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14 Hillside Ave, Winchester MA 01890

$2,380,000

Estimated $16,051/month Calculator

Single Family

4 Bedrooms

Baths

3881

Total Parking: 11 (1 Garage)

12,057 (0.28)

Built in 1870

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.

This home has been viewed 2 times

Last Checked: June 26th, 2026 at 7:23am (Source: MLS PIN #73541163)

Garage Parking

Air Conditioning

Lead Paint Free

General Information for 14 Hillside Ave, Winchester MA 01890

Listing ID73541163

Property TypeSingle Family / Detached

Price$2,380,000 ($613.24/SqFt)

StyleColonial

CityWinchester

CountyMiddlesex

Neighborhood(s)

Garage Parking1

ZoningRDB

Year Built1870

Year Built SourcePublic Records

Year Built DetailsActual,Approximate

Interior Features for 14 Hillside Ave, Winchester MA 01890

Approximate Living Area Total3881

Living Area Includes BasementYes

Rooms9

Bedrooms4

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric220 Volts

Exterior Features for 14 Hillside Ave, Winchester MA 01890

Approximate Lot Size (Acres)0.28

Approximate Lot Size (Square Feet)12057

Total Parking11 (1 Garage)

Garage Parking1

WaterPublic

SewerPublic Sewer

Lot Features

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction Materials

Road Frontage Type

Patio & PorchCovered

Roof Material

Utility Connections110 Volts

Water Views

Water Views Features

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 14 Hillside Ave, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourceOwner

Special Listing Conditions

ExclusionsFireplace Mantel In Living Room Is Excluded.

Compensation Based On

Financial Information for 14 Hillside Ave, Winchester MA 01890

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax16639

Tax Year2025

Assessed Value$1,500,400

Location Information for 14 Hillside Ave, Winchester MA 01890

Elementary SchoolLincoln

Middle SchoolMccall Middle

High SchoolWinchester Hs

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 14 Hillside Ave, Winchester MA 01890

Agent

Name: Rebecca Huang

Office

Name: William Raveis R.E. & Home Services

Phone: 617-322-3933

Payment Calculator

, Interest

Property Taxes 1386.58

Principal & Interest 14664.8

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

William Raveis R.E. & Home Services

Rebecca Huang

Agent Phone

Office Phone

(617) 322-3933

Text Agent Call Agent Call Office

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EXIT

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