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22 Hollywood Rd, Winchester MA 01890

Winchester, MA 01890 • Winchester Highlands
$1,999,000
Est. $11,882/month
5
Beds
3
Baths
3,136
Sq Ft
$637
Price/Sq Ft
0.34
Acres
1962
Year Built
2
Garage Spaces
15
Days on Market
Pending Listed Jun 1, 2026 • MLS# 73527768 Copied! • Updated Jun 17, 2026

About this home

OFFER DEADLINE TUESDAY JUNE 9, 12PM. Beautifully appointed 5BR, 2 full/2 half bath home with 3,136 sq ft of thoughtfully designed living space on a flat, fully fenced .34 acre lot. Renovated kitchen with quartz countertops and luxury appliances. Expansive and bright living room with custom built-ins, window seating, and gas fireplace. The main living level also offers 3 spacious bedrooms and a serene primary suite with a walk-in closet and private en suite bath. Fully refreshed entry-level offers another bedroom, includes a custom mudroom off the 2-car attached garage, half bath, and laundry room. Completed with an oversized media room with walkout access. Generous, manicured yard with expanded patio--perfect for everyday living and entertaining outdoors. New systems, flexible layout, abundant natural light, and thoughtful updates throughout. Extra outdoor storage with included shed. Minutes from the Middlesex Fells Reservation, top-rated schools, and vibrant downtown Winchester.

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Recently Sold Nearby

Property History

Market Insights

Property Timeline

📋
Status: Active under contract
Jun 10, 2026
Active → Active Under Contract
Pending Sale
Jun 9, 2026
Offer accepted, sale pending
🏠
Listed for Sale
Jun 1, 2026
$1,999,000
Original listing
Agent: Andersen Group Realty Office: Keller Williams Realty Boston Northwest

Tax History

Year Taxes Assessment
2026 $18,886 $1,709,300

Financial Details

Annual Property Tax
$18,886
Tax Year 2026
Assessed Value
$1,709,300

Facts & Features

2 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1962
Living Area 3,136 sq ft
Lot Size 0.34 acres
Bedrooms 5
Full Baths 2
Half Baths 2
Total Rooms 11

Interior

Heating Forced Air, Baseboard, Heat Pump, Natural Gas
Cooling Central Air, Heat Pump
Flooring Wood, Stone / Slate
Appliances Gas Water Heater, Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Plumbed For Ice Maker
Fireplace Living Room
Fireplaces 2
Basement Finished
Laundry Exterior Access, Electric Dryer Hookup, Washer Hookup
Features None

Exterior

Construction Frame, Stone
Architecture None
Roof Shingle
Features Patio, Storage, Sprinkler System, Fenced Yard, Outdoor Gas Grill Hookup
Pool None
Spa None
Fencing Fenced/enclosed, Fenced
Patio/Porch Patio
Garage Spaces 2
Has Garage Yes
Features Attached, Garage Door Opener, Paved Drive, Paved
Total Spaces 6
Electric 200+ Amp Service
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Outdoor Gas Grill Hookup
Annual Tax $18,886
Assessed Value $1,709,300
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures None
Exclusions Wine And Wine Fridge Garage Excluded
Possession None
Accepted Financing None
Structure Type []
House Color Gray
Sq Ft Source Public Record
Sq Ft Disclosures Finished lower level includes 5th bedroom and entertainment room with exterior access
Documents None
County Middlesex
Total market time (incl. prior listings) 16 days

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1962
Bedrooms
5
Full Bathrooms
2
Half Bathrooms
2
Living Area
3,136 sq ft
Total Rooms
11
Levels
Multi/Split

Room Details

Other Floor

Bathroom1
Bathroom - Half
Bedroom5
Closet, Flooring - Stone/Ceramic Tile, Window(s) - Bay/Bow/Box
Bedroom4
Closet, Flooring - Hardwood, Window(s) - Picture
Bedroom3
Closet, Flooring - Hardwood, Window(s) - Picture
Dining Room
Flooring - Hardwood, Window(s) - Picture
Kitchen
Flooring - Hardwood, Window(s) - Picture
Bathroom2
Bathroom - Half
Bedroom2
Closet, Flooring - Hardwood, Window(s) - Picture
Living Room
Flooring - Hardwood, Window(s) - Bay/Bow/Box, Window(s) - Picture, Cable Hookup, Recessed Lighting
Bathroom3
Bathroom - Full
Master Bedroom
Bathroom - Full, Closet - Linen, Flooring - Hardwood, Window(s) - Picture
Office
Family Room
Master Bathroom

Interior Features

Flooring: Wood, Stone / Slate
Appliances: Gas Water Heater, Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Plumbed For Ice Maker
Interior Features:
Windows:
Basement: Finished
Laundry: Exterior Access, Electric Dryer Hookup, Washer Hookup
Security: Security System

Construction & Materials

Year Built: 1962
Structure Type:
Exterior Materials: Frame, Stone
Roof: Shingle
Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Forced Air, Baseboard, Heat Pump, Natural Gas
Heating Zones: 3
Cooling: Central Air, Heat Pump
Cooling Zones: 1
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Patio, Storage, Sprinkler System, Fenced Yard, Outdoor Gas Grill Hookup
Patio & Porch: Patio
Fencing: Fenced/Enclosed, Fenced
Other Structures:
Lot Features:
Road Surface: Paved

Parking & Garage

Garage Spaces: 2
Garage Type: Attached
Total Parking Spaces: 6
Parking Features: Attached, Garage Door Opener, Paved Drive, Paved

Special Features

Fireplaces: 2
Fireplace Type: Living Room
Community Amenities: Public Transportation, Pool, Tennis Court(s), Park, Golf, Medical Facility, Bike Path, Conservation Area, House of Worship, Public School
School District
Winchester School District local
A+
School Safety 2024-25
0.1% Very Low (Safest)
0.1% Suspensions 0.1% In-School
5.4% below state avg
E

Elementary Schools

10 schools
The Wilder School
1.6 mi
Grades K-12
Acera School
1.8 mi
Grades K-08
Children's Own School
0.5 mi
Grades PK-K
A+
Lincoln Elementary School
0.8 mi | #74 of 824 | Score: 60.7
Dropped 29 spots from last year
+2.5 above state avg
334 students Moderate
Strong Attendance
Grades K-05
St. Mary Elementary School
1.0 mi
Grades PK-05
A+
Muraco Elementary School
1.6 mi | #62 of 824 | Score: 61.6
Improved 62 spots from last year
+3.4 above state avg
352 students Diverse
Rising School Strong Attendance
Grades K-05
A+
Ambrose Elementary School
1.6 mi | #11 of 824 | Score: 66.1
Improved 36 spots from last year
+7.9 above state avg
398 students Moderate
Rising School Strong Attendance
Grades K-05
A
Lynch Elementary School
1.9 mi | #113 of 824 | Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students Diverse
Grades PK-05
Creative Corner School Inc
2.0 mi
Grades PK-K
A+
Vinson-Owen Elementary School
2.6 mi | #40 of 824 | Score: 63.2
Improved 112 spots from last year
+5 above state avg
441 students Diverse
Rising School Strong Attendance
Grades PK-05
M

Middle Schools

1 school
A+
McCall Middle School
0.8 mi | #16 of 352 | Score: 62.4
Dropped 3 spots from last year
+4.2 above state avg
1,036 students Diverse
Strong Attendance
Grades 06-08
H

High Schools

1 school
A+
Winchester High School
1.1 mi | #17 of 346 | Score: 73.6
Improved 18 spots from last year
+15.4 above state avg
1,404 students Diverse
20 sports • 2,818 athletes
Strong AP Program High Graduation Rate College Ready Curriculum Strong Athletics
Grades 09-12
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,574
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

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Payment Over Time

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Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Neighborhood

Winchester Highlands

22 Hollywood Rd, Winchester MA 01890

Winchester, MA 01890

Listing Information

Listing Agent Andersen Group Realty
Listing Office Keller Williams Realty Boston Northwest
Office Phone 781-862-2800
Agent MLS ID TM309803
Office MLS ID AN2627
Listing Data Updated Jun 17, 2026 4:10 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Steven Novak
Steven Novak
BMN Boston Real Estate
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BMN Boston Real Estate

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