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268 Highland St, Milton MA 02186 - Preview 1 268 Highland St, Milton MA 02186 - Preview 2 268 Highland St, Milton MA 02186 - Preview 3 268 Highland St, Milton MA 02186 - Preview 4 268 Highland St, Milton MA 02186 - Preview 5 268 Highland St, Milton MA 02186 - Preview 6 268 Highland St, Milton MA 02186 - Preview 7 268 Highland St, Milton MA 02186 - Preview 8 268 Highland St, Milton MA 02186 - Preview 9 268 Highland St, Milton MA 02186 - Preview 10 268 Highland St, Milton MA 02186 - Preview 11 268 Highland St, Milton MA 02186 - Preview 12 268 Highland St, Milton MA 02186 - Preview 13 268 Highland St, Milton MA 02186 - Preview 14 268 Highland St, Milton MA 02186 - Preview 15 268 Highland St, Milton MA 02186 - Preview 16 268 Highland St, Milton MA 02186 - Preview 17 268 Highland St, Milton MA 02186 - Preview 18 268 Highland St, Milton MA 02186 - Preview 19 268 Highland St, Milton MA 02186 - Preview 20 268 Highland St, Milton MA 02186 - Preview 21 268 Highland St, Milton MA 02186 - Preview 22 268 Highland St, Milton MA 02186 - Preview 23 268 Highland St, Milton MA 02186 - Preview 24 268 Highland St, Milton MA 02186 - Preview 25 268 Highland St, Milton MA 02186 - Preview 26 268 Highland St, Milton MA 02186 - Preview 27 268 Highland St, Milton MA 02186 - Preview 28 268 Highland St, Milton MA 02186 - Preview 29 268 Highland St, Milton MA 02186 - Preview 30 268 Highland St, Milton MA 02186 - Preview 31 268 Highland St, Milton MA 02186 - Preview 32 268 Highland St, Milton MA 02186 - Preview 33 268 Highland St, Milton MA 02186 - Preview 34 268 Highland St, Milton MA 02186 - Preview 35 268 Highland St, Milton MA 02186 - Preview 36 268 Highland St, Milton MA 02186 - Preview 37
268 Highland St, Milton MA 02186 - Preview 1 268 Highland St, Milton MA 02186 - Preview 2 268 Highland St, Milton MA 02186 - Preview 3 268 Highland St, Milton MA 02186 - Preview 4 268 Highland St, Milton MA 02186 - Preview 5 268 Highland St, Milton MA 02186 - Preview 6 268 Highland St, Milton MA 02186 - Preview 7 268 Highland St, Milton MA 02186 - Preview 8 268 Highland St, Milton MA 02186 - Preview 9 268 Highland St, Milton MA 02186 - Preview 10 268 Highland St, Milton MA 02186 - Preview 11 268 Highland St, Milton MA 02186 - Preview 12 268 Highland St, Milton MA 02186 - Preview 13 268 Highland St, Milton MA 02186 - Preview 14 268 Highland St, Milton MA 02186 - Preview 15 268 Highland St, Milton MA 02186 - Preview 16 268 Highland St, Milton MA 02186 - Preview 17 268 Highland St, Milton MA 02186 - Preview 18 268 Highland St, Milton MA 02186 - Preview 19 268 Highland St, Milton MA 02186 - Preview 20 268 Highland St, Milton MA 02186 - Preview 21 268 Highland St, Milton MA 02186 - Preview 22 268 Highland St, Milton MA 02186 - Preview 23 268 Highland St, Milton MA 02186 - Preview 24 268 Highland St, Milton MA 02186 - Preview 25 268 Highland St, Milton MA 02186 - Preview 26 268 Highland St, Milton MA 02186 - Preview 27 268 Highland St, Milton MA 02186 - Preview 28 268 Highland St, Milton MA 02186 - Preview 29 268 Highland St, Milton MA 02186 - Preview 30 268 Highland St, Milton MA 02186 - Preview 31 268 Highland St, Milton MA 02186 - Preview 32 268 Highland St, Milton MA 02186 - Preview 33 268 Highland St, Milton MA 02186 - Preview 34 268 Highland St, Milton MA 02186 - Preview 35 268 Highland St, Milton MA 02186 - Preview 36 268 Highland St, Milton MA 02186 - Preview 37

268 Highland St, Milton MA 02186

Milton, MA 02186
$1,895,000
Est. $11,105/month
3
Beds
2.5
Baths
2,987
Sq Ft
$634
Price/Sq Ft
1.40
Acres
1938
Year Built
Single Family Residence
Type
3 hours 44 minutes
Time on Market
Active Open House Listed May 26, 2026 • MLS# 73523755 Copied!

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 Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1938
Bedrooms
3
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,987 sq ft
Total Rooms
9

Open House Schedule

30
May
Saturday, May 30
11:30 AM - 1:00 PM EDT
31
May
Sunday, May 31
1:00 PM - 2:30 PM EDT
29
May
Friday, May 29
11:00 AM - 12:30 PM EDT

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

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:

Location

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Neighborhood

268 Highland St, Milton MA 02186

Milton, MA 02186

Walkability

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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
E

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
M

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
H

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
Learn about these ratings
School data provided by BMN Schools

Monthly Payment Calculator

Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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After down payment
Total Interest
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Over life of loan
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$0
Including down payment
%
Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,323
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

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$0/mo
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Current Rate
$0/mo
+0.5% Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Property Timeline

🏠
Listed for Sale
May 26, 2026
$1,895,000
Original listing
Agent: Beth Rooney Office: eXp Realty

Price & Status History

Date Event Price Change
May 26, 2026 New Listing Added $1,895,000 —

Market Statistics

Time on Market
3 hours 44 minutes
Price per Sq Ft
$634

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

Listing Information

Listing Agent Beth Rooney
Listing Office eXp Realty
Agent MLS ID BB803693
Office MLS ID AC0342
Listing Data Updated May 26, 2026 9:09 AM 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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Market Analytics for Milton, MA

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