Sold Aug 13, 2026
$780,000Upcoming open house
Sun, Oct 18 · 11:00 AM–12:00 PM
Arrive prepared. Get the October 2026 Winchester Bean Group Buyer’s Guide before you tour.
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.
Listing last checked: Listing updated:
Listed by The North Star Group · Keller Williams Realty Evolution · MLS #73546074
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Details at a glance
Interior5 property facts
- Rooms
- 7
- Heating
- Central, Natural Gas, Hydro Air, ENERGY STAR Qualified Equipment
- Cooling
- Central Air, ENERGY STAR Qualified Equipment
- Flooring
- Tile, Hardwood, Stone / Slate
- Basement
- Yes
Building4 property facts
- Style
- Condominium
- Year built
- 1920
- Parking
- 2
- Roof
- Rubber, Asphalt/Composition Shingles
Land & utilities5 property facts
- Lot size
- 0.16 acres
- Water
- Public
- Sewer
- Public Sewer
- Pool
- Not reported
- Zoning
- Res
Financial2 property facts
- Assessment year
- 2026
- HOA fee
- $81 (billing period not supplied)
Location
Estimated monthly cost
Explore costs at the $769,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$3,888 / monthAdjust
- Principal & interest
- $3,888
- Property tax
- Not entered
- Insurance
- Not entered
- HOA
- Not entered
Annual property taxes were not supplied. Listing HOA fee: $81. The billing period was not supplied; confirm the monthly amount before adding it.
Partial estimate: add property tax, insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
More property insights
Automated value estimate $815,981
Estimated range $710,614–$921,348.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisComparable properties 3 supplied
Sold Aug 11, 2026
$812,00045-47 Chestnut St #3
Sold Jul 18, 2026
$695,000106 Thirteenth #316
Photo-based condition insights
Overall presentation: above average
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About 50 Middlesex Street #50
Can I request a private showing?
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.