$1,549,000
50 Holland Street
Winchester, MA, 01890
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 Details
Price:
$1,549,000
MLS #:
73556633
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jul 29, 2026
Finished Sq Ft:
2,640
Total Sq Ft:
2,640
Lot Size:
6,625 sqft / 0.15 acres (approx)
Year Built:
1960
Schools
Elementary School:
Lynch
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
1790
Appliances
Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
850
Cooling
Ductless
Fireplaces Total
1
Flooring
Hardwood
Heating
Forced Air, Oil
Interior Features
Closet, Lighting – Overhead, Wet bar, Recessed Lighting, Home Office, Kitchen, Wet Bar
Laundry Features
In Basement
Exterior
Architectural Style
Cape
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access
Construction Materials
Frame
Exterior Features
Deck, Patio, Covered Patio/Deck, Cabana, Rain Gutters, Hot Tub/Spa, Storage, Paddock, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Garden, Stone Wall
Fencing
Fenced
Open Parking Spaces
4
Open Parking YN
1
Other Structures
Cabana
Parking Features
Paved Drive
Parking Spots
4
Parking Total
4
Patio And Porch Features
Deck, Patio, Covered
Roof
Shingle
Spa Features
Private
Window Features
Screens
Financial
Tax Year
2025
Taxes
$10,599
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of Jul 31, 2026
59
Single Family Listed
67
Avg DOM
557
Avg $ / SqFt
$1,993,317
Avg List Price
Community
- Address50 Holland Street Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 50 Holland Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,549,000 and features 3 beds, 3 baths, and has approximately 2,640 square feet of living space, and was originally constructed in 1960. The current price per square foot is $587. The average price per square foot for Single Family listings in Winchester is $557. The average listing price for Single Family in Winchester is $1,993,317. To schedule a showing of MLS#73556633 at 50 Holland Street in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Compass. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
50 Holland Street
Winchester, MA