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.
Sold for $2,000,000
$2,000,000
268 Highland St, Milton, MA 02186
3beds
2,987sqft
Single Family Residence
Built in 1938
1.4 Acres Lot
$2,007,400 Zestimate®
$670/sqft
$6,285 Estimated rent
Home value
$2,007,400
$1.89M - $2.13M
$6,285/mo
Zestimate® history
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$13,628/mo
Est. payment
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Est. payment
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List your homeWhat's special
Timeless brick-front colonialSlate roofMature landscapeExtraordinary three-story barnSweeping green lawnsCopper downspouts
Zillow last checked:
Listing updated:
Listed by:
Beth Rooney 617-922-2547,
eXp Realty LLC - Corporate Office 888-854-7493
Bought with:
Beth Rooney
eXp Realty LLC - Corporate Office
Source: MLS PIN,MLS#: 73523755
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s), Cedar Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood
- Level: Second
Bedroom 2
- Features: Flooring - Hardwood
- Level: Second
Bedroom 3
- Features: Flooring - Hardwood
- Level: Second
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Countertops - Stone/Granite/Solid
- Level: First
Bathroom 2
- Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower
- Level: Second
Bathroom 3
- Features: Bathroom - Full
- Level: Second
Dining room
- Features: Flooring - Hardwood
- Level: First
Family room
- Features: Cathedral Ceiling(s), Flooring - Hardwood, Window(s) - Picture, Wet Bar
- Level: First
Kitchen
- Features: Flooring - Hardwood, Window(s) - Picture, Dining Area, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Remodeled, Stainless Steel Appliances
- Level: First
Living room
- Features: Flooring - Hardwood
- Level: First
Office
- Level: First
Heating
- Baseboard, Natural Gas, Fireplace
Cooling
- Central Air, Ductless
Appliances
- Included: Oven, Dishwasher, Disposal, Range, Refrigerator
- Laundry: In Basement
Features
- Home Office, Bonus Room, Wet Bar
- Basement: Partially Finished
- Number of fireplaces: 3
- Fireplace features: Family Room, Living Room
Interior area
- Total structure area: 2,987
- Total interior livable area: 2,987 sqft
- Finished area above ground: 2,987
Property
Parking
- Total spaces: 10
- Parking features: Detached, Paved Drive
- Garage spaces: 2
- Uncovered spaces: 8
Features
- Patio & porch: Patio
- Exterior features: Patio, Rain Gutters, Barn/Stable, Professional Landscaping, Sprinkler System
Lot
- Size: 1.4 Acres
Details
- Additional structures: Barn/Stable
- Parcel number: M:J B:014 L:8,133098
- Zoning: RA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Foundation: Concrete Perimeter
- Roof: Slate
Condition
- Year built: 1938
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Milton
Financial & listing details
- Price per square foot: $670/sqft
- Tax assessed value: $1,431,900
- Annual tax amount: $15,880
- Date on market: 9/14/2026
Price history
| Date | Event | Price |
|---|---|---|
| 8/31/2026 | Sold | $2,000,000+5.5%$670/sqft |
Source: MLS PIN #73523755 Report a problem | ||
| 6/10/2026 | Pending sale | $1,895,000$634/sqft |
Source: MLS PIN #73523755 Report a problem | ||
| 6/2/2026 | Contingent | $1,895,000$634/sqft |
Source: MLS PIN #73523755 Report a problem | ||
| 5/26/2026 | Listed for sale | $1,895,000+136.9%$634/sqft |
Source: MLS PIN #73523755 Report a problem | ||
| 5/18/2006 | Sold | $800,000+23.1%$268/sqft |
Source: Public Record Report a problem | ||
| 12/1/2005 | Sold | $650,000$218/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $15,880 +3.6% | $1,431,900 +2% |
| 2024 | $15,333 +2.5% | $1,404,100 +7% |
| 2023 | $14,961 +5.2% | $1,312,400 +15% |
| 2022 | $14,226 -1.2% | $1,140,800 +4% |
| 2021 | $14,396 +2% | $1,096,400 +1.9% |
| 2020 | $14,118 +2.5% | $1,076,100 +3% |
| 2019 | $13,769 -1.2% | $1,044,700 +3.6% |
| 2018 | $13,930 +6.9% | $1,008,700 +5% |
| 2017 | $13,027 +9.5% | $960,700 +9% |
| 2016 | $11,894 +0.9% | $881,000 +4.2% |
| 2015 | $11,786 -3.4% | $845,500 +3.9% |
| 2014 | $12,202 +2% | $814,000 |
| 2013 | $11,966 +2.4% | $814,000 |
| 2012 | $11,681 +3.2% | $814,000 +1.2% |
| 2011 | $11,318 +2.9% | $804,400 -2.4% |
| 2010 | $11,000 +12.8% | $824,000 -0.8% |
| 2009 | $9,756 +0.7% | $831,000 -6% |
| 2008 | $9,684 +1% | $884,400 |
| 2007 | $9,587 +5.6% | $884,400 -1.1% |
| 2006 | $9,076 +10.3% | $894,200 +14.5% |
| 2005 | $8,231 +1.6% | $780,900 +16.8% |
| 2004 | $8,102 +1.9% | $668,500 -1.4% |
| 2003 | $7,954 -1.6% | $678,100 +41.5% |
| 2002 | $8,084 +18% | $479,200 +28% |
| 1999 | $6,853 | $374,300 |
Find assessor info on the county website
Neighborhood: 02186
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Nearby schools
GreatSchools rating
- 9/10Glover Elementary SchoolGrades: K-5Distance: 1.1 mi
- 8/10Charles S Pierce Middle SchoolGrades: 6-8Distance: 1 mi
- 10/10Milton High SchoolGrades: 9-12Distance: 0.8 mi
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Estimated market value
$2,007,400
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Estimated market value
$2,007,400
- Massachusetts
- Norfolk County
- Milton
- 02186
- 268 Highland St
