18 Middlesex St Winchester — Photo 1 of 32
Recent Drop: $100,000
$2,695,000
Investment Analysis — 18 Middlesex St
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 0.51% cap rate and $13,782/yr in estimated NOI at the $2,695,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
4.5
SqFt
5,233
Style
Single Family
Built
2004
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.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 5,233 sq ft principal dwelling). Lot size: 10,812 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Open Houses
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator
Neighborhood
Public Transportation • Shopping • Tennis Court(s) • Walk/Jog Trails • Medical Facility • Bike Path
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First26 x 19
Dining Room
Lvl First15 x 15
Kitchen
Lvl First20 x 14
Family Room
Lvl First18 x 11
Master Bedroom
Lvl First19 x 13
Bedroom 2
Lvl Second15 x 15
Bedroom 3
Lvl Second15 x 13
Bedroom 4
Lvl Basement15 x 13
Bathroom 1
Lvl First10 x 13
Bathroom 2
Lvl Second10 x 13
Bathroom 3
Lvl Second8 x 6
Property History
$2,695,000
Was $2,795,000
Aug 5, 2026
MLS® 73518621
$2,795,000
May 13, 2026
MLS® 73518621
$2,795,000
Nov 12, 2025
MLS® 73442182
$2,795,000
Oct 10, 2025
MLS® 73442182
$2,695,000
May 16, 2025
MLS® 73347754
$2,695,000
Mar 19, 2025
MLS® 73347754
$2,695,000
Nov 21, 2024
MLS® 73292156
$2,695,000
Sep 18, 2024
MLS® 73292156
Listing Agent: Tina Natale
Listing Office: Luxury Living Real Estate
MLS® Number: 73518621
