BMN Boston

Get our mobile app!

Download on the App Store

18 Middlesex St, Winchester MA 01890

Winchester, MA 01890
$2,795,000
Est. $16,316/month
4
Beds
4.5
Baths
5,233
Sq Ft
$534
Price/Sq Ft
0.25
Acres
2004
Year Built
2
Parking
60
Days on Market
Active Listed May 13, 2026 • MLS# 73518621 Copied! • Updated Jun 3, 2026

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.

View in the App

Save this property, schedule tours instantly, and get alerts when the price drops

Scan to download BMN Boston app Scan with phone
Get the full experience in the BMN Boston app

BMN Estimate

Get the number an algorithm can't give you

A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.

Recently Sold Nearby

Property History

Property Timeline

🏠
Listed for Sale
May 14, 2026
$2,795,000
Original listing
Agent: Tina Natale Office: Luxury Living Real Estate

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
Features Paved Drive, Off Street, Paved
Total Spaces 2
Electric Generator, 200+ Amp Service
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Gas Dryer, Washer Hookup
Annual Tax $23,792
Assessed Value $2,145,400
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures Room Dimensions Are Approximate And For Marketing Purposes Only.
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Documents None
County Middlesex
Total market time (incl. prior listings) 21 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

Room Details

First Floor

Bathroom1
10 x 13
Dining Room
15 x 15
Kitchen
20 x 14
Living Room
26 x 19
Master Bedroom
19 x 13
Family Room
18 x 11

Second Floor

Bedroom3
15 x 13
Bathroom2
10 x 13
Bedroom2
15 x 15
Bathroom3
8 x 6

Basement Floor

Bedroom4
15 x 13

Other Floor

Bedroom5
Office
Master Bathroom

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
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

3 schools
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
M

Middle Schools

3 schools
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
C+
Daniel L Joyce Middle School
2.2 mi | #217 of 352 | Score: 39.5
Dropped 14 spots from last year
-18.7 below state avg
455 students Moderate
Grades 06-08
B
John F Kennedy Middle School
2.4 mi | #176 of 352 | Score: 42.4
Improved 42 spots from last year
-15.8 below state avg
521 students Diverse
Rising School
Grades 06-08
H

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
B
Woburn High School
1.8 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
A-
Medford High School
2.1 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
Learn about these ratings

Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,983
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

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

Loading map...

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 Jun 3, 2026 7:56 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

Steven Novak
Steven Novak
BMN Boston Real Estate
Ask about this property — free, no obligation.

Similar Homes for Sale

Comparable Properties

Customize Comparable Search

Finding comparable properties...

Market Analytics for Winchester, MA

Real-time market trends and pricing data for this area

18 Middlesex St, Winchester MA 01890 - Photo 1 18 Middlesex St, Winchester MA 01890 - Photo 2 18 Middlesex St, Winchester MA 01890 - Photo 3 18 Middlesex St, Winchester MA 01890 - Photo 4 18 Middlesex St, Winchester MA 01890 - Photo 5 18 Middlesex St, Winchester MA 01890 - Photo 6 18 Middlesex St, Winchester MA 01890 - Photo 7 18 Middlesex St, Winchester MA 01890 - Photo 8 18 Middlesex St, Winchester MA 01890 - Photo 9 18 Middlesex St, Winchester MA 01890 - Photo 10 18 Middlesex St, Winchester MA 01890 - Photo 11 18 Middlesex St, Winchester MA 01890 - Photo 12 18 Middlesex St, Winchester MA 01890 - Photo 13 18 Middlesex St, Winchester MA 01890 - Photo 14 18 Middlesex St, Winchester MA 01890 - Photo 15 18 Middlesex St, Winchester MA 01890 - Photo 16 18 Middlesex St, Winchester MA 01890 - Photo 17 18 Middlesex St, Winchester MA 01890 - Photo 18 18 Middlesex St, Winchester MA 01890 - Photo 19 18 Middlesex St, Winchester MA 01890 - Photo 20 18 Middlesex St, Winchester MA 01890 - Photo 21 18 Middlesex St, Winchester MA 01890 - Photo 22 18 Middlesex St, Winchester MA 01890 - Photo 23 18 Middlesex St, Winchester MA 01890 - Photo 24 18 Middlesex St, Winchester MA 01890 - Photo 25 18 Middlesex St, Winchester MA 01890 - Photo 26 18 Middlesex St, Winchester MA 01890 - Photo 27 18 Middlesex St, Winchester MA 01890 - Photo 28 18 Middlesex St, Winchester MA 01890 - Photo 29 18 Middlesex St, Winchester MA 01890 - Photo 30 18 Middlesex St, Winchester MA 01890 - Photo 31 18 Middlesex St, Winchester MA 01890 - Photo 32
Steven Novak

Steven Novak

BMN Boston Real Estate

Your message will be sent to Steven Novak.

Schedule a Tour