OFF MARKET

Off Market Apr 2014 for $766K

$1,643,180

•

2,533

sq ft

44 Ledyard Rd, Winchester, MA 01890

About this home

Love nature, walking, biking, cross country skiing? Need easy access to Boston? Want a top rated school for your children? This colonial, near the Middlesex Fells Reservation area with its 2575 acres of woodlands, and in the Lincoln School District, has it all! The first level features a kitchen, dining room with built-ins, living room with wood burning fireplace and built-ins, half bath, laundry area, and screened porch. The second level boasts a master suite with ensuite bath, three additional bedrooms, all with hardwood, one providing access to a walk up attic with exceptional storage space, and full tiled bath. A lower level family room with a second wood burning fireplace provides space for family and friends to enjoy time together. Other features include: new oil tank, 2 car garage, storage shed, central vacuuming, patio, partially fenced yard, walk to train station.

Single-familyProperty Type

1940Year Built

10,000 sq ftLot Size

$649Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Sven Andersen • RE/MAX Leading Edge

Bought with Caroline Staudt • Better Homes and Gardens Real Estate - The Shanahan Group

Redfin checked: 2 minutes ago

•Source:MLS PIN #71639411

Redfin Estimate

$1,643,180

$877K since sold in April 2014$14K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17.9% higher than the average sale price ($1.39M) 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 NOV 20, 2025
$1,355,000
B
4 beds2.5 baths2,865 sq ft
4 Sargent Rd, Winchester, MA 01890
SOLD APR 22, 2026
$1,325,000
C
3 beds2.5 baths2,153 sq ft
6 Marchant Rd, Winchester, MA 01890
SOLD AUG 14, 2026
$1,500,000
D
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD MAR 25, 2026
$1,470,000
E
3 beds2.5 baths2,370 sq ft
2 Canterbury Rd, Winchester, MA 01890
SOLD NOV 14, 2025
$1,150,000
F
3 beds2.5 baths2,648 sq ft
89 Main St, Winchester, MA 01890

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Earn from this home

Sell

$1,118,744

Est. take-home

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Rent

$5,224/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

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OPEN THU, 4:30PM TO 6PM
$1,749,000
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NEW 15 HRS AGO
$675,000
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5 Willowdale Rd, Winchester, MA 01890
NEW 27 HRS AGO
$2,049,000
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NEW 28 HRS AGO
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EARLY ACCESS
$1,325,000
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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
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$1,050,000
5 beds2.5 baths2,801 sq ft
257 Cross St, Winchester, MA 01890
See all

Provided by Redfin

Redfin agents who toured

Traditional Colonial located in East side of Winchester. House is somewhat dated, but has good sized bedrooms, formal living and dining rooms. Kitchen is small and lacks cabinet space, most likely new owner will renovate. Finished basement. Couldn't...
13 years ago• May not reflect the current state of the home
Carol Stevenson
Redfin Associate agent

Sale history for 44 Ledyard Rd

Year

Property tax

Land + Additions

Assessment*

2025

$16,685 (+10.4%)

$924,000 + $580,500

$1,504,500

2023

$15,111 (+1.6%)

$858,000 + $541,000

$1,399,000

2022

$14,873 (+8.0%)

$693,000 + $495,900

$1,188,900

2021

$13,772 (+6.8%)

$577,500 + $495,900

$1,073,400

2020

$12,891 (+9.2%)

$544,500 + $495,900

$1,040,400

2019

$11,800 (+3.6%)

$478,500 + $495,900

$974,400

2018

$11,390 (+6.2%)

$451,300 + $483,100

$934,400

2017

$10,722 (+11.5%)

$424,900 + $448,200

$873,100

2016

$9,614 (+6.6%)

$424,900 + $398,200

$823,100

2015

$9,016 (+16.2%)

$386,100 + $356,600

$742,700

2014

$7,759 (+0.5%)

$321,800 + $291,100

$612,900

2013

$7,717 (+1.8%)

$321,800 + $282,500

$604,300

2012

$7,584 (+3.7%)

$321,800 + $282,500

$604,300

2011

$7,312 (+1.2%)

$321,800 + $282,500

$604,300

2010

$7,224 (+2.1%)

$344,900 + $282,700

$627,600

2009

$7,073

$344,900 + $282,700

$627,600

Tax history for 44 Ledyard Rd

Year

Property tax

Land + Additions

Assessment*

2025

$16,685 (+10.4%)

$924,000 + $580,500

$1,504,500

2023

$15,111 (+1.6%)

$858,000 + $541,000

$1,399,000

2022

$14,873 (+8.0%)

$693,000 + $495,900

$1,188,900

2021

$13,772 (+6.8%)

$577,500 + $495,900

$1,073,400

2020

$12,891 (+9.2%)

$544,500 + $495,900

$1,040,400

2019

$11,800 (+3.6%)

$478,500 + $495,900

$974,400

2018

$11,390 (+6.2%)

$451,300 + $483,100

$934,400

2017

$10,722 (+11.5%)

$424,900 + $448,200

$873,100

2016

$9,614 (+6.6%)

$424,900 + $398,200

$823,100

2015

$9,016 (+16.2%)

$386,100 + $356,600

$742,700

2014

$7,759 (+0.5%)

$321,800 + $291,100

$612,900

2013

$7,717 (+1.8%)

$321,800 + $282,500

$604,300

2012

$7,584 (+3.7%)

$321,800 + $282,500

$604,300

2011

$7,312 (+1.2%)

$321,800 + $282,500

$604,300

2010

$7,224 (+2.1%)

$344,900 + $282,700

$627,600

2009

$7,073

$344,900 + $282,700

$627,600

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

10,019 Sq. Ft.

Year renovated

—

Sq. Ft.

2,724

Year built

1940

Style

Single Family Residential

County

Middlesex County

APN

3756802S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 234
Length: 18
Width: 13
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #2 Information
Area: 208
Length: 16
Width: 13
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 130
Length: 13
Width: 10
Level: Second
Features: Closet,Flooring - Hardwood,Attic Access

Bedroom #4 Information
Area: 252
Length: 18
Width: 14
Level: Second
Features: Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 20
Length: 5
Width: 4
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Area: 40
Length: 8
Width: 5
Level: Second
Features: Bathroom - Full

Bathroom #3 Information
Area: 40
Length: 8
Width: 5
Level: Second
Features: Bathroom - Full

Living Room Information
Area: 294
Length: 21
Width: 14
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 364
Length: 28
Width: 13
Level: Basement
Features: Flooring - Wall to Wall Carpet

Dining Room Information
Area: 143
Length: 13
Width: 11
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box

Kitchen Information
Area: 176
Length: 16
Width: 11
Level: First
Features: Flooring - Vinyl,Dining Area

Basement Information
Basement: Partially Finished, Sump Pump

Laundry Information
Laundry Features: Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 7
Window Features: Insulated Windows, Storm Window(s), Screens
Flooring: Wood, Vinyl, Carpet, Hardwood, Flooring - Hardwood
Interior Features: Entrance Foyer, Central Vacuum, Walk-Up Attic

Exterior

Building Information
Building Area (Total): 2,533
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Roof: Shingle
Patio And Porch Features: Porch, Porch - Enclosed, Patio
Exterior Features: Porch, Porch - Enclosed, Patio, Rain Gutters, Screens

Property Information
Accessibility Features: Accessible Entrance
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat

Lot Information
Lot Size (Acres): 0.23
Lot Features: Wooded
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $7,759
Tax Year: 2014

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers

Heating & Cooling
Has Heating
Heating: Central, Forced Air, Oil

Location

Location Information
Directions: Pierrepont Road to Ledyard
UnparsedAddress: 44 Ledyard Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, Public School

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,724
Stories: 2.0
Lot Size: 10,019 square feet
Style: Single Family Residential
Year Built: 1940
Year Renovated: —
County: Middlesex County
APN: 3756802S

Home facts updated by county records on Jul 29, 2026

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
Exclusions: Washer, Dryer And Refrigerator
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.8mi

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

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 hot days expected this year, 15 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

Air Factor

We're working on getting current and accurate air risk information for this home.

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

$1.56M – $1.89M

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Home values near 44 Ledyard Rd

Data from public records.

Address	Redfin Estimate
49 Ledyard Rd, Winchester, MA 4 Beds \| 3 Baths \| 3050 Sq. Ft.	$1,924,612
48 Ledyard Rd, Winchester, MA 6 Beds \| 4.5 Baths \| 5213 Sq. Ft.	$2,795,218

Address	Redfin Estimate
53 Ledyard Rd, Winchester, MA 4 Beds \| 3 Baths \| 2325 Sq. Ft.	$1,498,044
38 Ledyard Rd, Winchester, MA 4 Beds \| 2 Baths \| 2016 Sq. Ft.	$1,621,525

Address	Redfin Estimate
52 Ledyard Rd, Winchester, MA 3 Beds \| 1.5 Baths \| 2191 Sq. Ft.	$1,488,178
34 Ledyard Rd, Winchester, MA 4 Beds \| 2 Baths \| - Sq. Ft.	$1,672,084

Property information provided by MLS PIN when last listed in 2014. This data may not match . Learn more.

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