OFF MARKET

Off Market Dec 2015 for $1.3M

$2,341,310

Est. refi paymentEst. refi $5,519/mo

•

3,010

sq ft

23 Jefferson Rd, Winchester, MA 01890

About this home

One of Winchester's most beautiful and well-positioned locations! This exquisite home is within walking distance to the Middlesex Fells Reservation, Winchester Center, schools, restaurants and commuter rail yet nestled away in a private and tranquil retreat. Charm and quality are evident throughout this beautifully renovated slate roofed Tudor style which offers three floors of living space, 5 bedrooms 4.5 baths, and 2 car garage with loft, paver driveway. Large, updated cherry and granite kitchen with stainless steel appliances, adjacent mudroom and laundry. Spacious living room and dining room with atrium doors leading to blue stone patio and exceptional 16,000 sq ft private yard & extensive garden offering a diverse array of ferns, wildflowers, shrubs and trees. Large master suite with steam shower, third floor is perfect for guest or aupair. Updated systems with C/A, gas heat, and replacement windows. Just minutes from Boston on Rt 93, located in the Lincoln School district.

Single-familyProperty Type

1929Year Built

0.37 acresLot Size

$778Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Theuer, Pirani & Wile • RE/MAX Leading Edge

Bought with Karen Garrett • Better Homes and Gardens Real Estate - The Shanahan Group

Redfin checked: 3 minutes ago

•Source:MLS PIN #71916377

Redfin Estimate

$2,341,310

$996K since sold in December 2015$10K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.5% higher than the average sale price ($2.01M) of 6 comparable homes.

SOLD JAN 9, 2026
$1,930,000
A
4 beds2.5 baths3,658 sq ft
8 Felsdale Close, Winchester, MA 01890
BOUGHT WITH REDFIN JUL 13, 2026
$2,150,000
B
5 beds3 baths3,136 sq ft
22 Hollywood Rd, Winchester, MA 01890
SOLD JUL 30, 2026
$2,255,000
C
4 beds3.5 baths3,494 sq ft
2 York Rd, Winchester, MA 01890
SOLD MAY 1, 2026
$1,755,000
D
4 beds4.5 baths3,906 sq ft
35 Hollywood Rd, Winchester, MA 01890
SOLD APR 28, 2026
$2,120,000
E
5 beds3.5 baths2,860 sq ft
4 Leslie Rd, 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

$1,399,275

Est. take-home

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Refinance

Est. cash available

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Rent

$5,882/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

NEW 1 HR AGO
$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 SAT, 2PM TO 3PM
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
$1,098,000
3 beds1.5 baths1,657 sq ft
17 Russell Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 23 Jefferson Rd

Date

Event

Price

MLSPIN #73481047

Apr 27, 2026

Rental Removed

$9,500

$3/sq ft

Mar 1, 2026

Listed for Rent

$9,500

$3/sq ft

MLSPIN #73359523

Jul 15, 2025

Rental Removed

$9,500

$3/sq ft

Apr 14, 2025

Listed for Rent

$9,500

$3/sq ft

MLS PIN #71916377

Dec 16, 2015

Sold

$1,345,000

$447/sq ft

Oct 16, 2015

Pending

—

Oct 8, 2015

Listed

$1,399,000

$465/sq ft

MLS PIN #70111736

Jan 7, 2005

Sold

$1,180,000

$392/sq ft

Nov 12, 2004

Listing Removed

—

Nov 1, 2004

Listed

$1,250,000

$415/sq ft

Nestled on a 16K lot with mature plantings and private backyard, this stately Tudor combines old world charm and fabulous updated conveniences for today's lifestyle! Large gathering kitchen w/huge center island,plus room for a reading area or large dinner table with chairs. New MBR w/bath. Take note of the cast iron FP in MBR. New windows, systems, 2-zone central A/C. 3rd Flr sports a large great rm plus add'l BR + BA. Could be au pair suite. Allow 48 hrs. on offer.

MLS PIN #50395573

Jul 23, 1998

Sold

$633,000

$210/sq ft

Jun 3, 1998

Listing Removed

—

Apr 13, 1998

Listed

$649,000

$216/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$21,589 (+5.2%)

$1,043,900 + $902,800

$1,946,700

2024

$20,520 (+1.1%)

$969,300 + $841,800

$1,811,100

2023

$20,303 (+8.1%)

$969,300 + $841,800

$1,811,100

2022

$18,779 (+1.9%)

$782,900 + $718,200

$1,501,100

2021

$18,423 (+3.6%)

$717,700 + $718,200

$1,435,900

2020

$17,791 (+9.4%)

$717,700 + $718,200

$1,435,900

2019

$16,260 (+3.0%)

$624,500 + $718,200

$1,342,700

2018

$15,791 (+2.0%)

$594,600 + $700,800

$1,295,400

2017

$15,479 (+7.3%)

$594,600 + $665,900

$1,260,500

2016

$14,429 (+3.3%)

$594,600 + $640,800

$1,235,400

2015

$13,966 (+5.6%)

$540,600 + $609,800

$1,150,400

2014

$13,222 (+0.4%)

$452,000 + $592,400

$1,044,400

2013

$13,163 (+1.7%)

$452,000 + $578,800

$1,030,800

2012

$12,937 (+3.7%)

$452,000 + $578,800

$1,030,800

2011

$12,473 (+5.4%)

$452,000 + $578,800

$1,030,800

2010

$11,837 (+2.1%)

$460,400 + $568,000

$1,028,400

2009

$11,590

$460,400 + $568,000

$1,028,400

Tax history for 23 Jefferson Rd

Year

Property tax

Land + Additions

Assessment*

2025

$21,589 (+5.2%)

$1,043,900 + $902,800

$1,946,700

2024

$20,520 (+1.1%)

$969,300 + $841,800

$1,811,100

2023

$20,303 (+8.1%)

$969,300 + $841,800

$1,811,100

2022

$18,779 (+1.9%)

$782,900 + $718,200

$1,501,100

2021

$18,423 (+3.6%)

$717,700 + $718,200

$1,435,900

2020

$17,791 (+9.4%)

$717,700 + $718,200

$1,435,900

2019

$16,260 (+3.0%)

$624,500 + $718,200

$1,342,700

2018

$15,791 (+2.0%)

$594,600 + $700,800

$1,295,400

2017

$15,479 (+7.3%)

$594,600 + $665,900

$1,260,500

2016

$14,429 (+3.3%)

$594,600 + $640,800

$1,235,400

2015

$13,966 (+5.6%)

$540,600 + $609,800

$1,150,400

2014

$13,222 (+0.4%)

$452,000 + $592,400

$1,044,400

2013

$13,163 (+1.7%)

$452,000 + $578,800

$1,030,800

2012

$12,937 (+3.7%)

$452,000 + $578,800

$1,030,800

2011

$12,473 (+5.4%)

$452,000 + $578,800

$1,030,800

2010

$11,837 (+2.1%)

$460,400 + $568,000

$1,028,400

2009

$11,590

$460,400 + $568,000

$1,028,400

*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

4.5

Stories

Lot width

—

Lot depth

—

Lot size

16,117

Year renovated

—

Sq. Ft.

3,010

Year built

1929

Style

Single Family Residential

County

Middlesex County

APN

3134277S

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Jan 5, 2021.

Property details

Parking

Parking Information
Has Garage
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 6
Parking Features: Detached

Interior

Master Bedroom Information
Area: 374
Length: 17
Width: 22
Level: Second
Features: Bathroom - 3/4,Flooring - Hardwood

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

Bedroom #3 Information
Area: 153
Length: 9
Width: 17
Level: Second
Features: Flooring - Hardwood

Bedroom #4 Information
Area: 117
Length: 9
Width: 13
Level: Second
Features: Flooring - Hardwood

Bedroom #5 Information
Area: 210
Length: 14
Width: 15
Level: Third
Features: Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Living Room Information
Area: 247
Length: 13
Width: 19
Level: First
Features: Beamed Ceilings,Flooring - Hardwood

Family Room Information
Area: 224
Length: 14
Width: 16
Level: Third
Features: Flooring - Wall to Wall Carpet

Dining Room Information
Area: 154
Length: 14
Width: 11
Level: First
Features: Flooring - Hardwood,French Doors

Kitchen Information
Area: 391
Length: 17
Width: 23
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Countertops - Stone/Granite/Solid

Basement Information
Basement: Sump Pump

Laundry Information
Laundry Dimen: 6X12
Laundry Features: Flooring - Stone/Ceramic Tile, Exterior Access, First Floor

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

Interior Features
# of Rooms (Total): 11
Window Features: Insulated Windows
Flooring: Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Interior Features: Library, Sun Room

Exterior

Building Information
Building Area (Total): 3,010
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Actual
Color: Beige

Exterior Features
Roof: Slate
Exterior Features: Storage, Professional Landscaping, Sprinkler System

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.37
Lot Features: Wooded

Financial

Tax Information
Tax Annual Amount: $13,966
Tax Year: 2015

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers

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

Location

Location Information
Directions: Highland Avenue to Jefferson Road
UnparsedAddress: 23 Jefferson Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Park, Medical Facility, Conservation Area, Highway Access, Public School

Public facts

Beds: 6
Baths: 4.5
Sq. Ft.: 3,010
Stories: 3.0
Parking Spaces: 8
Basement: Yes
Accessible: No
Lot Size: 0.37 acres
Style: Single Family Residential
Year Built: 1929
Year Renovated: —
County: Middlesex County
APN: 3134277S
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Jan 5, 2021

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.6mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.6mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.0mi

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

3/10 Fire Factor

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

5/10 Heat Factor

7 days above 96° expected this year, 14 days in 30 years

6/10 Wind Factor

50% chance of strong winds in next 30 years

3/10 Air Factor

3 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

$2.23M – $2.69M

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New listings for sale in 01890

NEW 1 HR AGO

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257 Cross St, Winchester, MA 01890

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

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EARLY ACCESSCOMPASS COMING SOON

$1,699,000

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OPEN SAT, 2PM TO 3PM3D & VIDEO TOUR

$2,849,000

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Home values near 23 Jefferson Rd

Data from public records.

Address	Redfin Estimate
11 Jefferson Road, Winchester, MA 6 Beds \| 2.5 Baths \| 5052 Sq. Ft.	$2,938,094
19 Jefferson Road, Winchester, MA 6 Beds \| 3.5 Baths \| 4830 Sq. Ft.	$2,521,762

Address	Redfin Estimate
15 Jefferson Road, Winchester, MA 4 Beds \| 4.5 Baths \| 3600 Sq. Ft.	$2,537,004
21 Jefferson Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2827 Sq. Ft.	$1,910,248

Address	Redfin Estimate
17 Jefferson Road, Winchester, MA 4 Beds \| 1.5 Baths \| 1714 Sq. Ft.	$1,575,864
25 Jefferson Road, Winchester, MA 3 Beds \| 3.5 Baths \| 3839 Sq. Ft.	$1,918,098

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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