OFF MARKET

Off Market Jun 2021 for $1.8M

$2,373,830

Est. refi paymentEst. refi $1,620/mo

•

3,750

sq ft

21 Leslie Rd, Winchester, MA 01890

About this home

Located in the coveted Ledgewood area, this striking colonial set on a gorgeous 1/2 acre is highlighted by a far-reaching backyard retreat. Lovely manicured grounds and a welcoming farmers porch await you. From the entry foyer, French doors lead to the open living & dining room areas brimming w/natural light. Updated kitchen w/breakfast bar, white cabinetry & SS appliances, opens to the inviting family rm. An expansive deck across the back of the home has sliders linking formal & informal rooms - a perfect flow for entertaining! 2nd floor has 4 bdrms (2 ensuite) & 2nd laundry. Sumptuous owner’s suite w/cathedral ceilings, spa bath, private balcony & walk-in closet. Oversized mudroom off the family room provides access to the garage & finished lower level, featuring full height windows & 2 large rooms for numerous flex space options. Abundant storage & hdwd floors throughout. 2006 addition, 2013 boiler, 2019 roof, 2020 A/C. Lincoln Elementary School. Steps to the Fells & Town Center.

Single-familyProperty Type

1956Year Built

0.54 acresLot Size

$633Est. Price/Sq.Ft.

2 garage spacesParking

Listed by The Lorrie Parajeckas Group • Compass

Bought with Karen Garrett • Better Homes and Gardens Real Estate - The Shanahan Group

Redfin checked: 2 minutes ago

•Source:MLS PIN #72820640

Redfin Estimate

$2,373,830

$514K since sold in June 2021$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.1% higher than the average sale price ($2.14M) of 6 comparable homes.

SOLD JUL 30, 2026
$2,255,000
A
4 beds3.5 baths3,494 sq ft
2 York Rd, Winchester, MA 01890
SOLD MAY 1, 2026
$1,755,000
B
4 beds4.5 baths3,906 sq ft
35 Hollywood Rd, Winchester, MA 01890
SOLD JUN 16, 2026
$2,575,000
C
4 beds4.5 baths3,945 sq ft
2 Edgewater Pl, Winchester, MA 01890
BOUGHT WITH REDFIN JUL 13, 2026
$2,150,000
D
5 beds3 baths3,136 sq ft
22 Hollywood Rd, Winchester, MA 01890
BOUGHT WITH REDFIN JAN 27, 2026
$1,965,000
E
4 beds3.5 baths3,475 sq ft
46 Church St, Winchester, MA 01890
SOLD APR 28, 2026
$2,120,000
F
5 beds3.5 baths2,860 sq ft
4 Leslie Rd, Winchester, MA 01890

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Sell

$920,183

Est. take-home

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Est. cash available

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Rent

$6,052/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

100.0%

0.9% MoM

Median sale price

$1.7M

$39K MoM

Avg. days on market

21d

3 days MoM

Recently sold homes

7 MoM

New listings for sale

NEW 8 HRS AGO
$1,080,000
3 beds1 bath1,382 sq ft
6 Reservoir St, Winchester, MA 01890
OPEN FRI, 12PM TO 1:45PM
$2,600,000
6 beds3 baths3,534 sq ft
7 Lakeview Ter, Winchester, MA 01890
OPEN FRI, 11AM TO 12PM
$1,350,000
2 beds2.5 baths1,573 sq ft
36 Elmwood Ave #11, Winchester, MA 01890
REDFIN OPEN SAT, 11AM TO 12:30PM
$495,000
2 beds1 bath822 sq ft
200 Swanton St #303, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$1,495,000
4 beds2.5 baths2,973 sq ft
7 Sherman Pl #7, Winchester, MA 01890
$1,899,000
4 beds3.5 baths3,257 sq ft
11 Bonad Rd, Winchester, MA 01890
OPEN TODAY, 5PM TO 6:30PM
$1,799,999
4 beds2.5 baths3,126 sq ft
30 Allen Rd, Winchester, MA 01890
OPEN SAT, 1PM TO 2:30PM
$3,200,000
8 beds6.5 baths5,750 sq ft
30 Willowdale Rd, Winchester, MA 01890
3D WALKTHROUGH
$974,900
3 beds2.5 baths1,719 sq ft
258 Cross St, Winchester, MA 01890
$769,000
2 beds2 baths1,170 sq ft
666 Main St #310, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 21 Leslie Rd

Year

Property tax

Land + Additions

Assessment*

2026

$23,828 (+5.9%)

$1,122,300 + $1,028,200

$2,150,500

2025

$22,496 (+5.4%)

$1,122,300 + $906,200

$2,028,500

2024

$21,346 (+1.8%)

$1,042,300 + $841,700

$1,884,000

2023

$20,969 (+13.6%)

$1,042,300 + $841,700

$1,884,000

2022

$18,462 (+2.4%)

$842,100 + $633,700

$1,475,800

2021

$18,036 (+3.5%)

$772,100 + $633,700

$1,405,800

2020

$17,418 (+10.1%)

$772,100 + $633,700

$1,405,800

2019

$15,813 (+3.1%)

$672,100 + $633,700

$1,305,800

2018

$15,334 (+1.8%)

$640,100 + $617,800

$1,257,900

2017

$15,057 (+6.5%)

$640,100 + $586,000

$1,226,100

2016

$14,134 (+2.8%)

$640,100 + $570,000

$1,210,100

2015

$13,755 (+7.1%)

$582,100 + $550,900

$1,133,000

2014

$12,841 (+0.4%)

$487,100 + $527,200

$1,014,300

2013

$12,789 (+1.8%)

$487,100 + $514,400

$1,001,500

2012

$12,569 (+3.7%)

$487,100 + $514,400

$1,001,500

2011

$12,118 (+5.2%)

$487,100 + $514,400

$1,001,500

2010

$11,518 (+2.1%)

$496,100 + $504,600

$1,000,700

2009

$11,278

$496,100 + $504,600

$1,000,700

Tax history for 21 Leslie Rd

Year

Property tax

Land + Additions

Assessment*

2026

$23,828 (+5.9%)

$1,122,300 + $1,028,200

$2,150,500

2025

$22,496 (+5.4%)

$1,122,300 + $906,200

$2,028,500

2024

$21,346 (+1.8%)

$1,042,300 + $841,700

$1,884,000

2023

$20,969 (+13.6%)

$1,042,300 + $841,700

$1,884,000

2022

$18,462 (+2.4%)

$842,100 + $633,700

$1,475,800

2021

$18,036 (+3.5%)

$772,100 + $633,700

$1,405,800

2020

$17,418 (+10.1%)

$772,100 + $633,700

$1,405,800

2019

$15,813 (+3.1%)

$672,100 + $633,700

$1,305,800

2018

$15,334 (+1.8%)

$640,100 + $617,800

$1,257,900

2017

$15,057 (+6.5%)

$640,100 + $586,000

$1,226,100

2016

$14,134 (+2.8%)

$640,100 + $570,000

$1,210,100

2015

$13,755 (+7.1%)

$582,100 + $550,900

$1,133,000

2014

$12,841 (+0.4%)

$487,100 + $527,200

$1,014,300

2013

$12,789 (+1.8%)

$487,100 + $514,400

$1,001,500

2012

$12,569 (+3.7%)

$487,100 + $514,400

$1,001,500

2011

$12,118 (+5.2%)

$487,100 + $514,400

$1,001,500

2010

$11,518 (+2.1%)

$496,100 + $504,600

$1,000,700

2009

$11,278

$496,100 + $504,600

$1,000,700

*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

0.54 Acres

Year renovated

—

Sq. Ft.

3,776

Year built

1956

Style

Single Family Residential

County

Middlesex County

APN

3571924S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Storage, Paved Drive, Paved

Interior

Master Bedroom Information
Area: 204
Length: 17
Width: 12
Level: Second
Features: Bathroom - Full,Cathedral Ceiling(s),Ceiling Fan(s),Walk-In Closet(s),Flooring - Hardwood,Balcony - Exterior,Recessed Lighting,Slider,Closet - Double,Pocket Door

Bedroom #2 Information
Area: 132
Length: 12
Width: 11
Level: Second
Features: Bathroom - 3/4,Flooring - Hardwood,Closet - Double

Bedroom #3 Information
Area: 165
Length: 15
Width: 11
Level: Second
Features: Flooring - Hardwood,Closet - Double

Bedroom #4 Information
Area: 132
Length: 12
Width: 11
Level: Second
Features: Flooring - Hardwood,Closet - Double

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 2
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Marble,Lighting - Sconce

Bathroom #2 Information
Area: 160
Length: 20
Width: 8
Level: Second
Features: Bathroom - Double Vanity/Sink,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Jacuzzi / Whirlpool Soaking Tub,Recessed Lighting,Lighting - Sconce,Pocket Door

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub,Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile

Living Room Information
Area: 260
Length: 20
Width: 13
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,French Doors,Crown Molding

Family Room Information
Area: 273
Length: 21
Width: 13
Level: First
Features: Flooring - Hardwood,Deck - Exterior,Recessed Lighting,Slider,Lighting - Pendant,Crown Molding

Dining Room Information
Area: 221
Length: 17
Width: 13
Level: First
Features: Flooring - Hardwood,Deck - Exterior,Slider,Lighting - Sconce,Lighting - Pendant,Crown Molding,Pocket Door

Kitchen Information
Area: 253
Length: 23
Width: 11
Level: First
Features: Flooring - Hardwood,Dining Area,Pantry,Countertops - Stone/Granite/Solid,Breakfast Bar / Nook,Cabinets - Upgraded,Recessed Lighting,Stainless Steel Appliances,Lighting - Pendant,Pocket Door

Office Room Information
Area: 121
Length: 11
Width: 11
Level: First
Features: Fireplace,Flooring - Hardwood,Window(s) - Bay/Bow/Box,French Doors,Crown Molding

Basement Information
Basement: Full, Finished, Interior Entry, Sump Pump

Laundry Information
Laundry Features: Laundry Closet, Electric Dryer Hookup, Washer Hookup, Second Floor

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

Interior Features
# of Rooms (Total): 11
Door Features: French Doors, Insulated Doors, Storm Door(s)
Window Features: Window(s) - Bay/Bow/Box, Insulated Windows, Storm Window(s), Screens
Flooring: Tile, Vinyl, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Vinyl
Interior Features: Crown Molding, Bathroom - 3/4, Bathroom - With Shower Stall, Lighting - Sconce, Closet/Cabinets - Custom Built, Recessed Lighting, Ceiling - Half-Vaulted, Bathroom - Half, Cedar Closet(s), Lighting - Overhead, Office, Bathroom, Mud Room, Bonus Room, Exercise Room, Finish - Cement Plaster, Finish - Sheetrock, Wired for Sound, Internet Available - Broadband, High Speed Internet

Exterior

Building Information
Building Area (Total): 3,750
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Taupe

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Porch, Deck - Composite
Exterior Features: Porch, Deck - Composite, Balcony, Rain Gutters, Storage, Sprinkler System, Screens, Fenced Yard

Property Information
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat
Security Features: Security System

Lot Information
Lot Size (Acres): 0.54
Lot Features: Easements, Level
Road Frontage Type: Private Road
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $18,036
Tax Year: 2021

Utilities

Utility Information
Utilities: for Electric Range, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: 110 Volts, 220 Volts, Circuit Breakers, 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Central, Hot Water, Oil, ENERGY STAR Qualified Equipment, Fireplace(s)
Cooling: Central Air, Dual, ENERGY STAR Qualified Equipment

Location

Location Information
Directions: Main St to Lawson Rd, across Highland Ave to Lawson Rd Extension; left onto Leslie Rd.
UnparsedAddress: 21 Leslie Rd, Winchester MA 01890

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

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 3,776
Stories: 2.0
Lot Size: 0.54 acres
Style: Single Family Residential
Year Built: 1956
Year Renovated: —
County: Middlesex County
APN: 3571924S

Home facts updated by county records on Sep 16, 2026

Other

Miscellaneous Information
Heat Zones: 7

Listing Information
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.6mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.6mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.9mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

9/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.46% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 14 days in 30 years

6/10 Wind Factor

50% 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

$2.26M – $2.73M

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Home values near 21 Leslie Rd

Data from public records.

Address	Redfin Estimate
11 Leslie Road, Winchester, MA 4 Beds \| 3 Baths \| 4300 Sq. Ft.	$3,050,337
27 Leslie Road, Winchester, MA 3 Beds \| 3.5 Baths \| 3399 Sq. Ft.	$1,908,397

Address	Redfin Estimate
17 Leslie Road, Winchester, MA 7 Beds \| 6 Baths \| 6881 Sq. Ft.	$2,782,633
29 Leslie Road, Winchester, MA 3 Beds \| 2.5 Baths \| 2895 Sq. Ft.	$1,892,658

Address	Redfin Estimate
23 Leslie Road, Winchester, MA 5 Beds \| 2 Baths \| 3191 Sq. Ft.	$1,771,425
31 Leslie Road, Winchester, MA 2 Beds \| 2 Baths \| 2281 Sq. Ft.	$1,668,780

Property information provided by MLS PIN when last listed in 2021. This data may not match . Learn more.

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