Single Family Residence at 14 Hillside Ave, Winchester MA 01890, Winchester
Single Family Residence at 14 Hillside Ave, Winchester MA 01890, Winchester, photo 2 of 40
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40 photos

$2,380,000

14 Hillside Ave, Winchester MA 01890
Winchester, MA 01890
Listed by Rebecca Huang
Bedrooms
4
Bathrooms
4.5
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
99
On market date
June 24, 2026
Stories
N/A
Total bathrooms
4.5
Garage spaces
1
Parking spaces
10
Lot size
0.28 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

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

Walkability

Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

86
Highly walkable
out of 100
EPA National Walkability Index
16.5 / 20 -- Most walkable
Google Places amenity density
90 / 100
Restaurants & cafes20
Grocery stores2
Parks17
Schools18
Transit stops20
Pharmacies3

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
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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.