44 Middlesex St, Winchester, MA 01890
Property image
Property image
OFF MARKET

44 Middlesex St
Winchester, MA 01890

  • 3 Beds
  • 1 Bath
  • 1,200 sqft
3 Beds
1 Bath
1,200 sqft

Local Information

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

Home Highlights

Property Type
Apartment
Living Area
1,200 sqft

About this House

3 bedrooms/1 bath
Washer/dryer hookups in basement
Off-street parking (private driveway)
Fully applianced eat-in kitchen
Large living/dining room with hardwood floors
Front and back porches
Private yard
Close to public transportation
Convenient to schools and downtown area
Storage in basement
Gas heat (not included in rent)
44 Middlesex St, Winchester, MA 01890 is a 3 bedroom, 1 bathroom, 1,200 sqft apartment. More recently, it was listed as a rental in October 2022 with an asking price of $2,700 per month. That rental listing was removed on October 15, 2022. It is currently off market. The Trulia Estimate rent is $3,257/month.

Home Details for 44 Middlesex St

Property Information

Property Type / Style
Property Type: Apartment

Interior Features

Appliances & Utilities
DryerWasher

Exterior Features

Parking & Garage
Parking: Off Street

Price History for 44 Middlesex St

DatePriceEventSource
10/15/2022ListingRemovedZillow Rental Manager
10/03/2022$2,700Listed For RentZillow Rental Manager
03/24/2021ListingRemovedN/A
08/19/2019$2,400ListingRemovedN/A
08/12/2019$2,400Listed For RentN/A

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.41M
Sale-to-List Price
101.7%
Price per sq ft
$571
Available listings
77
2MoM
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Comparable Sales for 44 Middlesex St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
200 Swanton St #228, Winchester, MA
0.30
Apartment
$330,000
07/28/26
1
1
606
14 Bradford Rd #14, Winchester, MA
0.70
Apartment
$620,000
07/30/26
3
1.5
1,168
380 Place Ln #380, Woburn, MA
2.19
Apartment
$600,000
04/01/26
2
2
1,600
74 Beach St #1-3, Woburn, MA
2.15
Apartment
$220,000
08/11/25
1
417
29 Harvard Ave, Medford, MA
2.60
Apartment
$430,000
01/26/26
1
1
610
3 Colonial Village Dr #10, Arlington, MA
3.05
Apartment
$370,000
09/17/25
2
1
669
157 Boston Ave, Somerville, MA
2.96
Apartment
$945,000
04/03/26
4
3
1,865
12 Colonial Village Dr, Arlington, MA
3.05
Apartment
$350,000
05/22/26
1
1
663
66 Freeman St #1, Arlington, MA
3.50
Apartment
$515,000
08/21/25
2
1
994
79 Fairfax St, Somerville, MA
3.19
Apartment
$685,000
10/15/25
2
1
9,999
Home facts updated by county records

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Middlesex St.
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 Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

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Homes for sale near 44 Middlesex St

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Off Market Homes Near 44 Middlesex St

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