OFF MARKET

Off Market Mar 2021 for $1.1M

$1,540,912

Est. refi paymentEst. refi $3,356/mo

•

2,958

sq ft

444 S Border Rd, Winchester, MA 01890

About this home

A wonderful house inside and out! This home boasts a spacious, open floor plan with vaulted ceilings. There are three generous bedrooms, two baths and three fireplaces. The large kitchen has granite countertops, lots of storage and a Thermador Induction Cooktop with down draft system. The finished basement with 3/4 bath, offers lots of possibilities...playroom, family room, home office. There's so much space, you can have all three! The homeowners throughout their ownership have cultivated gorgeous gardens, installed a new patio, garden wall and outdoor stairs, as well as a sodded lawn on the upper level yard. Feel like you're on vacation in your own backyard! It's just a short walk to Winchester Center with great shops and restaurants, train station and beautiful town common. But the walk is even shorter to the Middlesex Fells Reservation, it's right across the street! Absolutely a must see home!

Single-familyProperty Type

1955Year Built

0.31 acresLot Size

$521Est. Price/Sq.Ft.

1 garage spacesParking

Listed by John and Maria Reilly • JMR Real Estate Group LLC

Bought with Qi Tian • FlyHomes Brokerage LLC

Redfin checked: 2 minutes ago

•Source:MLS PIN #72790199

Redfin Estimate

$1,540,912

$351K since sold in March 2021$9,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.9% higher than the average sale price ($1.38M) of 6 comparable homes.

SOLD AUG 14, 2026
$1,500,000
A
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD JAN 9, 2026
$1,392,500
B
3 beds2.5 baths2,865 sq ft
53 Bacon St, Winchester, MA 01890
SOLD JUL 30, 2026
$1,160,000
C
3 beds1.5 baths1,996 sq ft
70 Grove St, Winchester, MA 01890
SOLD JUN 1, 2026
$1,607,000
D
4 beds2.5 baths3,298 sq ft
6 Oakland Cir, Winchester, MA 01890
SOLD JUN 25, 2026
$1,275,000
E
3 beds2 baths1,511 sq ft
6 Alden Ln, Winchester, MA 01890
SOLD APR 22, 2026
$1,325,000
F
3 beds2.5 baths2,153 sq ft
6 Marchant Rd, Winchester, MA 01890

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Sell

$612,544

Est. take-home

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Est. cash available

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Rent

$4,893/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.1%

+0.0% MoM

Median sale price

$1.4M

$57K MoM

Avg. days on market

20d

0 days MoM

Recently sold homes

14 MoM

New listings for sale

EARLY ACCESS
$1,699,000
3 beds2 baths2,327 sq ft
4 Churchill Rd, Winchester, MA 01890
3D & VIDEO TOUR
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
3D WALKTHROUGH
$1,699,000
5 beds3.5 baths3,180 sq ft
30 Farrow St, Winchester, MA 01890
$1,098,000
3 beds1.5 baths1,657 sq ft
17 Russell Rd, Winchester, MA 01890
$1,999,000
4 beds2.5 baths3,757 sq ft
85 High St, Winchester, MA 01890
EARLY ACCESS
Unknown
3 beds3 baths5,127 sq ft
187 High St, Winchester, MA 01890
$949,999
4 beds2 baths2,326 sq ft
96 Loring Ave, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 444 S Border Rd

Date

Event

Price

MLS PIN #72790199

Mar 30, 2021

Sold

$1,190,000

$402/sq ft

Feb 25, 2021

Listed

$1,189,000

$402/sq ft

MLS PIN #71341582

Jun 20, 2012

Sold

$636,500

$215/sq ft

Mar 2, 2012

Contingent

—

Feb 22, 2012

Price Changed

$635,000

$215/sq ft

Feb 22, 2012

Listed

$625,000

$211/sq ft

+11

Beautiful open-concept three bedroom two bath ranch across from the Fells. Updated kitchen, skylights, cathedral ceilings, recessed lighting and gleaming hardwood floors. Great Room with fireplace and panoramic view of the Fells. Private, professionally landscaped yard with playset, fire pit and open play area. Finished basement with mudroom, family/playroom, laundry, office/media room and storage room. One car attached garage. Close to town, schools and commuter rail with easy access to I-93

MLS PIN #70516149

Aug 21, 2007

Sold

$574,000

$194/sq ft

Jun 29, 2007

Listing Removed

—

May 30, 2007

Price Changed

$588,000

$199/sq ft

Jan 25, 2007

Listed

$633,000

$214/sq ft

Exceptional ranch with loads of living space. This beautiful open concept home offers wonderful natural light through multiple skylights and soaring ceilings, an updated kitchen, gleaming hardwood floors, 3 fireplaces, a much desired first floor family room, recessed lighting, and more. With the 500 perennials in the wonderful tiered yard this home is a real retreat. A great sense of privacy and wonderful views and access to the fells. An absolute must see!

MLS PIN #30439275

Oct 27, 2000

Sold

$500,000

$169/sq ft

Sep 14, 2000

Listing Removed

—

Aug 23, 2000

Listed

$499,900

$169/sq ft

MLS PIN #50491423

Jun 1, 1998

Sold

$294,000

$99/sq ft

Mar 9, 1998

Listing Removed

—

Feb 11, 1998

Listed

$294,000

$99/sq ft

Public Records

Jun 2, 1989

Sold

$242,500

$82/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$14,012 (+4.9%)

$885,700 + $377,800

$1,263,500

2023

$13,353 (+1.1%)

$885,700 + $376,900

$1,262,600

2022

$13,203 (+6.0%)

$708,500 + $346,900

$1,055,400

2021

$12,455 (+3.6%)

$637,700 + $333,100

$970,800

2020

$12,028 (+10.4%)

$637,700 + $333,100

$970,800

2019

$10,898 (+6.8%)

$566,800 + $333,100

$899,900

2018

$10,204 (+8.6%)

$511,900 + $325,200

$837,100

2017

$9,399 (+12.4%)

$440,200 + $325,200

$765,400

2016

$8,361 (−3.8%)

$414,500 + $301,300

$715,800

2015

$8,690 (+9.3%)

$414,500 + $301,300

$715,800

2014

$7,952 (+0.8%)

$345,400 + $282,700

$628,100

2013

$7,885 (+2.7%)

$345,400 + $272,100

$617,500

2012

$7,674 (+3.7%)

$345,400 + $266,100

$611,500

2011

$7,399 (+3.4%)

$345,400 + $266,100

$611,500

2010

$7,156 (+2.1%)

$344,900 + $276,800

$621,700

2009

$7,007

$344,900 + $276,800

$621,700

Tax history for 444 S Border Rd

Year

Property tax

Land + Additions

Assessment*

2025

$14,012 (+4.9%)

$885,700 + $377,800

$1,263,500

2023

$13,353 (+1.1%)

$885,700 + $376,900

$1,262,600

2022

$13,203 (+6.0%)

$708,500 + $346,900

$1,055,400

2021

$12,455 (+3.6%)

$637,700 + $333,100

$970,800

2020

$12,028 (+10.4%)

$637,700 + $333,100

$970,800

2019

$10,898 (+6.8%)

$566,800 + $333,100

$899,900

2018

$10,204 (+8.6%)

$511,900 + $325,200

$837,100

2017

$9,399 (+12.4%)

$440,200 + $325,200

$765,400

2016

$8,361 (−3.8%)

$414,500 + $301,300

$715,800

2015

$8,690 (+9.3%)

$414,500 + $301,300

$715,800

2014

$7,952 (+0.8%)

$345,400 + $282,700

$628,100

2013

$7,885 (+2.7%)

$345,400 + $272,100

$617,500

2012

$7,674 (+3.7%)

$345,400 + $266,100

$611,500

2011

$7,399 (+3.4%)

$345,400 + $266,100

$611,500

2010

$7,156 (+2.1%)

$344,900 + $276,800

$621,700

2009

$7,007

$344,900 + $276,800

$621,700

*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

0.31 Acres

Year renovated

—

Sq. Ft.

2,958

Year built

1955

Style

Single Family Residential

County

Middlesex County

APN

1565104S

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: 1
# of Covered Spaces: 1
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive, Off Street, Driveway, Paved

Interior

Bedroom Information
Main Level Bedrooms: 1

Master Bedroom Information
Area: 144
Length: 12
Width: 12
Level: Main,First
Features: Ceiling Fan(s),Flooring - Hardwood,Cable Hookup,Lighting - Overhead,Closet - Double

Bedroom #2 Information
Area: 182
Length: 14
Width: 13
Level: First
Features: Skylight,Vaulted Ceiling(s),Flooring - Hardwood,Recessed Lighting,Closet - Double

Bedroom #3 Information
Area: 156
Length: 13
Width: 12
Level: First
Features: Flooring - Hardwood,Lighting - Overhead,Closet - Double

Bathroom Information
# of Bathrooms (Full): 2
Main Level Bathrooms: 1

Bathroom #1 Information
Area: 48
Length: 6
Width: 8
Level: Main,First
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Area: 54
Length: 9
Width: 6
Level: Basement
Features: Bathroom - 3/4,Closet - Linen,Flooring - Laminate,Enclosed Shower - Fiberglass,Recessed Lighting,Lighting - Sconce

Living Room Information
Area: 340
Length: 17
Width: 20
Level: Main,First
Features: Cathedral Ceiling(s),Ceiling Fan(s),Vaulted Ceiling(s),Flooring - Hardwood,Cable Hookup,Recessed Lighting

Family Room Information
Area: 266
Length: 19
Width: 14
Level: Basement
Features: Flooring - Laminate,Cable Hookup,Recessed Lighting

Dining Room Information
Area: 143
Length: 11
Width: 13
Level: Main,First
Features: Skylight,Vaulted Ceiling(s),Flooring - Hardwood,Recessed Lighting

Kitchen Information
Area: 160
Length: 10
Width: 16
Level: Main,First
Features: Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Remodeled,Stainless Steel Appliances,Peninsula,Lighting - Overhead

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

Laundry Information
Laundry Dimen: 9X15
Laundry Features: Flooring - Laminate, Electric Dryer Hookup, Washer Hookup, Lighting - Overhead, Sink, In Basement

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

Interior Features
# of Rooms (Total): 6
Door Features: Insulated Doors
Window Features: Skylight(s), Insulated Windows
Flooring: Tile, Laminate, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Vinyl
Interior Features: Closet, Recessed Lighting, Ceiling - Half-Vaulted, Lighting - Overhead, Entrance Foyer, Game Room, Bonus Room

Exterior

Building Information
Building Area (Total): 2,958
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Garden, Stone Wall

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.31
Lot Features: Sloped
ViewYN: Has View
View: Scenic View(s)
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $12,028
Tax Year: 2020

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: 100 Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Oil, Fireplace
Cooling: Central Air

Location

Location Information
Directions: Located on South Border Road between Alice Lane and Leslie Road.
UnparsedAddress: 444 S Border Rd, Winchester MA 01890

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

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,958
Stories: 1.0
Lot Size: 0.31 acres
Style: Single Family Residential
Year Built: 1955
Year Renovated: —
County: Middlesex County
APN: 1565104S

Home facts updated by county records on Jul 30, 2026

Other

Listing Information
Exclusions: Washer/Dryer; Personal Belongings.
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.7mi

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

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

2/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 hot days expected this year, 14 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

$1.46M – $1.77M

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Nearby similar homes

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New listings for sale in 01890

EARLY ACCESSCOMPASS COMING SOON

$1,699,000

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4 Churchill Rd, Winchester, MA 01890

3D & VIDEO TOUR

$2,849,000

5 beds4.5 baths5,058 sq ft

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3D WALKTHROUGH

$1,699,000

5 beds3.5 baths3,180 sq ft

30 Farrow St, Winchester, MA 01890

$1,098,000

3 beds1.5 baths1,657 sq ft

17 Russell Rd, Winchester, MA 01890

$1,999,000

4 beds2.5 baths3,757 sq ft

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EARLY ACCESSCOMPASS COMING SOON

Unknown

3 beds3 baths5,127 sq ft

187 High St, Winchester, MA 01890

$949,999

4 beds2 baths2,326 sq ft

96 Loring Ave, Winchester, MA 01890

Home values near 444 S Border Rd

Data from public records.

Address	Redfin Estimate
432 S Border Road, Winchester, MA 5 Beds \| 5.5 Baths \| 6095 Sq. Ft.	$3,025,122
464 S Border Road, Winchester, MA 5 Beds \| 3.5 Baths \| 3224 Sq. Ft.	$1,947,466

Address	Redfin Estimate
438 S Border Road, Winchester, MA 2 Beds \| 2 Baths \| - Sq. Ft.	$1,297,172
424 S Border Road, Winchester, MA 3 Beds \| 2 Baths \| 2133 Sq. Ft.	—

Address	Redfin Estimate
446 S Border Road, Winchester, MA 5 Beds \| 3 Baths \| 3472 Sq. Ft.	$1,783,941
454 S Border Road, Winchester, MA 4 Beds \| 3 Baths \| 2814 Sq. Ft.	$1,757,290

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

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