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59 South Shore Road & 14/14R Tripp Drive, Nantucket MA 02554

ActiveSurfside1 FamilySingle Family Residence

$39,900,000

$3,932 / sqft

Bedrooms

Bathrooms

8 + 1 half

Sq Ft

10,147

Lot

6.57 acres

Year Built

2020

Days on Market

Description

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.

Property Details

MLS #92933

StatusActive

Property Type1 Family

Sub TypeSingle Family Residence

NeighborhoodSurfside

MLS AreaSurfside

CityNantucket

StateMA

Zip02554

List Price$39,900,000

Price / Sq Ft$3,932

Bedrooms8

Full Baths8

Half Baths1

Total Rooms16

Living Area10,147 sqft

Lot Size6.57 acres

Year Built2020

Days on Market37

ZoningLUG2

FurnishedPartially

Fireplaces2

PoolNo

GarageNo

SewerSeptic Tank

Water SourceWell

Second DwellingE/Sd

OwnerJames D Feeley Tr

Parcel #308

Tax Map #80

Annual Tax$44,236.44

Assessed Value$11,174,700

Tax Year2026

On Market DateMay 22, 2026

First ListedMay 23, 2026

Last UpdatedJul 3, 2026

Latitude41.2491114

Longitude-70.1045694

Heating

Other

Parking

14+

Exterior

PatioP/PoolGymDeckGardenPorchH/Tub

View

NonePasture

Utilities

Cbl

Flooring

Appliances

Stove: 2Washer: 2

Interior Features

A,AC,Disp,Ins,Irr,OSh,WdStoveFloor 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.

Foundation

Poured Concrete

Basement

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

Lot Features

Yes

Additional MLS Details

SewerSeptic Tank

ZoningLUG2

Tax Year2026

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

Flooring3

Garage YNfalse

LINK Psf3932.1967

FurnishedPartially

Owner NameJames D Feeley Tr

AppliancesStove: 2, Washer: 2

Rooms Total16

Lot FeaturesYes

Water SourceWell

On Market Date2026-05-22

Parcel Number308

Tax Map Number80

Pool Private YNfalse

Tax Annual Amount44236.44

Interior FeaturesA,AC,Disp,Ins,Irr,OSh,WdStove, 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.

Tax Assessed Value11174700

Fireplace Features2

Foundation DetailsPoured Concrete

Original List Price39900000

LINK Listing Dwell2E/Sd

Original Entry Timestamp2026-03-17T16:13:34.247Z

Listing Agent

J Pepper Frazier II

J Pepper Frazier Co.

Price History

Date	Event	Price	Change
May 23, 2026	Listed	$39,900,000

Tax History

Year	Tax Amount	Assessed Value	Land	Improvements
2026	$44,236.44	$11,174,700	—	—

Market Context

Surfside Avg

$13,582,222

Surfside Median

$6,995,000

Island Avg

$6,935,068

Island Median

$4,950,000

Property Context

Wetlands NearbyNo

Source: MassGIS / FEMA NFHL. For informational purposes only — verify with Town of Nantucket.

MLS Listing #92933 — Data as of 2026-07-03