OFF MARKET

Off Market Aug 2018 for $925K

$1,498,044

Est. refi paymentEst. refi $1,179/mo

•

2,325

sq ft

53 Ledyard Rd, Winchester, MA 01890

About this home

Welcome to 53 Ledyard Road! The high 8' 4" ceilings and oversized rooms of this Expanded Cape will amaze you. You'll immediately feel at home in the fireplaced living room complete with custom built-ins and window seats, all bathed in natural light. The first floor also features a spacious dining room, eat-in kitchen with stainless steel appliances and a family room with easy access to the deck and backyard. The second level boasts a master suite with a cathedral ceiling and walk-in closet, plus 3 additional bedrooms with generous closet space and a family bath. Bonus spaces in the basement could easily serve as play, music or workout rooms. Outside a beautifully landscaped yard complete with irrigation system awaits. Well maintained with newer windows, roof and hot water heater. Much loved Lincoln School neighborhood just a short distance to downtown Winchester Center, Commuter Rail and Middlesex Fells Reservation.

Single-familyProperty Type

1945Year Built

5,438 sq ftLot Size

$644Est. Price/Sq.Ft.

3 spacesParking

Listed by Anna Hood • Waterfield Sotheby's International Realty

Bought with Anne Spry • Waterfield Sotheby's International Realty

Redfin checked: a minute ago

•Source:MLS PIN #72345420

Redfin Estimate

$1,498,044

$573K since sold in August 2018$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12% higher than the average sale price ($1.34M) of 6 comparable homes.

SOLD APR 30, 2026
$1,560,000
A
4 beds2.5 baths2,578 sq ft
17 Cranston Rd, Winchester, MA 01890
SOLD JUL 29, 2026
$1,535,000
B
4 beds2.5 baths2,691 sq ft
375 Lawrence Rd, Medford, MA 02155
SOLD JUL 31, 2026
$975,000
C
3 beds2 baths1,852 sq ft
15 Judkins Rd, Medford, MA 02155
BOUGHT WITH REDFIN JUL 31, 2026
$1,225,000
D
3 beds2 baths2,172 sq ft
18 Roberts Rd, Medford, MA 02155
SOLD JUN 25, 2026
$1,405,000
E
3 beds2.5 baths2,365 sq ft
88 Damon Rd, Medford, MA 02155
SOLD APR 22, 2026
$1,325,000
F
3 beds2.5 baths2,153 sq ft
6 Marchant Rd, Winchester, MA 01890

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Sell

$804,801

Est. take-home

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Refinance

Est. cash available

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Rent

$5,440/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.9%

0.2% MoM

Median sale price

$1.6M

$175K MoM

Avg. days on market

19d

0 days MoM

Recently sold homes

17 MoM

New listings for sale

OPEN THU, 5PM TO 6:30PM
$2,199,000
4 beds3.5 baths3,570 sq ft
19 Hancock St, Winchester, MA 01890
OPEN THU, 4:30PM TO 6PM
$1,749,000
5 beds3.5 baths3,508 sq ft
17 Churchill Rd, Winchester, MA 01890
NEW 14 HRS AGO
$675,000
2 beds1.5 baths1,190 sq ft
60 Lake St Unit E, Winchester, MA 01890
NEW 15 HRS AGO
$1,679,900
3 beds2 baths2,483 sq ft
5 Willowdale Rd, Winchester, MA 01890
NEW 26 HRS AGO
$2,049,000
4 beds3.5 baths3,210 sq ft
26 N Gateway, Winchester, MA 01890
NEW 28 HRS AGO
$1,699,000
3 beds2 baths2,421 sq ft
4 Churchill Rd, Winchester, MA 01890
EARLY ACCESS
$1,325,000
4 beds2 baths1,922 sq ft
9 Priscilla Ln, Winchester, MA 01890
HOT HOME
$619,000
3 beds3 baths1,225 sq ft
23 Shepard Ct #23, Winchester, MA 01890
3D & VIDEO TOUR
$1,099,000
4 beds2.5 baths2,411 sq ft
24 Richardson St, Winchester, MA 01890
$1,050,000
5 beds2.5 baths2,801 sq ft
257 Cross St, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 53 Ledyard Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,177 (+8.9%)

$834,600 + $443,800

$1,278,400

2023

$13,018 (−0.3%)

$775,000 + $441,900

$1,216,900

2022

$13,054 (+8.3%)

$625,900 + $417,600

$1,043,500

2021

$12,050 (+6.9%)

$521,600 + $417,600

$939,200

2020

$11,267 (+9.5%)

$491,800 + $417,600

$909,400

2019

$10,291 (+3.9%)

$432,200 + $417,600

$849,800

2018

$9,903 (+5.7%)

$407,600 + $404,800

$812,400

2017

$9,370 (+6.3%)

$383,800 + $379,200

$763,000

2016

$8,815 (+3.2%)

$383,800 + $370,900

$754,700

2015

$8,545 (+6.2%)

$348,700 + $355,200

$703,900

2014

$8,043 (+0.8%)

$290,600 + $344,700

$635,300

2013

$7,980 (+1.8%)

$290,600 + $334,300

$624,900

2012

$7,842 (+3.7%)

$290,600 + $334,300

$624,900

2011

$7,561 (+1.9%)

$290,600 + $334,300

$624,900

2010

$7,418 (+2.1%)

$311,500 + $333,000

$644,500

2009

$7,264

$311,500 + $333,000

$644,500

Tax history for 53 Ledyard Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,177 (+8.9%)

$834,600 + $443,800

$1,278,400

2023

$13,018 (−0.3%)

$775,000 + $441,900

$1,216,900

2022

$13,054 (+8.3%)

$625,900 + $417,600

$1,043,500

2021

$12,050 (+6.9%)

$521,600 + $417,600

$939,200

2020

$11,267 (+9.5%)

$491,800 + $417,600

$909,400

2019

$10,291 (+3.9%)

$432,200 + $417,600

$849,800

2018

$9,903 (+5.7%)

$407,600 + $404,800

$812,400

2017

$9,370 (+6.3%)

$383,800 + $379,200

$763,000

2016

$8,815 (+3.2%)

$383,800 + $370,900

$754,700

2015

$8,545 (+6.2%)

$348,700 + $355,200

$703,900

2014

$8,043 (+0.8%)

$290,600 + $344,700

$635,300

2013

$7,980 (+1.8%)

$290,600 + $334,300

$624,900

2012

$7,842 (+3.7%)

$290,600 + $334,300

$624,900

2011

$7,561 (+1.9%)

$290,600 + $334,300

$624,900

2010

$7,418 (+2.1%)

$311,500 + $333,000

$644,500

2009

$7,264

$311,500 + $333,000

$644,500

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

5,227 Sq. Ft.

Year renovated

—

Sq. Ft.

2,701

Year built

1945

Style

Single Family Residential

County

Middlesex County

APN

1041946S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

Property details

Parking

Parking Information
Has Open Parking
Parking Spaces: 3
Parking Features: Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 323
Length: 19
Width: 17
Level: Second
Features: Bathroom - Full,Skylight,Cathedral Ceiling(s),Ceiling Fan(s),Walk-In Closet(s),Closet,Window(s) - Picture,Recessed Lighting

Bedroom #2 Information
Area: 140
Length: 14
Width: 10
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 168
Length: 14
Width: 12
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #4 Information
Area: 140
Length: 14
Width: 10
Level: Second
Features: Skylight,Closet,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 24
Length: 6
Width: 4
Level: First
Features: Bathroom - 3/4,Bathroom - With Shower Stall,Flooring - Vinyl

Bathroom #2 Information
Area: 45
Length: 9
Width: 5
Level: Second
Features: Bathroom - Full,Bathroom - With Tub & Shower,Flooring - Vinyl

Bathroom #3 Information
Area: 40
Length: 8
Width: 5
Level: Second
Features: Bathroom - Full,Bathroom - With Tub & Shower,Skylight,Cathedral Ceiling(s),Flooring - Stone/Ceramic Tile

Living Room Information
Area: 322
Length: 23
Width: 14
Level: First
Features: Flooring - Hardwood,French Doors

Family Room Information
Area: 340
Length: 20
Width: 17
Level: First
Features: Flooring - Hardwood,Flooring - Stone/Ceramic Tile,Deck - Exterior,Exterior Access,Recessed Lighting,Slider

Dining Room Information
Area: 180
Length: 15
Width: 12
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Chair Rail

Kitchen Information
Area: 182
Length: 13
Width: 14
Level: First
Features: Flooring - Vinyl,Stainless Steel Appliances

Basement Information
Basement: Full, Partially Finished, Interior Entry, Bulkhead

Laundry Information
Laundry Features: Gas Dryer Hookup, Washer Hookup, In Basement

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 8
Door Features: French Doors
Window Features: Insulated Windows
Flooring: Tile, Vinyl, Carpet, Laminate, Hardwood, Flooring - Wall to Wall Carpet
Interior Features: Bonus Room

Exterior

Building Information
Building Area (Total): 2,325
Foundation Details: Concrete Perimeter, Block
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate
Color: White

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck
Exterior Features: Deck, Rain Gutters, Sprinkler System, Garden

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.12
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $9,903
Tax Year: 2018

Utilities

Utility Information
Utilities: for Gas Range, for Electric Oven, for Gas Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Steam, Natural Gas
Cooling: Window Unit(s)

Location

Location Information
Directions: Highland Ave to Pierrepont Rd, right onto Ledyard Rd
UnparsedAddress: 53 Ledyard Road, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Public School

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,701
Stories: 2.0
Lot Size: 5,227 square feet
Style: Single Family Residential
Year Built: 1945
Year Renovated: —
County: Middlesex County
APN: 1041946S

Home facts updated by county records on Jul 29, 2026

Other

Miscellaneous Information
Heat Zones: 2

Listing Information
Exclusions: See Inclusion/Exclusion Sheet.
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.9mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.8mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.2mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winchester, MA • 01890

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.42M – $1.72M

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Home values near 53 Ledyard Rd

Data from public records.

Address	Redfin Estimate
49 Ledyard Road, Winchester, MA 4 Beds \| 3 Baths \| 3050 Sq. Ft.	$1,924,612
44 Ledyard Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2533 Sq. Ft.	$1,643,180

Address	Redfin Estimate
52 Ledyard Road, Winchester, MA 3 Beds \| 1.5 Baths \| 2191 Sq. Ft.	$1,488,178
43 Ledyard Road, Winchester, MA 4 Beds \| 2.5 Baths \| - Sq. Ft.	$1,732,913

Address	Redfin Estimate
48 Ledyard Road, Winchester, MA 6 Beds \| 4.5 Baths \| 5213 Sq. Ft.	$2,795,218
1 Alden Lane, Winchester, MA 5 Beds \| 3.5 Baths \| 3517 Sq. Ft.	$2,015,709

Property information provided by MLS PIN when last listed in 2018. This data may not match . Learn more.

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