Skip to content
Bean Group
← Back to search
Browse photos

Active

50 Holland Street

Winchester, MA 01890

Offered at$1,549,000

Residential · Active · MLS #73556633
Listing Courtesy of Compass | Kim Covino & Co. Team

3Bedrooms
3Bathrooms
2,640Square feet
1960Year built

Bean Group guidance

Useful next steps

Request property information

Select a document or report and Bean Group will help track it down.

Availability varies by property and source. Documents are requested from the appropriate source and may not be immediately available.

Considering this property?

Decide whether it deserves a closer look.

A local Bean Group agent can help you compare nearby inventory, understand the listing details, and identify the questions worth answering before you visit.

Compare nearby homes

MLS PIN data

About this home

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!

Property information

Details at a glance

Interior

Rooms
10
Heating
Forced Air, Oil
Cooling
Ductless
Flooring
Hardwood
Fireplaces
1

Building

Style
Single Family Residence
Year built
1960
Parking
4
Foundation
Concrete Perimeter
Roof
Shingle

Land & utilities

Lot size
0.15 acres
Water
Public
Sewer
Public Sewer
Zoning
RG

Financial

Annual taxes
$10,599
Assessment year
2025

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$1,605,724

Estimated range $1,526,980$1,684,468

Request a professional valuation →

Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Sold Jul 24, 2026$1,455,000

4 Westwood Road

Sold Jun 15, 2026$1,540,000

62 Shaw Rd

Sold Jul 1, 2026$1,459,450

63 Mossdale Rd

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Winchester

MetricThis propertyWinchester
List price$1,549,000$1,549,000Near the local benchmark
Price / sq ft$587$5654% above local
Days on market45192% below local
Explore homes in Winchester

Active city listing statistics from MLS PIN as of September 5, 2026. Asking prices are not completed-sale values.

Keep exploring

Similar homes nearby

Common questions

About 50 Holland Street

Can I schedule a private showing?

Yes. Request a tour of 50 Holland Street and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.