37 Ledyard Rd, Winchester, MA 01890
OFF MARKET

$1,444,700

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,250 sqft

37 Ledyard Rd, Winchester, MA 01890

Est. Refi. Payment $8,619/mo*
Refinance Your Home
Currently Off Market - Sold Feb 15, 2008 for $585,000

Home Value

Trulia Estimate
$1.45M
Since last month
Decreased$26K (-1.7%)
Since last year
Increased$48K (+3.4%)
Since last sale
Increased$860K (+147.1%)
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 +69% in the last 10 years
MonthEstimated value
2026
August 2026$1.45M
August 2026$1.44M
July 2026$1.47M
June 2026$1.48M
May 2026$1.48M
April 2026$1.47M
March 2026$1.44M
February 2026$1.38M
January 2026$1.35M
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
40 Sargent Rd, Winchester, MA
0.12
Single-Family Home
$1,290,000
12/05/25
3
1.5
1,492
446 Highland Ave, Winchester, MA
0.10
Single-Family Home
$940,000
12/23/25
2
1.5
2,033
17 Cranston Rd, Winchester, MA
0.05
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
6 Alden Ln, Winchester, MA
0.17
Single-Family Home
$1,275,000
06/25/26
3
2
1,511
89 Main St, Winchester, MA
0.16
Single-Family Home
$1,150,000
11/14/25
3
2.5
2,648
6 Marchant Rd, Winchester, MA
0.14
Single-Family Home
$1,325,000
04/22/26
3
2.5
2,153
26 Robinson Rd, Medford, MA
0.41
Single-Family Home
$780,000
10/24/25
3
1.5
1,344
4 Sargent Rd, Winchester, MA
0.10
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865
595 Winthrop St, Medford, MA
0.66
Single-Family Home
$685,000
12/17/25
3
1.5
1,944
17 Dennett Rd, Winchester, MA
0.28
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283

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
50 Allen Rd, Winchester, MA 01890
0.04
$1,712,800
3
2
2,769
Off Market
17 Cranston Rd, Winchester, MA 01890
0.05
$1,560,000
4
2.5
2,578
Recently Sold
49 Ledyard Rd, Winchester, MA 01890
0.07
$1,970,600
4
3
3,050
Off Market
27 Ledyard Rd, Winchester, MA 01890
0.05
$2,660,400
3
1.5
2,364
Off Market
29 Allen Rd, Winchester, MA 01890
0.07
$1,834,300
4
2.5
2,810
Off Market
21 Willowdale Rd, Winchester, MA 01890
0.12
$2,170,000
5
3.5
4,591
Recently Sold
22 Willowdale Rd, Winchester, MA 01890
0.14
$2,120,700
4
2.5
2,973
Off Market
40 Sargent Rd, Winchester, MA 01890
0.12
$1,290,000
3
1.5
1,492
Recently Sold
33 Sargent Rd, Winchester, MA 01890
0.12
$1,944,900
5
3.5
3,022
Off Market
4 Sargent Rd, Winchester, MA 01890
0.10
$1,355,000
4
2.5
2,865
Recently Sold
446 Highland Ave, Winchester, MA 01890
0.10
$940,000
2
1.5
2,033
Recently Sold
5 Clearwater Rd, Winchester, MA 01890
0.15
$2,942,800
6
7.5
5,658
Off Market

Local Information

  • Map ViewExplore the area around 37 Ledyard Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1954
2,250 sqft
$642/sqft

About this House

Step into this charming 8+room Col. w/ many, many updates! New kit w/granite countertops, sunfilled familyroom off kit. New fam. bath, mostly all new windows throughout! Fabulous 40' deck enhances your backyard living space. Pretty hardwood floors, updated elec., double width driveway. Possible expansion over garage. Great playroom in LL. Office could be 4th. bedroom.
37 Ledyard Rd, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 2,250 sqft single-family home built in 1954. It last sold for $585,000 on Feb 15, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,444,700, with a rent estimate of $4,657/month.

Home Details for 37 Ledyard Rd

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 7500 sqft

Price and Tax history

DateEventPrice
Feb 15, 2008
Source: N/A
Sold
$585,000
Jan 25, 2008
Source: Agent Provided
Listed For Sale
$599,000
May 6, 2004
Source: N/A
Sold
$515,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$62.83KMoM
Sale-to-List Price
101.9%
0.2%MoM
Price per sq ft
$574
$3MoM
Available listings
64
13MoM

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 37 Ledyard Rd

  • What is 37 Ledyard Rd estimated to be worth?
    Trulia's estimated value for 37 Ledyard Rd in Winchester, MA is $1,444,700.
  • What is the price history for 37 Ledyard Rd?
    37 Ledyard Rd in Winchester, MA last sold for $585,000 in February 2008.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.47M. That is up $62.83K from the prior month.
  • How big is the lot at 37 Ledyard Rd?
    The lot at 37 Ledyard Rd in Winchester, MA is about 0.17 acres (7,500 sq ft).

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