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14 Hillside Ave, Winchester MA 01890

Winchester, MA 01890
$2,380,000
Est. $13,621/month
4
Beds
4.5
Baths
3,881
Sq Ft
$613
Price/Sq Ft
0.28
Acres
1870
Year Built
1
Garage Space
20
Days on Market
Active Listed Jun 24, 2026 • MLS# 73541163 Copied! • Updated Jun 28, 2026

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.

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Recently Sold Nearby

Property History

Market Insights

44.1%
Price Range
1
Previous Sales

Property Timeline

🏠
Listed for Sale
Jun 24, 2026
$2,380,000
Original listing
Agent: Rebecca Huang Office: William Raveis R.E. & Home Services
Previous Transaction - MLS #73362145
Full transaction history available when tracking began
🏷️
Previously Sold
Aug 21, 2025
$1,330,000
MLS #73362145

Tax History

Year Taxes Assessment
2025 $16,639 $1,500,400

Financial Details

Annual Property Tax
$16,639
Tax Year 2025
Assessed Value
$1,500,400

Facts & Features

1 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1870
Living Area 3,881 sq ft
Lot Size 0.28 acres
Bedrooms 4
Full Baths 4
Half Baths 1
Total Rooms 9

Interior

Heating Central, Electric
Cooling Central Air, Heat Pump
Flooring Vinyl, Hardwood
Appliances Electric Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator
Fireplace None
Fireplaces 2
Basement Full, Finished
Laundry First Floor, Electric Dryer Hookup, Washer Hookup
Features Bonus Room, Wine Cellar

Exterior

Construction None
Architecture Colonial, Victorian, Italianate
Roof None
Features Deck
Pool None
Spa None
Fencing None
Patio/Porch Deck
Garage Spaces 1
Has Garage Yes
Features Detached, Paved Drive, Off Street
Total Spaces 10
Electric Circuit Breakers
Water Public
Sewer Public Sewer
Gas None
Other For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup
Annual Tax $16,639
Assessed Value $1,500,400
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures Buyer/ Buyer Agent Is Advised To Do Their Own Diligence.
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Owner
Documents None
County Middlesex
Total market time (incl. prior listings) 4 days

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1870
Bedrooms
4
Full Bathrooms
4
Half Bathrooms
1
Living Area
3,881 sq ft
Total Rooms
9

Room Details

First Floor

Bedroom5
Dining Room
Kitchen
Living Room
Family Room

Second Floor

Bathroom1
Bedroom3
Bathroom2
Bedroom2
Bathroom3
Master Bedroom

Basement Floor

Bedroom4

Other Floor

Office
Master Bathroom
Yes

Interior Features

Flooring: Vinyl, Hardwood
Appliances: Electric Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator
Interior Features: Bonus Room, Wine Cellar
Windows:
Basement: Full, Finished
Laundry: First Floor, Electric Dryer Hookup, Washer Hookup
Security:

Construction & Materials

Style: Colonial, Victorian, Italianate
Year Built: 1870
Structure Type:
Exterior Materials:
Roof:
Foundation: Stone

Heating, Cooling & Utilities

Heating: Central, Electric
Heating Zones: 2
Cooling: Central Air, Heat Pump
Cooling Zones: 2
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Deck
Patio & Porch: Deck
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Garage Spaces: 1
Total Parking Spaces: 10
Parking Features: Detached, Paved Drive, Off Street

Special Features

Fireplaces: 2
Fireplace Type:
Community Amenities: Park, Public School
School District
Winchester School District local
A+
School Safety 2024-25
0.1% Very Low (Safest)
0.1% Suspensions 0.1% In-School
5.4% below state avg
E

Elementary Schools

10 schools
The Wilder School
1.1 mi
Grades K-12
Acera School
1.2 mi
Grades K-08
A+
Lincoln Elementary School
0.2 mi | #74 of 824 | Score: 60.7
Dropped 29 spots from last year
+2.5 above state avg
334 students Moderate
Strong Attendance
Grades K-05
St. Mary Elementary School
0.4 mi
Grades PK-05
Children's Own School
0.7 mi
Grades PK-K
A+
Muraco Elementary School
1.0 mi | #62 of 824 | Score: 61.6
Improved 62 spots from last year
+3.4 above state avg
352 students Diverse
Rising School Strong Attendance
Grades K-05
A
Lynch Elementary School
1.3 mi | #113 of 824 | Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students Diverse
Grades PK-05
A+
Ambrose Elementary School
1.3 mi | #11 of 824 | Score: 66.1
Improved 36 spots from last year
+7.9 above state avg
398 students Moderate
Rising School Strong Attendance
Grades K-05
Creative Corner School Inc
1.3 mi
Grades PK-K
A+
Vinson-Owen Elementary School
2.2 mi | #40 of 824 | Score: 63.2
Improved 112 spots from last year
+5 above state avg
441 students Diverse
Rising School Strong Attendance
Grades PK-05
M

Middle Schools

1 school
A+
McCall Middle School
0.2 mi | #16 of 352 | Score: 62.4
Dropped 3 spots from last year
+4.2 above state avg
1,036 students Diverse
Strong Attendance
Grades 06-08
H

High Schools

1 school
A+
Winchester High School
0.5 mi | #17 of 346 | Score: 73.6
Improved 18 spots from last year
+15.4 above state avg
1,404 students Diverse
20 sports • 2,818 athletes
Strong AP Program High Graduation Rate College Ready Curriculum Strong Athletics
Grades 09-12
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,387
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

14 Hillside Ave, Winchester MA 01890

Winchester, MA 01890

Listing Information

Listing Agent Rebecca Huang
Listing Office William Raveis R.E. & Home Services
Office Phone 617-322-3933
Agent MLS ID CN207682
Office MLS ID AN0762
Listing Data Updated Jun 28, 2026 4:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Steven Novak
Steven Novak
BMN Boston Real Estate
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