59 South Shore Road & 14 Tripp Drive • $39,900,000
Surfside, Nantucket, MA 02554
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.
Floor 1: 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
Floor 2: 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
Floor 3: Living room. Two bedrooms. One bathroom.
Basement: Additional bedrooms and full bathrooms and gym
Parking:> 14
Listed by Compass MA LLC
59 South Shore Road & 14 Tripp Drive Location
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xProperty Information for 59 South Shore Road & 14 Tripp Drive
Property Summary
Type: 1 Family
Rooms: 11
Year Built: 2020
Remodeled: 2020
Water View:
Other View: Pasture
Zoning: LUG2
Lot Size(SF): 10147
Furnished: Unfurnished
2nd Dwelling: None
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:
Lead Paint:
Recreation and Outdoor Spaces: Patio, P/Pool, Gym
Amenities:
Taxes and Fees
Building Assessment:
Land Assessment:
Total Assessment: 0
Tax Year: 2025
Property History for 59 South Shore Road & 14 Tripp Drive
$1,495,000
$1,325,000
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