14 Hillside Ave Winchester, MA ^$ 2,380,000

14 Hillside Ave

^$ 2,380,000

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Recently Listed

Open House 6/27 2:30pm - 4pm

14 Hillside Ave

Winchester, MA, 01890

^$ 2,380,000

Bedrooms4 Baths4.1 Sq 3,881

Monthly Estimate*

^$ 15,028

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Single Family Home for sale in Winchester, MA

for $2,380,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,881 square foot home was built in 1870 on a lot size of 0.28.

Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester's most sought-after neighborhoods.

Open House

6/27/2026 2:30 PM - 4:00 PM

6/28/2026 1:00 PM - 2:30 PM

14 Hillside Ave 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

^$ 2,380,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 16,639

Style

Colonial,Victorian,Italianate

Lot Size

0.28

Year Built

1870

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73541163

List By

Rebecca Huang

Listing Agent

William Raveis R.E. & Home Services

Broker

Affordability Calculator

$16,414

Per Month

Monthly Principal & Interest: $15,028
Monthly Property Taxes: $1,387
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% 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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Trends

Single family listings in Winchester, MA

Average List Price ^$2,200,268

Percent of Sale Price 8%

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
6/24/2026	$2,380,000		Listed Price

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14 Hillside Ave, Winchester, MA, 01890 is a Single Family Home for sale at $2,380,000 with 3,881 sqft and a lot size of 0.28. 14 Hillside Ave has 4 bedrooms, 4.1 baths, and was built in 1870. 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 6.49% 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 6/25/2026.

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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14 Hillside Ave

Single Family Home for sale in Winchester, MA

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