Dimensions15 x 13
LevelSecond
18 Middlesex St, Winchester MA 01890
Winchester, MA 01890
$2,795,000
$2,695,000
Est. $15,810/month
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About this home
This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate. A lifestyle of luxury/convenience steps away from town, commuter rail, school and walking trails.
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Recently Sold Nearby
Property History
Market Insights
1
Price Changes
47.6%
Price Range
1
Previous Sales
Property Timeline
Price Reduced
Aug 5, 2026
$2,695,000
$100,000
(-3.58%)
From $2,795,000 to $2,695,000 (-3.6%)
Listed for Sale
May 14, 2026
$2,795,000
Original listing
Agent: Tina Natale
Office: Luxury Living Real Estate
Previous Transaction - MLS #72044797
Full transaction history available when tracking began
Previously Sold
Oct 28, 2016
$1,465,000
MLS #72044797
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/05/2026 | ↓ Price Reduced | $2,695,000 | $100,000 | - | From $2,795,000 to $2,695,000 (-3.6%) |
| 05/14/2026 | 🏠 Listed for Sale | $2,795,000 | - | - | Original listing |
| 10/28/2016 | 🏷️ Previously Sold | $1,465,000 | - | - | MLS #72044797 |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $23,792 | $2,145,400 |
Financial Details
Annual Property Tax
$23,792
Tax Year 2025
Assessed Value
$2,145,400
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
2004
Living Area
5,233 sq ft
Lot Size
0.25 acres
Bedrooms
4
Full Baths
4
Half Baths
1
Total Rooms
10
Interior
Heating
Forced Air, Radiant, Natural Gas
Cooling
Central Air
Flooring
Wood, Marble, Stone / Slate
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
Fireplace
None
Fireplaces
2
Basement
Full, Finished, Interior Entry, Sump Pump
Laundry
Gas Dryer Hookup, Washer Hookup
Features
Bathroom, Central Vacuum
Exterior
Construction
None
Architecture
Contemporary, Villa
Roof
None
Features
Patio, Covered Patio/deck, Pool - Inground, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall
Pool
In Ground
Spa
None
Fencing
Fenced/enclosed, Fenced
Patio/Porch
Patio, Covered
Parking
Features
Paved Drive, Off Street, Paved
Total Spaces
2
Utilities
Electric
Generator, 200+ Amp Service
Water
Public
Sewer
Public Sewer
Gas
None
Other
For Gas Range, For Gas Dryer, Washer Hookup
Financial
Annual Tax
$23,792
Assessed Value
$2,145,400
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
Room Dimensions Are Approximate And For Marketing Purposes Only.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Middlesex
Total market time (incl. prior listings)
88 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2004
Bedrooms
4
Full Bathrooms
4
Half Bathrooms
1
Living Area
5,233 sq ft
Total Rooms
10
Floor Layout
Interactive room guide
Floor Layout
Finished Area
4,331 sq ft above grade
902 sq ft below grade
Dimensions10 x 13
LevelSecond
Dimensions15 x 15
LevelSecond
Dimensions8 x 6
LevelSecond
Dimensions10 x 13
LevelFirst
Dimensions15 x 15
LevelFirst
Dimensions20 x 14
LevelFirst
Dimensions26 x 19
LevelFirst
Dimensions19 x 13
LevelFirst
Dimensions18 x 11
LevelFirst
Dimensions15 x 13
LevelBasement
Display Options
Outdoor Areas
PoolIn Ground
Patio & porchPatio, Covered
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:
Wood, Marble, Stone / Slate
Appliances:
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
Interior Features:
Bathroom, Central Vacuum
Windows:
Insulated Windows
Basement:
Full, Finished, Interior Entry, Sump Pump
Laundry:
Gas Dryer Hookup, Washer Hookup
Security:
Security System
Construction & Materials
Style:
Contemporary, Villa
Year Built:
2004
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Forced Air, Radiant, Natural Gas
Heating Zones:
4
Cooling:
Central Air
Cooling Zones:
4
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio, Covered Patio/Deck, Pool - Inground, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall
Patio & Porch:
Patio, Covered
Fencing:
Fenced/Enclosed, Fenced
Other Structures:
Lot Features:
Road Surface:
Paved
Parking & Garage
Total Parking Spaces:
2
Parking Features:
Paved Drive, Off Street, Paved
Special Features
Fireplaces:
2
Fireplace Type:
Pool:
Private Pool
Pool Features:
In Ground
Community Amenities:
Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School, T-Station
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
10 schools
Acera School
0.8 mi
Grades K-08
The Wilder School
0.9 mi
Grades K-12
A
Lynch Elementary School
0.5 mi
|
#113 of 824
|
Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students
Diverse
Grades PK-05
Creative Corner School Inc
0.6 mi
Grades PK-K
St. Mary Elementary School
0.6 mi
Grades PK-05
A+
Lincoln Elementary School
0.6 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
A+
Muraco Elementary School
0.7 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+
Ambrose Elementary School
1.1 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
Children's Own School
1.4 mi
Grades PK-K
A+
Vinson-Owen Elementary School
1.7 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
Middle Schools
1 school
A+
McCall Middle School
0.7 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
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
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Property Tax
$1,983
Homeowners Insurance
$200
PMI (if <20% down)
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Loan Summary
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
18 Middlesex St, Winchester MA 01890
Winchester, MA 01890
Listing Information
Listing Agent
Tina Natale
Listing Office
Luxury Living Real Estate
Office Phone
617-227-7007
Agent MLS ID
CN214185
Office MLS ID
AN6147
Listing Data Updated
Aug 9, 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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