22 Hollywood Rd Winchester, MA ^$ 1,999,000

22 Hollywood Rd

^$ 1,999,000

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Open House 6/4 5:30pm - 6:30pm

22 Hollywood Rd

Winchester, MA, 01890

^$ 1,999,000

Bedrooms5 Baths2.2 Sq 3,136

Monthly Estimate*

^$ 12,308

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Single Family Home for sale in Winchester, MA

for $1,999,000 with 5 bedrooms and 2 full baths, 2 half baths. This 3,136 square foot home was built in 1962 on a lot size of 0.34.

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.

Open House

6/4/2026 5:30 PM - 6:30 PM

6/5/2026 5:30 PM - 6:30 PM

6/6/2026 11:00 AM - 12:00 PM

6/7/2026 11:00 AM - 12:00 PM

22 Hollywood Rd Winchester, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

^$ 1,999,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 18,886

Style

Lot Size

0.34

Year Built

1962

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73527768

List By

Andersen Group Realty

Listing Agent

Keller Williams Realty Boston Northwest

Broker

Affordability Calculator

$13,882

Per Month

Monthly Principal & Interest: $12,308
Monthly Property Taxes: $1,574
Monthly Home Insurance: --

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Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Winchester, MA

Average List Price ^$2,299,613

Percent of Sale Price 15%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

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Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
6/1/2026	$1,999,000		Listed Price

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22 Hollywood Rd, Winchester, MA, 01890 is a Single Family Home for sale at $1,999,000 with 3,136 sqft and a lot size of 0.34. 22 Hollywood Rd has 5 bedrooms, 2.2 baths, and was built in 1962. The property's zip code is 01890 which is in Winchester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 6/3/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, 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, 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. 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.

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22 Hollywood Rd

Single Family Home for sale in Winchester, MA

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