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PROPERTIES Off Market

Surfside- 59 South Shore Road & 14 Tripp Drive

$39,900,000
Dec 23 2025
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Nantucket Coastal Equestrian Estate includes 59 S Shore Rd, 14 Tripp Dr front and 14 Tripp Dr. Just minutes from Surfside Beach, this newly built 9-bedroom, 8.5-bath estate sleeps 23 and blends equestrian charm with coastal luxury. The private, manicured grounds feature paddocks, a resort-style pool, spa, and fire pits, blending the freedom and beauty of open pasture with the luxury of wellness retreat amenities. Inside, soaring barn-inspired ceilings, hand-hewn beams, and refined finishes create rustic elegance with modern sophistication. The chef’s kitchen, designed for large gatherings, boasts an 8-burner range, dual ovens, two dishwashers, and expansive prep space. A home office, gym, and southern-style game room with shuffleboard, billiards, bar, and band set-up add practicality and entertainment. Days begin with horseback rides or beach walks, afternoons by the pool, and evenings under Nantucket’s starry skies. Conveniently located near bike paths, bridle trails, cafés, and Town, this estate is more than a home—it’s a lifestyle.

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Additional Details

The main level welcomes you with a modern entry that leads you into a bright, open living, dining and kitchen area with soaring ceilings! A spacious island with bar seating. Large living room with wood stove and indoor/ outdoor living connecting to pool and porch. East wing entertainment hall offers full bar, shuffleboard, band stage and wood stove. Chef catering kitchen as well

Private primary suite with walk in custom closets, spa bathroom with soaking tub, glass shower and private balcony overlooking the courtyard with indoor/ outdoor shower. A lofted sitting area and office space

Additional bedrooms and full bathrooms and gym

Cabana with bedroom and bathroom

Property Information

  • 11
  • 8
  • 8
  • 1
  • 6.57 acres
  • 2020
  • 2020
  • LUG2
  • -
  • Well
  • Septic Tank
  • None, Pastoral
  • -
  • 3

Amenities

listing property icon Property

  • Central A/C
  • Disposal
  • Outdoor Shower
  • Wood Stove

listing outdoor icon Outdoors

  • Gym
  • Private Pool
  • Patio
  • 14

listing household icon Household

  • Cable
  • Other
  • 2
  • 2

Location

Google Map of 59 South Shore Road & 14 Tripp Drive, Nantucket, MA, USA

NEIGHBORHOOD

Surfside

This family-friendly part of the island offers traditional, easy summer living with popular beaches, snack shacks, shuttle services to town and a sandy coastline ideal for kicking back and catching some sun. This neighborhood also has a three-mile bike path…

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Request More Information

Surfside- 59 South Shore Road & 14 Tripp Drive

$39,900,000

  • 8 Beds
  • 8 + 1 half baths
  • 6.57 acres

Listing History

Surfside- 59 South Shore Road & 14 Tripp Drive

Property Type: Single-Family
$39,900,000
Surfside- 59 South Shore Road & 14 Tripp Drive Image