Sold
Last Sold Price
3 beds3,055 sqft

20 Hollywood Rd, Winchester, MA 01890

Single FamilyProperty Type
0.34 acresLot Size
1962Year Built
$363/sq ftPrice per sq ft
4 carsParking Spaces

Description

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...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.
  • Listed by: Alison Kee • RE/MAX Realty Experts
Listing closed: 11/20/2017 12:00 AM • Source: MLS PIN, MLS#: 72215241
See It First™ on Compass

Find homes before they're listed on other real estate sites.

Start your search

Recent comparable sales

Median sold price

$1,325,000

Avg days on market

29

Sale-to-list ratio

100.6%

Winchester, MA

9 comparable properties found

$1,392,500 | 53 Bacon Street, Winchester, MA 01890
1/34
1

$1,392,500

Sold 01/09/26

3
Bedrooms
2,865
Square Feet
0.28
Acres
a front view of a house with garden
1/43
2

$1,350,000

Sold 05/30/25

3
Bedrooms
3,351
Square Feet
0.34
Acres
a house view with a outdoor space
1/28
3

$975,000

Sold 05/07/25

3
Bedrooms
2,873
Square Feet
0.15
Acres
$1,165,000 | 59 Johnson Road, Winchester, MA 01890
1/25
4

$1,165,000

Sold 10/14/25

3
Bedrooms
2,458
Square Feet
0.39
Acres
a front view of a house with garden
1/40
5

$1,770,000

Sold 09/12/25

3
Bedrooms
2,850
Square Feet
0.15
Acres
an aerial view of residential houses with outdoor space
1/43
6

$1,325,000

Sold 04/22/26

3
Bedrooms
2,153
Square Feet
0.26
Acres
a front view of a house with garden
1/26
7

$1,226,000

Sold 07/15/25

3
Bedrooms
2,534
Square Feet
0.23
Acres
a front view of a house with garden
1/34
8

$1,325,000

Sold 12/22/25

3
Bedrooms
1,942
Square Feet
0.23
Acres
a front view of a house with garden
1/32
9

$1,355,000

Sold 11/20/25

4
Bedrooms
2,865
Square Feet
0.23
Acres

Location

Listing Courtesy of RE/MAX Realty Experts, Alison Kee

Sold By Compass, Adam Geragosian

Add your commute
Payment Calculator

$6,846 per month

30 year fixed, 7.03% Interest

Principal and Interest

$5,926

Property Taxes

$920

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.
Know your buying power with a preapproval and custom rate in minutes
Rocket Mortgage1

Property Information for 20 Hollywood Road

Property Details

  • Taxes: $11,041 / year
  • MLS Type: Single Family / Detached
  • Town: Winchester
  • Area: MA-Winchester
  • Architectural Style: Colonial
  • Style: Colonial
  • Garage Spaces: 2
  • Parking Spaces Total: 4

Building Information

  • Year Built: 1962
  • Lot Size: 0.34 AC / 15,000 SF

General Details

Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access
  • Current Financing: Conv. Fixed
  • Living Area: 3055.0
  • Color: beige
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Location/School
  • Grade School: Lincoln
  • High School: Whs
  • Middle School: Mccall
  • Neighborhood: East Hill

Features

Interior Features
  • Appliances: Range, Dishwasher, Disposal, Microwave, Countertop Range, Refrigerator, Washer, Dryer, ENERGY STAR Qualified Refrigerator, Gas Water Heater, Water Heater, Utility Connections for Gas Range, Utility Connections for Gas Dryer
  • Basement Features: Full, Finished, Bulkhead, Sump Pump
  • Num of Baths: 3.0
  • Num of Full Baths: 2
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 2.50
  • Bathrooms Total Integer: 3
  • DoorFeatures: Storm Door(s)
  • FireplaceFeatures: Living Room
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Flooring: Wood, Tile, Carpet, Flooring - Wall to Wall Carpet
  • Interior Features: Closet - Cedar, Walk-in Storage, Closet, Home Office, Play Room, Foyer
  • Interior Features: Window AC
  • Laundry Features: In Basement, Washer Hookup
  • Primary Bath: Yes
Exterior Features
  • Construction: Frame
  • Exterior Features: Rain Gutters, Professional Landscaping, Sprinkler System
  • Exterior Features: Professional Landscaping, Sprinkler System, Patio
  • Lot Description: Wooded
  • Patio And Porch Features: Patio
  • Roof Material: Shingle
  • Waterfront Features: Beach Front, Lake/Pond, 1/2 to 1 Mile To Beach
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Paved Drive
  • Open Parking: Yes
  • Parking Features: Attached, Paved Drive
Utilities
  • Cooling: Window AC
  • Cooling: Yes
  • Electric: 100 Amp Service
  • Heating: Baseboard, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, for Gas Dryer, Washer Hookup
  • Water: Public

Room Information

Primary Bedroom
  • Room Primary Bedroom Area: 247.0
  • Room Primary Bedroom Features: Bathroom - 3/4,Walk-In Closet(s),Closet/Cabinets - Custom Built
  • Room Primary Bedroom Length: 19.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 13.0
Bedroom 2
  • Bedroom2 Area: 156.0
  • Bedroom2 Features: Closet,Flooring - Hardwood
  • Bedroom2 Length: 12.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 13.0
Bedroom 3
  • Bedroom3 Area: 221.0
  • Bedroom3 Features: Walk-In Closet(s),Flooring - Hardwood,Attic Access
  • Bedroom3 Length: 13.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 17.0
Bedroom 4
  • Bedroom4 Area: 247.0
  • Bedroom4 Features: Closet,Flooring - Wall to Wall Carpet,Recessed Lighting
  • Bedroom4 Length: 19.0
  • Bedroom4 Level: Basement
  • Bedroom4 Width: 13.0
Bathroom 1
  • Bathroom1 Area: 20.0
  • Bathroom1 Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Countertops - Upgraded,Cabinets - Upgraded,Recessed Lighting
  • Bathroom1 Length: 4.0
  • Bathroom1 Level: First
  • Bathroom1 Width: 5.0
Bathroom 2
  • Bathroom2 Area: 30.0
  • Bathroom2 Features: Bathroom - Full,Bathroom - Tiled With Tub,Flooring - Marble,Countertops - Stone/Granite/Solid,Countertops - Upgraded
  • Bathroom2 Length: 5.0
  • Bathroom2 Level: Second
  • Bathroom2 Width: 6.0
Bathroom 3
  • Bathroom3 Area: 20.0
  • Bathroom3 Features: Bathroom - 3/4,Bathroom - Tiled With Shower Stall,Flooring - Marble,Countertops - Stone/Granite/Solid
  • Bathroom3 Length: 5.0
  • Bathroom3 Level: Second
  • Bathroom3 Width: 4.0
Dining Room
  • Dining Room Area: 169.0
  • Dining Room Features: Flooring - Hardwood,Chair Rail
  • Dining Room Length: 13.0
  • Dining Room Level: First
  • Dining Room Width: 13.0
Family Room
  • Family Room Area: 195.0
  • Family Room Features: Skylight,Cathedral Ceiling(s),Beamed Ceilings,Slider
  • Family Room Length: 15.0
  • Family Room Level: First
  • Family Room Width: 13.0
Kitchen
  • Kitchen Area: 238.0
  • Kitchen Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Dining Area,Countertops - Stone/Granite/Solid,Cabinets - Upgraded,Recessed Lighting,Stainless Steel Appliances
  • Kitchen Length: 14.0
  • Kitchen Level: First
  • Kitchen Width: 17.0
Laundry
  • Laundry Dimen: 6X9
Living Room
  • Room Living Room Area: 299.0
  • Room Living Room Features: Flooring - Hardwood
  • Room Living Room Length: 23.0
  • Room Living Room Level: First
  • Room Living Room Width: 13.0
Other Room 1
  • Room Office Area: 81.0
  • Room Office Features: Exterior Access
  • Room Office Length: 9.0
  • Room Office Level: First
  • Room Office Width: 9.0

Property Information

Property Info
  • UFFI: Unknown
  • Farm Land Area Units: Square Feet
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Road Surface Type: Paved
  • Disclosures: Subject to seller finding suitable housing,property already identified. Small ice dam in 2015 in back 2nd floor bedroom,taken care of right away.
Tax Information
  • Tax ID: M:006 B:0439 L:0,896187
  • Assessments: $899,100
  • Book: 48776
  • Tax Year: 2017
  • Zoning: RDB

Building / Association Information

Living Characteristics
  • Beds Total: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Foundation Area: 1829.0
  • Cooling Zones: 0
  • Heat Zones: 4

Market and Agent Information

Sale Info
  • Buyer Broker Comp: 2%
  • Other Agent Compensation: 0

Property History for 20 Hollywood Road

DateEvent & SourcePriceAppreciation
Nov 21, 2017

Sold (Public Record)

Public Record #610770754

$1,110,000

+2.8% / yr

Nov 20, 2017

Sold

MLS PIN #72215241

$1,110,000—
Oct 2, 2017

Under Agreement

MLS PIN #72215241

—
DateEvent & SourcePrice
11/21/2017

Sold (Public Record)

Public Record #610770754

$1,110,000

+2.8% / yr

11/20/2017

Sold

MLS PIN #72215241

$1,110,000
10/02/2017

Under Agreement

MLS PIN #72215241

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public records

20 Hollywood Road

Beds

5

Baths

2.5

Total Finished SqFt

3,729 SqFt

Above Grade Finished SqFt

3,729 SqFt

Unfinished Basement SqFt

209 SqFt

Stories

2

Schools near 20 Hollywood Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Lincoln Elementary School
PublicK to 5

McCall Middle School
Public6 to 8

Winchester High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 01890

$1,299,000 | 39 Forest Street, Winchester, MA 01890
1/38
Open: 10/10 12:00PM - 02:00PMNew

$1,299,000

3
Bedrooms
2,350
Square Feet
0.26
Acres
$1,399,000 | 15 Lloyd Street, Winchester, MA 01890
1/40
Listed By CompassOpen: 10/10 01:00PM - 02:30PM

$1,399,000

5
Bedrooms
2,071
Square Feet
0.11
Acres
$2,199,000 | 42 Everett Avenue, Winchester, MA 01890
1/40
Open: 10/10 01:00PM - 02:30PM

$2,199,000

6
Bedrooms
4,947
Square Feet
0.41
Acres
$2,049,000 | 21 Amberwood Drive, Winchester, MA 01890
1/42
Listed By CompassOpen: 10/10 11:00AM - 01:00PM

$2,049,000

5
Bedrooms
4,063
Square Feet
0.46
Acres
$329,900 | 20 Arthur Street, Unit 20, Winchester, MA 01890

$329,900

2
Bedrooms
1,084
Square Feet
$2,399,000 | 63 Wedgemere Avenue, Winchester, MA 01890
1/39
Open: 10/10 11:00AM - 12:30PMVirtual Tour

$2,399,000

4
Bedrooms
3,550
Square Feet
0.43
Acres
$899,000 | 39 Henry Street, Winchester, MA 01890
1/23
Listed By Coldwell Banker RealtyOpen: 10/10 12:00PM - 01:30PM

$899,000

3
Bedrooms
1,313
Square Feet
0.36
Acres
a view of house with a yard
1/28
Open: 10/10 01:00PM - 02:30PM

$3,299,000

7
Bedrooms
7,226
Square Feet
0.43
Acres
$18,000,000 | 15 Vinson Circle, Winchester, MA 01890
1/42

$18,000,000

6
Bedrooms
10,000
Square Feet
0.98
Acres

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 20 Hollywood Road, Winchester, MA 01890
$1,110,000
3
3,055
15,000
$725,000
4
1,900
10,300
$600,000
5
3,526
–
$2,250,000
5
5,677
15,926
$1
4
3
2,127
–
$365,000
4
–
–

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of RE/MAX Realty Experts, Alison Kee

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.