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$2,380,000

14 Hillside Ave, Winchester MA 01890
Winchester, MA 01890
Listed by Rebecca Huang
Bedrooms
4
Bathrooms
4.1
Living area
3,881 sqft
Year built
1870

About this home

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.

Highlights

Fireplace

Property details

MLS #
73541163
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
57
On market date
June 24, 2026
Stories
N/A
Garage spaces
1
Lot size
0.28 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Lincoln Elementary
0.2 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
347
Student:teacher ratio
12.4:1
District
Winchester
Middle
McCall Middle
0.17 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Winchester High School
0.56 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,349
Student:teacher ratio
13.8:1
District
Winchester

Mortgage calculator

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Est. monthly payment
$14,483/mo
$476,000 down
$1,904,000 loan
Principal & interest$12,349
Property tax (est.)$1,983
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 28, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.