27 Middlesex St, Winchester, MA 01890
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OFF MARKET

27 Middlesex St
Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,434 sqft

$910,700

Trulia Estimate
as of Jul 13, 2026
Est. Refi. Payment $5,375/mo*
Refinance Your Home

$910,700

Trulia Estimate
as of Jul 13, 2026
Est. Refi. Payment $5,375/mo*
Refinance Your Home
3 Beds
2 Baths
1,434 sqft

Local Information

  • Map ViewExplore the area around 27 Middlesex St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Great location, close proximity to Winchester Center, commuter rail station, restaurants, library, bike path and shopping. All of the schools are nearby, McCall Middle School, Winchester High,and Lynch Elementary School. This 2/3 Cape offers 1.5 baths, three season porch, hardwood floors on first floor, basement room, and a fenced backyard. Yard, which is fenced and small dogs are allowed. Owner requires full credit report.
27 Middlesex St, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 1,434 sqft single-family home built in 1947. It last sold for $240,000 on Mar 1, 1999. More recently, it was listed as a rental in May 2019 with an asking price of $2,700 per month. That rental listing was removed on May 18, 2019. It is currently off market. The Trulia Estimate is $910,700, with a rent estimate of $4,363/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27 Middlesex St

Interior Features

Interior Details
BasementNumber of Rooms: 6Types of Rooms: Dining Room, Sun Room
Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1947
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 6534 sqft

Building

Fitness & Sports
Tennis Court

Price History for 27 Middlesex St

DatePriceEventSource
05/18/2019$2,700ListingRemovedAgent Provided
05/16/2019$2,700Listed For RentAgent Provided
11/26/2013$2,300ListingRemovedAgent Provided
10/27/2013$2,300PriceChange
Agent Provided
09/14/2013$2,500Listed For RentAgent Provided
03/01/1999$240,000Sold
N/A
08/09/1991$158,500Sold
N/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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Property Tax and Assessment

Year2025
Tax$9,371
Assessment$845,000
Home facts updated by county records

Comparable Sales for 27 Middlesex St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
49 Spruce St, Winchester, MA
0.42
Single-Family Home
$815,000
03/09/26
3
1.5
1,710
76 Woodside Rd, Winchester, MA
0.50
Single-Family Home
$1,080,000
05/12/26
4
2
1,552
104 Wendell St, Winchester, MA
0.54
Single-Family Home
$1,100,000
05/28/26
3
1.5
1,675
9 Sylvester Ct, Winchester, MA
0.43
Single-Family Home
$1,015,000
12/01/25
4
1.5
2,001
136 Sylvester Ave, Winchester, MA
0.49
Single-Family Home
$1,156,000
02/25/26
3
1.5
1,608
149 Horn Pond Brook Rd, Winchester, MA
0.40
Single-Family Home
$1,020,000
06/05/26
5
2
2,331
26 Olive St, Winchester, MA
0.56
Single-Family Home
$1,000,000
08/01/25
3
2
1,977
320 Washington St, Winchester, MA
0.72
Single-Family Home
$1,015,000
03/20/26
3
1.5
1,749
4 Fairfield Pl, Winchester, MA
0.11
Single-Family Home
$2,200,000
07/14/25
4
3.5
3,896
9 Emerson Ct, Winchester, MA
0.64
Single-Family Home
$790,001
08/15/25
3
2
1,441

Nearby homes

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Assigned Schools

These are the assigned schools for 27 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 27 Middlesex St

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Off Market Homes Near 27 Middlesex St

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