59 South Shore Road & 14/14R Tripp Drive • $39,900,000
Surfside, 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.
Floor 1: 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.
Floor 2: 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.
Basement: The lower level offers additional bedrooms and full bathrooms alongside a dedicated gym.
Parking: 14+
Listed by J Pepper Frazier Co.
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59 South Shore Road & 14/14R Tripp Drive Location
J Pepper Frazier II
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xProperty Information for 59 South Shore Road & 14/14R Tripp Drive
Property Summary
Type: 1 Family
Rooms: 16
Year Built: 2020
Remodeled:
Water View:
Other View: Pasture
Zoning: LUG2
Lot Size(SF): 10147
Furnished: Partially
2nd Dwelling: E/Sd
Water: Well
Sewer: Septic Tank
Lot Size(A): 6.57
Beds/Baths: 8/8
Wtr Frontage:
Total SqFt(GLA): 286189
Amenities
First Floor Bedrooms: 1
Heating: Other
Fireplaces: 2
Floors: 3
Yard:
Parking: 14+
Foundation: Poured Concrete
Lead Paint:
Recreation and Outdoor Spaces: Patio, P/Pool, Gym, Deck, Garden, Porch, H/Tub
Amenities:
Taxes and Fees
Building Assessment: 11174700
Land Assessment: 3498700
Total Assessment: 14673400
Tax Year: 2026
Property History for 59 South Shore Road & 14/14R Tripp Drive
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