OFF MARKET

Off Market Jun 2023 for $1.5M

$1,634,712

Est. refi paymentEst. refi $3,270/mo

•

2,592

sq ft

59 Woodside Rd, Winchester, MA 01890

About this home

Welcome to your dream home located nearby picturesque Winter Pond. This remodeled 5 bed, 2.5 bath Colonial has all the features you've been looking for & more. From the moment you step inside, you'll be greeted by an inviting living area, featuring a cozy fireplace & windows that bathe the space in natural light. The open floor plan seamlessly flows into the dining area. The kitchen is a chef's delight, complete with SS appliances, granite countertops, & plenty of counter space for meal prep. The primary bedroom is a tranquil retreat, with full bath & large closet space. The remaining 4 bedrooms are equally generous. But that's not all – this home also boasts a dedicated office space, mudroom, a finished basement perfect for a theater, gym, or family room. Large backyard with a patio area, plus, 2-car garage with plenty of room for your vehicles & additional storage. Located minutes away from top-rated schools, shops, restaurants, & all the amenities this vibrant community has to offer

Single-familyProperty Type

1930Year Built

10,563 sq ftLot Size

$631Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Pirani & Wile Group • Leading Edge Real Estate

Bought with Candor Realty Group • Four Points Real Estate, LLC

Redfin checked: 2 minutes ago

•Source:MLS PIN #73102498

Redfin Estimate

$1,634,712

$85K since sold in June 2023$14K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.2% lower than the average sale price ($1.66M) of 6 comparable homes.

SOLD AUG 14, 2026
$2,200,000
A
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
SOLD MAY 15, 2026
$2,300,000
B
4 beds2.5 baths3,283 sq ft
12 Yale St, Winchester, MA 01890
SOLD BY REDFIN JUN 5, 2026
$1,020,000
C
5 beds2 baths2,331 sq ft
149 Horn Pond Brook 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 MAY 29, 2026
$1,250,000
E
4 beds2 baths2,046 sq ft
87 Wendell St, Winchester, MA 01890
SOLD AUG 7, 2026
$1,660,000
F
4 beds3.5 baths2,768 sq ft
10 Farrow St, Winchester, MA 01890

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Earn from this home

Sell

$388,696

Est. take-home

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Refinance

Est. cash available

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Rent

$5,146/mo

Redfin rental estimate

List your home for rent

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

3D WALKTHROUGH
$974,900
4 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
VIDEO TOUR
$775,000
3 beds2 baths1,643 sq ft
189 Washington St #2, Winchester, MA 01890
$1,599,000
5 beds2 baths2,944 sq ft
143 Arlington St, Winchester, MA 01890
$4,299,000
5 beds5.5 baths6,526 sq ft
4 Dartmouth, Winchester, MA 01890
$1,300,000
4 beds2.5 baths2,666 sq ft
465 Washington St, Winchester, MA 01890
$1,300,000
4 beds2.5 baths2,666 sq ft
465 Washington St #465, Winchester, MA 01890
$1,299,000
4 beds1.5 baths3,307 sq ft
253 Pond St, Winchester, MA 01890
$2,995,000
5 beds5.5 baths6,500 sq ft
8 Priscilla Ln, Winchester, MA 01890
$3,149,000
7 beds7.5 baths8,540 sq ft
37 Mayflower Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 59 Woodside Rd

Date

Event

Price

MLS PIN #73102498

Jun 12, 2023

Sold

$1,550,000

$598/sq ft

May 5, 2023

Contingent

—

Apr 24, 2023

Listed

$1,489,000

$574/sq ft

MLS PIN #30547008

Jan 2, 2002

Sold

$437,000

$169/sq ft

Nov 21, 2001

Listing Removed

—

Sep 28, 2001

Listed

$454,000

$175/sq ft

Public Records

Jun 26, 1998

Sold

$335,000

$129/sq ft

Public Records

Aug 17, 1988

Sold

$235,000

$91/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$14,761 (+5.5%)

$834,800 + $496,200

$1,331,000

2023

$13,995 (+2.0%)

$834,800 + $460,900

$1,295,700

2022

$13,725 (+3.8%)

$667,900 + $429,200

$1,097,100

2021

$13,219 (+4.6%)

$601,100 + $429,200

$1,030,300

2020

$12,640 (+9.5%)

$601,100 + $419,100

$1,020,200

2019

$11,546 (+6.4%)

$534,300 + $419,100

$953,400

2018

$10,855 (+10.4%)

$482,500 + $408,000

$890,500

2017

$9,833 (+10.0%)

$414,900 + $385,800

$800,700

2016

$8,940 (−2.1%)

$390,700 + $374,700

$765,400

2015

$9,130 (+6.7%)

$390,700 + $361,400

$752,100

2014

$8,553 (+0.5%)

$325,600 + $350,000

$675,600

2013

$8,514 (+1.8%)

$325,600 + $341,100

$666,700

2012

$8,367 (+3.7%)

$325,600 + $341,100

$666,700

2011

$8,067 (+6.7%)

$325,600 + $341,100

$666,700

2010

$7,561 (+2.1%)

$325,100 + $331,800

$656,900

2009

$7,403

$325,100 + $331,800

$656,900

Tax history for 59 Woodside Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,761 (+5.5%)

$834,800 + $496,200

$1,331,000

2023

$13,995 (+2.0%)

$834,800 + $460,900

$1,295,700

2022

$13,725 (+3.8%)

$667,900 + $429,200

$1,097,100

2021

$13,219 (+4.6%)

$601,100 + $429,200

$1,030,300

2020

$12,640 (+9.5%)

$601,100 + $419,100

$1,020,200

2019

$11,546 (+6.4%)

$534,300 + $419,100

$953,400

2018

$10,855 (+10.4%)

$482,500 + $408,000

$890,500

2017

$9,833 (+10.0%)

$414,900 + $385,800

$800,700

2016

$8,940 (−2.1%)

$390,700 + $374,700

$765,400

2015

$9,130 (+6.7%)

$390,700 + $361,400

$752,100

2014

$8,553 (+0.5%)

$325,600 + $350,000

$675,600

2013

$8,514 (+1.8%)

$325,600 + $341,100

$666,700

2012

$8,367 (+3.7%)

$325,600 + $341,100

$666,700

2011

$8,067 (+6.7%)

$325,600 + $341,100

$666,700

2010

$7,561 (+2.1%)

$325,100 + $331,800

$656,900

2009

$7,403

$325,100 + $331,800

$656,900

*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

10,454 Sq. Ft.

Year renovated

—

Sq. Ft.

2,546

Year built

1930

Style

Single Family Residential

County

Middlesex County

APN

1431148S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 10, 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, Paved

Interior

Master Bedroom Information
Area: 280
Length: 14
Width: 20
Level: Second
Features: Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #2 Information
Area: 110
Length: 10
Width: 11
Level: Second
Features: Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #3 Information
Area: 121
Length: 11
Width: 11
Level: Second
Features: Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #4 Information
Area: 99
Length: 9
Width: 11
Level: Second
Features: Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #5 Information
Area: 88
Length: 8
Width: 11
Level: Second
Features: Closet,Flooring - Hardwood,Recessed Lighting

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

Bathroom #1 Information
Area: 80
Length: 8
Width: 10
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Area: 35
Length: 5
Width: 7
Level: Second
Features: Bathroom - Full,Bathroom - With Tub & Shower

Bathroom #3 Information
Area: 80
Length: 8
Width: 10
Level: Second
Features: Bathroom - Full,Bathroom - With Tub & Shower

Living Room Information
Area: 567
Length: 21
Width: 27
Level: Main,First
Features: Flooring - Hardwood,Open Floorplan,Recessed Lighting

Family Room Information
Area: 273
Length: 13
Width: 21
Level: Basement
Features: Flooring - Wall to Wall Carpet,Recessed Lighting

Dining Room Information
Area: 121
Length: 11
Width: 11
Level: First
Features: Flooring - Hardwood,Open Floorplan,Recessed Lighting,Lighting - Pendant

Kitchen Information
Area: 121
Length: 11
Width: 11
Level: Main,First
Features: Flooring - Hardwood,Kitchen Island,Open Floorplan,Recessed Lighting,Lighting - Pendant

Office Room Information
Area: 48
Length: 6
Width: 8
Level: Second
Features: Flooring - Hardwood,Recessed Lighting

Basement Information
Basement: Partially Finished

Laundry Information
Laundry Features: Electric Dryer Hookup

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

Interior Features
# of Rooms (Total): 10
Flooring: Wood, Tile, Carpet, Flooring - Hardwood
Interior Features: Recessed Lighting, Home Office

Exterior

Building Information
Building Area (Total): 2,592
Foundation Details: Block
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: White

Exterior Features
Fencing: Invisible
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Sprinkler System, Invisible Fence

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.24
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $13,995
Tax Year: 2023

Utilities

Utility Information
Utilities: for Electric Range, for Electric Dryer
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Wildwood Street to Woodside Road
UnparsedAddress: 59 Woodside Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, Public School

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 2,546
Stories: 2.0
Lot Size: 10,454 square feet
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Middlesex County
APN: 1431148S

Home facts updated by county records on Sep 10, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Lynch Elementary School

Public PreK-5 • Assigned • 0.1mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.0mi

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

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, 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

$1.55M – $1.88M

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Nearby similar homes

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Home values near 59 Woodside Rd

Data from public records.

Address	Redfin Estimate
48 Woodside Road, Winchester, MA 3 Beds \| 2.5 Baths \| 1818 Sq. Ft.	$1,337,695
56 Woodside Road, Winchester, MA 3 Beds \| 1.5 Baths \| 1712 Sq. Ft.	$1,560,423

Address	Redfin Estimate
50 Woodside Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2376 Sq. Ft.	$1,405,378
60 Woodside Road, Winchester, MA 3 Beds \| 1.5 Baths \| 1235 Sq. Ft.	$1,217,219

Address	Redfin Estimate
54 Woodside Road, Winchester, MA 5 Beds \| 3 Baths \| 2630 Sq. Ft.	$1,762,334
70 Woodside Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2566 Sq. Ft.	$1,671,064

Property information provided by MLS PIN when last listed in 2023. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 01890, MA

Sale history for 59 Woodside Rd

Tax history for 59 Woodside Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01890

Home values near 59 Woodside Rd

More real estate resources