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Active

50 Middlesex Street #50

Winchester, MA 01890

Offered at$789,000

Residential · Active · MLS #73546074
Listing Courtesy of Keller Williams Realty Evolution | The North Star Group

2Bedrooms
2Bathrooms
1,036Square feet
1920Year built

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MLS PIN data

About this home

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.

Property information

Details at a glance

Interior

Rooms
7
Heating
Central, Natural Gas, Hydro Air, ENERGY STAR Qualified Equipment
Cooling
Central Air, ENERGY STAR Qualified Equipment
Flooring
Tile, Hardwood, Stone / Slate

Building

Style
Condominium
Year built
1920
Parking
2
Roof
Rubber, Asphalt/Composition Shingles

Land & utilities

Lot size
0.16 acres
Water
Public
Sewer
Public Sewer
Zoning
Res

Financial

Assessment year
2026
HOA fee
81.2

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$815,981

Estimated range $710,614$921,348

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Sold Jul 14, 2026$735,000

67 Webster St #2

Sold Jul 5, 2026$760,000

8-10 Fordham St. #1

Sold Jun 16, 2026$787,000

61 North Street #1

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Winchester

MetricThis propertyWinchester
List price$789,000$1,549,00049% below local
Price / sq ft$762$56535% above local
Days on market585114% above local
Explore homes in Winchester

Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 50 Middlesex Street #50

Can I schedule a private showing?

Yes. Request a tour of 50 Middlesex Street #50 and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.