OFF MARKET

Off Market Jul 2021 for $1.6M

$2,226,677

Est. refi paymentEst. refi $3,634/mo

•

3,861

sq ft

44 Glen Rd, Winchester, MA 01890

About this home

Welcome to 44 Glen Road - where old meets new with stunning results! Updated eleven room Antique Colonial fashioned for today's comfortable living. Beautifully renovated chef's kitchen with large, granite center island. A bonus breakfast area with fireplace and large dining room make the 'heart of the home' ideal for family gatherings and holiday get-togethers. Enjoy outdoor living with direct access from the kitchen to a magnificent mahogany deck overlooking a beautifully landscaped yard and stone patio! Large living room with fireplace. Open floor plan with family room adjacent to the kitchen and a sweet sitting area complete the first floor. Master suite with a deck plus 4 additional bedrooms and a common play area on the 2nd floor. Located in one of Winchester's finest neighborhoods, close to the town center, schools and all the amenities Winchester has to offer. Imagine being part of the history of this special property! Perfectly suited for working/learning from home.

Single-familyProperty Type

1867Year Built

0.34 acresLot Size

$577Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Nancy Fleming • Barrett Sotheby's International Realty

Bought with Erin Bertrand • Lakewalk Properties, Inc.

Redfin checked: 3 minutes ago

•Source:MLS PIN #72832591

Redfin Estimate

$2,226,677

$627K since sold in July 2021$49K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.4% higher than the average sale price ($2.17M) of 6 comparable homes.

SOLD JUN 9, 2026
$2,100,000
A
6 beds2.5 baths4,104 sq ft
15 Wildwood St, Winchester, MA 01890
SOLD AUG 14, 2026
$2,200,000
B
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
SOLD AUG 28, 2026
$2,300,000
C
5 beds3.5 baths5,230 sq ft
78 Bacon St, Winchester, MA 01890
SOLD JUL 21, 2026
$2,300,000
D
5 beds3.5 baths4,744 sq ft
30 Rangeley Rd, Winchester, MA 01890
SOLD MAY 15, 2026
$2,300,000
E
4 beds2.5 baths3,283 sq ft
12 Yale St, Winchester, MA 01890
SOLD MAR 26, 2026
$1,850,000
F
5 beds3.5 baths3,294 sq ft
20 Grove Pl, Winchester, MA 01890

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Earn from this home

Sell

$962,323

Est. take-home

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Refinance

Est. cash available

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Rent

$5,464/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 SUN, 11AM TO 12PM
$619,000
3 beds3.5 baths1,225 sq ft
23 Shepard Ct #23, Winchester, MA 01890
OPEN SUN, 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 SUN, 12:30PM TO 1:30PM
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 44 Glen Rd

Date

Event

Price

MLS PIN #72832591

Jul 27, 2021

Sold

$1,600,000

$414/sq ft

Jun 18, 2021

Contingent

—

Jun 7, 2021

Price Changed

$1,675,000

$434/sq ft

May 27, 2021

Relisted

—

May 26, 2021

Contingent

—

May 17, 2021

Listed

$1,750,000

$453/sq ft

MLS PIN #71863713

Nov 20, 2015

Sold

$1,295,000

$335/sq ft

Sep 27, 2015

Pending

—

Sep 11, 2015

Price Changed

$1,325,000

$343/sq ft

Jul 28, 2015

Price Changed

$1,349,000

$349/sq ft

Jun 25, 2015

Listed

$1,399,900

$363/sq ft

+19

44 Glen Road - where old meets new with stunning results! Updated eleven plus room Antique Colonial fashioned for today's comfortable living. Beautifully renovated chef's kitchen with large, granite center island. A bonus breakfast room with fireplace and large dining room make the 'heart of the home' ideal for family gatherings and holiday get-togethers. Enjoy outdoor living with direct access from the kitchen to a magnificent mahogany deck overlooking a beautifully landscaped yard. Oversized first floor family room with fireplace - so hard to find in an older home! Private formal living room and sitting area complete the first floor. Combination master suite and home office (or bedroom) plus three additional bedrooms with common play area on the 2nd floor. Located in one of Winchester's finest neighborhoods, close to the town center, schools and all the amenities Winchester has to offer. Imagine being part of the history of this special property!

MLS PIN #30313467

Jul 29, 1999

Sold

$496,750

$129/sq ft

Jun 25, 1999

Listing Removed

—

Apr 23, 1999

Listed

$532,500

$138/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$19,875 (−4.4%)

$1,240,200 + $552,000

$1,792,200

2023

$20,794 (+2.4%)

$1,203,800 + $617,400

$1,821,200

2022

$20,301 (+2.4%)

$1,021,400 + $601,400

$1,622,800

2021

$19,819 (+3.0%)

$893,700 + $651,000

$1,544,700

2020

$19,242 (+10.1%)

$902,000 + $651,000

$1,553,000

2019

$17,470 (+1.8%)

$791,600 + $651,000

$1,442,600

2018

$17,154 (+4.6%)

$773,200 + $634,000

$1,407,200

2017

$16,400 (+6.9%)

$735,400 + $600,100

$1,335,500

2016

$15,344 (+3.1%)

$735,400 + $578,300

$1,313,700

2015

$14,886 (+2.4%)

$668,200 + $558,000

$1,226,200

2014

$14,539 (+0.3%)

$607,500 + $540,900

$1,148,400

2013

$14,493 (+4.0%)

$607,500 + $527,400

$1,134,900

2012

$13,932 (+3.7%)

$584,500 + $525,600

$1,110,100

2011

$13,432 (+9.3%)

$584,500 + $525,600

$1,110,100

2010

$12,290 (+2.1%)

$595,300 + $472,500

$1,067,800

2009

$12,034

$595,300 + $472,500

$1,067,800

Tax history for 44 Glen Rd

Year

Property tax

Land + Additions

Assessment*

2025

$19,875 (−4.4%)

$1,240,200 + $552,000

$1,792,200

2023

$20,794 (+2.4%)

$1,203,800 + $617,400

$1,821,200

2022

$20,301 (+2.4%)

$1,021,400 + $601,400

$1,622,800

2021

$19,819 (+3.0%)

$893,700 + $651,000

$1,544,700

2020

$19,242 (+10.1%)

$902,000 + $651,000

$1,553,000

2019

$17,470 (+1.8%)

$791,600 + $651,000

$1,442,600

2018

$17,154 (+4.6%)

$773,200 + $634,000

$1,407,200

2017

$16,400 (+6.9%)

$735,400 + $600,100

$1,335,500

2016

$15,344 (+3.1%)

$735,400 + $578,300

$1,313,700

2015

$14,886 (+2.4%)

$668,200 + $558,000

$1,226,200

2014

$14,539 (+0.3%)

$607,500 + $540,900

$1,148,400

2013

$14,493 (+4.0%)

$607,500 + $527,400

$1,134,900

2012

$13,932 (+3.7%)

$584,500 + $525,600

$1,110,100

2011

$13,432 (+9.3%)

$584,500 + $525,600

$1,110,100

2010

$12,290 (+2.1%)

$595,300 + $472,500

$1,067,800

2009

$12,034

$595,300 + $472,500

$1,067,800

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.34 Acres

Year renovated

—

Sq. Ft.

3,861

Year built

1867

Style

Single Family Residential

County

Middlesex County

APN

3083137S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 29, 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, Storage, Garage Faces Side, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 315
Length: 21
Width: 15
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Walk-In Closet(s),Closet,Flooring - Hardwood,French Doors,Deck - Exterior

Bedroom #2 Information
Area: 216
Length: 12
Width: 18
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 130
Length: 13
Width: 10
Level: Second
Features: Closet,Flooring - Hardwood

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

Bedroom #5 Information
Area: 228
Length: 19
Width: 12
Level: Second
Features: Closet,Flooring - Hardwood

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

Bathroom #1 Information
Area: 56
Length: 7
Width: 8
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Area: 70
Length: 10
Width: 7
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Shower Stall

Bathroom #3 Information
Area: 72
Length: 9
Width: 8
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub

Living Room Information
Area: 378
Length: 21
Width: 18
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 192
Length: 16
Width: 12
Level: First
Features: Flooring - Hardwood,French Doors

Dining Room Information
Area: 171
Length: 19
Width: 9
Level: First
Features: Bathroom - Half,Flooring - Hardwood,French Doors

Kitchen Information
Area: 234
Length: 18
Width: 13
Level: First
Features: Flooring - Hardwood,Pantry,Countertops - Stone/Granite/Solid,French Doors,Kitchen Island,Deck - Exterior,Exterior Access,Stainless Steel Appliances,Gas Stove,Lighting - Pendant

Basement Information
Basement: Full, Walk-Out Access, Interior Entry, Unfinished

Laundry Information
Laundry Dimen: 5X7
Laundry Features: Gas Dryer Hookup, Washer Hookup, First Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3
Fireplace Features: Living Room, Master Bedroom

Interior Features
# of Rooms (Total): 11
Door Features: French Doors
Flooring: Tile, Hardwood, Flooring - Hardwood
Interior Features: Dining Area, Pantry, Sitting Room

Exterior

Building Information
Building Area (Total): 3,861
Foundation Details: Stone
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Renovated Since
Color: Gray

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Porch, Deck, Deck - Wood, Patio, Covered
Exterior Features: Porch, Deck, Deck - Wood, Patio, Covered Patio/Deck, Rain Gutters, Sprinkler System, Decorative Lighting, Fenced Yard

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

Lot Information
Lot Size (Acres): 0.34
Lot Features: Level
Road Surface Type: Paved
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $19,919
Tax Year: 2021

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers, 200+ Amp Service

Heating & Cooling
Has Heating
Heating: Hot Water, Oil, Natural Gas, Fireplace

Location

Location Information
Directions: Church Street and/or Cambridge Street to Glen Road
UnparsedAddress: 44 Glen Road, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Medical Facility, House of Worship, Public School, Sidewalks

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 3,861
Stories: 2.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1867
Year Renovated: —
County: Middlesex County
APN: 3083137S

Home facts updated by county records on Jul 29, 2026

Other

Miscellaneous Information
Heat Zones: 6

Listing Information
StandardStatus: Closed

Around this home

Schools

Ambrose Elementary School

Public K-5 • Assigned • 0.3mi

10/10

McCall Middle School

Public 6-8 • Assigned • 0.9mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.2mi

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

Minor risk of being in a wildfire over 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

$2.12M – $2.56M

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Home values near 44 Glen Rd

Data from public records.

Address	Redfin Estimate
34 Glen Road, Winchester, MA 8 Beds \| 2.5 Baths \| 3036 Sq. Ft.	$2,122,442
40 Glen Road, Winchester, MA 5 Beds \| 3 Baths \| 2743 Sq. Ft.	$2,166,661

Address	Redfin Estimate
36 Glen Road, Winchester, MA 5 Beds \| 1.5 Baths \| 1999 Sq. Ft.	$1,372,513
46 Glen Road, Winchester, MA 6 Beds \| 2 Baths \| 2754 Sq. Ft.	$1,713,991

Address	Redfin Estimate
38 Glen Road, Winchester, MA 5 Beds \| 2.5 Baths \| 3938 Sq. Ft.	$2,391,181
50 Glen Road, Winchester, MA 5 Beds \| 2.5 Baths \| 2476 Sq. Ft.	$1,804,851

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 44 Glen Rd

Tax history for 44 Glen 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 44 Glen Rd

More real estate resources