35 Hollywood Rd Winchester, MA ^$ 1,888,000

35 Hollywood Rd

^$ 1,888,000

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Open House 3/15 1:30pm - 3pm

35 Hollywood Rd

Winchester, MA, 01890

^$ 1,888,000

Bedrooms4 Baths4.1 Sq 3,906

Monthly Estimate*

^$ 11,625

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Single Family Home for sale in Winchester, MA

for $1,888,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,906 square foot home was built in 1963 on a lot size of 0.37.

Tucked at the end of a cul-de-sac and bordering the Fells, this classic brick-and-wood Colonial blends generous living spaces with comfortable, easy flow. The fireplaced living room and spacious dining room are filled with natural light and framed by peaceful woodland views. The kitchen features stone counters, stainless appliances, and a peninsula that connects to the dining area and opens to a vaulted, beamed family room with fireplace and French doors to the outdoors. A home office offers added flexibility. Upstairs, four inviting bedrooms include a tranquil primary suite with walk-in, cedar closet and private bath, and a second bedroom with its own ensuite bath. The walk-out lower level offers additional living space with a playroom, wet bar, and full bath. Porch, patio, and fenced yard create welcoming outdoor areas, complemented by central air and an attached 2 car garage. With its thoughtful layout and cul-de-sac setting near the Fells, this home offers enduring appeal.

Open House

3/15/2026 1:30 PM - 3:00 PM

35 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

^$ 1,888,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 19,624

Style

Colonial

Lot Size

0.37

Year Built

1963

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73485418

List By

Anne Spry

Listing Agent

Barrett Sotheby's International Realty

Broker

Affordability Calculator

$13,260

Per Month

Monthly Principal & Interest: $11,625
Monthly Property Taxes: $1,635
Monthly Home Insurance: --

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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 ^$2,562,872

Percent of Sale Price 36%

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
3/11/2026	$1,888,000		Listed Price

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35 Hollywood Rd, Winchester, MA, 01890 is a Single Family Home for sale at $1,888,000 with 3,906 sqft and a lot size of 0.37. 35 Hollywood Rd has 4 bedrooms, 4.1 baths, and was built in 1963. 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 3/15/2026.

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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35 Hollywood Rd

Single Family Home for sale in Winchester, MA

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