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Properties

  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
  • 14 Hillside Ave, Winchester, Massachusetts, 4 Bedrooms Bedrooms, 9 Rooms Rooms,4.5 BathroomsBathrooms,Residential,For Sale,Hillside Ave,73541163
Property Description

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.

Features
Heating System:
Central, Electric
Cooling System:
Central Air, Heat Pump
Basement:
Full, Finished
Parking:
Off Street, Detached, Paved Drive
Appliances:
Disposal, Range, Dishwasher, Refrigerator, Electric Water Heater, Oven
Exterior Unit Features:
Deck
Flooring:
Vinyl, Hardwood
Sewer:
Public Sewer
Style:
Colonial, Victorian, Italianate
Water:
Public
Disclosure:
THIS PROPERTY IS CONTINGENT ON SELLERS FINDING SUITABLE HOUSING.
Electric Feature:
Circuit Breakers
Garage Parking:
Yes
Interior Features:
Bonus Room, Wine Cellar
Lead Paint:
Unknown
Laundry Features:
Washer Hookup, First Floor, Electric Dryer Hookup
Additional Information
Grade School:
Lincoln
High School:
Winchester Hs
Middle School:
Mccall Middle
Market Time:
4
Parking Spaces:
10
Tax Year:
2025
Status:
Active
Price Per Sqft:
$613
Zoning:
RDB
Orig Price:
$2,380,000
Fireplaces:
2
Waterfront:
No
MlsStatus:
Active
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 52' 5''
Latitude:
N42° 26' 55.8''
  • Google Map

Residential

14 Hillside Ave, Winchester, Massachusetts

4 Bedrooms
4.5 Total Bathrooms
3,881 Sqft
$2,380,000
Listing ID #73541163
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$2,380,000
Bedrooms :
4
Rooms :
9
Total Bathrooms :
4.5
Full Bathrooms :
4
Half Bathrooms :
1
Square Footage :
3,881 Sqft
Year Built :
1870
Lot Area :
0.28 Acre
Listing ID :
73541163
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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