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50 Middlesex Street 50Winchester, MA 01890

For Sale

$799,000

Smart Buyer Rebate $3,480

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.

Listed by Taylor Johnson

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Keller Williams Realty Evolution

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617-820-8964

Listed by The North Star Group

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Keller Williams Realty Evolution

Last updated July 31, 2026

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Source: MLSPin #73546074

Listing Facts

  • TypeCondo
  • NeighborhoodNorth Main
  • Bedrooms2
  • Bathrooms2
  • Days on Prevu25
  • HOA/Maint. Fees$81.2/month
  • Size1,036 sqft
  • Price per sqft$771

Amenities

  • Private Outdoor Space
  • Pets Allowed
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

07/07/2026
Listed by Keller Williams Realty Evolution
$799,000

Property Details for 50 Middlesex Street 50

Association

Amenities

  • Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House Of Worship, Private School, Public School, T-Station, University
  • Pets Allowed: Yes

Fees

  • Association Fee: $81.20 Monthly
  • Association Fee Includes: Sewer, Insurance

Exterior

Construction

  • Number Of Units Total: 2
  • Roof: Rubber, Asphalt/Composition Shingles
  • Stories: 2
  • Stories Total: 2
  • Structure Type: Townhouse
  • Window Features: Insulated Windows, Screens
  • Year Built: 1920
  • Year Built Details: Actual
  • Building Name: 50-52 Middlesex St Townhomes
  • Common Walls: End Unit
  • Construction Materials: Stone, Post & Beam, Conventional (2x4-2x6)
  • Entry Level: 1
  • Exterior Features: Deck - Composite, Patio - Enclosed, Covered Patio/Deck, Storage, Fenced Yard, Garden, Screens, Rain Gutters, Professional Landscaping

Features

  • Fencing: Security, Fenced
  • Patio And Porch Features: Deck - Composite, Patio - Enclosed, Covered
  • Waterfront Features: Lake/Pond, 1/2 To 1 Mile To Beach, Beach Ownership(Public)

Measurements

  • Building Area Total: 1,036
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.16
  • Lot Size Area: 0
  • Lot Size Square Feet: 7,009
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 898750
  • Tax Assessed Value: $999,999,999.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Disposal, Microwave, Freezer, ENERGY STAR Qualified Refrigerator, ENERGY STAR Qualified Dishwasher, Range
  • Flooring: Tile, Hardwood, Stone / Slate
  • Interior Features: Finish - Sheetrock, Internet Available - Unknown

Measurements

  • Living Area: 1,036
  • Living Area Source: Unit Floor Plan

Rooms

  • Basement: Y
  • Bathrooms Full: 2
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 2
  • Main Level Bedrooms: 1
  • Rooms Total: 7

Other

Environmental

  • Green Energy Efficient: Thermostat

Parking

Parking

  • Open Parking Spaces: 2
  • Open Parking: Yes
  • Parking Features: Off Street, Tandem, Deeded, Paved
  • Parking Total: 2

Schools

Elementary School

  • Elementary School: Lynch Elementary

High School

  • High School: Winchester High

Middle or Junior School

  • Middle Or Junior School: Mccall Middle

Utilities

Equipment

  • Cooling: Central Air, ENERGY STAR Qualified Equipment
  • Has Cooling: Yes
  • Electric: Circuit Breakers, 100 Amp Service
  • Heating: Central, Natural Gas, Hydro Air, ENERGY STAR Qualified Equipment
  • Has Heating: Yes
  • Laundry Features: In Building, In Unit, Electric Dryer Hookup
  • Sewer: Public Sewer
  • Utilities: For Gas Range, For Electric Dryer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this condo have?

There are 2 bedrooms and 2 bathrooms in this condo at 50 Middlesex Street 50.

What schools are nearby to 50 Middlesex Street 50?

Nearby schools include the Lynch Elementary, Mccall Middle, and Winchester High.

Does this condo have parking?

Yes, there are 2 parking spaces available for 50 Middlesex Street 50.

Are pets allowed at 50 Middlesex Street?

Yes, 50 Middlesex Street allows pets.

How does 50 Middlesex Street 50 compare to other condos in North Main?

This condo is listed 3% below the average price for condos in North Main and has been on the market for 21 less days than the typical home in this area.

What building or home owners association is the condo part of?

This condo is in the 50-52 Middlesex St Townhomes building.

What is the square footage on this condo?

According to the MLS, this listing is 1,036 sqft.

50 Middlesex Street 50 is a 2-bedroom, 2-bath condo for sale in Winchester MA 01890. On Prevu for 25 days at $799,000. This residence features 1,036 square feet of living space, located in North Main. The median listing price for condos in this area is $1,131,500. Nearby schools include Lynch Elementary, Mccall Middle, and Winchester High. The home offers private outdoor space, pets allowed, air conditioning, parking, and swimming pool. View other condo listings in Middlesex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.