OFF MARKET

Off Market Mar 2024 for $2.4M

$2,745,777

Est. refi paymentEst. refi $364/mo

•

4,678

sq ft

20 Winthrop Rd, Lexington, MA 02421

About this home

Proudly presenting this rare offering to welcome you to 20 Winthrop Road; one of Lexington’s most coveted streets in historic Munroe Hill. Sitting on nearly half an acre of professionally landscaped grounds, you will find this magnificent home designed by Lexington's highly regarded local twentieth century architect Willard Brown and enhanced by renowned artist William Henry Grueby. Exquisitely maintained and updated over the years since, this home showcases the early 1900’s charm and seamlessly blends the best of modern living filled with luxury amenities. This six-bedroom home showcases warmth and light throughout with many spaces for formal or casual entertaining inside and out. The exterior features a spacious deck with pergola leading to a beautifully lit yard surrounded by mature plantings. This home is just a short walk to the town center, schools, trails, and a quick drive to commuting routes. OPEN HOUSE CANCELLED.

Single-familyProperty Type

1882Year Built

0.41 acresLot Size

$587Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Rachel Gallant • Century 21 North East

Bought with Rachel Gallant • Century 21 North East

Redfin checked: a few seconds ago

•Source:MLS PIN #73201408

Redfin Estimate

$2,745,777

$247K since sold in March 2024$25K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 37.1% higher than the average sale price ($2.00M) of 5 comparable homes.

SOLD APR 30, 2026
$2,010,000
A
6 beds4.5 baths4,500 sq ft
2380 Massachusetts Ave, Lexington, MA 02421
SOLD JUN 29, 2026
$2,705,000
B
5 beds4.5 baths4,559 sq ft
16 Hastings Rd, Lexington, MA 02421
SOLD MAY 1, 2026
$2,156,500
C
6 beds2.5 baths3,162 sq ft
51 Bloomfield St, Lexington, MA 02421
SOLD JUL 13, 2026
$1,285,000
D
5 beds3.5 baths2,492 sq ft
50 Kendall Rd, Lexington, MA 02421
SOLD JUL 28, 2026
$1,860,000
E
4 beds3 baths3,528 sq ft
32 Baskin Rd, Lexington, MA 02421

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Earn from this home

Sell

$695,696

Est. take-home

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Refinance

Est. cash available

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Rent

$7,406/mo

Redfin rental estimate

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Market trends in 02421, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.4%

0.7% MoM

Median sale price

$1.7M

$12K MoM

Avg. days on market

22d

3 days MoM

Recently sold homes

26 MoM

New listings for sale

3D WALKTHROUGH
$999,000
3 beds1.5 baths1,372 sq ft
1 Constitution Rd, Lexington, MA 02421
3D WALKTHROUGH
$3,195,000
7 beds5 baths5,114 sq ft
16 Middleby Rd, Lexington, MA 02421
See all

Provided by Redfin

Sale history for 20 Winthrop Rd

Date

Event

Price

MLS PIN #73201408

Mar 28, 2024

Sold

$2,499,000

$534/sq ft

Feb 16, 2024

Contingent

—

Feb 11, 2024

Listed

$2,499,000

$534/sq ft

MLS PIN #71643737

May 15, 2015

Sold

$1,528,000

$327/sq ft

Mar 6, 2015

Pending

—

Mar 4, 2015

Relisted

—

Feb 25, 2015

Pending

—

Sep 18, 2014

Price Changed

$1,598,000

$342/sq ft

Jun 18, 2014

Price Changed

$1,698,000

$363/sq ft

May 19, 2014

Price Changed

$1,749,000

$374/sq ft

Mar 12, 2014

Listed

$1,799,000

$385/sq ft

+13

Unusual and interesting Arts and Crafts Shingle style home was designed by Lexington's highly regarded local twentieth century architect Willard Brown and enhanced by renowned artist William Henry Grueby. This very unique home is filled with natural light with an open floor plan which is perfect for entertaining. Many updates include architect designed kitchen with Sub Zero refrigerator, GE Profile appliances, granite and corian, All updated baths, one with whirlpool. Updated wiring, plumbing, heating system, plus addition of central air and central alarm. Other special features include leaded glass windows, leaded glass cabinets and an exceptional living room fireplace surround with carved scenic "Pines by Grueby.

Public Records

Feb 22, 1995

Sold

$60,000

$13/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$30,356 (+5.2%)

$1,139,000 + $1,327,000

$2,466,000

2025

$28,851 (+17.5%)

$1,084,000 + $1,275,000

$2,359,000

2024

$24,561 (+1.6%)

$1,033,000 + $972,000

$2,005,000

2023

$24,180 (+4.2%)

$939,000 + $921,000

$1,860,000

2022

$23,212 (+1.8%)

$853,000 + $829,000

$1,682,000

2021

$22,808 (+0.5%)

$813,000 + $772,000

$1,585,000

2020

$22,691 (+4.6%)

$813,000 + $802,000

$1,615,000

2019

$21,688 (+3.5%)

$774,000 + $762,000

$1,536,000

2018

$20,964 (+1.4%)

$717,000 + $749,000

$1,466,000

2017

$20,677 (+2.1%)

$683,000 + $744,000

$1,427,000

2016

$20,250 (+11.3%)

$627,000 + $760,000

$1,387,000

2014

$18,193 (+2.0%)

$510,000 + $663,000

$1,173,000

2013

$17,830 (−0.2%)

$510,000 + $663,000

$1,173,000

2012

$17,874 (+0.4%)

$534,000 + $660,000

$1,194,000

2011

$17,798 (+3.9%)

$538,000 + $698,000

$1,236,000

2010

$17,131 (+4.5%)

$538,000 + $698,000

$1,236,000

2009

$16,394

$566,000 + $698,000

$1,264,000

Tax history for 20 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2026

$30,356 (+5.2%)

$1,139,000 + $1,327,000

$2,466,000

2025

$28,851 (+17.5%)

$1,084,000 + $1,275,000

$2,359,000

2024

$24,561 (+1.6%)

$1,033,000 + $972,000

$2,005,000

2023

$24,180 (+4.2%)

$939,000 + $921,000

$1,860,000

2022

$23,212 (+1.8%)

$853,000 + $829,000

$1,682,000

2021

$22,808 (+0.5%)

$813,000 + $772,000

$1,585,000

2020

$22,691 (+4.6%)

$813,000 + $802,000

$1,615,000

2019

$21,688 (+3.5%)

$774,000 + $762,000

$1,536,000

2018

$20,964 (+1.4%)

$717,000 + $749,000

$1,466,000

2017

$20,677 (+2.1%)

$683,000 + $744,000

$1,427,000

2016

$20,250 (+11.3%)

$627,000 + $760,000

$1,387,000

2014

$18,193 (+2.0%)

$510,000 + $663,000

$1,173,000

2013

$17,830 (−0.2%)

$510,000 + $663,000

$1,173,000

2012

$17,874 (+0.4%)

$534,000 + $660,000

$1,194,000

2011

$17,798 (+3.9%)

$538,000 + $698,000

$1,236,000

2010

$17,131 (+4.5%)

$538,000 + $698,000

$1,236,000

2009

$16,394

$566,000 + $698,000

$1,264,000

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.41 Acres

Year renovated

—

Sq. Ft.

4,402

Year built

1882

Style

Single Family Residential

County

Middlesex County

APN

872294S

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: 8
AttachedGarageYN: Yes
Parking Features: Under, Garage Door Opener, Heated Garage, Insulated, Off Street, Driveway, Paved

Interior

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Closet - Linen,Walk-In Closet(s),Flooring - Hardwood,Double Vanity,Remodeled,Crown Molding,Window Seat

Bedroom #2 Information
Level: Second
Features: Bathroom - Full,Flooring - Hardwood

Bedroom #3 Information
Level: Second
Features: Fireplace,Flooring - Hardwood

Bedroom #4 Information
Level: Second
Features: Flooring - Hardwood

Bedroom #5 Information
Level: Third
Features: Bathroom - Half,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 3
Main Level Bathrooms: 1

Bathroom #1 Information
Level: Main,First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Living Room Information
Level: First
Features: Flooring - Hardwood,Open Floorplan,Recessed Lighting,Remodeled,Archway,Crown Molding

Dining Room Information
Level: First
Features: Flooring - Hardwood,Open Floorplan

Kitchen Information
Level: First
Features: Flooring - Hardwood,Dining Area,Pantry,Countertops - Upgraded,Kitchen Island,Breakfast Bar / Nook,Cabinets - Upgraded,Deck - Exterior,Exterior Access,Remodeled,Storage,Gas Stove,Window Seat

Basement Information
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Garage Access, Concrete

Laundry Information
Laundry Features: Second Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 12
Door Features: French Doors, Storm Door(s)
Window Features: Insulated Windows, Storm Window(s)
Flooring: Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Interior Features: Bedroom, Sun Room, Bonus Room

Exterior

Building Information
Building Area (Total): 4,678
Foundation Details: Stone
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Green

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

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

Lot Information
Lot Size (Acres): 0.41
Lot Features: Corner Lot
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $24,561
Tax Year: 2024

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Hot Water, Radiant, Oil, Propane
Cooling: Central Air, Dual

Location

Location Information
Directions: Mass Ave or Waltham Street to Winthrop Street
UnparsedAddress: 20 Winthrop Road, Lexington MA 02421

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School

Public facts

Beds: 6
Baths: 3.5
Sq. Ft.: 4,402
Stories: 2.0
Lot Size: 0.41 acres
Style: Single Family Residential
Year Built: 1882
Year Renovated: —
County: Middlesex County
APN: 872294S

Home facts updated by county records on Jul 29, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools
Places
Transit

Maria Hastings Elementary School

Public K-5 • Assigned • 1.5mi

10/10

Wm Diamond Middle School

Public 6-8 • Assigned • 1.4mi

9/10

Lexington High School

Public 9-12 • Assigned • 0.4mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Lexington continues to be a competitive Seller's market driven by its historic appeal & location. With buildable land exhausted, true inventory growth is very constrained; development mostly replaces existing homes. New zoning laws will eventually...
2 months ago • Lexington
Benjamin Ginsburg
Redfin Premier agent
151 deals
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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 96° expected this year, 15 days in 30 years

6/10 Wind Factor

50% 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

Lexington, MA • 02421

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 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.61M – $3.16M

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Nearby similar homes

3D WALKTHROUGH

$999,000

3 beds1.5 baths1,372 sq ft

1 Constitution Rd, Lexington, MA 02421

$2,998,000

6 beds5.5 baths6,131 sq ft

22 Constitution Rd, Lexington, MA 02421

$2,599,000

5 beds4.5 baths4,288 sq ft

4 Augustus Rd, Lexington, MA 02421

$5,495,000

5 beds7 baths9,357 sq ft

16 Solomon Pierce Rd, Lexington, MA 02420

$2,688,000

5 beds5.5 baths4,973 sq ft

19 Cottage St, Lexington, MA 02420

$3,100,000

6 beds5.5 baths5,353 sq ft

50 Oak St, Lexington, MA 02421

New listings for sale in 02421

3D WALKTHROUGH

$999,000

3 beds1.5 baths1,372 sq ft

1 Constitution Rd, Lexington, MA 02421

3D WALKTHROUGH

$3,195,000

7 beds5 baths5,114 sq ft

16 Middleby Rd, Lexington, MA 02421

Home values near 20 Winthrop Rd

Data from public records.

Address	Redfin Estimate
25 Winthrop Road, Lexington, MA 6 Beds \| 2.5 Baths \| 2499 Sq. Ft.	$2,139,219
16 Winthrop Road, Lexington, MA 5 Beds \| 4.5 Baths \| 5758 Sq. Ft.	$3,113,761

Address	Redfin Estimate
21 Winthrop Road, Lexington, MA 6 Beds \| 4.5 Baths \| 5343 Sq. Ft.	$3,092,537
18 Winthrop Road, Lexington, MA 6 Beds \| 2.5 Baths \| 2874 Sq. Ft.	$2,662,464

Address	Redfin Estimate
17 Winthrop Road, Lexington, MA 5 Beds \| 4.5 Baths \| 4065 Sq. Ft.	$2,999,758
28 Winthrop Road, Lexington, MA 3 Beds \| 2.5 Baths \| 2561 Sq. Ft.	$1,944,052

Property information provided by MLS PIN when last listed in 2024. 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 02421, MA

Sale history for 20 Winthrop Rd

Tax history for 20 Winthrop Rd

Public record

Property details

Around this home

Lifestyle

Local insights from Redfin agents

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02421

Home values near 20 Winthrop Rd

More real estate resources