268 Highland St Milton, MA ^$ 1,895,000

268 Highland St

^$ 1,895,000

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Open House 5/29 11am - 12:30pm

268 Highland St

Milton, MA, 02186

^$ 1,895,000

Bedrooms3 Baths2.1 Sq 2,987

Monthly Estimate*

^$ 11,668

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Single Family Home for sale in Milton, MA

for $1,895,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,987 square foot home was built in 1938 on a lot size of 1.4.

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.

Open House

5/29/2026 11:00 AM - 12:30 PM

5/30/2026 11:30 AM - 1:00 PM

5/31/2026 1:00 PM - 2:30 PM

268 Highland St Milton, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

^$ 1,895,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 15,880

Style

Colonial

Lot Size

1.4

Year Built

1938

Town/City

Milton

County/Region

Norfolk

MLS | Web ID

73523755

List By

Beth Rooney

Listing Agent

Exp Realty

Broker

Affordability Calculator

$12,991

Per Month

Monthly Principal & Interest: $11,668
Monthly Property Taxes: $1,323
Monthly Home Insurance: --

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Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Milton, MA

Average List Price ^$2,392,328

Percent of Sale Price 26%

About Milton, MA

27,252 Population

4% Since 2002

^$123,529 Median Income

42.17 Median Age

36% Households with Children

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Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
5/26/2026	$1,895,000		Listed Price

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268 Highland St, Milton, MA, 02186 is a Single Family Home for sale at $1,895,000 with 2,987 sqft and a lot size of 1.4. 268 Highland St has 3 bedrooms, 2.1 baths, and was built in 1938. The property's zip code is 02186 which is in Milton, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 5/28/2026.

The real estate information and related content displayed on this site 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.

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 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 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, or as to the accuracy of any of the Images, set forth herein.

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268 Highland St

Single Family Home for sale in Milton, MA

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