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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.

More Info

Basic Information

  • Bedrooms4
  • Mls StatusNew
  • Bathroom5
  • Parcel Number M:005 B:0269 L:0,895722

Tax Information

  • Tax Assessed Value $1,500,400
  • Tax Year 2025
  • Taxes$16,639

School Information

  • High School Winchester Hs
  • Elementary SchoolLincoln
  • High SchoolWinchester
  • Junior HighMccall Middle

Parking

  • Parking Spaces5
  • Covered Spaces 1
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Detached, Paved Drive, Off Street

Rooms

  • Bathroom 1 Second
  • Bathroom 2 Second
  • Bathroom 3 Third
  • Bathrooms Total Decimal 4.5
  • Bedroom 2 Second
  • Bedroom 3 Second
  • Bedroom 4 Basement
  • Bedroom 5 First
  • Dining Room First
  • Family Room First
  • Full Bath4
  • Half Baths1
  • Kitchen First
  • Living Room First
  • Master Bedroom Second

Basic Information

  • List Price$2,380,000
  • MLS Number73541163
  • Modification Date06/24/2026
  • Property SubTypeSingle Family Residence

Location

  • Address14 Hillside Avenue
  • Building Number14
  • CountyMiddlesex
  • StateMA
  • StreetHillside Avenue
  • TownWinchester
  • Zip01890

Building

  • BasementFull, Finished
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplaces Total 2
  • FoundationStone
  • Garage Spaces1
  • Patio And Porch Features Deck
  • Property StyleColonial, Victorian, Italianate
  • Rooms9
  • Utilities For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup
  • Year Built1870
  • Year Built Details Actual, Approximate
  • Year Built Source Public Records

Property

  • Acreage0.28

Interior

  • Flooring Vinyl, Hardwood
  • Interior Features Bonus Room, Wine Cellar

Exterior

  • Exterior Features Deck

Utilities

  • Cooling Central Air, Heat Pump
  • Cooling YN Yes
  • Electric Circuit Breakers
  • Heat SystemYes
  • Heating Central, Electric
  • Sewer Public Sewer
  • Water Source Public

Property Information

  • Square Feet3,881
  • Building Area Source Owner
  • Living Area 3,881
  • Lot Size Square Feet 12,057
  • Lot Size Units Acres

Amenities

  • AmenitiesPark, Public School
  • Appliances IncludedElectric Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator

Legal

  • ZoningRDB

Other

  • Date Listed06/24/2026
  • Farm Land Area Units Square Feet

Map Location

Driving Directions

Listed by Rebecca Huang of William Raveis R.E. & Home Services

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