18 Middlesex St, Winchester, MA 01890
Property image
Property image
FOR SALE
0.25 ACRES

18 Middlesex St
Winchester, MA 01890

  • 4 Beds
  • 4.5 Baths
  • 5,233 sqft (on 0.25 acres)

$2,795,000

Est. Mortgage $16,531/mo*
Get Pre-Qualified

$2,795,000

Est. Mortgage $16,531/mo*
Get Pre-Qualified
4 Beds
4.5 Baths
5,233 sqft
(on 0.25 acres)

Home Highlights

Parking
2 Open Spaces
Outdoor
Patio, Pool
Climate Control
Heating & Cooling
Price/Sqft
$534
Listed
70 days ago

Local Information

  • Map ViewExplore the area around 18 Middlesex St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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.

Home Details for 18 Middlesex St

Interior Features

Interior Details
Basement: Full,Finished,Interior Entry,Sump PumpNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5233 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas Dryer, Washer HookupAppliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Gas Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Radiant,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a FireplaceNo Spa
Gas & Electric
Electric: Generator, 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: French DoorsFlooring: Wood, Marble, Stone / Slate
Levels, Entrance, & Accessibility
Floors: Wood, Marble, Stone Slate
Security
Security: Security System

Exterior Features

Exterior Home Features
Patio / Porch: Patio, CoveredFencing: Fenced/Enclosed, FencedExterior: Patio, Covered Patio/Deck, Pool - Inground, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone WallFoundation: Concrete PerimeterHas a Private PoolSprinkler System
Parking & Garage
Open Parking Spaces: 2No GarageHas Open ParkingParking Spaces: 2Parking: Paved Drive,Off Street,Paved
Pool
Pool: In GroundPool
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4331Finished Area (below surface): 902

Days on Market

Days on Market: 70

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary,Villa
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:015 B:0016 L:0, 898747

Price & Status

Price
List Price: $2,795,000Price Per Sqft: $534

Active Status

MLS Status: Active

Location

Direction & Address
City: Winchester
School Information
Elementary School: LynchJr High / Middle School: MccallHigh School: Winchester

Agent Information

Listing Agent
Listing ID: 73518621

Building

Building Area
Building Area: 5233 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 10812 sqft

Miscellaneous

BasementMls Number: 73518621Above Grade Unfinished Area: 4331

Additional Information

Public TransportationShoppingTennis Court(s)Walk/Jog TrailsMedical FacilityBike PathConservation AreaPublic SchoolT-Station
Last check for updates: about 13 hours ago
Listing courtesy of Tina Natale, (617) 794-8460
Luxury Living Real Estate, (617) 227-7007
Source: MLS PIN, MLS#73518621
Also Listed on MLS PIN.

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.41M
Sale-to-List Price
101.7%
Price per sq ft
$571
Available listings
77
2MoM

Price History for 18 Middlesex St

DatePriceEventSource
05/14/2026$2,795,000Listed For SaleMLS PIN #73518621
11/12/2025$2,795,000ListingRemovedMLS PIN #73442182
10/10/2025$2,795,000Listed For SaleMLS PIN #73442182
05/16/2025$2,695,000ListingRemovedMLS PIN #73347754
03/19/2025$2,695,000Listed For SaleMLS PIN #73347754
11/21/2024$2,695,000ListingRemovedMLS PIN #73292156
09/19/2024$2,695,000Listed For SaleMLS PIN #73292156
11/01/2023$2,550,000ListingRemovedMLS PIN #73147332
10/13/2023$2,550,000PriceChange
MLS PIN #73147332
09/28/2023$2,599,000PriceChange
MLS PIN #73147332
08/11/2023$2,650,000Listed For SaleMLS PIN #73147332
07/01/2023$2,695,000ListingRemovedMLS PIN #73107084
05/04/2023$2,695,000Listed For SaleMLS PIN #73107084
12/13/2022$2,595,000ListingRemovedMLS PIN #73047571
11/03/2022$2,595,000PriceChange
MLS PIN #73047571
10/13/2022$2,695,000Listed For SaleMLS PIN #73047571
10/28/2016$1,465,000Sold
N/A
08/17/2016$1,499,000PendingAgent Provided
07/28/2016$1,499,000Listed For SaleAgent Provided
06/07/2002$450,000Sold
N/A
05/01/2002$25,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$23,792
Assessment$2,145,400
Home facts updated by county records

Comparable Sales for 18 Middlesex St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6 Ivy Cir, Winchester, MA
0.34
Single-Family Home
$1,500,000
04/15/26
6
4
3,403
237 Swanton St, Winchester, MA
0.35
Single-Family Home
$1,850,000
05/29/26
5
4
4,334
19 Glengarry Rd, Winchester, MA
0.38
Single-Family Home
$1,825,000
12/08/25
6
3.5
3,521
46 Church St, Winchester, MA
0.48
Single-Family Home
$1,965,000
01/27/26
4
3.5
3,475
29 Shepard Ct, Winchester, MA
0.43
Single-Family Home
$2,450,000
01/09/26
6
5
4,594
49 Sheridan Cir, Winchester, MA
0.53
Single-Family Home
$2,409,000
07/10/26
5
4.5
5,881
4 Norwood St, Winchester, MA
0.54
Single-Family Home
$3,242,250
10/17/25
5
4.5
5,250
15 Wildwood St, Winchester, MA
0.41
Single-Family Home
$2,100,000
06/09/26
6
2.5
4,104
9 Norfolk Rd, Winchester, MA
0.53
Single-Family Home
$2,400,000
12/23/25
6
3.5
4,320
112 Wendell St, Winchester, MA
0.57
Single-Family Home
$1,335,000
02/04/26
4
3
2,854

Nearby homes

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Assigned Schools

These are the assigned schools for 18 Middlesex St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
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  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

Tina Natale, Luxury Living Real Estate, (617) 227-7007
Agent Phone: (617) 794-8460
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
18 Middlesex St, Winchester, MA 01890 is a 4 bedroom, 5 bathroom, 5,233 sqft single-family home built in 2004. This property is currently available for sale and was listed by MLS PIN on May 14, 2026. The MLS # for this home is MLS# 73518621.