OFF MARKET

Off market nov 2017 for $1.1M

$1,806,178

Est. refi paymentEst. refi $6,433/mo

•

3,055

sq ft

20 Hollywood Rd, Winchester, MA 01890

About this home

Searching for a solid and inviting home that you will love? Imagine how happy you will be celebrating life's milestones in your new home, located on a tranquil street in a superb East Hills location. 20 Hollywood Road is that home for you and your family and friends to gather. Enjoy this terrific colonial home that offers you 3-4 large bedrooms, a large kitchen, and a home office with a fantastic view. Relax in your light-filled family room with vaulted ceilings and skylights. Spend your fall evenings enjoying your near-perfect yard and stone patio. Is being able to walk everywhere important to you? From here you can walk to Winchester center, local schools, the train, and The Fells (one of the top 5 State Parks in MA with over 2,200 acres of trails and protected landscape). Hollywood awaits you, and it's a house you don't want to miss.its you.

Single-familyProperty Type

1962Year Built

0.34 acresLot Size

$591Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Lorie Glantz • RE/MAX Realty Experts

Bought with Adam Geragosian • Gibson Sotheby's International Realty

Redfin checked: a minute ago

•Source:MLS PIN #72215241

Redfin Estimate

$1,806,178

$696K since sold in November 2017$11K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12.2% higher than the average sale price ($1.61M) of 5 comparable homes.

BOUGHT WITH REDFIN JUL 13, 2026
$2,150,000
A
5 beds3 baths3,136 sq ft
22 Hollywood Rd, 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 JUN 30, 2026
$1,399,000
C
3 beds3.5 baths2,936 sq ft
71 Sargent Rd, 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 AUG 14, 2026
$1,500,000
E
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$994,664

Est. take-home

List your home with Redfin and save $9,031

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$5,700/mo

Redfin rental estimate

List your home for rent

Market trends in 01890, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.0%

0.0% MoM

Median sale price

$1.8M

$87K MoM

Avg. days on market

22d

1 days MoM

Recently sold homes

14 MoM

New listings for sale

$1,450,000
8 beds5 baths6,200 sq ft
67-69 Hemingway St, Winchester, MA 01890
$2,999,000
5 beds4.5 baths4,900 sq ft
5 Forest Cir, Winchester, MA 01890
$1,049,000
4 beds2 baths2,226 sq ft
16-18 Russell Rd, Winchester, MA 01890
OPEN TODAY, 11:30AM TO 1PM
$2,650,000
4 beds4.5 baths5,233 sq ft
18 Middlesex St, Winchester, MA 01890
$3,799,000
8 beds5 baths7,081 sq ft
15 Foxcroft Rd, Winchester, MA 01890
OPEN TODAY, 11:30AM TO 1PM
$1,299,000
6 beds2 baths2,946 sq ft
419-421 Washington St, Winchester, MA 01890
$2,950,000
6 beds4 baths4,752 sq ft
18 Surrey Rd, Winchester, MA 01890
EARLY ACCESS
$4,199,000
6 beds6 baths7,175 sq ft
7 Aquinas Path, Winchester, MA 01890
OPEN TODAY, 11:30AM TO 1PM
$890,000
2 beds1 bath1,489 sq ft
80 Nelson St, Winchester, MA 01890
OPEN TODAY, 1PM TO 2:30PM
$1,985,000
4 beds3.5 baths4,241 sq ft
30 Surrey Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 20 Hollywood Rd

Date

Event

Price

MLS PIN #72215241

Nov 20, 2017

Sold

$1,110,000

$363/sq ft

Oct 2, 2017

Pending

—

Sep 5, 2017

Price Changed

$1,130,000

$370/sq ft

Aug 31, 2017

Relisted

—

Aug 24, 2017

Pending

—

Aug 17, 2017

Listed

$1,180,000

$386/sq ft

MLS PIN #70463035

Jan 3, 2007

Sold

$825,000

$270/sq ft

Oct 18, 2006

Listing Removed

—

Sep 22, 2006

Listed

$879,000

$288/sq ft

Charming Central Entrance Colonial offers new roof in 2001, new gutters and clapboard siding in 2005. Many updates include, three new baths, laundry, garage doors and windows. Fireplace living room opens to first floor skylight family room. A generous front to back master bedroom with bath. Two additional bedrooms with walkin closet. Large finished basement has family room, den or 4th bedroom. Well landscaped private yard. East Hill location. Walk to train and center. Offered at $879,000

Year

Property tax

Land + Additions

Assessment*

2026

$19,480 (+1.3%)

$1,022,000 + $736,100

$1,758,100

2025

$19,234 (+19.4%)

$1,022,000 + $712,400

$1,734,400

2023

$16,115 (+2.0%)

$949,000 + $547,900

$1,496,900

2022

$15,806 (+8.5%)

$766,500 + $497,000

$1,263,500

2021

$14,572 (+7.0%)

$638,800 + $497,000

$1,135,800

2020

$13,620 (+9.6%)

$602,300 + $497,000

$1,099,300

2019

$12,428 (+6.9%)

$529,300 + $497,000

$1,026,300

2018

$11,629 (+5.3%)

$499,100 + $454,900

$954,000

2017

$11,041 (+6.7%)

$469,900 + $429,200

$899,100

2016

$10,351 (+2.9%)

$469,900 + $416,300

$886,200

2015

$10,058 (+5.9%)

$427,100 + $401,400

$828,500

2014

$9,496 (+0.5%)

$355,900 + $394,200

$750,100

2013

$9,445 (+1.8%)

$355,900 + $383,700

$739,600

2012

$9,282 (+3.7%)

$355,900 + $383,700

$739,600

2011

$8,949 (+1.7%)

$355,900 + $383,700

$739,600

2010

$8,801 (+2.1%)

$381,400 + $383,200

$764,600

2009

$8,617

$381,400 + $383,200

$764,600

Tax history for 20 Hollywood Rd

Year

Property tax

Land + Additions

Assessment*

2026

$19,480 (+1.3%)

$1,022,000 + $736,100

$1,758,100

2025

$19,234 (+19.4%)

$1,022,000 + $712,400

$1,734,400

2023

$16,115 (+2.0%)

$949,000 + $547,900

$1,496,900

2022

$15,806 (+8.5%)

$766,500 + $497,000

$1,263,500

2021

$14,572 (+7.0%)

$638,800 + $497,000

$1,135,800

2020

$13,620 (+9.6%)

$602,300 + $497,000

$1,099,300

2019

$12,428 (+6.9%)

$529,300 + $497,000

$1,026,300

2018

$11,629 (+5.3%)

$499,100 + $454,900

$954,000

2017

$11,041 (+6.7%)

$469,900 + $429,200

$899,100

2016

$10,351 (+2.9%)

$469,900 + $416,300

$886,200

2015

$10,058 (+5.9%)

$427,100 + $401,400

$828,500

2014

$9,496 (+0.5%)

$355,900 + $394,200

$750,100

2013

$9,445 (+1.8%)

$355,900 + $383,700

$739,600

2012

$9,282 (+3.7%)

$355,900 + $383,700

$739,600

2011

$8,949 (+1.7%)

$355,900 + $383,700

$739,600

2010

$8,801 (+2.1%)

$381,400 + $383,200

$764,600

2009

$8,617

$381,400 + $383,200

$764,600

*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.

3,729

Year built

1962

Style

Single Family Residential

County

Middlesex County

APN

3865052S

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: 2
# of Covered Spaces: 2
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive

Interior

Master Bedroom Information
Area: 247
Length: 19
Width: 13
Level: Second
Features: Bathroom - 3/4,Walk-In Closet(s),Closet/Cabinets - Custom Built

Bedroom #2 Information
Area: 156
Length: 12
Width: 13
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 221
Length: 13
Width: 17
Level: Second
Features: Walk-In Closet(s),Flooring - Hardwood,Attic Access

Bedroom #4 Information
Area: 247
Length: 19
Width: 13
Level: Basement
Features: Closet,Flooring - Wall to Wall Carpet,Recessed Lighting

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

Bathroom #1 Information
Area: 20
Length: 4
Width: 5
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Countertops - Upgraded,Cabinets - Upgraded,Recessed Lighting

Bathroom #2 Information
Area: 30
Length: 5
Width: 6
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub,Flooring - Marble,Countertops - Stone/Granite/Solid,Countertops - Upgraded

Bathroom #3 Information
Area: 20
Length: 5
Width: 4
Level: Second
Features: Bathroom - 3/4,Bathroom - Tiled With Shower Stall,Flooring - Marble,Countertops - Stone/Granite/Solid

Living Room Information
Area: 299
Length: 23
Width: 13
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 195
Length: 15
Width: 13
Level: First
Features: Skylight,Cathedral Ceiling(s),Beamed Ceilings,Slider

Dining Room Information
Area: 169
Length: 13
Width: 13
Level: First
Features: Flooring - Hardwood,Chair Rail

Kitchen Information
Area: 238
Length: 14
Width: 17
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Dining Area,Countertops - Stone/Granite/Solid,Cabinets - Upgraded,Recessed Lighting,Stainless Steel Appliances

Office Room Information
Area: 81
Length: 9
Width: 9
Level: First
Features: Exterior Access

Basement Information
Basement: Full, Finished, Bulkhead, Sump Pump

Laundry Information
Laundry Dimen: 6X9
Laundry Features: In Basement, Gas Dryer Hookup, Washer Hookup

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

Interior Features
# of Rooms (Total): 8
Door Features: Storm Door(s)
Flooring: Wood, Tile, Carpet, Flooring - Wall to Wall Carpet
Interior Features: Cedar Closet(s), Storage, Closet, Home Office, Play Room, Foyer, Walk-Up Attic

Exterior

Building Information
Building Area (Total): 3,055
Foundation Area: 1,829
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate
Color: beige

Exterior Features
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Rain Gutters, Professional Landscaping, Sprinkler System

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.34
Lot Features: Wooded
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $11,041
Tax Year: 2017

Utilities

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

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Natural Gas
Cooling: Window Unit(s)

Location

Location Information
Directions: Highland Ave to Pierrepont to Hollywood
UnparsedAddress: 20 Hollywood Rd, Winchester MA 01890

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

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 3,729
Stories: 2.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1962
Year Renovated: —
County: Middlesex County
APN: 3865052S

Home facts updated by county records on Sep 16, 2026

Other

Miscellaneous Information
Heat Zones: 4

Listing Information
Exclusions: Living Room And Dining Room Curtains.
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.8mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.8mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.1mi

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

0.46% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 14 days in 30 years

6/10 Wind Factor

52% 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

$1.72M – $2.08M

Reach more buyers when you sell with Redfin. Save up to $18,062 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

OPEN TODAY, 12PM TO 1:30PM

$1,450,000

4 beds3.5 baths2,370 sq ft

6 Burbank Rd, Medford, MA 02155

OPEN TODAY, 12PM TO 2PM

$1,199,000

3 beds3 baths2,226 sq ft

422 Mystic St, Arlington, MA 02474

VIDEO TOUR

$1,899,000

4 beds4.5 baths3,818 sq ft

11 Mary Kenney Way, Medford, MA 02155

$2,195,000

4 beds2.5 baths3,060 sq ft

65 Crocker Rd, Medford, MA 02155

OPEN TODAY, 11:30AM TO 1PM

$890,000

2 beds1 bath1,489 sq ft

80 Nelson St, Winchester, MA 01890

OPEN TODAY, 1PM TO 2:30PM

$3,200,000

8 beds6.5 baths5,750 sq ft

30 Willowdale Rd, Winchester, MA 01890

New listings for sale in 01890

$1,450,000

8 beds5 baths6,200 sq ft

67-69 Hemingway St, Winchester, MA 01890

$2,999,000

5 beds4.5 baths4,900 sq ft

5 Forest Cir, Winchester, MA 01890

$1,049,000

4 beds2 baths2,226 sq ft

16-18 Russell Rd, Winchester, MA 01890

OPEN TODAY, 11:30AM TO 1PM

$2,650,000

4 beds4.5 baths5,233 sq ft

18 Middlesex St, Winchester, MA 01890

$3,799,000

8 beds5 baths7,081 sq ft

15 Foxcroft Rd, Winchester, MA 01890

OPEN TODAY, 11:30AM TO 1PM

$1,299,000

6 beds2 baths2,946 sq ft

419-421 Washington St, Winchester, MA 01890

$2,950,000

6 beds4 baths4,752 sq ft

18 Surrey Rd, Winchester, MA 01890

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$4,199,000

6 beds6 baths7,175 sq ft

7 Aquinas Path, Winchester, MA 01890

OPEN TODAY, 11:30AM TO 1PM

$890,000

2 beds1 bath1,489 sq ft

80 Nelson St, Winchester, MA 01890

Home values near 20 Hollywood Rd

Data from public records.

Address	Redfin Estimate
18 Hollywood Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 1900 Sq. Ft.	$1,470,336
17 Hollywood Rd, Winchester, MA 5 Beds \| 4 Baths \| 4557 Sq. Ft.	$1,926,484

Address	Redfin Estimate
16 Hollywood Rd, Winchester, MA 4 Beds \| 3 Baths \| 2550 Sq. Ft.	$1,839,034
19 Hollywood Rd, Winchester, MA 4 Beds \| 3 Baths \| 2127 Sq. Ft.	$1,476,532

Address	Redfin Estimate
10 Hollywood Rd, Winchester, MA 3 Beds \| 1.5 Baths \| 1921 Sq. Ft.	$1,351,365
21 Hollywood Rd, Winchester, MA 4 Beds \| 2.5 Baths \| - Sq. Ft.	$1,703,395

Property information provided by MLS PIN when last listed in 2017. This data may not match . Learn more.

More real estate resources

Zip Codes
Neighborhoods
Minor Civil Divisions
Cities
Popular Searches

02155 homes for sale
02474 homes for sale
01890 homes for sale
01801 homes for sale
02420 homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Winchester	Agents near me	Quincy, MA homes for sale	Winchester Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Winchester Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Cambridge homes for sale
Boston homes for sale
Newton homes for sale