OFF MARKET

Off Market Oct 2020 for $1.3M

$1,841,548

•

2,550

sq ft

16 Hollywood Rd, Winchester, MA 01890

About this home

Sunday Open House CANCELLED. Offer accepted. Welcome to this beautiful contemporary home, a perfect mid-century modern architectural achievement set amidst lush gardens and framed by natural woodlands. There are 4 generously sized bedrooms, one of which is perfect for a home office, study space, home gym or combo. The well equipped kitchen features updated SS appliances including a Viking range and a sweet dining area overlooking the garden. Dine al fresco on the brick patio while enjoying the tranquil babbling of the goldfish pond. The family room opens to the gorgeous back garden with lush perennials and mature trees. The 2nd level primary bedroom has a luxurious, spa inspired bathroom and an enviable walk-in dressing room with ample storage. This truly special home has been carefully, lovingly maintained. Enjoy the convenience of the direct entry 2 car garage and central AC. Easy distance to Commuter Rail, schools and town center

Single-familyProperty Type

1973Year Built

0.36 acresLot Size

$722Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Naomi DeLairre • Waterfield Sotheby's International Realty

Bought with Brennan, Shifman & Lee Team • Unlimited Sotheby's International Realty

Redfin checked: 2 minutes ago

•Source:MLS PIN #72724250

Redfin Estimate

$1,841,548

$492K since sold in October 2020$21K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.5% higher than the average sale price ($1.75M) of 6 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 APR 30, 2026
$1,560,000
B
4 beds2.5 baths2,578 sq ft
17 Cranston Rd, 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 JUL 30, 2026
$2,255,000
D
4 beds3.5 baths3,494 sq ft
2 York Rd, Winchester, MA 01890
SOLD JUN 1, 2026
$1,607,000
E
4 beds2.5 baths3,298 sq ft
6 Oakland Cir, Winchester, MA 01890
SOLD OCT 9, 2025
$1,500,000
F
3 beds2.5 baths2,283 sq ft
17 Dennett Rd, Winchester, MA 01890

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Earn from this home

Sell

$794,281

Est. take-home

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Rent

$5,661/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

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OPEN TODAY, 11AM TO 12PM
$1,099,000
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$1,050,000
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257 Cross St, Winchester, MA 01890
EARLY ACCESS
$675,000
2 beds2 baths1,124 sq ft
60 Lake St Unit E, Winchester, MA 01890
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$1,699,000
3 beds2 baths2,327 sq ft
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OPEN TODAY, 12:30PM TO 1:30PM
$2,849,000
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See all

Provided by Redfin

Sale history for 16 Hollywood Rd

Date

Event

Price

MLS PIN #72724250

Oct 28, 2020

Sold

$1,350,000

$529/sq ft

Sep 12, 2020

Contingent

—

Sep 10, 2020

Listed

$1,289,000

$505/sq ft

MLS PIN #72128883

Jun 1, 2017

Sold

$1,165,000

$457/sq ft

Mar 25, 2017

Pending

—

Mar 9, 2017

Listed

$1,200,000

$471/sq ft

+25

Mid-Century Modern/Asian Influence..Much sought after East Hill location. Close to Middlesex Fells, Community Music School, Winchester Center, trains to Boston. The large Zen inspired yard offers much space to relax while soaking in the sights and sounds of the Koi pond and low maintenance mature plantings. All rooms are well sized with much of the living space offering cathedral ceilings. Hardwood flooring and warm neutral tones throughout. The large kitchen has been updated with high end stainless steel appliances, custom cabinetry & counters. Two of the Four generously sized bedrooms are en-suite with the Master Bedroom offering five piece bath including soaking tub plus a large walk-in closet/dressing room. Two Car attached garage, Central Air, Irrigation system with private well. Don't miss out on your opportunity to own this unique property. Shown by appointment only.

Year

Property tax

Land + Additions

Assessment*

2025

$17,582 (+9.8%)

$1,031,800 + $553,600

$1,585,400

2023

$16,014 (+1.3%)

$958,100 + $525,400

$1,483,500

2022

$15,815 (+12.6%)

$773,900 + $490,300

$1,264,200

2021

$14,048 (+7.2%)

$644,900 + $450,000

$1,094,900

2020

$13,109 (+10.0%)

$608,000 + $450,000

$1,058,000

2019

$11,920 (+9.6%)

$534,300 + $450,000

$984,300

2018

$10,872 (+3.3%)

$503,900 + $388,000

$891,900

2017

$10,525 (+6.6%)

$474,400 + $382,700

$857,100

2016

$9,877 (+6.6%)

$474,400 + $371,200

$845,600

2015

$9,262 (+6.2%)

$431,100 + $331,800

$762,900

2014

$8,720 (−0.9%)

$359,300 + $329,500

$688,800

2013

$8,796 (+1.8%)

$359,300 + $329,500

$688,800

2012

$8,644 (+3.7%)

$359,300 + $329,500

$688,800

2011

$8,334 (+1.1%)

$359,300 + $329,500

$688,800

2010

$8,240 (+2.1%)

$385,100 + $330,800

$715,900

2009

$8,068

$385,100 + $330,800

$715,900

Tax history for 16 Hollywood Rd

Year

Property tax

Land + Additions

Assessment*

2025

$17,582 (+9.8%)

$1,031,800 + $553,600

$1,585,400

2023

$16,014 (+1.3%)

$958,100 + $525,400

$1,483,500

2022

$15,815 (+12.6%)

$773,900 + $490,300

$1,264,200

2021

$14,048 (+7.2%)

$644,900 + $450,000

$1,094,900

2020

$13,109 (+10.0%)

$608,000 + $450,000

$1,058,000

2019

$11,920 (+9.6%)

$534,300 + $450,000

$984,300

2018

$10,872 (+3.3%)

$503,900 + $388,000

$891,900

2017

$10,525 (+6.6%)

$474,400 + $382,700

$857,100

2016

$9,877 (+6.6%)

$474,400 + $371,200

$845,600

2015

$9,262 (+6.2%)

$431,100 + $331,800

$762,900

2014

$8,720 (−0.9%)

$359,300 + $329,500

$688,800

2013

$8,796 (+1.8%)

$359,300 + $329,500

$688,800

2012

$8,644 (+3.7%)

$359,300 + $329,500

$688,800

2011

$8,334 (+1.1%)

$359,300 + $329,500

$688,800

2010

$8,240 (+2.1%)

$385,100 + $330,800

$715,900

2009

$8,068

$385,100 + $330,800

$715,900

*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

0.36 Acres

Year renovated

—

Sq. Ft.

2,550

Year built

1973

Style

Single Family Residential

County

Middlesex County

APN

3683163S

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: 2
# of Covered Spaces: 2
Parking Spaces: 2
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Window(s) - Picture,Lighting - Sconce

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

Bedroom #3 Information
Level: First
Features: Bathroom - 3/4,Closet,Flooring - Hardwood

Bedroom #4 Information
Level: First
Features: Closet,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Full,Bathroom - With Tub & Shower,Flooring - Stone/Ceramic Tile,Dryer Hookup - Dual

Bathroom #2 Information
Level: First
Features: Bathroom - 3/4,Bathroom - With Shower Stall,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Jacuzzi / Whirlpool Soaking Tub,Bidet,Lighting - Sconce

Living Room Information
Level: Main,First
Features: Flooring - Hardwood,Recessed Lighting

Family Room Information
Level: Main,First
Features: Ceiling Fan(s),Flooring - Hardwood,Exterior Access,Recessed Lighting

Dining Room Information
Level: Main,First
Features: Flooring - Stone/Ceramic Tile,Recessed Lighting

Kitchen Information
Level: Main
Features: Skylight,Ceiling Fan(s),Flooring - Hardwood,Window(s) - Picture,Dining Area,Countertops - Stone/Granite/Solid,Exterior Access,Stainless Steel Appliances,Gas Stove,Lighting - Pendant

Laundry Information
Laundry Features: First Floor, Washer Hookup

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

Interior Features
# of Rooms (Total): 8
Window Features: Insulated Windows, Screens
Flooring: Tile, Hardwood

Exterior

Building Information
Building Area (Total): 2,550
Foundation Details: Slab
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Grey

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.36
Lot Features: Level
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $13,109
Tax Year: 2020

Utilities

Utility Information
Utilities: for Gas Range, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers, 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Electric Baseboard, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Highland Ave to Pierrepont Rd to Hollywood Rd
UnparsedAddress: 16 Hollywood Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,550
Stories: 2.0
Lot Size: 0.36 acres
Style: Single Family Residential
Year Built: 1973
Year Renovated: —
County: Middlesex County
APN: 3683163S

Home facts updated by county records on Jul 29, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Lincoln Elementary School

Public K-5 • Assigned • 0.8mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.7mi

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

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

5/10 Heat Factor

7 days above 97° 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

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

$1.75M – $2.12M

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Home values near 16 Hollywood Rd

Data from public records.

Address	Redfin Estimate
18 Hollywood Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 1900 Sq. Ft.	$1,494,565
2 Hollywood Rd, Winchester, MA 2 Beds \| 1.5 Baths \| 1574 Sq. Ft.	$1,297,469

Address	Redfin Estimate
10 Hollywood Rd, Winchester, MA 3 Beds \| 1.5 Baths \| 1921 Sq. Ft.	$1,336,434
5 Hollywood Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 2624 Sq. Ft.	$1,921,348

Address	Redfin Estimate
4 Hollywood Rd, Winchester, MA 4 Beds \| 3.5 Baths \| 5000 Sq. Ft.	$2,198,905
17 Hollywood Rd, Winchester, MA 5 Beds \| 4 Baths \| 4557 Sq. Ft.	$2,013,307

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

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