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.
- 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:
- a three family also available for sale MLS #73553833 as a package.Seller will be recording a rite of way and parking arrangement as well as a maintenance agreement deed restriction for both properties.
- 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
- Grade School:
- Lincoln
- High School:
- Winchester Hs
- Middle School:
- Mccall Middle
- Market Time:
- 30
- Parking Spaces:
- 10
- Tax Year:
- 2025
- Status:
- Active
- Price Per Sqft:
- $593
- Zoning:
- RDB
- Orig Price:
- $2,380,000
- Fireplaces:
- 2
- Waterfront:
- No
- MlsStatus:
- Active
- City:
- Winchester
- State:
- MA
- County:
- Middlesex
- Postal Code:
- 01890
- Longitude:
- W72° 52' 5''
- Latitude:
- N42° 26' 55.8''
Residential
14 Hillside Ave, Winchester, Massachusetts
- Property Type :
- Residential
- Listing Type :
- For Sale
- Price :
- $2,300,000
- 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
- Stephen E. Robb
- View website
- 617-212-0251
-
srobb@robbenterprises.com
