Skip to content
All Winchester homes
1 / 38
ActiveListed 62 days ago

$1,899,000

85 High St, Winchester, MA 01890

4
beds
2.5
baths
3,757
sqft
Lot sizeThe land that comes with the home, as reported to the MLS.
0.29 acres
Year builtThe year the building was originally built, as reported by the listing agent.
1931
On the marketDays since the home was listed. New listings tend to move fastest.
62 days ago
Property type
Single Family Residence
Price per sqftList price divided by interior living area — handy for comparing homes of different sizes.
$505
ParkingSpaces that come with the home, as reported to the MLS.
6 spaces
Annual taxesLast annual property tax bill reported to the MLS. A new owner's bill can differ.
$15,671

What’s Special

  • Heated Garage
  • Central Air
  • Patio
  • Fenced Yard

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

Listing courtesy of Catherine Albiani, Better Homes and Gardens Real Estate - The Shanahan Group · MLS PIN #73565817

Facts & Features

Status
Active
Active status flag
Active
Bedrooms
4
Bathrooms
2 full, 1 half
Living area
3,757 sqft

Interior

4
  • Dining Area
  • Breakfast Bar / Nook
  • Foyer
  • Bonus Room

Exterior

6
  • Patio
  • Rain Gutters
  • Professional Landscaping
  • Sprinkler System
  • Screens
  • Fenced Yard

Parking

6
  • Detached
  • Garage Door Opener
  • Heated Garage
  • Storage
  • Off Street
  • Paved

Laundry

3
  • Second Floor
  • Electric Dryer Hookup
  • Washer Hookup

Heating

2
  • Steam
  • Natural Gas

Cooling

1
  • Central Air

Appliances

8
  • Water Heater
  • Oven
  • Dishwasher
  • Disposal
  • Range
  • Refrigerator
  • Washer
  • Dryer

MLS PIN #73565817 · Listed August 19, 2026

Location

85 High St, Winchester · All Winchester homes

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.

$1,899,000

85 High St

Similar Homes

All Winchester homes →
1 Overlook Way1 / 40
Active

$1,750,000

4 bd · 2.5 ba · 3,604 sqft · Single Family

1 Overlook Way

Winchester, MA 01890

Listing courtesy of Lynne Russo, Better Homes and Gardens Real Estate - The Shanahan Group · MLS PIN #73581571

9 Plymouth Rd1 / 37
Active

$2,250,000

5 bd · 3 ba · 4,071 sqft · Single Family

9 Plymouth Rd

Winchester, MA 01890

Listing courtesy of Steph Crawford Group, Real Broker MA, LLC · MLS PIN #73544924

25 Arlington St1 / 32
Active

$1,529,000

4 bd · 3.5 ba · 2,709 sqft · Single Family

25 Arlington St

Winchester, MA 01890

Listing courtesy of Domingo Medina, Coldwell Banker Realty - Lexington · MLS PIN #73584817

30 Surrey Rd1 / 42
ActiveNew · 6 days ago

$1,985,000

4 bd · 3.5 ba · 4,241 sqft · Single Family

30 Surrey Rd

Winchester, MA 01890

Listing courtesy of Anne Spry, Barrett Sotheby's International Realty · MLS PIN #73589478

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.