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50 Holland StreetWinchester, MA 01890

For Sale

$1,549,000

Smart Buyer Rebate $7,745

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!

Listed by Kim Covino

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Compass

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781-249-3854

Listed by Kim Covino & Co. Team

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Compass

Last updated July 30, 2026

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Source: MLSPin #73556633

Listing Facts

  • TypeSingle-family
  • NeighborhoodWinchester Town Center
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu3
  • Taxes$10,599/year
  • Size2,640 sqft
  • Price per sqft$587

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Parking

Location

Mortgage Calculator

Listing History

07/29/2026
Listed by Compass
$1,549,000

Property Details for 50 Holland Street

Association

Amenities

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access

Exterior

Construction

  • Roof: Shingle
  • Window Features: Screens
  • Year Built: 1960
  • Year Built Details: Renovated Since
  • Architectural Style: Cape
  • 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

Features

  • Fencing: Fenced
  • Other Structures: Cabana
  • Patio And Porch Features: Deck, Patio, Covered
  • Road Frontage Type: Public

Measurements

  • Building Area Total: 2,640
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.15
  • Lot Size Area: 0
  • Lot Size Square Feet: 6,625
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:010 B:0086 L:0,897033
  • Tax Annual Amount: $10,599.00
  • Tax Assessed Value: $955,700.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Hardwood
  • Interior Features: Closet, Lighting - Overhead, Wet Bar, Recessed Lighting, Home Office, Kitchen, Wet Bar
  • Spa Features: Private
  • Spa: Yes

Measurements

  • Living Area: 2,640
  • Living Area Source: Measured

Rooms

  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3
  • Rooms Total: 10

Parking

Parking

  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Paved Drive
  • Parking Total: 4

Schools

Elementary School

  • Elementary School: Lynch

High School

  • High School: Whs

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Ductless
  • Has Cooling: Yes
  • Heating: Forced Air, Oil
  • Has Heating: Yes
  • Laundry Features: In Basement
  • Sewer: Public Sewer
  • Utilities: For Electric Range
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 3 bathrooms in this single-family home at 50 Holland Street.

What schools are nearby to 50 Holland Street?

Nearby schools include the Lynch Elementary School, Mccall Middle School, and Whs High School.

Does this single-family home have parking?

Yes, there are 4 parking spaces available for 50 Holland Street.

What are the annual taxes for 50 Holland Street?

Annual taxes for this single-family home are estimated at $10,599.

How does 50 Holland Street compare to other single-family homes in Winchester Town Center?

This single-family home is listed 11% below the average price for single-family homes in Winchester Town Center and has been on the market for 39 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,640 sqft.

50 Holland Street is a 3-bedroom, 3-bath single-family home for sale in Winchester MA 01890. On Prevu for 3 days at $1,549,000. This home features 2,640 square feet of living space, located in Winchester Town Center. The median listing price for single-family homes in this area is $999,900. Nearby schools include Lynch Elementary School, Mccall Middle School, and Whs High School. Additional amenities include private outdoor space, dishwasher, parking, and washer/dryer. View other single-family home listings in Middlesex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.