271 River Rd, Winthrop, MA 02152
Property image
Property image
OFF MARKET

$865,700

Trulia Estimate
as of Sep 23, 2026
  • 4 Beds
  • 2.5 Baths
  • 2,786 sqft

271 River Rd, Winthrop, MA 02152

Home Highlights

Apartment
2,786 sqft
$311/sqft

Local Information

  • Map ViewExplore the area around 271 River Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Formal dining roomGood sized yardExtra-large closetsHalf bathLarge center islandTile backsplash
Just Listed! Tastefully renovated 4 bedroom/2.5 bath Victorian located on one of Winthrop s most desirable streets! Recent upgrades are highlighted by a chef s granite kitchen with a large center island, stainless appliances, tile backsplash, natural maple cabinetry. The 1st floor also features a stacked stone gas fireplace with a reclaimed wood mantle formal dining room. The 2nd floor features 3 large bedrooms, an updated bathroom with a jacuzzi tub a double vanity with granite counters. The finished attic includes two additional bedrooms with extra-large closets. The offering is complete with a partially finished basement that works as a recreational room includes a half bath storage area with laundry hook-ups. A large deck off the kitchen leads to a good sized yard driveway big enough for 4 cars. Extremely well located close to beaches, yacht clubs, golf club, the new high school, Logan Airport, Boston, restaurants/shops in downtown Winthrop. Available 9/1.
Tenant pays
271 River Rd, Winthrop, MA 02152 is a 4 bedroom, 3 bathroom, 2,786 sqft apartment. It last sold for $479,000 on Jun 12, 2015 (11,875% above the $4,000 asking price). More recently, it was listed as a rental in July 2026 with an asking price of $4,000 per month. That rental listing was removed on July 10, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $865,700, with a rent estimate of $4,152/month.

Home Details for 271 River Rd

Interior Features

Heating & Cooling
Heating: Natural GasHeating Fuel: Natural Gas

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Comparable Sales for 271 River Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
125 Pleasant St #2, Winthrop, MA
0.53
Apartment
$706,250
07/07/26
3
2
1,517 sqft
600 Governors Dr #32, Winthrop, MA
0.86
Apartment
$350,000
10/30/25
2
1
821 sqft
77 Bennington St #508, Revere, MA
1.83
Apartment
$316,500
09/16/26
2
2
891 sqft
58 Homer St, East Boston, MA
2.23
Apartment
$480,000
07/10/26
3
1
2,214 sqft
95-97 Addison St, East Boston, MA
2.35
Apartment
$684,900
04/24/26
3
2
1,146 sqft
7 Wordsworth St, East Boston, MA
2.42
Apartment
$465,000
06/05/26
12
10
6,000 sqft
246 Bremen St, East Boston, MA
2.93
Apartment
$699,000
07/03/26
3
2
2,262 sqft
595 Revere Beach Pkwy #40, Revere, MA
2.75
Apartment
$359,000
09/16/26
2
2
945 sqft
249 Lexington St, East Boston, MA
2.88
Apartment
$575,000
07/02/26
2
2
1,200 sqft
320 Maverick St, East Boston, MA
2.91
Apartment
$525,000
06/22/26
2
2
1,056 sqft
Home facts updated by county records

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Winthrop

Last updated Sep 2026
Trulia Rent Estimate$4,152/mo
Average rent
$2.6K
$95MoM
Available listings
74
View rental market trends in Winthrop, MA

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

Price and Tax history

DateEventPrice
Jul 10, 2026
Source: Zillow Rentals
ListingRemoved
$4,000
Jul 1, 2026
Source: Zillow Rentals
Listed For Rent
$4,000
Oct 2, 2024
Source: Zillow Rentals
ListingRemoved
$3,600
Sep 12, 2024
Source: Zillow Rentals
Listed For Rent
$3,600
Aug 2, 2024
Source: Zillow Rentals
ListingRemoved

Frequently asked questions about 271 River Rd

  • What is 271 River Rd estimated to be worth?
    Trulia's estimated value for 271 River Rd in Winthrop, MA is $865,700.
  • What is the price history for 271 River Rd?
    271 River Rd in Winthrop, MA last sold for $479,000 in June 2015.
  • Is Winthrop a buyer's or seller's market?
    Winthrop is currently a balanced 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.

Homes for rent near 271 River Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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