14 Risley Rd, Winchester, MA 01890
OFF MARKET

14 Risley Rd
Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,398 sqft

$2,182,900

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $13,111/mo*
Refinance Your Home

$2,182,900

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $13,111/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,398 sqft

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

Property Type
Single-Family Home
Year Built
1947
Living Area
3,398 sqft
Price/Sqft
$642
Parking
Garage

About this House

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. It is currently off market. The Trulia Estimate is $2,182,900, with a rent estimate of $7,172/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 History for 14 Risley Rd

DatePriceEventSource
12/23/2021$1,820,000Sold
MLS PIN #72913415
11/02/2021$1,799,000PendingRE/MAX International #72913415
10/27/2021$1,799,000Listed For SaleMLS PIN #72913415
06/30/2000$330,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$21,365
Assessment$1,926,500
Home facts updated by county records

Comparable Sales for 14 Risley Rd

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
163 Main St, Winchester, MA
0.26
Single-Family Home
$1,175,000
08/18/25
4
2.5
2,335
19 Town Way, Winchester, MA
0.08
Single-Family Home
$2,750,000
04/03/26
5
5.5
5,257

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 14 Risley Rd.
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

11 pet-friendly rentals in Winchester, MA

Explore by feature - Garage

11 rentals with a garage in Winchester, MA

Explore by feature - Air Conditioning

27 rentals with air conditioning in Winchester, MA

Explore by feature - Pool

9 rentals with a pool in Winchester, MA

Explore by feature - Washer/dryer

28 rentals with a washer/dryer in Winchester, MA

Explore by feature - Outdoor Space

11 rentals with an outdoor space in Winchester, MA

Homes for sale near 14 Risley Rd

Skip to last item
Skip to first item

Off Market Homes Near 14 Risley Rd

Skip to last item
Skip to first item