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15 Skyline Drive • $4,495,000

Surfside, Nantucket, MA 02554

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Just minutes from the South Shore beaches yet worlds away, this spectacular Surfside estate offers over 3 acres of unparalleled privacy surrounded by mature trees and natural beauty. The winding driveway leads through a canopy of lush trees to a beautifully remodeled, classic Nantucket home—spacious, serene, and designed for effortless island living.The main level features a sun-drenched living room with a grand vaulted ceiling, wood burning fireplace, and exposed wood beams, flowing seamlessly into the dining area and newly renovated kitchen. With a total of 5 bedrooms, 4 full baths, and 2 powder rooms on three finished floors this property provides the perfect layout for entertaining guests and extended family in a private setting. Outdoors, the property truly shines. The oval swimming pool with hot tub is framed by patios and lush landscaping. A built-in grill, screened porch, and raised vegetable and herb gardens invite al fresco living, while a two-car garage and generous driveway complete this exceptional offering. A rare find in Surfside, 15 Skyline Drive combines coastal proximity, acreage, and total privacy—a timeless island retreat that feels both expansive and intimate, designed to be shared with family and friends for generations to come.

Floor 1: Step through the front door into a bright and airy living room where vaulted ceilings, exposed wood beams, and a wood-burning fireplace set a tone of relaxed sophistication. The open-concept layout flows naturally into the dining area and newly remodeled kitchen, featuring a Thermador six-burner range, Sub-Zero double refrigerator, and elegant tile backsplash. Double sliders open from the family room to the screened-in porch and outdoor dining deck, creating an easy connection to the pool and gardens.
A first-floor primary suite offers a peaceful retreat with double closets, dual pedestal sinks, a soaking tub, and glass-enclosed shower. Completing this level are a laundry room, powder room, and a breezeway that leads to the attached two-car garage.

Floor 2: The upper level hosts three additional bedrooms, each with plenty of natural light and thoughtful design. One en suite bedroom features double vanities and a freestanding tub, while the other two bedrooms share a full bathroom with updated fixtures and timeless Nantucket charm. Above the garage is a private guest suite—a comfortable bedroom with an en suite bath that provides separation while remaining fully integrated into the home.The layout is ideal for family or guests, providing both privacy and proximity. High ceilings, wide-plank flooring, and classic millwork carry the home’s coastal elegance throughout this floor.

Floor 3: A loft off the second floor leads to the widow’s walk, offering distant views of the harbor.

Basement: Designed for entertaining and relaxation, the finished lower level offers a remarkable blend of comfort and function. A soundproofed home theater invites cozy movie nights, while the custom mahogany cocktail bar adds a touch of sophistication complete with ice maker and bar fridge. An additional living room with two gas fireplaces providing a cozy extra space for gatherings, and a multi-purpose room can flex as a home gym, office, or playroom. With generous square footage and thoughtful design, the lower level ensures there’s space for everyone to unwind. Additional half bath and cedar storage closet on this level complete the lower level living.

Parking:> Yes ample parking for multiple cars on belgian block drive

Listed by Maury People Sotheby's International Realty

15 Skyline Drive Location
Property Code: #92714
Bedrooms:
5 beds
Bathrooms:
4 and 2 half
Lot:
142,876 sq ft
Year Built:
1992
Heating Type:
GFHA
Listed:
36 ago
Assessed Value:
$4,168,000

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Property Information for 15 Skyline Drive
Property Summary

Type: 1 Family

Rooms: 11

Year Built: 1992

Remodeled: 2025

Water View:

Other View: Trees/Woods

Zoning: LUG2

Lot Size(SF): 3528

Furnished: Furnished

2nd Dwelling: P/Sd

Water: Well

Sewer: Septic Tank

Lot Size(A): 3.28

Beds/Baths: 5/4

Wtr Frontage:

Total SqFt(GLA): 142876

Amenities

First Floor Bedrooms: 1

Heating: GFHA

Fireplaces: 3

Floors: Hardwood, Tile, Carpet

Yard:

Parking: Yes ample parking for multiple cars on belgian block drive

Foundation: Concrete Pour

Lead Paint:

Recreation and Outdoor Spaces: H/Tub, P/Pool, Patio, Deck, Garden

Amenities:

Taxes and Fees

Building Assessment: 2743800

Land Assessment: 1424200

Total Assessment: 4168000

Tax Year: 2025

Property History for 15 Skyline Drive
Nov 15, 2025
Active
15 Skyline Drive :: Surfside
$4,495,000
1 Family
36 Days on Market
Listed by: Maury People Sotheby's International Realty
Oct 29, 2025
Withdrawn
15 Skyline Drive - Surfside
$4,790,000
1 Family
194 Days on Market
Listed by: William Raveis Nantucket
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