Active
64 Days on market
50 Middlesex Street #50 Winchester — Photo 1 of 21

50 Middlesex Street #50 Winchester — Photo 1 of 21

Recent Drop: $10,000

$799,000
$789,000

$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

This Property
Size (SqFt) →Price →
This Property$762/sqft
Local Avg (Winchester)$599/sqft
27% AboveMarket Average

* Analysis is based on 11 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$799,000
Annual Taxes--
HOA Fee$81.2

Parking

Garage0
Off-Street2

Interior Specifications

Total Rooms7
FireplacesNone
FlooringTile, Hardwood, Stone / Slate
BasementY

Climate & Utilities

HeatingCentral, Natural Gas, Hydro Air, ENERGY STAR Qualified Equipment
CoolingCentral Air, ENERGY STAR Qualified Equipment
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionStone, Post & Beam, Conventional (2x4-2x6)
RoofRubber, Asphalt/Composition Shingles
Foundation--
ZoningRes

Property & Lot

Acres0.16
SqFt Lot7,009
Lot Features--

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

Second
Master Bedroom
Main,First
Living RoomDining RoomKitchenBedroom 2
Living Room
Lvl Main,First

13.4 x 11.4

Bathroom - Full, Closet, Flooring - Hardwood, Open Floorplan, Recessed Lighting, Remodeled

Dining Room
Lvl Main,First

10.3 x 15

Bathroom - Full, Closet, Flooring - Hardwood, Open Floorplan, Recessed Lighting, Remodeled

Kitchen
Lvl Main,First

9 x 8.1

Flooring - Hardwood, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Cabinets - Upgraded, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled

Master Bedroom
Lvl Second

11.2 x 9.2

Closet, Flooring - Hardwood, Recessed Lighting

Bedroom 2
Lvl Main,First

11.3 x 9

Property History

Price Drop
$789,000

Was $799,000

Aug 24, 2026

MLS® 73546074

Listed
$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 Provided By

Listing Agent: The North Star Group

Listing Office: Keller Williams Realty Evolution

MLS® Number: 73546074

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