50 Middlesex Street #50 Winchester — Photo 1 of 21
Recent Drop: $10,000
$789,000
Investment Analysis — 50 Middlesex Street #50
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 2-bedroom in 01890 carries an estimated $3,110/mo in gross rent — about a 2.27% cap rate and $17,921/yr in estimated NOI at the $789,000 list price. Adjust every assumption in the calculator below.
Beds
2
Baths
2
SqFt
1,036
Style
Condominium
Built
1920
Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen with quartz countertops and full-height backsplash, Bosch stainless steel appliances, and beautifully designed baths with custom tile and premium Kohler fixtures. Additional upgrades include a new roof, central A/C and heat, recessed lighting, and all-new systems throughout. Winchester is renowned for its award-winning schools, charming New England downtown filled with shops, restaurants, and cafés, easy commuter rail access to Boston, and convenient proximity to major highways—offering the perfect blend of suburban tranquility and city convenience.
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 MLS and other third-party data may be inaccurate or out of date.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.
Immersive Experience
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Disposal • Microwave • Freezer • ENERGY STAR Qualified Refrigerator • ENERGY STAR Qualified Dishwasher • Range
Neighborhood
Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First13.4 x 11.4
Bathroom - Full, Closet, Flooring - Hardwood, Open Floorplan, Recessed Lighting, Remodeled
Dining Room
Lvl Main,First10.3 x 15
Bathroom - Full, Closet, Flooring - Hardwood, Open Floorplan, Recessed Lighting, Remodeled
Kitchen
Lvl Main,First9 x 8.1
Flooring - Hardwood, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Cabinets - Upgraded, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled
Master Bedroom
Lvl Second11.2 x 9.2
Closet, Flooring - Hardwood, Recessed Lighting
Bedroom 2
Lvl Main,First11.3 x 9
Property History
$789,000
Was $799,000
Aug 24, 2026
MLS® 73546074
$799,000
Jul 7, 2026
MLS® 73546074
Listing Agent: The North Star Group
Listing Office: Keller Williams Realty Evolution
MLS® Number: 73546074