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$2,380,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,881 Sq. Ft.
  • 0.28 Acres
  • 1 Car Garage
  • Updated 3 hours ago

Next open house:

Open House: 2:30 PM - 4:00 PM

Saturday 6/27 2:30 PM - 4:00 PM

14 Hillside Ave,Winchester, MA 01890

14 Hillside AveWinchesterMA01890

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Join us at 14 Hillside Ave on:

  • Open House: 1:00 PM - 2:30 PM

    Sunday 6/28 1:00 PM - 2:30 PM

    14 Hillside Ave,Winchester, MA 01890
    14 Hillside AveWinchesterMA01890
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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.

Full Property Details for 14 Hillside Ave

General

  • Price: $2,380,000
  • Taxes: $16,639 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73541163
  • Updated: 6/25/2026
  • Added to Site: 1 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Bathroom 1: Second
  • Bathroom 2: Second
  • Bathroom 3: Second

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Second
  • Bedroom 2: Second
  • Bedroom 3: Second
  • Bedroom 4: Basement

Other Rooms

  • Living Room: First
  • Family Room: First
  • Kitchen: First
  • Dining Room: First

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Parking Features: Detached, Paved Drive, Off Street

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Colonial, Victorian, Italianate
  • Basement: Yes
  • Square Feet: 3,881
  • Year Built: 1870

Lot Features

  • Lot Size (Acres): 0.28

Financial Considerations

  • Tax Amount: $16,639
  • Tax Year: 2025

Disclosures and Reports

  • Disclosures/Rstr.: buyer/ buyer agent is advised to do their own diligence.
  • Property ID: M:005 B:0269 L:0, 895722

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

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Listing agent

— 14 Hillside Ave —

  • Rebecca Huang

    William Raveis R.E. & Home Services

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 14 Hillside Ave

School District:Winchester School District, Winchester, MA
NameGradesDistance
Lincoln Elementary School, Winchester, MA
161 Mystic Valley Parkway, Winchester, MA 01890
K-50.2 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-80.2 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-120.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14 Hillside Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/24/2026
Listed
$2,380,000
78.95%
MLS
8/20/2025
Sold
$1,330,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14 Hillside Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$16,639
6%
$1,500,400
8%
2024
$15,734
2%
$1,388,700
6%
2023
$15,437
5%
$1,308,200
11%
2022
$14,741
3%
$1,178,300
5%
2021
$14,344
4%
$1,118,000
—
2020
$13,852
11%
$1,118,000
8%
2019
$12,496
3%
$1,031,900
4%
2018
$12,080
2%
$991,000
3%
2017
$11,843
7%
$964,400
2%
2016
$11,033
3%
$944,600
7%
2015
$10,678
8%
$879,600
12%
2014
$9,932
—
$784,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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

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14 Hillside Ave, Winchester, MA 01890 (MLS# 73541163) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 14 Hillside Ave is currently listed for $2,380,000 and was received on June 24, 2026. Want to learn more about 14 Hillside Ave? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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