44 Winter St #4, Boston, MA 02108
Property image
Property image
OFF MARKET

$781,500

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,300 sqft

44 Winter St #4, Boston, MA 02108

Downtown Crossing
Est. Refi. Payment $4,595/mo*
Refinance Your Home

Home Value

Trulia Estimate
$782K
Since last month
Increased$147K (+15.6%)
Since last year
Increased$25K (+2.3%)
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 decreased by -9% in the last 10 years
MonthEstimated value
2026
September 2026$1.09M
August 2026$782K
July 2026$943K
June 2026$909K
May 2026$913K
April 2026$911K
March 2026$973K
February 2026$993K
January 2026$999K
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
0.21
Multi-Family Home
$2,760,000
12/05/25
3
3
1,750
0.50
Multi-Family Home
$2,495,000
07/20/26
5
4
2,376
0.85
Multi-Family Home
$1,250,000
02/12/26
3
3
1,377
0.06
Multi-Family Home
$4,025,000
04/15/26
10
9
4,920
0.85
Multi-Family Home
$1,600,000
10/27/25
5
3
2,040
0.46
Multi-Family Home
$5,500,000
06/26/26
7
4
5,779
0.78
Multi-Family Home
$1,950,000
08/03/26
5
4
2,805
0.98
Multi-Family Home
$2,100,000
07/31/26
4
3
2,402
0.89
Multi-Family Home
$2,337,200
03/06/26
3
2
3,130
1.12
Multi-Family Home
$875,000
06/15/26
2
2
971

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
0.02
$1,197,600
2
2
1,465
Off Market
0.02
$1,428,500
2
2
1,380
Off Market
0.02
$995,000
2
1.5
1,435
For Sale
0.03
$694,500
Studio
-
-
Off Market
0.03
$2,292,800
2
2
2,233
Off Market
0.03
$3,096,500
2
2.5
3,357
Off Market
0.06
$8,513,400
Studio
-
19,075
Off Market
0.06
$4,025,000
10
9
4,920
Recently Sold
0.06
$1,299,000
2
2
2,058
For Sale
0.06
$699,999
1
1
841
For Sale
0.06
$642,100
1
1
830
Off Market
0.06
-
2
1
1,124
Off Market

Local Information

  • Map ViewExplore the area around 44 Winter St #4.
  • Schools30 Preschool Schools31 Elementary Schools20 Middle Schools19 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
1,300 sqft
$601/sqft

About this House

Introducing the Residences at 44 Winter St, Midtown's newest luxury apartments. Prepare to be impressed by these finely appointed Manhattan style loft residences, which offer upscale urban finishes with generously apportioned living space. The units feature designer kitchens, rustic flooring, industrial lighting, high ceilings with stainless steel duct, exposed brick, original period details and inspiring color schemes, all fit with Nest thermostats, W/D on each floor, and central A/C. Ideally situated steps to the Boston Common, local restaurants, shopping, entertainment, the Green/Orange/Red line T, bus routes and South Station. Be the first to live in this vibrant, pace setting downtown development. Studio, 3, and 4 bedroom units available.
44 Winter St #4, Boston, MA 02108 is a 4 bedroom, 2 bathroom, 1,300 sqft multi-family in Downtown Crossing. More recently, it was listed as a rental in April 2015 with an asking price of $6,000 per month. That rental listing was removed on May 20, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $781,500, with a rent estimate of $4,689/month.

Home Details for 44 Winter St #4

Property Information

Property Type / Style
Property Type: Multi Family

Price and Tax history

DateEventPrice
May 20, 2015
Source: Agent Provided
ListingRemoved
$6,000
Apr 24, 2015
Source: Agent Provided
Listed For Rent
$6,000

Market trends in Boston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$830K
$6.67K
MoM
Sale-to-List Price
99.3%
0.3%
MoM
Price per sq ft
$759
$20
MoM
Available listings
1905
310
MoM

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Downtown Crossing

  • Woman
    "I have enjoyed my time at Millenium Tower. The building is awesome- easy to get in & out, the staff is friendly & efficient. The restaurant & bar is convenient & the food is awesome. Pool, hot tub, great gym - & many options to commune w/other residents. I will miss it!"
  • Roshan R.
    "love my neighborhood. great people making music here. Mature people snd friendly. people help people. "
  • Ahmed G.
    "Almost everyone is friendly, because of theirs kids who are going to school. the neighborhoods are cleaned"
  • Howard W.
    "A true urban neighborhood in the heart of the city. Up and coming restaurants and incredible potential to restore the crossroads where the US began"

LGBTQ Local Legal Protections

Frequently asked questions about 44 Winter St #4

  • What is 44 Winter St #4 estimated to be worth?
    Trulia's estimated value for 44 Winter St #4 in Boston, MA is $781,500.
  • Is Boston a buyer's or seller's market?
    Boston is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Boston?
    The median sale price in Boston is $830K. That is down $6.67K from the prior month.
  • What are the closest schools to 44 Winter St #4?
    The closest schools to 44 Winter St #4 in Boston, MA are Albert D Holland School of Technology (Middle/High, rated 2/10), Baldwin Early Learning Center (Pre-K/Elementary), Blackstone Elementary School (Pre-K, rated 3/10).

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Off Market Homes Near 44 Winter St #4

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