$1,895,000
268 Highland St
Milton, MA, 02186
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.
Property Details
Price:
$1,895,000
MLS #:
73523755
Status:
Active Under Contract
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
May 26, 2026
Finished Sq Ft:
2,987
Total Sq Ft:
2,987
Lot Size:
60,949 sqft / 1.40 acres (approx)
Year Built:
1938
Schools
Interior
Above Grade Finished Area
2987
Appliances
Oven, Dishwasher, Disposal, Range, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Ductless
Fireplaces Total
3
Heating
Baseboard, Natural Gas, Fireplace
Interior Features
Home Office, Bonus Room, Wet Bar
Laundry Features
In Basement
Exterior
Architectural Style
Colonial
Covered Spaces
2
Exterior Features
Patio, Rain Gutters, Barn/Stable, Professional Landscaping, Sprinkler System
Garage Spaces
2
Open Parking Spaces
8
Open Parking YN
1
Other Structures
Barn/Stable
Parking Features
Detached, Paved Drive
Parking Spots
10
Parking Total
10
Patio And Porch Features
Patio
Roof
Slate
Financial
Tax Year
2025
Taxes
$15,880
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 Milton as of Jun 02, 2026
65
Single Family Listed
58
Avg DOM
569
Avg $ / SqFt
$2,111,335
Avg List Price
Community
- Address268 Highland St Milton MA
- CityMilton
- CountyNorfolk
- Zip Code02186
Subdivisions in Milton
Similar Listings Nearby
Property Summary
- 268 Highland St Milton MA is a Single Family for sale in Milton, MA, 02186. It is listed for $1,895,000 and features 3 beds, 3 baths, and has approximately 2,987 square feet of living space, and was originally constructed in 1938. The current price per square foot is $634. The average price per square foot for Single Family listings in Milton is $569. The average listing price for Single Family in Milton is $2,111,335. To schedule a showing of MLS#73523755 at 268 Highland St in Milton, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Senné. 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.
268 Highland St
Milton, MA