LevelSecond
14 Hillside Ave, Winchester MA 01890
Winchester, MA 01890
$2,380,000
$2,300,000
Est. $13,217/month
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
1
Price Changes
44.1%
Price Range
1
Previous Sales
Property Timeline
Price Reduced
Jul 20, 2026
$2,300,000
$80,000
(-3.36%)
From $2,380,000 to $2,300,000 (-3.4%)
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
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/20/2026 | ↓ Price Reduced | $2,300,000 | $80,000 | - | From $2,380,000 to $2,300,000 (-3.4%) |
| 06/24/2026 | 🏠 Listed for Sale | $2,380,000 | - | - | Original listing |
| 08/21/2025 | 🏷️ Previously Sold | $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
Parking
Garage Spaces
1
Has Garage
Yes
Features
Detached, Paved Drive, Off Street
Total Spaces
10
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
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
Buyer/ Buyer Agent Is Advised To Do Their Own Diligence.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Owner
Documents
None
County
Middlesex
Total market time (incl. prior listings)
30 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
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,615 sq ft above grade
1,266 sq ft below grade
LevelSecond
LevelSecond
LevelSecond
LevelSecond
LevelSecond
LevelFirst
LevelFirst
LevelFirst
LevelFirst
LevelFirst
LevelBasement
FeaturesYes
Display Options
Outdoor Areas
Patio & porchDeck
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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
Nearby Schools
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
Elementary Schools
3 schools
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
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
High Schools
3 schools
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
A-
Medford High School
1.3 mi
|
#94 of 346
|
Score: 60.6
Improved 24 spots from last year
+2.3 above state avg
1,195 students
Diverse
19 sports
• 1,212 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades PK-12
B
Woburn High School
2.4 mi
|
#143 of 346
|
Score: 56.1
Dropped 21 spots from last year
-2.1 below state avg
1,259 students
Diverse
18 sports
• 2,056 athletes
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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Monthly Payment Breakdown
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Property Tax
$1,387
Homeowners Insurance
$200
PMI (if <20% down)
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Loan Summary
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Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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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
Jul 24, 2026 3:05 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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