OFF MARKET

Off Market Mar 2020 for $1.3M

$1,993,917

Est. refi paymentEst. refi $2,398/mo

•

3,113

sq ft

4 Penn Rd, Winchester, MA 01890

About this home

Picture Perfect and beautifully renovated home in desirable Ambrose neighborhood! Recently expanded with direct entry mudroom & bath from rear yard & 2 car garage. Large sunny country kitchen w/high end appliances, Wolf range, hands free foot pedal faucet, prep sink, soapstone countertops, and oversized island with seating. adj. family room off kitchen with brilliant sunlight, high ceilings, and beautiful windows overlooking the yard. This beautiful home with an english cottage look encompasses the best of both worlds offering character and charm along with modern amenities and a contemporary flair~ Formal living room w/fplc & built in shelving, spacious dining room, & sunroom/office complete this floor. Second floor offers 4 spacious corner bedrooms with 2 full baths. Third floor features a large bonus room or 5th bedroom. Gorgeous fenced private rear yard with bluestone patio and perennial plantings~ Updated systems, roof, windows, a/c, electric etc..must see this very special home!

Single-familyProperty Type

1930Year Built

7,735 sq ftLot Size

$641Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Kim Covino • Leading Edge Real Estate

Bought with Kim Covino • Leading Edge Real Estate

Redfin checked: a minute ago

•Source:MLS PIN #72612091

Redfin Estimate

$1,993,917

$614K since sold in March 2020$13K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.7% lower than the average sale price ($2.34M) of 6 comparable homes.

SOLD JUN 26, 2026
$3,500,000
A
5 beds3.5 baths5,128 sq ft
50 Oxford 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 JUN 1, 2026
$1,440,150
C
6 beds3 baths2,658 sq ft
65 High St, Winchester, MA 01890
SOLD AUG 14, 2026
$2,200,000
D
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
SOLD OCT 31, 2025
$1,750,000
E
4 beds2.5 baths2,397 sq ft
15 Westland Ave, Winchester, MA 01890
SOLD JUN 23, 2026
$2,830,000
F
5 beds3.5 baths4,792 sq ft
56 Yale St, Winchester, MA 01890

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Sell

$932,098

Est. take-home

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Est. cash available

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Rent

$5,780/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

EARLY ACCESS
$1,325,000
4 beds2 baths1,922 sq ft
9 Priscilla Ln, Winchester, MA 01890
OPEN TODAY, 11AM TO 12PM
$619,000
3 beds3.5 baths1,225 sq ft
23 Shepard Ct #23, Winchester, MA 01890
OPEN TODAY, 11AM TO 12PM
$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
EARLY ACCESS
$675,000
2 beds2 baths1,124 sq ft
60 Lake St Unit E, Winchester, MA 01890
EARLY ACCESS
$1,699,000
3 beds2 baths2,327 sq ft
4 Churchill Rd, Winchester, MA 01890
OPEN TODAY, 2PM TO 3PM
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 4 Penn Rd

Date

Event

Price

MLS PIN #72612091

Mar 13, 2020

Sold

$1,380,000

$443/sq ft

Feb 12, 2020

Pending

—

Feb 10, 2020

Contingent

—

Jan 26, 2020

Listed

$1,499,000

$482/sq ft

MLS PIN #71069288

Aug 3, 2010

Listing Removed

—

Aug 2, 2010

Sold

$850,000

$273/sq ft

May 4, 2010

Contingent

—

Apr 22, 2010

Listed

$840,228

$270/sq ft

Enchanting English cottage style home nestled within one of Winchester's coziest neighborhoods offers all the space and amenties that you desire. This updated home exudes with charm from the outside on in.You''ll love the new kitchen! Designed by a chef, it's a cook's delight featuring high end appliances, slate countertops and center island, a cork floor and nice finishes throughout! The lovely private backyard is great for family summertime fun, outdoor dining and gardening. Your new home!

MLS PIN #50381442

Sep 15, 1997

Sold

$394,000

$127/sq ft

Jul 24, 1997

Listing Removed

—

Jul 19, 1997

Listed

$389,000

$125/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$17,168 (+12.2%)

$879,600 + $668,500

$1,548,100

2023

$15,306 (−0.8%)

$816,800 + $622,000

$1,438,800

2022

$15,437 (+9.7%)

$659,700 + $574,300

$1,234,000

2021

$14,078 (+7.3%)

$534,000 + $563,300

$1,097,300

2020

$13,126 (+5.4%)

$502,600 + $556,800

$1,059,400

2019

$12,449 (+2.6%)

$471,200 + $556,800

$1,028,000

2018

$12,134 (+7.9%)

$453,900 + $541,500

$995,400

2017

$11,241 (+6.9%)

$404,500 + $510,900

$915,400

2016

$10,513 (+6.3%)

$404,500 + $495,600

$900,100

2015

$9,893 (−2.3%)

$337,700 + $477,200

$814,900

2014

$10,123 (+4.9%)

$337,700 + $461,900

$799,600

2013

$9,654 (+1.7%)

$306,300 + $449,700

$756,000

2012

$9,488 (+3.7%)

$306,300 + $449,700

$756,000

2011

$9,148 (+3.3%)

$306,300 + $449,700

$756,000

2010

$8,858 (+2.1%)

$328,300 + $441,300

$769,600

2009

$8,673

$328,300 + $441,300

$769,600

Tax history for 4 Penn Rd

Year

Property tax

Land + Additions

Assessment*

2025

$17,168 (+12.2%)

$879,600 + $668,500

$1,548,100

2023

$15,306 (−0.8%)

$816,800 + $622,000

$1,438,800

2022

$15,437 (+9.7%)

$659,700 + $574,300

$1,234,000

2021

$14,078 (+7.3%)

$534,000 + $563,300

$1,097,300

2020

$13,126 (+5.4%)

$502,600 + $556,800

$1,059,400

2019

$12,449 (+2.6%)

$471,200 + $556,800

$1,028,000

2018

$12,134 (+7.9%)

$453,900 + $541,500

$995,400

2017

$11,241 (+6.9%)

$404,500 + $510,900

$915,400

2016

$10,513 (+6.3%)

$404,500 + $495,600

$900,100

2015

$9,893 (−2.3%)

$337,700 + $477,200

$814,900

2014

$10,123 (+4.9%)

$337,700 + $461,900

$799,600

2013

$9,654 (+1.7%)

$306,300 + $449,700

$756,000

2012

$9,488 (+3.7%)

$306,300 + $449,700

$756,000

2011

$9,148 (+3.3%)

$306,300 + $449,700

$756,000

2010

$8,858 (+2.1%)

$328,300 + $441,300

$769,600

2009

$8,673

$328,300 + $441,300

$769,600

*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

Stories

Lot width

—

Lot depth

—

Lot size

7,841 Sq. Ft.

Year renovated

—

Sq. Ft.

3,113

Year built

1930

Style

Single Family Residential

County

Middlesex County

APN

1554167S

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
Parking Features: Detached, Off Street, Paved

Interior

Master Bedroom Information
Area: 192
Length: 16
Width: 12
Level: Second
Features: Walk-In Closet(s),Flooring - Hardwood,Cable Hookup,Recessed Lighting

Bedroom #2 Information
Area: 228
Length: 12
Width: 19
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 182
Length: 13
Width: 14
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #4 Information
Area: 204
Length: 12
Width: 17
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #5 Information
Area: 324
Length: 12
Width: 27
Level: Third
Features: Closet,Closet/Cabinets - Custom Built,Flooring - Hardwood,Cable Hookup

Bathroom Information
# of Bathrooms (Full): 3
Main Level Bathrooms: 1

Bathroom #1 Information
Area: 56
Length: 7
Width: 8
Level: Main,First
Features: Bathroom - Full,Bathroom - Tiled With Tub,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Area: 54
Length: 6
Width: 9
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub,Flooring - Stone/Ceramic Tile

Bathroom #3 Information
Area: 54
Length: 6
Width: 9
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub,Flooring - Stone/Ceramic Tile

Living Room Information
Area: 247
Length: 19
Width: 13
Level: Main,First
Features: Flooring - Hardwood,Open Floorplan

Family Room Information
Area: 216
Length: 12
Width: 18
Level: Main,First
Features: Bathroom - Full,Flooring - Hardwood,Cable Hookup,Recessed Lighting

Dining Room Information
Area: 192
Length: 16
Width: 12
Level: Main,First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood

Kitchen Information
Area: 300
Length: 15
Width: 20
Level: Main,First
Features: Closet/Cabinets - Custom Built,Flooring - Wood,Pantry,Countertops - Stone/Granite/Solid,Kitchen Island,Exterior Access,Recessed Lighting,Pot Filler Faucet,Washer Hookup

Office Room Information
Area: 144
Length: 16
Width: 9
Level: Main
Features: Flooring - Hardwood

Basement Information
Basement: Full, Concrete, Unfinished

Laundry Information
Laundry Dimen: 7X8
Laundry Features: Electric Dryer Hookup, Washer Hookup, First Floor

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

Interior Features
# of Rooms (Total): 9
Flooring: Tile, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Interior Features: Closet, Office, Mud Room

Exterior

Building Information
Building Area (Total): 3,113
Foundation Details: Concrete Perimeter, Stone
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Renovated Since
Color: Blue

Exterior Features
Fencing: Fenced
Roof: Shingle
Exterior Features: Rain Gutters, Professional Landscaping, Sprinkler System, Fenced Yard, Stone Wall

Property Information
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat

Lot Information
Lot Size (Acres): 0.18
Lot Features: Gentle Sloping
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $12,449
Tax Year: 2019

Utilities

Utility Information
Utilities: for Gas Range, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard
Cooling: Central Air

Location

Location Information
Directions: Cambridge Street to Oneida to Penn Road
UnparsedAddress: 4 Penn Road, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Highway Access, House of Worship, Marina, Private School, Public School

Public facts

Beds: 5
Baths: 3.0
Sq. Ft.: 3,113
Stories: 2.0
Lot Size: 7,841 square feet
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Middlesex County
APN: 1554167S

Home facts updated by county records on Jul 30, 2026

Other

Miscellaneous Information
Heat Zones: 5

Listing Information
Exclusions: Drawer Storage In Basement Across From Work Bench Area
StandardStatus: Closed

Around this home

Schools

Ambrose Elementary School

Public K-5 • Assigned • 0.1mi

10/10

McCall Middle School

Public 6-8 • Assigned • 1.1mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.3mi

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

1/10 Fire Factor

Unlikely to be 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

$1.90M – $2.29M

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Home values near 4 Penn Rd

Data from public records.

Address	Redfin Estimate
2 Penn Rd, Winchester, MA 4 Beds \| 2 Baths \| 2016 Sq. Ft.	$1,547,052
9 Penn Rd, Winchester, MA 5 Beds \| 4.5 Baths \| 5353 Sq. Ft.	$2,720,015

Address	Redfin Estimate
6 Penn Rd, Winchester, MA 5 Beds \| 2.5 Baths \| 2555 Sq. Ft.	$1,629,855
7 Penn Rd, Winchester, MA 4 Beds \| 1.5 Baths \| 3069 Sq. Ft.	$1,692,239

Address	Redfin Estimate
8 Penn Rd, Winchester, MA 3 Beds \| 2 Baths \| 1593 Sq. Ft.	$1,338,767
5 Penn Rd, Winchester, MA 5 Beds \| 2.5 Baths \| 2429 Sq. Ft.	$1,805,386

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

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