14 Hillside Ave, Winchester MA 01890

Winchester, MA 01890

$2,380,000

Est. $13,621/month

Beds

4.5

Baths

3,881

Sq Ft

$613

Price/Sq Ft

0.28

Acres

1870

Year Built

Single Family Residence

Type

1 hour 25 minutes

Time on Market

Active Open House Listed Jun 24, 2026 • MLS# 73541163 Copied!

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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Property Overview

Property Type

Single Family Residence

Listing Type

For Sale

Year Built

1870

Bedrooms

Full Bathrooms

Half Bathrooms

Living Area

3,881 sq ft

Total Rooms

Open House Schedule

Jun

Sunday, June 28

1:00 PM - 2:30 PM EDT

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

Parking

Garage Spaces 1

Has Garage Yes

Features Detached, Paved Drive, Off Street

Total Spaces 5

Utilities

Electric Circuit Breakers

Water Public

Sewer Public Sewer

Gas None

Other For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup

Financial

Annual Tax $16,639

Assessed Value $1,500,400

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: 5

Parking Features: Detached, Paved Drive, Off Street

Special Features

Fireplaces: 2

Fireplace Type:

Community Amenities: Park, Public School

Location

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Neighborhood

14 Hillside Ave, Winchester MA 01890

Winchester, MA 01890

Walkability

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Down Payment

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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

Total interest 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.

Property History

Market Insights

44.1%

Price Range

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

View Listing →

Date	Event	Price	Change	$/sqft	Details
06/24/2026	🏠 Listed for Sale	$2,380,000	-	-	Original listing
08/21/2025	🏷️ Previously Sold	$1,330,000	-	-	MLS #73362145

Price & Status History

Date	Event	Price	Change
Jun 24, 2026	New Listing Added	$2,380,000	—
Aug 21, 2025	Sold	$1,330,000	—

Market Statistics

Time on Market

1 hour 25 minutes

Price per Sq Ft

$613

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

Listing Information

Listing Agent Rebecca Huang

Listing Office William Raveis R.E. & Home Services

Agent MLS ID CN207682

Office MLS ID AN0762

Listing Data Updated Jun 24, 2026 4:12 PM 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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Monthly Payment Breakdown

Loan Summary

Listed for Sale

Previous Transaction - MLS #73362145

Previously Sold

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14 Hillside Ave, Winchester MA 01890

About this home

Property Overview

Open House Schedule

Facts & Features

Home Facts

Interior

Exterior

Parking

Utilities

Financial

Interior Features

Construction & Materials

Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

Special Features

Location

Neighborhood

Walkability

Nearby Schools

Elementary Schools

Middle Schools

High Schools

Monthly Payment Calculator

Monthly Payment Breakdown

Loan Summary

Rate Impact

Payment Over Time

Property History

Market Insights

Property Timeline

Listed for Sale

Previous Transaction - MLS #73362145

Previously Sold

Detailed History Table ▼

Price & Status History

Market Statistics

Tax History

Financial Details

Listing Information

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