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Surfside- 59 South Shore Road & 14/14R Tripp Drive

$39,900,000
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Just minutes from Surfside Beach, Rhythm Ranch is a rare nearly seven-acre equine estate opportunity spanning three contiguous properties that balance coastal sanctuary and countryside retreat. The main residence at 59 South Shore Road brings together two storied barn-styled structures into one expansive 9,500+ square foot home, incorporating a salvaged custom Benson timberframe from the historic Vanderbilt / Egan Estate. Inside, soaring barn-inspired ceilings set the tone for refined, rustic elegance, while a home office, gym, game room with shuffleboard, billiards, and a full bar round out the experience. The grounds are built to host, with a grand pool, spa, pool house, multiple fire pits, 36 fruit trees in its orchard and tucked-away garden spaces. The two adjacent one-acre lots at 14 Tripp Drive offer a vast canvas of open, manicured land with direct access to Nantucket's conservation trails. Conceptual drawings for an equestrian program including HDC-approved plans are available. Offering an unmatched connection to Nantucket's natural landscape, from its celebrated trails to its beloved beaches, this is a rare chance to claim something truly extraordinary. Your island legacy starts here.

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Additional Details

The main level opens into a bright, airy living, dining, and kitchen space beneath soaring ceilings. A large island with bar seating anchors the room, while the living area — complete with a wood stove — connects seamlessly to the pool and porch. The east wing brings the entertainment with a full bar, shuffleboard, band stage, and a second wood stove, plus a dedicated catering kitchen for hosting at scale.

The second level is crowed by a private primary suite with custom walk-in closets and a spa bathroom featuring a soaking tub and glass shower. A private balcony overlooks the courtyard, complete with an indoor/outdoor shower. A lofted sitting area and dedicated office space round out the level.

The lower level offers additional bedrooms and full bathrooms alongside a dedicated gym.

Cabana studio with bathroom.

Property Information

  • 16
  • 8
  • 8
  • 1
  • 6.57 acres
  • 2020
  • LUG2
  • Existing
  • Well
  • Septic Tank
  • None, Pastoral
  • Poured Concrete
  • 3

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Amenities

listing property icon Property

  • Alarm
  • Central A/C
  • Disposal
  • Insulation
  • Irrigation
  • Outdoor Shower
  • Wood Stove

listing outdoor icon Outdoors

  • Deck
  • Garden
  • Gym
  • Hot Tub
  • Private Pool
  • Patio
  • Porch
  • Yes
  • 14+

listing household icon Household

  • Cable
  • Other
  • 2
  • 2

Location

Google Map of 59 South Shore Road & 14/14R 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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Surfside- 59 South Shore Road & 14/14R Tripp Drive

$39,900,000

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

Listing History

Surfside- 59 South Shore Road & 14/14R Tripp Drive

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