Perched above the shore of Harpswell Sound, this classic Cape Cod-style home sets the tone for easy coastal living. With timeless lines and 245 ft of owned ocean frontage, it feels like the kind of place where stories are told, food and drinks are shared, and time slows to match the rhythm of the tides. Inside hardwood floors, formal and informal spaces give you the opportunity to comfortably accommodate everything from a cozy evening to vibrant celebrations. The second floor offers a functional layout with a spacious primary bedroom with a walk-in closet, two additional bedrooms and full bath - complete with a double vanity, a custom tile shower and soaking tub overlooking the bay. Tucked above the garage is a bonus room that is a true Maine treasure. With cathedral ceilings, a charming cupola that lets in natural light, and wide pine floors, the space is wrapped floor to ceiling in warm pine paneling - giving it that cozy, cabin-in-the woods feel, right at home. Use the space for your home office away from the pace of the rest of the home or a place to dive into your next hobby. Outside the salt air greets you along with the scent of pine and sounds of the sea. Wander through the trees to a deck perched right at the shoreline, where a set of stairs leads you to the rocks below. It's the perfect launchpad for a morning paddle or an impromptu saltwater dip. As part of the beloved High Head Yacht Club community, you'll have access to a dock and clubhouse just around the bend—so boating out for a sunset cruise or joining friends for a gathering on the water is made easy. Cherished by the same family for the last forty years this is your opportunity to own part of Maine in a beautiful coastal community.
Single-familyProperty Type
1985Year Built
1.1 acresLot Size
$656Est. Price/Sq.Ft.
2 car garageParking
Listed by Jennifer Tabb• Portside Real Estate Group
Bought with Richard Bisson Jr• Keller Williams Realty
Sewer: Septic Tank, Private Sewer, Septic Design Available
Water Source: Well, Private
Water Heater: On Demand, Tankless
Location
HOA Information
Has Association
Association Fee: $1,892
Association Fee Frequency: Annually
Location Information
Unparsed Address: 56 Headland Road, Harpswell, ME 04079
Directions: From Route 1 in Brunswick continue onto Pleasant St towards downtown Brunswick, turn right onto Maine St, turn left onto Bath Rd, turn right onto Route 123, turn left onto High Head Rd, turn left onto Headland Rd continue to #56 on the right.
Public facts
Beds: 3
Baths: 2.5
Sq. Ft.: 2,326
Stories: 2.0
Lot Size: 1.1 acres
Style: Single Family Residential
Year Built: 1985
Year Renovated: —
County: Cumberland County
APN: 145947
Home facts updated by county records on Jul 27, 2026
Around this home
Schools
Harpswell Community School
Public K-5 • Assigned • 3.7mi
9/10
Mt Ararat Middle School
Public 6-8 • Assigned • 10.4mi
6/10
Mt Ararat High School
Public 9-12 • Assigned • 10.0mi
4/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
3/10 Heat Factor
7 days above 85° expected this year, 17 days in 30 years
8/10 Wind Factor
80% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Harpswell, ME • 04079
Average low and high temperatures (°F)
30
16
33
15
42
28
50
37
60
47
71
57
75
62
74
58
69
54
59
45
49
35
36
21
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.3 hours in
June and 4 hours in December, placing it below the
U.S. average for solar exposure.
8.3 hrs
4 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.45M – $1.76M
Reach more buyers when you sell with Redfin. Save up to $15,267 in fees.3 minutes to get started.
Get a free, detailed breakdown of how we calculated your estimate.