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        • Madaket
        • Madequecham
        • Miacomet
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        • Muskeget
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        • Naushop
        • Pocomo
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        • Madequecham
        • Miacomet
        • Mid Island
        • Middle Moors
        • Monomoy
        • Muskeget
        • Nashaquisett
        • Naushop
        • Pocomo
        • Polpis
        • Quaise
        • Quidnet
        • Sandpiper Place
        • Sconset
        • Shawkemo
        • Shimmo
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      • Cliff
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      • Hummock Pond
      • Madaket
      • Madequecham
      • Miacomet
      • Mid Island
      • Middle Moors
      • Monomoy
      • Muskeget
      • Nashaquisset
      • Naushop
      • Pocomo
      • Polpis
      • Quaise
      • Quidnet
      • Sandpiper Place
      • Sconset
      • Shawkemo
      • Shimmo
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          • Miacomet
          • Mid Island
          • Middle Moors
          • Monomoy
          • Muskeget
          • Nashaquisett
          • Naushop
          • Pocomo
          • Polpis
          • Quaise
          • Quidnet
          • Sandpiper Place
          • Sconset
          • Shawkemo
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        • Miacomet
        • Mid Island
        • Middle Moors
        • Monomoy
        • Muskeget
        • Nashaquisset
        • Naushop
        • Pocomo
        • Polpis
        • Quaise
        • Quidnet
        • Sandpiper Place
        • Sconset
        • Shawkemo
        • Shimmo
        • South of Town
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59 South Shore Road & 14 & 14R Tripp Drive, Nantucket, MA 02554

$39,900,000

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  • 8 BedBeds
  • 8.5 BathBaths
  • SqftSqft
  • TypeSingle Family
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  • Listing # 93104
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Property Description 59 South Shore Road & 14 & 14R Tripp Drive, Nantucket, MA 02554

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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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.

Area

With close proximity to Town and one of the most well known beaches on the island, Surfside is a popular area for year-round and seasonal residents. This family-friendly area offers bike paths, soft sand beaches, places to explore and more. Being nearby to all Mid Island shopping and dining is a plus and with Cisco and Hummock Pond not far either there are lots of options for activities. From modest homes to large family estates, there are ample options for all.

  • 2.3 miles to Town
  • Surfside Beach is one of the most popular beaches on the island for all ages. It's ocean surf and wide soft sand provides everything you could want for a day at the beach.
  • Nobadeer Beach is a popular spot amongst the younger crowd and a great spot for surfing or plane spotting as they land and take off from the airport.
  • Between Surfside and Nobadeer beaches there are several small parking areas and beach entry spots for a quieter day by the sea.
  • The Surf at Surfside beach whips up traditional fare for Breakfast, Lunch and Dinner. From breakfast sandwiches to burgers, salads and more. Take your order down to the beach or sit at one of their picnic tables.
  • Brix Wine shop is located just off Surfside Road and offers a great nearby location to peruse their vast wine selection.

community

Property Details

  • Property Type: Single Family
  • List Date: 05/22/2026
  • Year Built: 2020
  • Year Renovated: 2020
  • Area: Surfside
  • Zoning: LUG2
  • Beds: 8
  • Full Bath: 8
  • Half Bath: 1
  • Total Baths: 9
  • Annual Taxes: $44,236.44
  • Water Frontage: No
  • Water Views: No
  • Other Views: None, Pasture
  • Water: Well
  • Sewer: Septic Tank

Amenities

Interior FeaturesInterior Features
  • Furnished: Unfurnished
  • Heat: Other
  • Fireplaces: 2
Exterior FeaturesExterior Features
  • Private Pool: No
  • Community Pool: No
  • Private Tennis: No
  • Community Tennis: No
  • Hot Tub: No
  • Parking: 14
Other StructuresOther Structures
  • Cabana studio with bathroom.

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      59 South Shore Road & 14/14R Tripp Drive Nantucket MA 02554
      $39,900,000
      8 BED 8 BEDS 8.5 BATH 8.5 BATHS SQ. FT.
      MLS# 92933Single Family
      Listing Courtesy of J Pepper Frazier Co.
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