59 South Shore Road & 14/14R Tripp Drive • $39,900,000

Surfside, Nantucket, MA

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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.

59 South Shore Road & 14/14R Tripp Drive Location
Property Code: #92933
Sold Date:
Sep 3, 2026
Asking Price:
$39,900,000
Original Price:
$39,900,000
Bedrooms:
8 beds
Bathrooms:
8 and 1 half
Lot:
286,189 sq ft
Year Built:
2020
Heating Type:
Other
Listed:
104 ago
Assessed Value:
$14,673,400
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