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14 Hillside AveWinchester, MA 01890

For Sale

$2,300,000

Smart Buyer Rebate $11,500

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.

Listed by Rebecca Huang

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William Raveis R.E. & Home Services

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617-888-0018

Last updated July 24, 2026

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Source: MLSPin #73541163

Listing Facts

  • TypeSingle-family
  • NeighborhoodWinchester Town Center
  • Bedrooms4
  • Bathrooms5
  • Days on Prevu38
  • Taxes$16,639/year
  • Size3,881 sqft
  • Price per sqft$593

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

07/20/2026
Price Decreased
$2,300,000
06/24/2026
Listed by William Raveis R.E. & Home Services
$2,380,000

Property Details for 14 Hillside Ave

Association

Amenities

  • Community Features: Park, Public School

Exterior

Construction

  • Year Built: 1870
  • Year Built Details: Actual,Approximate
  • Architectural Style: Colonial, Victorian, Italianate
  • Exterior Features: Deck

Features

  • Patio And Porch Features: Deck

Measurements

  • Building Area Total: 3,881
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.28
  • Lot Size Area: 0
  • Lot Size Square Feet: 12,057
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:005 B:0269 L:0,895722
  • Tax Annual Amount: $16,639.00
  • Tax Assessed Value: $1,500,400.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Electric Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Vinyl, Hardwood
  • Interior Features: Bonus Room, Wine Cellar

Measurements

  • Living Area: 3,881
  • Living Area Source: Owner

Rooms

  • Basement: Full, Finished
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4
  • Rooms Total: 9

Parking

Parking

  • Covered Spaces: 1
  • Garage Spaces: 1
  • Garage: Yes
  • Open Parking Spaces: 9
  • Open Parking: Yes
  • Parking Features: Detached, Paved Drive, Off Street
  • Parking Total: 10

Schools

Elementary School

  • Elementary School: Lincoln

High School

  • High School: Winchester Hs

Middle or Junior School

  • Middle Or Junior School: Mccall Middle

Utilities

Equipment

  • Cooling: Central Air, Heat Pump
  • Has Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Central, Electric
  • Has Heating: Yes
  • Laundry Features: First Floor, Electric Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Utilities: For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 5 bathrooms in this single-family home at 14 Hillside Ave.

What schools are nearby to 14 Hillside Ave?

Nearby schools include the Lincoln Elementary School, Mccall Middle, and Winchester Hs High School.

Does this single-family home have parking?

Yes, there is 1 parking space available for 14 Hillside Ave.

What are the annual taxes for 14 Hillside Ave?

Annual taxes for this single-family home are estimated at $16,639.

How does 14 Hillside Ave compare to other single-family homes in Winchester Town Center?

This single-family home is listed 32% above the average price for single-family homes in Winchester Town Center and has been on the market for 4 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 3,881 sqft.

14 Hillside Ave is a 4-bedroom, 5-bath single-family home for sale in Winchester MA 01890. Listed on Prevu for 38 days at $2,300,000. This includes a recent price decrease of $80,000. This property features 3,881 square feet of living space, located in Winchester Town Center. The median listing price for single-family homes in this area is $999,900. Nearby schools include Lincoln Elementary School, Mccall Middle, and Winchester Hs High School. The home offers private outdoor space, dishwasher, air conditioning, and parking. View other single-family home listings in Middlesex County.

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.