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Jared McBride
REALTOR®
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268 Highland St, Milton, MA 02186

$1,895,000
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Active Under Contract
BEDS3 BATHS2 full 1 partial SQUARE FEET2,987 MLS#73523755
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family

Property Description

Set on over 1.4 acres in one of Miltons 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.

268 Highland St | MLS# 73523755

This single family home located at 268 Highland St, Milton, MA 02186 is currently listed for sale with an asking price of $1,895,000. This property was built in 1938 and has 3 bedrooms and 2 full and 1 partial baths with 2987 sq. ft. Search Milton real estate on jaredmcbride.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Partially Finished
Basement: Yes
Cooling: Central Air, Ductless
Fireplaces: 3
Garage: 2
Heating: Baseboard, Natural Gas, Fireplace
Home Style: Colonial
Lot Size: 1.40 Acres
Roof Type: Slate
Taxes: $15,880
Year Built: 1938

Amenities

Home Office
Bonus Room
Wet Bar
Patio
Rain Gutters
Barn/Stable
Professional Landscaping
Sprinkler System

Feature Descriptions

Appliances: Oven, Dishwasher, Disposal, Range, Refrigerator
Building Area Total: 2987
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 9
Dining Room: Flooring - Hardwood
Family Room: Cathedral Ceiling(s), Flooring - Hardwood, Window(s) - Picture, Wet Bar
Fireplace Features: Family Room, Living Room
Fireplace Y/N: Yes
GarageY/N: Yes
HeatingY/N: 1
Kitchen: Flooring - Hardwood, Window(s) - Picture, Dining Area, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Remodeled, Stainless Steel Appliances
Laundry: In Basement
Living Room: Flooring - Hardwood
Master Bathroom: Yes
Master Bedroom: Walk-In Closet(s), Cedar Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood
Open Parking Y/N: Yes
Other Structures: Barn/Stable
Parcel Number: M:J B:014 L:8,133098
Parking Features: Detached, Paved Drive
Parking Total: 10
Patio And Porch: Patio
Rooms Total: 9
Sewer: Public Sewer
Water: Public

Listed By / Shown By

Listed By

Agency Name: eXp Realty LLC - Corporate Office
Agent Name: Beth Rooney
Agency Phone: 888-854-7493

Shown By

Agent Name: Jared McBride
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 6,093.49 per month $4,217.45 Principal & Interest $1,323.33 Property Tax $552.71 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/04/2026. The listing information on this page last changed on 06/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 06/04/2026 12:01:23 AM EST) or MLSPIN MLS (last updated Wed 06/03/2026 11:38:42 PM EST) or Prime MLS (last updated Wed 06/03/2026 11:33:45 PM EST) or MREIS (last updated Wed 06/03/2026 11:55:16 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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