Active
67 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

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!

Key facts

It was listed on July 29, 2026. The annual property taxes are $10,599 (2025 tax year). It sits on a 0.15-acre (6,625 sq ft) lot.

Immersive Experience

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$587/sqft
Local Avg (Winchester)$559/sqft
5% 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

HeatingBaseboard, 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
Primary 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

Primary 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

Questions about this home

When was 50 Holland Street, Winchester listed?

50 Holland Street, Winchester was listed on July 29, 2026.

Has the price of 50 Holland Street, Winchester changed?

The price hasn't changed since it was listed at $1,549,000.

What are the property taxes for 50 Holland Street, Winchester?

The annual property taxes for 50 Holland Street, Winchester are $10,599 (2025 tax year).

How big is the lot at 50 Holland Street, Winchester?

50 Holland Street, Winchester sits on a 0.15-acre (6,625 sq ft) lot.

What is the status of 50 Holland Street, Winchester?

50 Holland Street, Winchester is actively listed for sale.

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

2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '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