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For Sale

50 Holland Street, Winchester MA 01890

Winchester, MA 01890

$1.55M
3 BD · 3 BA · 2,640 sf · 0.15 ac · Built 1960
The residence

Private showings available! Resort living just steps from the town center! Completely remodeled with 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 primary 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!

At a glance
Property type
Single Family Residence
Status
Active
Year built
1960
Lot size
0.15 acres
Living area
2,640 sf
MLS#
c554bde0b2e2d9ea14331fbfe0bc0305
Beds · Baths
3 · 3
Location

Winchester, MA.

Winchester, Massachusetts, is a market our advisors follow closely — its streets, housing stock and setting each shape what a residence here is worth and how it lives day to day. We are glad to walk you through the locale in detail, and how this particular address sits within it.

Estimated Monthly Payment+
$8K/mo
Approximate · principal & interest only
Display Currency
$1.55M

Indicative conversion — settlement always in USD.

Private Showing

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Listing courtesy of Compass · MLSPIN

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Listings updated Sep 27, 2026

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