44 Winter St, Lexington, MA 02420
OFF MARKET

$1,854,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,432 sqft (on 0.69 acres)

44 Winter St, Lexington, MA 02420

Est. Refi. Payment $11,071/mo*
Refinance Your Home
Currently Off Market - Sold Mar 11, 1998 for $510,000

Home Value

Trulia Estimate
$1.85M
Since last month
Decreased$10K (-0.5%)
Since last year
Decreased$27K (-1.5%)
Since last sale
Increased$1M (+263.6%)
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 +56% in the last 10 years
MonthEstimated value
2026
August 2026$1.85M
July 2026$1.86M
June 2026$1.91M
May 2026$1.96M
April 2026$1.94M
March 2026$1.91M
February 2026$1.84M
January 2026$1.82M
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
28 Sullivan St, Lexington, MA
0.12
Single-Family Home
$1,835,000
11/19/25
4
3.5
3,309
6 Hadley Rd, Lexington, MA
0.43
Single-Family Home
$1,635,000
12/02/25
4
3
3,062
49 Eldred St, Lexington, MA
0.54
Single-Family Home
$1,100,000
10/06/25
4
2
2,692
30 Volunteer Way, Lexington, MA
0.34
Single-Family Home
$1,840,000
06/30/26
4
4.5
3,284
29 Dewey Rd, Lexington, MA
0.68
Single-Family Home
$1,450,000
07/15/26
4
2.5
2,984
24 Gray Ter, Bedford, MA
0.36
Single-Family Home
$805,000
11/13/25
3
1.5
1,132
7 Curve St, Bedford, MA
0.45
Single-Family Home
$780,000
08/21/26
3
2
1,525
37 Pine St, Bedford, MA
0.36
Single-Family Home
$849,000
03/30/26
3
2
1,547
16 Sunnyfield Rd, Bedford, MA
0.38
Single-Family Home
$860,000
04/10/26
3
2
1,620
52 Turning Mill Rd, Lexington, MA
0.91
Single-Family Home
$1,215,000
08/05/26
4
3
2,300

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
15 Fifer Ln #15, Lexington, MA 02420
0.08
$699,000
2
2.5
1,555
For Sale
12 Fifer Ln #12, Lexington, MA 02420
0.10
-
3
2
1,513
Off Market
6 Magnolia Ln, Lexington, MA 02420
0.06
$1,723,200
3
2.5
3,212
Off Market
27 Fifer Ln #27, Lexington, MA 02420
0.10
-
3
2
1,509
Off Market
28 Sullivan St, Lexington, MA 02420
0.12
$1,835,000
4
3.5
3,309
Recently Sold
2 Drummer Boy Way #2, Lexington, MA 02420
0.17
-
2
1.5
1,254
Off Market
4 Drummer Boy Way #4, Lexington, MA 02420
0.17
$850,000
3
2
1,509
Recently Sold
14 Pine Knoll Rd, Lexington, MA 02420
0.16
$2,229,300
5
3.5
4,410
Off Market
12 Sullivan St, Lexington, MA 02420
0.13
$2,441,700
4
2.5
3,713
Off Market
18 Drummer Boy Way #18, Lexington, MA 02420
0.17
$852,800
3
2
1,511
Recently Sold
24 Pine Knoll Rd, Lexington, MA 02420
0.16
$2,400,000
6
5.5
5,761
Recently Sold
3 Woodland Rd, Bedford, MA 01730
0.17
$874,100
2
1
1,391
Off Market

Local Information

  • Map ViewExplore the area around 44 Winter St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
0.69 acres
Living Area
2,432 sqft
Price/Sqft
$762
Parking
Garage

About this House

This single-family home is located at 44 Winter St, Lexington, MA. 44 Winter St is in Lexington, MA and in ZIP code 02420. This property has 4 bedrooms, 3 bathrooms and approximately 2,432 sqft of floor space. This property has a lot size of 0.69 acres and was built in 1997.
44 Winter St, Lexington, MA 02420 is a 4 bedroom, 3 bathroom, 2,432 sqft single-family home built in 1997. It last sold for $510,000 on Mar 11, 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,854,300, with a rent estimate of $5,733/month.

Home Details for 44 Winter St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Office
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposal
Fireplace & Spa
FireplaceJetted Bath Tub

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: ShingleLawnPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Price and Tax history

DateEventPrice
Mar 11, 1998
Source: N/A
Sold
$510,000
Sep 16, 1997
Source: N/A
Sold
$524,000
Jan 10, 1997
Source: N/A
Sold
$230,000

Market trends in Lexington

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.55M
$14.67KMoM
Sale-to-List Price
102.1%
0.4%MoM
Price per sq ft
$580
$21MoM
Available listings
123
33MoM

Around this home

What Locals Say about Lexington

At least 146 Trulia users voted on each feature.

  • 84 % Say parking is easy

  • 83 % Say it's dog friendly

  • 83 % Say car is needed

  • 80 % Say it's quiet

  • 76 % Say people would walk alone at night

  • 75 % Say yards are well-kept

  • 71 % Say there's wildlife

  • 71 % Say there are sidewalks

  • 71 % Say kids play outside

  • 70 % Say there's holiday spirit

  • 63 % Say they plan to stay for at least 5 years

  • 58 % Say streets are well-lit

  • 56 % Say neighbors are friendly

  • 49 % Say there are community events

  • 44 % Say it's walkable to grocery stores

  • 43 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Klaus Raupp
    "The whole neighborhood is friendly, with walking/biking paths like the Minuteman and many dog specific areas."
    0
    Flag
  • Sbastien Godard
    "We have neighborhood parties. And a lot of community with the neighbors. This is a great place to live "
    0
    Flag
  • Lexliv
    "Great neighborhood! Safe place to live and many things are easily accessible, short drive into Boston"
    1
    Flag
  • Fmcgovern
    "Good With multiple options including Bus versus MBTA train versus Uber Multiple options for routes into Boston"
    1
    Flag
  • 77sunrise
    "Easy access to bus 62 and 76, also the Rev bus from 128business council from depot square is super convenient to get to Alewife."
    0
    Flag
  • 77sunrise
    "There are a lot of dogs. If your dog does not like other dogs, then you will have a hard time to avoid them."
    0
    Flag
  • Joao C.
    "Lexington is one of the best town the I ever live Everyone around my neighborhood is friendly and they respect which other "
    0
    Flag
  • 77sunrise
    "Voice on the green, Concerts and winter solstice service at First Paris Lexington are great events. Summer concerts at Depot Square are also nice relaxing for a summer night."
    2
    Flag
  • Kamesh K.
    "We have neighborhood potluck block parties where we meet neighbors and kids enjoy food, music and games"
    1
    Flag
  • Tim K.
    "I have live here and my business is in the center of town so convenient and safe love my town my kids going to the public school and they learn so much they’re always busy with their spots I cannot be happy than this safe for me and my family "
    0
    Flag
  • Laura Manlief
    "Wonderful schools, nice community, small town feeling, and very safe. Birthplace of the United States."
    4
    Flag
  • Michelleolson
    "There are lots of dogs. All on leashes. I don’t know if any dog parks. Very walkable neighborhood. We don’t own a dog so I don’t know too much more."
    2
    Flag
  • Johnnybutera
    "Historical events and neighborhood get togethers are very common and a blast. They all revolve around families "
    1
    Flag
  • Michelleolson
    "A historic town, ethnically diverse, well educated and close to Boston. Expensive to buy into however."
    2
    Flag
  • Etpmullis
    "Lovely area schools transportation economy is great! What more can you ask for!! Maybe warmer winter "
    0
    Flag
  • Vipin
    " Wet nice neighborhood as my friends live here and we are regular visitors. Very nice school system and well connected to Boston "
    0
    Flag
  • Hunt m.
    "It’s a wonderfully walkable neighborhood with obscenely overpriced homes and increasing number of teardowns and McMansions."
    0
    Flag
  • emil w.
    "It is the best: Quiet, safe, airy, not subject to flooding, private."
    0
    Flag
  • crowleyt
    "Haved lived in this area for almost 30 years. Terrific school system, tradionally one of the top 5 in state every year. Great proximity to major transportation routes to Boston / Cambridge and Rte 128 / 95. Higly educated residents with strong emphasis on getting children to attend college. Convenient to conservation land, and a terrific family run farm. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 44 Winter St

  • What is 44 Winter St estimated to be worth?
    Trulia's estimated value for 44 Winter St in Lexington, MA is $1,854,300.
  • What is the price history for 44 Winter St?
    44 Winter St in Lexington, MA last sold for $510,000 in March 1998.
  • Is Lexington a buyer's or seller's market?
    Lexington is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Lexington?
    The median sale price in Lexington is $1.55M. That is up $14.67K from the prior month.
  • Does 44 Winter St have air conditioning?
    Yes, 44 Winter St in Lexington, MA has air conditioning.
  • Does 44 Winter St have laundry facilities?
    Yes, 44 Winter St in Lexington, MA has laundry facilities.

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