21 Fairmount St, Winchester, MA 01890
Property image
Property image
OFF MARKET

$1,519,100

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,188 sqft (on 0.27 acres)

21 Fairmount St, Winchester, MA 01890

Est. Refi. Payment $9,456/mo*
Refinance Your Home
Currently Off Market - Sold Dec 30, 2019 for $680,000

Home Value

Trulia Estimate
$1.52M
Since last month
Increased$30K (+2%)
Since last year
Increased$151K (+11.1%)
Since last sale
Increased$833K (+122.5%)
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 +94% in the last 10 years
MonthEstimated value
2026
September 2026$1.51M
August 2026$1.48M
July 2026$1.48M
June 2026$1.5M
May 2026$1.51M
April 2026$1.5M
March 2026$1.5M
February 2026$1.44M
January 2026$1.42M
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
41 Englewood Rd, Winchester, MA
0.19
Single-Family Home
$1,038,500
12/01/25
3
1.5
1,683
40 Englewood Rd, Winchester, MA
0.16
Single-Family Home
$1,218,000
05/20/26
4
2
1,841
1 Orient St, Winchester, MA
0.16
Single-Family Home
$1,330,000
05/28/26
3
1.5
2,222
10 Bonad Rd, Winchester, MA
0.17
Single-Family Home
$1,620,000
07/06/26
4
2.5
2,233
162 Forest St, Winchester, MA
0.31
Single-Family Home
$1,280,000
10/03/25
4
1.5
1,900
24 Hinds Rd, Winchester, MA
0.31
Single-Family Home
$1,750,000
07/09/26
4
3
2,814
102 Hillcrest Pkwy, Winchester, MA
0.40
Single-Family Home
$1,425,000
12/01/25
4
2
1,755
18 Grayson Rd, Winchester, MA
0.12
Single-Family Home
$1,738,000
07/28/26
3
2.5
2,992
15 Englewood Rd, Winchester, MA
0.22
Single-Family Home
$1,425,000
05/07/26
4
3
1,903
147 Highland Ave, Winchester, MA
0.41
Single-Family Home
$1,200,000
09/25/25
3
2
1,884

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
29 Kenwin Rd, Winchester, MA 01890
0.06
$1,621,300
4
2
2,132
Off Market
64 Highland Ave #5, Winchester, MA 01890
0.10
$473,700
1
1
734
Off Market
64 Highland Ave #11, Winchester, MA 01890
0.10
$911,700
3
2.5
2,650
Off Market
64 Highland Ave #18, Winchester, MA 01890
0.10
$433,900
1
1
758
Off Market
19 Kenwin Rd, Winchester, MA 01890
0.09
$1,470,500
3
2
1,875
Off Market
6 Reservoir St, Winchester, MA 01890
0.10
$1,080,000
3
1
1,382
For Sale
32 Grayson Rd, Winchester, MA 01890
0.10
$1,570,400
3
1.5
1,996
Off Market
7 Appalachian Rd, Winchester, MA 01890
0.12
$2,150,000
4
4.5
3,263
Recently Sold
5 Alben St, Winchester, MA 01890
0.12
$1,923,800
4
2.5
3,381
Off Market
20 Grayson Rd, Winchester, MA 01890
0.12
$1,995,600
5
4.5
3,825
Off Market
18 Grayson Rd, Winchester, MA 01890
0.12
$1,738,000
3
2.5
2,992
Recently Sold
14 Bonad Rd, Winchester, MA 01890
0.15
$1,746,000
3
2.5
2,516
Off Market

Local Information

  • Map ViewExplore the area around 21 Fairmount St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
0.27 acre lot
2,188 sqft
$694/sqft
Garage

About this House

Great opportunity to live in Winchester! This spacious Colonial, boasts large rooms, a master suite, large living room, and original flooring. With some update, this house could be spectacular! So many possibilities with such a large lot and so much room for expansion. One car garage, porch off of the back of the house can either be closed in or enjoyed as is. Don't miss out on this opportunity!! Close to the Middlesex Fells Reservation with beautiful hiking and biking trails. Easy access to the commuter rail to Boston and Maine.
21 Fairmount St, Winchester, MA 01890 is a 4 bedroom, 3 bathroom, 2,188 sqft single-family home built in 1940. It last sold for $680,000 on Dec 30, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,519,100, with a rent estimate of $5,509/month.

Home Details for 21 Fairmount St

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: SlateExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 0.27 acres

Price and Tax history

DateEventPrice
Dec 30, 2019
Source: N/A
Sold
$680,000
Nov 7, 2019
Source: Agent Provided
Pending
$727,000
Oct 23, 2019
Source: Agent Provided
PriceChange
$727,000
Price decreased by 8%
Sep 6, 2019
Source: Agent Provided
PriceChange
$788,000
Price decreased by 1%
Aug 15, 2019
Source: Agent Provided
Listed For Sale
$799,900

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 21 Fairmount St

  • What is 21 Fairmount St estimated to be worth?
    Trulia's estimated value for 21 Fairmount St in Winchester, MA is $1,519,100.
  • What is the price history for 21 Fairmount St?
    21 Fairmount St in Winchester, MA last sold for $680,000 in December 2019.
  • 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 21 Fairmount St have air conditioning?
    Yes, 21 Fairmount St in Winchester, MA has air conditioning.
  • How big is the lot at 21 Fairmount St?
    The lot at 21 Fairmount St in Winchester, MA is about 0.27 acres (11,556 sq ft).

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