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

86 Middlesex St
Winchester, MA 01890

  • 2 Beds
  • 1.5 Baths
  • 1,192 sqft

$921,300

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $5,538/mo*
Refinance Your Home

$921,300

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $5,538/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,192 sqft

Local Information

  • Map ViewExplore the area around 86 Middlesex St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Home Sweet Home! 86 Middlesex St is a lovingly maintained home, featuring gorgeous oak flooring throughout and a great open floor plan. An updated kitchen with induction range, stainless appliances, granite counters and plenty of space for cooking opens to a sunny dining room, ready to fit a big table. The family room has great space for hanging out, opens to an office area with sliders to a private fenced in yard, including a patio and shed. The second floor offers two large bedrooms and one full bathroom, updated with modern fixtures and lots of storage space. Unfinished basement provides laundry, additional storage and ample ceiling height for your home gym! The house comes with smart home features, including wireless/voice enabled recess lighting, door lock, Nest and built in speakers. Centrally located in a fantastic neighborhood with potential for expansion. Enjoy outdoors with immediate access to bike path, tennis, splash park and less than a mile from town, train and schools.
86 Middlesex St, Winchester, MA 01890 is a 2 bedroom, 2 bathroom, 1,192 sqft single-family home built in 1900. It last sold for $685,000 on Oct 5, 2020. It is currently off market. The Trulia Estimate is $921,300, with a rent estimate of $3,617/month.

Home Highlights

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

Home Details for 86 Middlesex St

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatioSprinkler System
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 3484 sqft

Building

Fitness & Sports
Tennis Court

Price History for 86 Middlesex St

DatePriceEventSource
10/05/2020$685,000Sold
N/A
08/25/2020$675,000PendingAgent Provided
08/13/2020$675,000Listed For SaleAgent Provided
08/01/2017$620,000Sold
N/A
07/01/2017$569,000PendingAgent Provided
06/24/2017$569,000Listed For SaleAgent Provided
08/31/2012$413,000Sold
N/A
08/23/2012$429,000PendingAgent Provided
07/07/2012$429,000PriceChange
Agent Provided
05/24/2012$439,000PriceChange
Agent Provided
04/27/2012$449,000Listed For SaleAgent Provided
06/15/1987$175,000Sold
N/A

Market trends in Winchester

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
75
7MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$9,136
Assessment$823,800
Home facts updated by county records

Comparable Sales for 86 Middlesex St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
49 Spruce St, Winchester, MA
0.54
Single-Family Home
$815,000
03/09/26
3
1.5
1,710
76 Woodside Rd, Winchester, MA
0.36
Single-Family Home
$1,080,000
05/12/26
4
2
1,552
9 Emerson Ct, Winchester, MA
0.75
Single-Family Home
$790,001
08/15/25
3
2
1,441
136 Sylvester Ave, Winchester, MA
0.36
Single-Family Home
$1,156,000
02/25/26
3
1.5
1,608
9 Sylvester Ct, Winchester, MA
0.31
Single-Family Home
$1,015,000
12/01/25
4
1.5
2,001
2 Maria Ct, Woburn, MA
0.59
Single-Family Home
$780,000
04/23/26
2
2
1,824
104 Wendell St, Winchester, MA
0.48
Single-Family Home
$1,100,000
05/28/26
3
1.5
1,675
149 Horn Pond Brook Rd, Winchester, MA
0.26
Single-Family Home
$1,020,000
06/05/26
5
2
2,331
18 Hemingway St, Winchester, MA
0.27
Single-Family Home
$1,280,000
07/16/25
5
3.5
2,137
108 Arlington Rd, Woburn, MA
0.82
Single-Family Home
$660,000
08/28/25
3
1
1,030

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 86 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

8 pet-friendly rentals in Winchester, MA

Explore by feature - Garage

9 rentals with a garage in Winchester, MA

Explore by feature - Air Conditioning

25 rentals with air conditioning in Winchester, MA

Explore by feature - Pool

6 rentals with a pool in Winchester, MA

Explore by feature - Washer/dryer

31 rentals with a washer/dryer in Winchester, MA

Explore by feature - Outdoor Space

8 rentals with an outdoor space in Winchester, MA

Homes for sale near 86 Middlesex St

Skip to last item
Skip to first item

Off Market Homes Near 86 Middlesex St

Skip to last item
Skip to first item