14 Risley Rd, Winchester, MA 01890
OFF MARKET

$2,133,200

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,398 sqft

14 Risley Rd, Winchester, MA 01890

Est. Refi. Payment $13,362/mo*
Refinance Your Home
Currently Off Market - Sold Dec 23, 2021 for $1,820,000

Home Value

Trulia Estimate
$2.13M
Since last month
Increased$3K (+0.1%)
Since last year
Increased$62K (+3%)
Since last sale
Increased$319K (+17.5%)
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 +82% in the last 10 years
MonthEstimated value
2026
September 2026$2.14M
August 2026$2.14M
July 2026$2.18M
June 2026$2.18M
May 2026$2.2M
April 2026$2.2M
March 2026$2.17M
February 2026$2.08M
January 2026$2.06M
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
17 Cranston Rd, Winchester, MA
0.14
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
4 Sargent Rd, Winchester, MA
0.18
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865
2 Priscilla Ln, Winchester, MA
0.14
Single-Family Home
$2,649,000
05/29/26
4
3.5
4,255
21 Willowdale Rd, Winchester, MA
0.13
Single-Family Home
$2,170,000
07/31/26
5
3.5
4,591
71 Sargent Rd, Winchester, MA
0.21
Single-Family Home
$1,399,000
06/30/26
3
3.5
2,936
8 Felsdale Close, Winchester, MA
0.40
Single-Family Home
$1,930,000
01/09/26
4
2.5
3,658
89 Main St, Winchester, MA
0.14
Single-Family Home
$1,150,000
11/14/25
3
2.5
2,648
6 Marchant Rd, Winchester, MA
0.11
Single-Family Home
$1,325,000
04/22/26
3
2.5
2,153
19 Town Way, Winchester, MA
0.08
Single-Family Home
$2,750,000
04/03/26
5
5.5
5,257
22 Hollywood Rd, Winchester, MA
0.28
Single-Family Home
$2,150,000
07/13/26
5
3
3,136

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
49 Ledyard Rd, Winchester, MA 01890
0.03
$1,993,400
4
3
3,050
Off Market
50 Allen Rd, Winchester, MA 01890
0.06
$1,716,000
3
2
2,769
Off Market
40 Sargent Rd, Winchester, MA 01890
0.05
$1,290,000
3
1.5
1,492
Recently Sold
18 Town Way, Winchester, MA 01890
0.06
$2,259,200
4
3.5
4,026
Off Market
6 Alden Ln, Winchester, MA 01890
0.07
$1,275,000
3
2
1,511
Recently Sold
33 Sargent Rd, Winchester, MA 01890
0.08
$1,962,400
5
3.5
3,022
Off Market
19 Town Way, Winchester, MA 01890
0.08
$2,750,000
5
5.5
5,257
Recently Sold
22 Standish Ln, Winchester, MA 01890
0.09
$2,880,900
5
4.5
5,044
Off Market
39 Town Way, Winchester, MA 01890
0.10
$3,200,000
6
6
5,709
Recently Sold
30 Willowdale Rd, Winchester, MA 01890
0.12
$3,200,000
8
6.5
5,750
For Sale
6 Marchant Rd, Winchester, MA 01890
0.11
$1,325,000
3
2.5
2,153
Recently Sold
17 Cranston Rd, Winchester, MA 01890
0.14
$1,560,000
4
2.5
2,578
Recently Sold

Local Information

  • Map ViewExplore the area around 14 Risley Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1947
3,398 sqft
$628/sqft
Garage

About this House

What's unique:Patio
Exquisite custom built center entrance colonial in East Hill, beautifully re-envisioned, gutted & rebuilt w/expansive addition in 05 boasts 3 impressive levels of thoughtfully designed amazing space that reflects beauty & warmth in every detail. Gracious 1st level w/its easy flow & well-appointed living area is highlighted by fine features+ that will surprise & delight at every turn. (See tour/list). Elegant DR opens to large kit w/sleek granite counters & island, custom maple cabs & dining area w/sliders to lovely patio & yard: THE PLACE to relax & entertain. Kit flows seamlessly to spacious FR w/cath ceiling, custom windows & doors that also lead to patio. LR has Fr doors to in-demand home office. MBR suite w/walk-in closet & chic bath, plus 3 BRs w/double closets & spa bath await on 2nd level. Fin lower level with inlaw potential has full bath & access to 2C gar. Fab expansion possibilities in walk-up attic. Close to town Center, T, schools & Fells, close to 93 & minutes to Boston.
14 Risley Rd, Winchester, MA 01890 is a 4 bedroom, 4 bathroom, 3,398 sqft single-family home built in 1947. It last sold for $1,820,000 on Dec 23, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,133,200, with a rent estimate of $6,145/month.

Home Details for 14 Risley Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1947Year Updated: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Price and Tax history

DateEventPrice
Dec 23, 2021
Source: MLS PIN #72913415
Sold
$1,820,000
Nov 2, 2021
Source: RE/MAX International #72913415
Pending
$1,799,000
Oct 27, 2021
Source: MLS PIN #72913415
Listed For Sale
$1,799,000
Jun 30, 2000
Source: N/A
Sold
$330,000

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 14 Risley Rd

  • What is 14 Risley Rd estimated to be worth?
    Trulia's estimated value for 14 Risley Rd in Winchester, MA is $2,133,200.
  • What is the price history for 14 Risley Rd?
    14 Risley Rd in Winchester, MA last sold for $1,820,000 in December 2021.
  • 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.
  • How big is the lot at 14 Risley Rd?
    The lot at 14 Risley Rd in Winchester, MA is about 0.21 acres (8,939 sq ft).
  • Does 14 Risley Rd have a garage?
    Yes, 14 Risley Rd in Winchester, MA has a garage.

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Off Market Homes Near 14 Risley Rd

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