59 S Shore & 14 Tripp Drive

$39,900,000
Price
9
Beds
10,147 Sq. Ft.
$3,932 / Sq. Ft.
10,147
Sq. Ft.
$3,932
per Sq. Ft.

Description

Nantucket Coastal Equestrian Estate! 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 with a resort-style pool, spa, fire pits and will feature paddocks. 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,...Nantucket Coastal Equestrian Estate! 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 with a resort-style pool, spa, fire pits and will feature paddocks. 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. This estate is more than a home—it’s a lifestyle.

Property Details for 59 South Shore & 14 Tripp Drive

Town
Nantucket
MLS Area
Surfside
Area
MA-Nantucket-Surfside, MA-Nantucket
Architectural Style
Other (See Remarks)
Style
Garden, Other (See Remarks)
Garage Spaces
0
Parking Spaces
14.00
Parking Spaces Total
14
LISTING UPDATED: 11/19/2025 05:45 PM

Property Details for 59 South Shore & 14 Tripp Drive

StatusActive
MLS #73437103
Days on Market88
Taxes$33,908 / year
HOA Fees-
Compass TypeSingle Family
MLS TypeRental / Single Family Residence
Year Built2020
CountyNantucket County

Location

Listing Courtesy of: .

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Building Information for 59 South Shore & 14 Tripp Drive

Stories-Year Built2020Building Size-Lot Size6.58 AC / 286,624 SF

Payment Calculator

$199,986 per month

30 year fixed, 6.28% Interest

Principal and Interest

$197,160

Property Taxes

$2,826

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 59 South Shore & 14 Tripp Drive

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Swimming Pool, Stables, Bike Path, Conservation Area
  • Living Area: 10147.0
  • SqFt with Basement: No
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Appraiser
Features
Interior Features
  • Appliances: Stove: 2, Washer: 2
  • Num of Baths: 9.0
  • Num of Full Baths: 8
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 8.50
  • Bathrooms Total Integer: 9
  • FireplaceFeatures: 2
  • FireplaceYN: Yes
  • Fireplaces: 3
  • Flooring: 3
  • Interior Features: AC,Disp,OSh,WdStove, 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
  • Main Level Bedrooms: 1
  • Primary Bath: Yes
  • SpaYN: No
Exterior Features
  • Exterior Features: Porch, Deck, Patio, Pool - Inground, Pool - Above Ground Heated, Cabana, Barn/Stable, Paddock, Professional Landscaping, Decorative Lighting, Garden, Horses Permitted
  • Exterior Features: Pool - Inground, Pool - Above Ground Heated, Paddock, Cabana, Barn/Stable, Professional Landscaping, Decorative Lighting, Garden Area, Horses Permitted, Porch, Deck, Patio
  • Frontage Type: None
  • Lot Description: Wooded, Easements, Additional Land Avail.
  • Other Structures: Cabana, Barn/Stable
  • Patio And Porch Features: Porch, Deck, Patio
  • Pool Features: In Ground, Heated
  • Pool Private: Yes
  • View: Scenic View(s)
  • View: Yes
  • Waterfront Features: Ocean, 0 to 1/10 Mile To Beach, Beach Ownership(Public)
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Paved Drive
  • Open Parking: Yes
  • Parking Features: Paved Drive
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Heating: Central
  • Heating: Yes
  • Sewer: Private Sewerage
  • Utility Connections: Cbl
  • Water: Private
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Private Road
Tax Information
  • Tax ID: M:00080 P:00308
  • Assessments: $10,337,800
  • Book: 1784
  • Lot: 6
  • Map: 80
  • Tax Year: 2025
  • Zoning: LUG2
Building / Association Information
Living Characteristics
  • Beds Total: 9
Other Building Characteristics
  • Foundation: Concrete Perimeter
Complex & Association Information
  • Adult Community: No
Rental Info
Rental Info
  • HorseAmenities: Paddocks
  • Horse: Yes

Property History for 59 South Shore & 14 Tripp Drive

DateEvent & SourcePriceAppreciation
Sep 30, 2025

Listed (Active)

NANTUCKET_LINK #92653

$39,900,000
Sep 29, 2025

Listed (Active)

MLS PIN #73437103

$39,900,000
Dec 1, 2020

Sold

NANTUCKET_LINK #86700

$1,325,000
Mar 6, 2020

Listed (Active)

NANTUCKET_LINK #86700

$1,495,000
DateEvent & SourcePrice
09/30/2025

Listed (Active)

NANTUCKET_LINK #92653

$39,900,000
09/29/2025

Listed (Active)

MLS PIN #73437103

$39,900,000
12/01/2020

Sold

NANTUCKET_LINK #86700

$1,325,000
03/06/2020

Listed (Active)

NANTUCKET_LINK #86700

$1,495,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 59 South Shore & 14 Tripp Drive

Taxable ValueLand$977,000Additions$9,360,800Total$10,337,800
Tax Record2025$33,908 ($2,826 / month)
Home Facts
Beds0Lot Size199,354 SqFtStyleSingle Family ResidenceZoningLUG2CountyNANTUCKETAPNNANT M:00080 P:00308

Schools near 59 South Shore & 14 Tripp Drive

This home is within Nantucket School District.
Rating
School
Type
Grades
Distance
Public - PK to 2
Public - 6 to 8
Public - 9 to 12
Public - 3 to 5
Rating
School
Distance
Nantucket Elementary School
PublicPK to 2

Cyrus Peirce Middle School
Public6 to 8

Nantucket High School
Public9 to 12

Nantucket Intermediate School
Public3 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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59 South Shore & 14 Tripp Drive is a single family home for sale in Nantucket, MA 02554. This property was listed for sale on September 29, 2025 by Compass, it's currently listed at $39,900,000. It has been on the market for a total of 88 days and was last sold on December 1, 2020. This listing's school district is Nantucket School District. Nearby schools include Nantucket Elementary School, Cyrus Peirce Middle School and Nantucket High School. 59 South Shore & 14 Tripp Drive is a 9-bed, 9-bath, 10,147 sqft single family home built in 2020.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.