,300Listed For RentZillow Rentals
08/15/2015$1,950ListingRemovedAgent Provided
06/02/2015$1,950Listed For RentAgent Provided

Market trends in Winthrop

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
74
6MoM
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Comparable Sales for 2 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Summit Ave, Winthrop, MA
0.29
Multi-Family Home
$890,000
12/17/25
4
2
2,386
37-39 Hutchinson St, Winthrop, MA
0.24
Multi-Family Home
$830,000
08/30/25
5
2
2,958
89-91 Sagamore Ave, Winthrop, MA
0.31
Multi-Family Home
$830,000
11/14/25
4
2.5
2,000
68-70 Floyd St, Winthrop, MA
0.13
Multi-Family Home
$930,000
08/22/25
4
3.5
3,432
144 Quincy Ave, Winthrop, MA
0.06
Multi-Family Home
$1,600,000
03/12/26
5
4
3,866
22 Upland Rd, Winthrop, MA
0.03
Multi-Family Home
$1,175,000
04/15/26
6
3.5
4,062
80 Shirley St, Winthrop, MA
0.43
Multi-Family Home
$880,000
12/15/25
4
2
2,366
76 Pearl Ave, Revere, MA
0.49
Multi-Family Home
$690,000
07/30/25
4
3
1,507
50-52 Wilshire St, Winthrop, MA
0.52
Multi-Family Home
$990,000
04/16/26
6
2
2,212
441 Winthrop St, Winthrop, MA
0.49
Multi-Family Home
$725,000
03/24/26
6
2
2,454

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Upland Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
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  • 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
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  • Trulia User
    "Winthrop is close to downtown Boston, the beach, Logan Airport and the MBTA (both bus and train lines)."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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Apartments for Rent

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Explore by feature - Pet Friendly

24 pet-friendly rentals in Winthrop, MA

Explore by feature - Air Conditioning

35 rentals with air conditioning in Winthrop, MA

Explore by feature - Washer/dryer

38 rentals with a washer/dryer in Winthrop, MA

Homes for sale near 2 Upland Rd

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Off Market Homes Near 2 Upland Rd

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