50 Middlesex Street #50 Winchester — Photo 1 of 21
Recent Drop: $14,100
$774,900
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.
Key facts
It was listed on July 7, 2026. The price has come down from an original $799,000 to $774,900 across 2 changes, most recently on September 14, 2026. The condo fee is $81 per month.
Immersive Experience
Market Value Analysis
* Analysis is based on 19 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
Primary Bedroom
Lvl Second11.2 x 9.2
Closet, Flooring - Hardwood, Recessed Lighting
Bedroom 2
Lvl Main,First11.3 x 9
Property History
$774,900
Was $789,000
Sep 14, 2026
MLS® 73546074
$789,000
Was $799,000
Aug 24, 2026
MLS® 73546074
$799,000
Jul 7, 2026
MLS® 73546074
Questions about this home
When was 50 Middlesex Street #50, Winchester listed?
50 Middlesex Street #50, Winchester was listed on July 7, 2026.
Has the price of 50 Middlesex Street #50, Winchester changed?
The price has come down from an original $799,000 to $774,900 across 2 changes, most recently on September 14, 2026.
What is the condo fee at 50 Middlesex Street #50, Winchester?
The condo fee is $81 per month.
What is the status of 50 Middlesex Street #50, Winchester?
50 Middlesex Street #50, Winchester is actively listed for sale.
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
2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: The North Star Group
Listing Office: Keller Williams Realty Evolution
MLS® Number: 73546074
