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Set on over 1.4 acres in one of Milton's most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn-offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.

More Info

Basic Information

  • Bedrooms3
  • Mls StatusNew
  • Bathroom3
  • Parcel Number M:J B:014 L:8,133098

Basic Information

  • List Price$1,895,000
  • MLS Number73523755
  • Modification Date05/26/2026
  • Property SubTypeSingle Family Residence

Building

  • BasementPartially Finished
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplace Features Family Room, Living Room
  • Fireplaces Total 3
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Patio And Porch Features Patio
  • Property StyleColonial
  • Rooms9
  • Year Built1938
  • Year Built Details Actual
  • Year Built Source Public Records

Amenities

  • Appliances IncludedOven, Dishwasher, Disposal, Range, Refrigerator

Tax Information

  • Tax Assessed Value $1,431,900
  • Tax Year 2025
  • Taxes$15,880

Rooms

  • Bathroom 1 First
  • Bathroom 2 Second
  • Bathroom 3 Second
  • Bathrooms Total Decimal 2.5
  • Bedroom 2 Second
  • Bedroom 3 Second
  • Dining Room First
  • Family Room First
  • Full Bath2
  • Half Baths1
  • Kitchen First
  • Living Room First
  • Master Bedroom Second
  • Office First

Exterior

  • Exterior Features Patio, Rain Gutters, Barn/Stable, Professional Landscaping, Sprinkler System
  • RoofSlate

Property Information

  • Square Feet2,987
  • Building Area Source Public Records
  • Living Area 2,987
  • Lot Size Square Feet 60,949
  • Lot Size Units Acres

Parking

  • Parking Spaces10
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Detached, Paved Drive

Location

  • Address268 Highland Street
  • Building Number268
  • CountyNorfolk
  • StateMA
  • StreetHighland Street
  • TownMilton
  • Zip02186

Property

  • Acreage1.4
  • Other Structures Barn/Stable

Interior

  • Interior Features Home Office, Bonus Room, Wet Bar

Utilities

  • Cooling Central Air, Ductless
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Baseboard, Natural Gas, Fireplace
  • Sewer Public Sewer
  • Water Source Public

Other

  • Date Listed05/26/2026
  • Farm Land Area Units Square Feet

Map Location

Listed by Beth Rooney of eXp Realty

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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 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. MLSPIN 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.

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