Single Family Residence at 50 Holland Street, Winchester MA 01890
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 2 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 3 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 4 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 5 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 6 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 7 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 8 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 9 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 10 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 11 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 12 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 13 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 14 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 15 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 16 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 17 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 18 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 19 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 20 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 21 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 22 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 23 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 24 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 25 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 26 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 27 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 28 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 29 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 30 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 31 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 32 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 33 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 34 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 35 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 36 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 37 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 38 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 39 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 40 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 41 of 42
Single Family Residence at 50 Holland Street, Winchester MA 01890, photo 42 of 42
42 photos

$1,549,000

50 Holland Street, Winchester MA 01890
Winchester, MA 01890
Listed by Kim Covino & Co. Team
Bedrooms
3
Bathrooms
2.5
Living area
2,640 sqft
Year built
1960

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!

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73556633
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
84
On market date
July 29, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
N/A
Parking spaces
4
Lot size
0.15 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Muraco Elementary
0.37 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
345
Student:teacher ratio
11.9:1
District
Winchester
Middle
McCall Middle
0.56 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Winchester High School
0.11 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,349
Student:teacher ratio
13.8:1
District
Winchester

Walkability

Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

88
Highly walkable
out of 100
EPA National Walkability Index
17.3 / 20 -- Most walkable
Google Places amenity density
90 / 100
Restaurants & cafes20
Grocery stores2
Parks15
Schools20
Transit stops20
Pharmacies3

Market position

How this listing compares to current activity in Winchester, from live MLS data.

On the market 84 days -- 1 more days than Winchester's current average of 83 days.
For reference, the median list price across 176 active listings in Winchester right now is $799,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$9,478/mo
$309,800 down
$1,239,200 loan
Principal & interest$8,037
Property tax (est.)$1,291
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 25 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.