Active
42 Days on market
50 Holland Street Winchester — Photo 1 of 42

50 Holland Street Winchester — Photo 1 of 42

$1,549,000

50 Holland Street, Winchester, MA 01890

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!

Immersive Experience

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$587/sqft
Local Avg (Winchester)$555/sqft
6% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$1,549,000
Annual Taxes$10,599

Parking

Garage0
Off-Street4

Interior Specifications

Total Rooms10
Fireplaces1
FlooringHardwood
BasementNone

Climate & Utilities

HeatingForced Air, Oil
CoolingDuctless
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRG

Property & Lot

Acres0.15
SqFt Lot6,625
Lot Features--

Amenities & Appliances

Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator

Neighborhood

Public Transportation • Shopping • Tennis Court(s) • Park • Golf • Medical Facility

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bathroom 2
First
Living RoomDining RoomBedroom 3Bathroom 1
Basement
OfficeFamily RoomBathroom 3
Main,First
Kitchen
Living Room
Lvl First

18 x 14

Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood

Dining Room
Lvl First

14 x 12

Closet/Cabinets - Custom Built, Flooring - Hardwood, Wine Chiller, Lighting - Overhead

Kitchen
Lvl Main,First

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

Office
Lvl Basement

14 x 11

Closet, Lighting - Overhead

Family Room
Lvl Basement

17 x 13

Ceiling Fan(s), Closet, Recessed Lighting

Master Bedroom
Lvl Second

23 x 15

Ceiling Fan(s), Closet, Flooring - Hardwood

Bedroom 2
Lvl Second

23 x 13

Bedroom 3
Lvl First

15 x 12

Ceiling Fan(s), Closet, Flooring - Hardwood, Deck - Exterior, Exterior Access, Slider

Bathroom 1
Lvl First

8 x 8

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Recessed Lighting

Bathroom 2
Lvl Second

8 x 5

Bathroom - Tiled With Tub & Shower, Lighting - Overhead

Bathroom 3
Lvl Basement

11 x 10

Bathroom - Half

Population

23,406

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$230K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

18.3%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Middlesex County

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)

ADU Potential

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 Provided By

Listing Agent: Kim Covino & Co. Team

Listing Office: Compass

MLS® Number: 73556633

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