FeaturesFlooring - Hardwood
LevelSecond
268 Highland St, Milton MA 02186
Milton, MA 02186
$1,895,000
Est. $11,105/month
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About this home
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.
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Property History
Market Insights
Property Timeline
Status: Active under contract
Jun 2, 2026
Active → Active Under Contract
Pending Sale
Jun 2, 2026
Offer accepted, sale pending
Listed for Sale
May 26, 2026
$1,895,000
Original listing
Agent: Beth Rooney
Office: eXp Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/02/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 06/02/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 05/26/2026 | 🏠 Listed for Sale | $1,895,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $15,880 | $1,431,900 |
Financial Details
Annual Property Tax
$15,880
Tax Year 2025
Assessed Value
$1,431,900
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1938
Living Area
2,987 sq ft
Lot Size
1.40 acres
Bedrooms
3
Full Baths
2
Half Baths
1
Total Rooms
9
Interior
Heating
Baseboard, Natural Gas, Fireplace
Cooling
Central Air, Ductless
Flooring
None
Appliances
Oven, Dishwasher, Disposal, Range, Refrigerator
Fireplace
Family Room, Living Room
Fireplaces
3
Basement
Partially Finished
Laundry
In Basement
Features
Home Office, Bonus Room, Wet Bar
Exterior
Construction
None
Architecture
Colonial
Roof
Slate
Features
Patio, Rain Gutters, Barn/stable, Professional Landscaping, Sprinkler System
Pool
None
Spa
None
Fencing
None
Patio/Porch
Patio
Parking
Garage Spaces
2
Has Garage
Yes
Features
Detached, Paved Drive
Total Spaces
10
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$15,880
Assessed Value
$1,431,900
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Home Was Originally A 4 Bedroom, One Bedroom Was Converted Into Walk In Closet. Three Story Barn With Much Potential. Barn Sold As-is. Buyer To Do Due Diligence To Determine Future Use As An Adu.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
brick
Sq Ft Source
Public Record
Documents
None
County
Norfolk
Total market time (incl. prior listings)
15 days
Property Overview
Property Type
Single Family Residence
Listing Type
Sale Pending
Year Built
1938
Bedrooms
3
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,987 sq ft
Total Rooms
9
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,987 sq ft above grade
FeaturesBathroom - Full, Bathroom - Tiled With Tub & Shower
LevelSecond
FeaturesFlooring - Hardwood
LevelSecond
FeaturesBathroom - Full
LevelSecond
FeaturesWalk-In Closet(s), Cedar Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood
LevelSecond
FeaturesBathroom - Half, Countertops - Stone/Granite/Solid
LevelFirst
FeaturesFlooring - Hardwood
LevelFirst
FeaturesFlooring - Hardwood, Window(s) - Picture, Dining Area, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Remodeled, Stainless Steel Appliances
LevelFirst
FeaturesFlooring - Hardwood
LevelFirst
LevelFirst
FeaturesCathedral Ceiling(s), Flooring - Hardwood, Window(s) - Picture, Wet Bar
LevelFirst
FeaturesYes
Display Options
Outdoor Areas
Patio & porchPatio
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Oven, Dishwasher, Disposal, Range, Refrigerator
Interior Features:
Home Office, Bonus Room, Wet Bar
Windows:
Basement:
Partially Finished
Laundry:
In Basement
Security:
Construction & Materials
Style:
Colonial
Year Built:
1938
Structure Type:
Exterior Materials:
Roof:
Slate
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Baseboard, Natural Gas, Fireplace
Cooling:
Central Air, Ductless
Cooling Zones:
2
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio, Rain Gutters, Barn/Stable, Professional Landscaping, Sprinkler System
Patio & Porch:
Patio
Fencing:
Other Structures:
Barn/Stable
Lot Features:
Road Surface:
Parking & Garage
Garage Spaces:
2
Total Parking Spaces:
10
Parking Features:
Detached, Paved Drive
Special Features
Fireplaces:
3
Fireplace Type:
Family Room, Living Room
Community Amenities:
Nearby Schools
School District
Milton School District local
A+
School Safety
2024-25
0.3%
Low
0.2%
Suspensions
0.1%
In-School
0.1%
Emergency
5.2% below state avg
Elementary Schools
10 schools
Milton Academy
0.8 mi
Grades K-12
St. Mary of the Hills Elementary School
1.4 mi
Grades PK-08
Delphi Academy
1.6 mi
Grades K-08
St. Agatha Elementary School
1.8 mi
Grades K-08
Thacher Montessori School
2.8 mi
Grades PK-08
A+
Glover School
1.1 mi
|
#48 of 824
|
Score: 62.5
Improved 61 spots from last year
+4.3 above state avg
593 students
Moderate
Rising School
Strong Attendance
Grades K-05
A+
Collicot School
1.2 mi
|
#36 of 824
|
Score: 63.5
Improved 68 spots from last year
+5.3 above state avg
623 students
Moderate
Rising School
Strong Attendance
Grades K-05
A+
Cunningham School
1.2 mi
|
#46 of 824
|
Score: 62.6
Improved 54 spots from last year
+4.4 above state avg
612 students
Moderate
Rising School
Grades PK-05
Wilson-Kindelan School
1.5 mi
Grades K-04
A-
Tucker School
1.5 mi
|
#188 of 824
|
Score: 55.7
Improved 99 spots from last year
-2.5 below state avg
454 students
Very Diverse
Rising School
Diverse Student Body
Grades PK-05
Middle Schools
1 school
A
Charles S Pierce Middle School
1.0 mi
|
#47 of 352
|
Score: 57.5
Improved 17 spots from last year
-0.8 below state avg
1,002 students
Diverse
Grades 06-08
High Schools
2 schools
A+
Milton High School
0.8 mi
|
#22 of 346
|
Score: 73.1
Improved 4 spots from last year
+14.9 above state avg
1,083 students
Diverse
21 sports
• 2,432 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
Fontbonne Academy
1.2 mi
12 sports
• 564 athletes
Grades 09-12
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Homeowners Insurance
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Loan Summary
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95% Interest
Year 15
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Location
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Neighborhood
268 Highland St, Milton MA 02186
Milton, MA 02186
Listing Information
Listing Agent
Beth Rooney
Listing Office
eXp Realty LLC - Corporate Office
Office Phone
888-854-7493
Agent MLS ID
BB803693
Office MLS ID
AC0342
Listing Data Updated
Aug 13, 2026 12:04 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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