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

$1,938,100

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 3,992 sqft

98 Middlesex St, Winchester, MA 01890

Est. Refi. Payment $12,622/mo*
Refinance Your Home
Currently Off Market - Sold Jun 25, 2020 for $1,555,000

Home Value

Trulia Estimate
$1.94M
Since last month
Decreased$17K (-0.9%)
Since last year
Increased$59K (+3.2%)
Since last sale
Increased$379K (+24.4%)
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 +199% in the last 10 years
MonthEstimated value
2026
October 2026$1.93M
September 2026$1.91M
August 2026$1.95M
July 2026$2.01M
June 2026$2M
May 2026$2.03M
April 2026$2M
March 2026$1.99M
February 2026$1.9M
January 2026$1.87M
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
10 Farrow St, Winchester, MA
0.10
Single-Family Home
$1,660,000
08/07/26
4
3.5
2,768
237 Swanton St, Winchester, MA
0.34
Single-Family Home
$1,850,000
05/29/26
5
4
4,334
149 Horn Pond Brook Rd, Winchester, MA
0.23
Single-Family Home
$1,020,000
06/05/26
5
2
2,331
40 Pickering St, Winchester, MA
0.39
Single-Family Home
$1,330,000
04/14/26
4
2.5
2,454
6 Ivy Cir, Winchester, MA
0.38
Single-Family Home
$1,500,000
04/15/26
6
4
3,403
9 Norfolk Rd, Winchester, MA
0.36
Single-Family Home
$2,400,000
12/23/25
6
3.5
4,320
307 Cross St, Winchester, MA
0.57
Single-Family Home
$1,730,000
07/24/26
5
5
3,500
46 Clark St, Winchester, MA
0.19
Single-Family Home
$1,035,000
09/18/26
4
1.5
1,777
29 Shepard Ct, Winchester, MA
0.39
Single-Family Home
$2,450,000
01/09/26
6
5
4,594
49 Sheridan Cir, Winchester, MA
0.35
Single-Family Home
$2,409,000
07/10/26
5
4.5
5,881

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
94 Middlesex St, Winchester, MA 01890
0.01
$840,300
4
2
1,650
Off Market
100 Middlesex St, Winchester, MA 01890
0.02
$1,255,400
4
2
3,018
Off Market
90 Middlesex St, Winchester, MA 01890
0.02
$1,196,900
4
3
1,700
Off Market
92 Middlesex St, Winchester, MA 01890
0.02
$1,040,400
4
2.5
1,680
Off Market
90 Middlesex St #90, Winchester, MA 01890
0.02
$1,079,200
4
2.5
1,682
Off Market
92 Middlesex St #92, Winchester, MA 01890
0.02
$1,084,300
4
2.5
1,680
Off Market
92 Middlesex St #0, Winchester, MA 01890
0.02
$913,100
4
2.5
1,680
Off Market
90 Middlesex St #0, Winchester, MA 01890
0.02
$948,100
4
3
1,700
Off Market
95 Middlesex St, Winchester, MA 01890
0.03
$941,100
3
2
1,330
Off Market
97 Middlesex St, Winchester, MA 01890
0.03
$842,600
4
1
1,625
Off Market
91 Middlesex St, Winchester, MA 01890
0.03
$1,175,800
4
2
2,372
Off Market
102 Middlesex St, Winchester, MA 01890
0.03
$1,260,100
3
3
2,180
Off Market
86 Middlesex St, Winchester, MA 01890
0.03
$886,800
2
1.5
1,192
Off Market
87 Middlesex St, Winchester, MA 01890
0.04
$982,400
3
2
1,243
Off Market
82 Middlesex St, Winchester, MA 01890
0.04
$951,000
3
2
1,508
Off Market
106 Middlesex St, Winchester, MA 01890
0.04
$1,282,600
4
3
2,568
Off Market
8 Horn Pond Brook Rd, Winchester, MA 01890
0.05
$1,367,400
3
3
1,924
Off Market
81 Middlesex St, Winchester, MA 01890
0.05
$1,305,100
6
2
2,505
Off Market
6 Horn Pond Brook Rd, Winchester, MA 01890
0.05
$1,068,000
3
2
1,727
Off Market
78 Middlesex St, Winchester, MA 01890
0.05
$1,459,100
3
2.5
2,650
Off Market

Local Information

  • Map ViewExplore the area around 98 Middlesex St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2018
3,992 sqft
$485/sqft
Garage

About this House

OPEN HOUSES CANCELLED! SELLER ACCEPTED AN OFFER! Pristine 2018-construction located in an ultra-convenient Winchester neighborhood! An impressive build with a thoughtful, high-end design executed with precision by a well known Winchester-based builder, this 5-bedroom / 3.5 bathroom Colonial delivers the space and quality that youâve been waiting for. With an expansive, open floor plan, the main level features a sitting room with a gas fireplace, a gourmet kitchen with an 8â center island, and a mud-room with custom-built cubbies. On the 2nd floor you will find 3 full bathrooms and 4 large bedrooms including a stunning master with dramatic vaulted ceilings. The recently finished 3rd level includes the 5th bedroom and an oversized family room. A 2-car garage, a back deck and yard, and a partially finished basement round out this offering. Less than a mile to the commuter rail, downtown, Winchester High, Lynch Elementary, Horn Pond, and the newly built Tri-Community Greenway.
98 Middlesex St, Winchester, MA 01890 is a 5 bedroom, 4 bathroom, 3,992 sqft single-family home built in 2018. It last sold for $1,555,000 on Jun 25, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,938,100, with a rent estimate of $8,176/month.

Home Details for 98 Middlesex St

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowave
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood, Cement Concrete
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 6647 sqft

Price and Tax history

DateEventPrice
Jun 25, 2020
Source: N/A
Sold
$1,555,000
May 29, 2020
Source: Agent Provided
Pending
$1,549,000
May 26, 2020
Source: Agent Provided
Listed For Sale
$1,549,000
Oct 16, 2018
Source: N/A
Sold
$1,380,000
Jul 28, 2018
Source: Agent Provided
Pending
$1,399,900

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

Around this home

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

Frequently asked questions about 98 Middlesex St

  • What is 98 Middlesex St estimated to be worth?
    Trulia's estimated value for 98 Middlesex St in Winchester, MA is $1,938,100.
  • What is the price history for 98 Middlesex St?
    98 Middlesex St in Winchester, MA last sold for $1,555,000 in June 2020.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • Does 98 Middlesex St have air conditioning?
    Yes, 98 Middlesex St in Winchester, MA has air conditioning.
  • How big is the lot at 98 Middlesex St?
    The lot at 98 Middlesex St in Winchester, MA is about 0.15 acres (6,647 sq ft).

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Off Market Homes Near 98 Middlesex St

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