
50 Holland Street Winchester — Photo 1 of 42
$1,549,000
Winchester, MA 01890
Beds
3
Baths
2.5
SqFt
2,640
Style
Single Family
Built
1960
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!
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator
Public Transportation • Shopping • Tennis Court(s) • Park • Golf • Medical Facility
18 x 14
Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood
14 x 12
Closet/Cabinets - Custom Built, Flooring - Hardwood, Wine Chiller, Lighting - Overhead
22 x 12
Flooring - Stone/Ceramic Tile, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Lighting - Pendant
14 x 11
Closet, Lighting - Overhead
17 x 13
Ceiling Fan(s), Closet, Recessed Lighting
23 x 15
Ceiling Fan(s), Closet, Flooring - Hardwood
23 x 13
15 x 12
Ceiling Fan(s), Closet, Flooring - Hardwood, Deck - Exterior, Exterior Access, Slider
8 x 8
Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Recessed Lighting
8 x 5
Bathroom - Tiled With Tub & Shower, Lighting - Overhead
11 x 10
Bathroom - Half
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,640 sq ft principal dwelling). Lot size: 6,625 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73556633
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