$1,999,000
22 Hollywood Rd
Winchester, MA, 01890
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.
Property Details
Price:
$1,999,000
MLS #:
73527768
Status:
Active Under Contract
Beds:
5
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
winchesterhighlands
Listed Date:
Jun 1, 2026
Finished Sq Ft:
3,136
Total Sq Ft:
3,136
Lot Size:
15,002 sqft / 0.34 acres (approx)
Year Built:
1962
Schools
Elementary School:
Lincoln
Middle School:
Mccall
High School:
Winchester
Interior
Above Grade Finished Area
3136
Appliances
Gas Water Heater, Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Plumbed For Ice Maker
Bathrooms
2 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air, Heat Pump
Fireplaces Total
2
Flooring
Wood, Stone / Slate
Heating
Forced Air, Baseboard, Heat Pump, Natural Gas
Laundry Features
Exterior Access, Electric Dryer Hookup, Washer Hookup
Levels
Multi/Split
Exterior
Attached Garage YN
1
Community Features
Public Transportation, Pool, Tennis Court(s), Park, Golf, Medical Facility, Bike Path, Conservation Area, House of Worship, Public School
Construction Materials
Frame, Stone
Covered Spaces
2
Exterior Features
Patio, Storage, Sprinkler System, Fenced Yard, Outdoor Gas Grill Hookup
Fencing
Fenced/Enclosed, Fenced
Garage Spaces
2
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Attached, Garage Door Opener, Paved Drive, Paved
Parking Spots
6
Parking Total
6
Patio And Porch Features
Patio
Roof
Shingle
Security Features
Security System
Financial
Tax Year
2026
Taxes
$18,886
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of Jun 13, 2026
70
Single Family Listed
53
Avg DOM
547
Avg $ / SqFt
$2,230,783
Avg List Price
Community
- Address22 Hollywood Rd Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 22 Hollywood Rd Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,999,000 and features 5 beds, 3 baths, and has approximately 3,136 square feet of living space, and was originally constructed in 1962. The current price per square foot is $637. The average price per square foot for Single Family listings in Winchester is $547. The average listing price for Single Family in Winchester is $2,230,783. To schedule a showing of MLS#73527768 at 22 Hollywood Rd in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Keller Williams Realty Boston Northwest. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
22 Hollywood Rd
Winchester, MA