257 Cross Street Winchester — Photo 1 of 40
$1,050,000
Investment Analysis — 257 Cross Street
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 2.64% cap rate and $27,725/yr in estimated NOI at the $1,050,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
2.5
SqFt
2,801
Style
Single Family
Built
1960
Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!
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 2,801 sq ft principal dwelling). Lot size: 10,365 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 MLS and other third-party data may be inaccurate or out of date.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
Range • Dishwasher • Refrigerator • Freezer
Neighborhood
Public Transportation • Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Golf
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First17 x 15
Flooring - Hardwood, Window(s) - Picture
Dining Room
Lvl First20 x 13
Kitchen
Lvl Main,First18 x 12
Flooring - Hardwood, Dining Area
Family Room
Lvl Basement22 x 20
Master Bedroom
Lvl First14 x 12
Bathroom - Half, Closet, Flooring - Hardwood
Bedroom 2
Lvl First14 x 11
Bedroom 3
Lvl First11 x 11
Closet, Flooring - Hardwood
Bedroom 4
Lvl Basement17 x 11
Closet
Bedroom 5
Lvl Basement14 x 10
Closet
Bathroom 1
Lvl First12 x 7
Bathroom - Full
Bathroom 2
Lvl First5 x 4
Bathroom - Half
Bathroom 3
Lvl Basement9 x 6
Bathroom - Full
Property History
$1,050,000
Sep 2, 2026
MLS® 73571418
$488,000
Jan 19, 2011
MLS® 71176694
$499,990
Jan 8, 2011
MLS® 71176694
$1,800
May 5, 2010
MLS® 71028758
$1,800
Feb 5, 2010
MLS® 71028758
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73571418
