
50 Middlesex Street #50 Winchester — Photo 1 of 21
Recent Drop: $10,000
$789,000
50 Middlesex Street #50, Winchester, MA 01890
Winchester, MA 01890
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.
Immersive Experience
Market Value Analysis
* Analysis is based on 11 actively listed and recently sold comparable properties strictly within Winchester, MA.
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
Population
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Middlesex County
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Listing Agent: The North Star Group
Listing Office: Keller Williams Realty Evolution
MLS® Number: 73546074
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