Pending

$1,895,000

268 Highland St, Milton, MA 02186

3beds

2,987sqft

$11,599/mo

Get pre-qualified

Single Family Residence

Built in 1938

1.4 Acres Lot

$1,973,400 Zestimate^®

$634/sqft

$-- HOA

What's special

Timeless brick-front colonialSlate roofMature landscapeExtraordinary three-story barnSweeping green lawnsCopper downspouts

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.

18 days

56

2

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: $634/sqft
Tax assessed value: $1,431,900
Annual tax amount: $15,880
Date on market: 8/7/2026

Estimated market value

$1,973,400

$1.87M - $2.07M

$5,813/mo

Price history

Date	Event	Price
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