OFF MARKET

Off Market Oct 2021 for $851K

$1,302,083

•

2,113

sq ft

5 Upland Rd, Winchester, MA 01890

About this home

Rare opportunity to make this property your dream home & become part of the Winchester community. Situated on a side street – this home offers a multitude of opportunities. Live in as-is or create your own vision for this lovely 3 bed, 2.5 bath 1930s old style colonial. Hardwood floors throughout with ample living space and natural light fill the home. The first floor offers an updated kitchen, first floor bedroom with half bath, dining, substantial living room and enclosed front porch. Two oversized bedrooms with generously size closets and a full bath are upstairs. The versatile lower level offers a living space perfect for a den or home office, full bath, laundry and storage. There’s a spacious backyard and detached 1 car garage and plus a bonus storage shed. Convenient location walkable to Lynch Elementary school, Horn Pond Reservation, Tri-Community Bike Path. Easy access to commuter rail and minutes to downtown shops and restaurants.

Single-familyProperty Type

1930Year Built

5,001 sq ftLot Size

$616Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Pirani & Wile Group • Leading Edge Real Estate

Bought with Nancy Pallotta • Leading Edge Real Estate

Redfin checked: a minute ago

•Source:MLS PIN #72890386

Redfin Estimate

$1,302,083

$451K since sold in October 2021$40K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.3% higher than the average sale price ($1.12M) of 6 comparable homes.

SOLD SEP 17, 2026
$675,000
A
3 beds2 baths1,219 sq ft
64 Garfield Ave, Woburn, MA 01801
SOLD JUL 16, 2026
$1,280,000
B
3 beds2 baths2,192 sq ft
2 Eaton Ct, Winchester, MA 01890
SOLD SEP 1, 2026
$784,500
C
3 beds2 baths2,212 sq ft
24 Carter St, Woburn, MA 01801
SOLD SEP 18, 2026
$1,035,000
D
4 beds1.5 baths1,777 sq ft
46 Clark St, Winchester, MA 01890
SOLD AUG 14, 2026
$1,325,000
E
3 beds1.5 baths2,006 sq ft
3 Chesterford Ter, Winchester, MA 01890
SOLD JUL 6, 2026
$1,620,000
F
4 beds2.5 baths2,233 sq ft
10 Bonad Rd, Winchester, MA 01890

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Earn from this home

Sell

$620,552

Est. take-home

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Rent

$5,309/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

EARLY ACCESS
$1,529,000
4 beds4 baths2,709 sq ft
25 Arlington St, Winchester, MA 01890
$1,195,000
3 beds1.5 baths2,239 sq ft
4 Stone Ave, Winchester, MA 01890
VIDEO TOUR
$1,000,000
3 beds1 bath1,908 sq ft
23 Stone Ave, Winchester, MA 01890
VIDEO TOUR
$1,850,000
4 beds2.5 baths3,092 sq ft
1 Overlook Way, Winchester, MA 01890
$700,000
2 beds2 baths1,240 sq ft
666 Main St #217, Winchester, MA 01890
$349,900
1 bed1 bath602 sq ft
200 Swanton St Unit T14, Winchester, MA 01890
$1,325,000
4 beds2 baths1,922 sq ft
9 Priscilla Ln, Winchester, MA 01890
$399,000
1 bed1 bath613 sq ft
200 Swanton St #727, Winchester, MA 01890
$1,080,000
3 beds1 bath1,382 sq ft
6 Reservoir St, Winchester, MA 01890
$2,600,000
6 beds3 baths3,534 sq ft
7 Lakeview Ter, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 5 Upland Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,456 (+4.1%)

$590,000 + $624,400

$1,214,400

2025

$12,928 (+35.8%)

$560,500 + $605,200

$1,165,700

2023

$9,517 (+4.0%)

$531,000 + $330,200

$861,200

2022

$9,152 (+5.8%)

$442,500 + $289,100

$731,600

2021

$8,654 (+3.6%)

$376,100 + $298,400

$674,500

2020

$8,357 (+14.9%)

$376,100 + $298,400

$674,500

2019

$7,276 (+1.9%)

$302,400 + $298,400

$600,800

2018

$7,143 (+6.7%)

$287,600 + $298,400

$586,000

2017

$6,696 (+8.9%)

$272,900 + $272,400

$545,300

2016

$6,147 (+1.5%)

$272,900 + $253,400

$526,300

2015

$6,054 (+6.2%)

$247,100 + $251,600

$498,700

2014

$5,701 (+5.8%)

$213,900 + $236,400

$450,300

2013

$5,390 (+5.2%)

$199,100 + $223,000

$422,100

2012

$5,122 (+3.7%)

$185,100 + $223,000

$408,100

2011

$4,938 (+5.0%)

$185,100 + $223,000

$408,100

2010

$4,701 (+2.1%)

$186,300 + $222,100

$408,400

2009

$4,603

$186,300 + $222,100

$408,400

Tax history for 5 Upland Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,456 (+4.1%)

$590,000 + $624,400

$1,214,400

2025

$12,928 (+35.8%)

$560,500 + $605,200

$1,165,700

2023

$9,517 (+4.0%)

$531,000 + $330,200

$861,200

2022

$9,152 (+5.8%)

$442,500 + $289,100

$731,600

2021

$8,654 (+3.6%)

$376,100 + $298,400

$674,500

2020

$8,357 (+14.9%)

$376,100 + $298,400

$674,500

2019

$7,276 (+1.9%)

$302,400 + $298,400

$600,800

2018

$7,143 (+6.7%)

$287,600 + $298,400

$586,000

2017

$6,696 (+8.9%)

$272,900 + $272,400

$545,300

2016

$6,147 (+1.5%)

$272,900 + $253,400

$526,300

2015

$6,054 (+6.2%)

$247,100 + $251,600

$498,700

2014

$5,701 (+5.8%)

$213,900 + $236,400

$450,300

2013

$5,390 (+5.2%)

$199,100 + $223,000

$422,100

2012

$5,122 (+3.7%)

$185,100 + $223,000

$408,100

2011

$4,938 (+5.0%)

$185,100 + $223,000

$408,100

2010

$4,701 (+2.1%)

$186,300 + $222,100

$408,400

2009

$4,603

$186,300 + $222,100

$408,400

*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

4,792 Sq. Ft.

Year renovated

—

Sq. Ft.

3,600

Year built

1930

Style

Single Family Residential

County

Middlesex County

APN

1530292S

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: 1
# of Covered Spaces: 1
Parking Spaces: 3
Parking Features: Detached, Paved Drive, Off Street, Tandem

Interior

Master Bedroom Information
Area: 143
Length: 13
Width: 11
Level: First
Features: Ceiling Fan(s),Flooring - Hardwood

Bedroom #2 Information
Area: 144
Length: 12
Width: 12
Level: Second
Features: Ceiling Fan(s),Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 198
Length: 11
Width: 18
Level: Second
Features: Ceiling Fan(s),Closet,Flooring - Hardwood

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

Bathroom #1 Information
Level: First
Features: Bathroom - Half

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

Bathroom #3 Information
Area: 45
Length: 5
Width: 9
Level: Basement
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall

Living Room Information
Area: 228
Length: 12
Width: 19
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 224
Length: 16
Width: 14
Level: Basement
Features: Flooring - Wall to Wall Carpet,Recessed Lighting

Dining Room Information
Area: 143
Length: 13
Width: 11
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 150
Length: 15
Width: 10
Level: Main,First
Features: Ceiling Fan(s),Flooring - Hardwood,Countertops - Stone/Granite/Solid,Cable Hookup,Recessed Lighting

Basement Information
Basement: Finished

Laundry Information
Laundry Dimen: 9X10
Laundry Features: Flooring - Wall to Wall Carpet, In Basement

Interior Features
# of Rooms (Total): 11
Window Features: Window(s) - Picture
Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood
Interior Features: Ceiling Fan(s), Sun Room

Exterior

Building Information
Building Area (Total): 2,113
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Blue

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Storage, Fenced Yard

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.11
Lot Features: Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $8,654
Tax Year: 2021

Utilities

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

Heating & Cooling
Has Heating
Heating: Baseboard, Natural Gas

Location

Location Information
Directions: Main St to Hemingway St to Upland Rd
UnparsedAddress: 5 Upland Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Bike Path, Public School

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 3,600
Stories: 2.0
Lot Size: 4,792 square feet
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Middlesex County
APN: 1530292S

Home facts updated by county records on Sep 16, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Lynch Elementary School

Public PreK-5 • Assigned • 0.2mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.0mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.8mi

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 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

53% chance of strong winds in next 30 years

3/10 Air Factor

2 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

$1.24M – $1.50M

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Home values near 5 Upland Rd

Data from public records.

Address	Redfin Estimate
12 Upland Road, Winchester, MA 2 Beds \| 1 Baths \| 1455 Sq. Ft.	$813,350
2 Upland Road, Winchester, MA 3 Beds \| 1.5 Baths \| 1902 Sq. Ft.	$1,352,756

Address	Redfin Estimate
6 Upland Road, Winchester, MA 3 Beds \| 2 Baths \| 1800 Sq. Ft.	$1,080,406
7 Upland Road, Winchester, MA 3 Beds \| 2 Baths \| 1810 Sq. Ft.	$1,180,059

Address	Redfin Estimate
4 Upland Road, Winchester, MA 3 Beds \| 2.5 Baths \| 2052 Sq. Ft.	$1,380,691
9 Upland Road, Winchester, MA 3 Beds \| 2.5 Baths \| 1468 Sq. Ft.	$1,210,122

Property information provided by MLS PIN when last listed in 2021. 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 5 Upland Rd

Tax history for 5 Upland 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 5 Upland Rd

More real estate resources