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

$2,695,000

Original price: $2,795,000
  • 4 Beds
  • 4.5 Baths
  • 5,233 sqft (on 0.25 acres)

18 Middlesex St, Winchester, MA 01890

Est. Mortgage $16,716/mo*
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Home Highlights

Single-Family Home
Built in 2004
0.25 acre lot
$515/sqft
2 Open Spaces

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

About this House

Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. 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.
Last check for updates: about 9 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.

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: 128

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: $2,695,000Price Per Sqft: $515

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

Around this home

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
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  • 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
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  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
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Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

Home Value

Trulia Estimate
$2.59M
Since last month
Increased$36K (+1.4%)
Since last year
Increased$20K (+0.8%)
Since last sale
Increased$1M (+76.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +76% in the last 10 years
MonthEstimated value
2026
September 2026$2.59M
August 2026$2.55M
July 2026$2.66M
June 2026$2.27M
May 2026$2.78M
April 2026$2.7M
March 2026$2.7M
February 2026$2.69M
January 2026$2.68M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Farrow St, Winchester, MA
0.19
Single-Family Home
$1,660,000
08/07/26
4
3.5
2,768
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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
36 Middlesex St #36, Winchester, MA 01890
0.03
$1,380,000
4
3.5
2,259
Recently Sold
37-39 Middlesex St, Winchester, MA 01890
0.04
-
6
3
2,355
Off Market
44-46 Middlesex St, Winchester, MA 01890
0.06
-
5
2
2,392
Off Market
50 Middlesex St #50, Winchester, MA 01890
0.07
$774,900
2
2
1,036
For Sale
52 Middlesex St #52, Winchester, MA 01890
0.08
$1,200,000
4
2.5
2,303
Recently Sold
61 Lake St, Winchester, MA 01890
0.09
$1,352,300
4
1.5
1,985
Off Market
4 Fairfield Pl, Winchester, MA 01890
0.10
$2,238,100
4
3.5
3,896
Off Market
63 Middlesex St, Winchester, MA 01890
0.10
$1,015,800
3
2
1,614
Off Market
60 Lake St #I, Winchester, MA 01890
0.11
$653,900
2
1.5
1,464
Off Market
53 Lake St, Winchester, MA 01890
0.11
$1,075,000
3
2.5
2,235
For Sale
2 Fairfield Pl, Winchester, MA 01890
0.11
$1,988,400
5
2.5
3,746
Off Market

Price and Tax history

DateEventPrice
Aug 5, 2026
Source: MLS PIN #73518621
PriceChange
$2,695,000
Price decreased by 4%
May 14, 2026
Source: MLS PIN #73518621
Listed For Sale
$2,795,000
Nov 12, 2025
Source: MLS PIN #73442182
ListingRemoved
$2,795,000
Oct 10, 2025
Source: MLS PIN #73442182
Listed For Sale
$2,795,000
May 16, 2025
Source: MLS PIN #73347754
ListingRemoved
$2,695,000

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.

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Frequently asked questions about 18 Middlesex St

  • What is the estimated monthly payment for 18 Middlesex St?
    Based on a $2,695,000 list price with 20% down at today's rates, the estimated monthly payment for 18 Middlesex St in Winchester, MA is approximately $16,984 (about $14,641 principal & interest, $2,268 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Winchester, MA.
  • What are the closest schools to 18 Middlesex St?
    The closest schools to 18 Middlesex St in Winchester, MA are Lynch Elementary School (Pre-K, rated 9/10), McCall Middle School (rated 9/10), Winchester High School (rated 10/10).
  • What is 18 Middlesex St estimated to be worth?
    Trulia's estimated value for 18 Middlesex St in Winchester, MA is $2,588,600.
  • Does 18 Middlesex St have air conditioning?
    Yes, 18 Middlesex St in Winchester, MA has air conditioning.
  • Does 18 Middlesex St have a pool?
    Yes, 18 Middlesex St in Winchester, MA has a pool.
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.