Single Family Residence at 5 Gap Head Rd, Rockport MA 01966
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$5,500,000

5 Gap Head Rd, Rockport MA 01966
Rockport, MA 01966
Listed by Ann Rick Gloucester Group
Bedrooms
4
Bathrooms
3.5
Living area
4,096 sqft
Year built
1998

About this home

Tucked away on a private, no-through-traffic oceanfront way, this property enjoys a rare combination of tranquility, privacy, and stunning waterfront surroundings on Straitsmouth Point between Rockport’s legendary twin lighthouses on Thacher Island to the south; Sandy Bay and the Atlantic Ocean to the west and north and the rocky shoreline below. Every spacious room within the easy-flowing floor plan features an ocean view via massive windows and exudes a cozy, yet refined ambiance that meets today’s needs and desires for daily living and when entertaining. With 4 bedrooms – the primary suite has a massive closet - 3.5 baths and 4,000+ sf of air-conditioned living space, this spectacular residence with beautiful gardens, ample outdoor play spaces, palazzo-like covered patio, 2-car heated garage with a workshop, and substantial storage accommodates a multitude of must-haves as well as amenities you didn’t even know you wanted. A year-round property destined to become a generational treasure

Highlights

WaterfrontViewFireplace

Property details

MLS
MLS Property Information Network
MLS #
73555738
Property type
Single Family Residence
Subdivision
Gap Head
Status
Active
Days on market
85
On market date
July 28, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
2
Parking spaces
6
Lot size
0.74 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Rockport Elementary
0.92 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
312
Student:teacher ratio
10.1:1
District
Rockport
Middle
Rockport Middle
0.85 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
205
Student:teacher ratio
7.6:1
District
Rockport
High
Rockport High
0.79 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
231
Student:teacher ratio
7.7:1
District
Rockport

Walkability

Blended score for Rockport's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

82
Highly walkable
out of 100
EPA National Walkability Index
14.7 / 20 -- Above average walkable
Google Places amenity density
95 / 100
Restaurants & cafes20
Grocery stores4
Parks13
Schools4
Transit stops9
Pharmacies1

Market position

How this listing compares to current activity in Rockport, from live MLS data.

On the market 85 days -- 14 fewer days than Rockport's current average of 99 days.
For reference, the median list price across 86 active listings in Rockport right now is $727,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$33,272/mo
$1,100,000 down
$4,400,000 loan
Principal & interest$28,538
Property tax (est.)$4,583
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated August 17, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.