50 Holland Street · Winchester

FOR SALE · MLS #73556633

$1,549,000

beds
3
baths
2.5
sqft
2,640

50 Holland Street

Winchester, MA 01890

LOCATION

Property location

Directions

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50 Holland Street, Winchester, MA 01890Open Street View

Nelson to Holland

Home type
Single Family Residence
Interior living area
2,640 sqft
Year built
1960
Lot size
6,625 sqft (about 0.15 acres)
Parking spaces
4
Price per sqft
$587/sqft

About this home

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!

Listed by Kim Covino & Co. Team · Compass
MLS PIN #73556633 · Updated 9/27/2026, 5:09:00 PM ET

Facts & features

Home overview
Property subtype
Single Family Residence
Property category
Residential
MLS status
Active
Bedrooms
3
Full bathrooms
2
Half bathrooms
1
Total bathrooms
2.5
Total rooms
10
Living area
2,640 sqft
Living area source
Measured
Above grade finished area
1,790 sqft
Below grade finished area
850 sqft
Building area
2,640
Building area units
Square Feet
Building area source
Measured
Area includes basement
Yes
Area disclosures
Measurements are for marketing purposes only.
Interior & systems
Heating
Baseboard · Oil
Heating available
Yes
Heating zones
3
Cooling
Ductless
Cooling available
Yes
Cooling zones
3
Appliances
Oven · Dishwasher · Disposal · Microwave · Range · Refrigerator · Freezer · Washer · Dryer · Wine Refrigerator
Flooring
Hardwood
Interior features
Closet · Lighting - Overhead · Wet bar · Recessed Lighting · Home Office · Kitchen · Wet Bar
Laundry
In Basement
Laundry dimensions
11X10
Fireplace
Yes
Fireplaces
1
Fireplace features
Living Room
Windows
Screens
Room details

Primary bedroom

Level
Second
Area
345 sqft
Length
23 ft
Width
15 ft
Features
Ceiling Fan(s) · Closet · Flooring - Hardwood

Bedroom 2

Level
Second
Area
299 sqft
Length
23 ft
Width
13 ft
Features
Ceiling Fan(s) · Closet · Flooring - Hardwood

Bedroom 3

Level
First
Area
180 sqft
Length
15 ft
Width
12 ft
Features
Ceiling Fan(s) · Closet · Flooring - Hardwood · Deck - Exterior · Exterior Access · Slider

Living room

Level
First
Area
252 sqft
Length
18 ft
Width
14 ft
Features
Ceiling Fan(s) · Closet/Cabinets - Custom Built · Flooring - Hardwood

Dining room

Level
First
Area
168 sqft
Length
14 ft
Width
12 ft
Features
Closet/Cabinets - Custom Built · Flooring - Hardwood · Wine Chiller · Lighting - Overhead

Family room

Level
Basement
Area
221 sqft
Length
17 ft
Width
13 ft
Features
Ceiling Fan(s) · Closet · Recessed Lighting

Kitchen

Level
Main,First
Area
264 sqft
Length
22 ft
Width
12 ft
Features
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

Level
Basement
Area
154 sqft
Length
14 ft
Width
11 ft
Features
Closet · Lighting - Overhead

Bathroom 1

Level
First
Area
64 sqft
Length
8 ft
Width
8 ft
Features
Bathroom - Full · Bathroom - Tiled With Tub & Shower · Flooring - Stone/Ceramic Tile · Recessed Lighting

Bathroom 2

Level
Second
Area
40 sqft
Length
8 ft
Width
5 ft
Features
Bathroom - Tiled With Tub & Shower · Lighting - Overhead

Bathroom 3

Level
Basement
Area
110 sqft
Length
11 ft
Width
10 ft
Features
Bathroom - Half

Price & tax details

Current asking price$1,549,000
Original asking price$1,549,000
Listed on2026-07-29
Days on market60
Tax record supplied by MLS
YearProperty taxAssessed value
2025$10,599$955,700

These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.

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SCHOOLS & EDUCATION

Schools & performance

2026 MA DESE

School names, grades and state-reported measures are listed below.

Schools named in the listing

93DESE percentile

MLS-listed elementary

Lynch Elementary

Grades PK · K · 1 · 2 · 3 · 4 · 5

Progress toward targets 78%

95DESE percentile

MLS-listed middle

McCall Middle

Grades 6 · 7 · 8

Progress toward targets 86%

—DESE percentile

MLS-listed high school

Whs

School name supplied by the listing; confirm with the district.

MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.
What do these numbers mean?

DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.

School names link to available school or district websites.

Information is deemed reliable but is not guaranteed. © 2026 MLS Property Information Network, Inc. All rights reserved.

Listings updated