OFF MARKET

Off Market Sep 2024 for $1.3M

$1,498,499

Est. refi paymentEst. refi $590/mo

•

2,364

sq ft

27 Ledyard Rd, Winchester, MA 01890

About this home

Discover the endless potential of this charming 3-bedroom, 1.5-bathroom home, perfectly positioned on a sought-after Winchester lot with excellent frontage and a generously sized yard. The finished lower level features a convenient walkout to a private backyard, creating additional living space and ample opportunities for outdoor enjoyment. This property presents a fantastic opportunity for a full renovation or teardown, allowing you to design and construct your dream home from the ground up. Situated near top-tier schools, a variety of convenient amenities, and the scenic Middlesex Fells Conservation area, this location offers the best of both worlds—serenity and accessibility. Don't miss the chance to create a custom living space in a prime location that caters to your lifestyle and preferences. Embrace this unique opportunity to bring your vision to life and make this desirable Winchester address your own.

Single-familyProperty Type

1940Year Built

0.28 acresLot Size

$634Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Andersen Group Realty • Keller Williams Realty Boston Northwest

Bought with Andersen Group Realty • Keller Williams Realty Boston Northwest

Redfin checked: 3 minutes ago

•Source:MLS PIN #73268304

Redfin Estimate

$1,498,499

$118K since sold in September 2024$10K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.5% higher than the average sale price ($1.29M) of 6 comparable homes.

SOLD JUN 26, 2026
$985,000
A
3 beds2 baths2,030 sq ft
19 Wildwood Rd, Medford, MA 02155
SOLD JUL 30, 2026
$1,160,000
B
3 beds1.5 baths1,996 sq ft
70 Grove St, Winchester, MA 01890
SOLD AUG 14, 2026
$1,500,000
C
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD APR 22, 2026
$1,325,000
D
3 beds2.5 baths2,153 sq ft
6 Marchant Rd, 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 JUN 25, 2026
$1,275,000
F
3 beds2 baths1,511 sq ft
6 Alden Ln, Winchester, MA 01890

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Earn from this home

Sell

$360,233

Est. take-home

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Refinance

Est. cash available

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Rent

$3,915/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 21 HRS AGO
$675,000
2 beds1.5 baths1,190 sq ft
60 Lake St Unit E, Winchester, MA 01890
NEW 22 HRS AGO
$1,679,900
3 beds2 baths2,483 sq ft
5 Willowdale Rd, Winchester, MA 01890
$2,049,000
4 beds3.5 baths3,210 sq ft
26 N Gateway, Winchester, MA 01890
$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 27 Ledyard Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,211 (+3.5%)

$968,400 + $313,000

$1,281,400

2024

$13,725 (+6.5%)

$899,200 + $312,200

$1,211,400

2023

$12,886 (+0.7%)

$899,200 + $312,200

$1,211,400

2022

$12,796 (+10.6%)

$726,300 + $296,600

$1,022,900

2021

$11,570 (+7.7%)

$605,200 + $296,600

$901,800

2020

$10,745 (+11.2%)

$570,600 + $296,600

$867,200

2019

$9,665 (+4.3%)

$501,500 + $296,600

$798,100

2018

$9,269 (+5.6%)

$472,900 + $287,500

$760,400

2017

$8,775 (+6.5%)

$445,300 + $269,300

$714,600

2016

$8,239 (+8.2%)

$445,300 + $260,100

$705,400

2015

$7,614 (+8.8%)

$404,600 + $222,600

$627,200

2014

$7,001 (+0.4%)

$337,200 + $215,800

$553,000

2013

$6,974 (+1.8%)

$337,200 + $208,900

$546,100

2012

$6,854 (+3.7%)

$337,200 + $208,900

$546,100

2011

$6,608

$337,200 + $208,900

$546,100

2010

$6,604 (+2.1%)

$361,400 + $212,400

$573,800

2009

$6,467

$361,400 + $212,400

$573,800

Tax history for 27 Ledyard Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,211 (+3.5%)

$968,400 + $313,000

$1,281,400

2024

$13,725 (+6.5%)

$899,200 + $312,200

$1,211,400

2023

$12,886 (+0.7%)

$899,200 + $312,200

$1,211,400

2022

$12,796 (+10.6%)

$726,300 + $296,600

$1,022,900

2021

$11,570 (+7.7%)

$605,200 + $296,600

$901,800

2020

$10,745 (+11.2%)

$570,600 + $296,600

$867,200

2019

$9,665 (+4.3%)

$501,500 + $296,600

$798,100

2018

$9,269 (+5.6%)

$472,900 + $287,500

$760,400

2017

$8,775 (+6.5%)

$445,300 + $269,300

$714,600

2016

$8,239 (+8.2%)

$445,300 + $260,100

$705,400

2015

$7,614 (+8.8%)

$404,600 + $222,600

$627,200

2014

$7,001 (+0.4%)

$337,200 + $215,800

$553,000

2013

$6,974 (+1.8%)

$337,200 + $208,900

$546,100

2012

$6,854 (+3.7%)

$337,200 + $208,900

$546,100

2011

$6,608

$337,200 + $208,900

$546,100

2010

$6,604 (+2.1%)

$361,400 + $212,400

$573,800

2009

$6,467

$361,400 + $212,400

$573,800

*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

1.5

Stories

Lot width

—

Lot depth

—

Lot size

0.28 Acres

Year renovated

—

Sq. Ft.

1,969

Year built

1940

Style

Single Family Residential

County

Middlesex County

APN

1693084S

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: 1
# of Covered Spaces: 1
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Under, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Level: Second
Features: Closet,Flooring - Hardwood,Lighting - Sconce

Bedroom #2 Information
Level: Second
Features: Closet,Flooring - Hardwood,Lighting - Overhead

Bedroom #3 Information
Level: Second
Features: Closet,Flooring - Hardwood,Lighting - Overhead

Bathroom Information
# of Bathrooms (Full): 1
# of Bathrooms (Half): 1
Main Level Bathrooms: 1

Bathroom #1 Information
Level: Main,First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Lighting - Overhead

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile,Lighting - Sconce

Living Room Information
Level: Main,First
Features: Flooring - Hardwood,Lighting - Sconce,Crown Molding

Family Room Information
Level: Basement
Features: Flooring - Hardwood,Exterior Access,Recessed Lighting,Slider

Dining Room Information
Level: Main,First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Lighting - Overhead

Kitchen Information
Level: Main,First
Features: Flooring - Stone/Ceramic Tile,Lighting - Overhead

Basement Information
Basement: Full, Finished, Walk-Out Access, Garage Access

Laundry Information
Laundry Features: Flooring - Stone/Ceramic Tile, Main Level, Lighting - Overhead, First Floor, Electric Dryer Hookup

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

Interior Features
# of Rooms (Total): 7
Door Features: Insulated Doors
Window Features: Insulated Windows, Screens
Flooring: Wood

Exterior

Building Information
Building Area (Total): 2,364
Foundation Details: Concrete Perimeter, Block
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: White

Exterior Features
Roof: Shingle
Patio And Porch Features: Porch, Porch - Enclosed, Screened
Exterior Features: Porch, Porch - Enclosed, Porch - Screened, Rain Gutters, Professional Landscaping, Decorative Lighting, Screens, Stone Wall

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.28
Lot Features: Wooded, Gentle Sloping
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $13,725
Tax Year: 2024

Utilities

Utility Information
Utilities: for Electric Range, for Electric Dryer
Sewer: Public Sewer
Water Source: Public
Electric: 110 Volts

Heating & Cooling
Has Heating
Has Cooling
Heating: Central, Forced Air, Natural Gas
Cooling: Window Unit(s)

Location

Location Information
Directions: Highland Avenue to Pierrepont Road to Ledyard Road
UnparsedAddress: 27 Ledyard Rd, Winchester MA 01890

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

Public facts

Beds: 3
Baths: 1.5
Sq. Ft.: 1,969
Stories: 2.0
Lot Size: 0.28 acres
Style: Single Family Residential
Year Built: 1940
Year Renovated: —
County: Middlesex County
APN: 1693084S

Home facts updated by county records on Jul 30, 2026

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
Exclusions: None
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.7mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.7mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.1mi

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 hot days expected this year, 14 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

$1.42M – $1.72M

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Home values near 27 Ledyard Rd

Data from public records.

Address	Redfin Estimate
38 Ledyard Road, Winchester, MA 4 Beds \| 2 Baths \| 2016 Sq. Ft.	$1,621,525
24 Ledyard Road, Winchester, MA 2 Beds \| 2 Baths \| 1393 Sq. Ft.	$1,128,590

Address	Redfin Estimate
34 Ledyard Road, Winchester, MA 4 Beds \| 2 Baths \| - Sq. Ft.	$1,672,084
20 Ledyard Road, Winchester, MA 3 Beds \| 2 Baths \| 2400 Sq. Ft.	$1,421,691

Address	Redfin Estimate
28 Ledyard Road, Winchester, MA 3 Beds \| 1.5 Baths \| 1728 Sq. Ft.	$1,734,739
16 Ledyard Road, Winchester, MA 3 Beds \| 2 Baths \| 1636 Sq. Ft.	$1,326,974

Property information provided by MLS PIN when last listed in 2024. This data may not match . Learn more.

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