
Active
50 Holland Street
Winchester, MA 01890
Residential · Active · MLS #73556633
Listing Courtesy of Compass | Kim Covino & Co. Team
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MLS PIN data
About this home
Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!
Property information
Details at a glance
Interior
- Rooms
- 10
- Heating
- Forced Air, Oil
- Cooling
- Ductless
- Flooring
- Hardwood
- Fireplaces
- 1
Building
- Style
- Single Family Residence
- Year built
- 1960
- Parking
- 4
- Foundation
- Concrete Perimeter
- Roof
- Shingle
Land & utilities
- Lot size
- 0.15 acres
- Water
- Public
- Sewer
- Public Sewer
- Zoning
- RG
Financial
- Annual taxes
- $10,599
- Assessment year
- 2025
Listing history
Price and status timeline
No additional public listing history was supplied for this property.
Property value estimate
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Comparable sales
Recent properties for context


62 Shaw Rd

63 Mossdale Rd
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Generated from listing photography; not a substitute for an inspection.
Local market context
How this home compares in Winchester
Active city listing statistics from MLS PIN as of September 5, 2026. Asking prices are not completed-sale values.
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Common questions
About 50 Holland Street
Can I schedule a private showing?
Yes. Request a tour of 50 Holland Street 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.




