12 & 13 Shimmo Pond Road
Shimmo
$4,795,000
Days on Market: 149
Bed: 6 Bath: 6
Your Nantucket sanctuary awaits in one of the island’s most desirable enclaves. Welcome to 12 Shimmo Pond Road, where you’ll find a 4-Bedroom Main Home and a 2-Bedroom Guest Cottage on expansive grounds. This exceptional property is set on an oversized and private parcel, surrounded by lush gardens and mature trees that create a serene sense of seclusion. Included in this offering is 13 Shimmo Pond Road, located directly across the street, adding to the estate’s privacy and potential. Perfectly suited for hosting family and friends or for enjoying private retreat spaces, the property offers peace, comfort, and enduring character. Meandering garden paths, sunny terraces, and shady nooks lend a sense of magic, while the thoughtful layout allows for both quiet solitude and welcoming gatherings. Just a stone’s throw from the shimmering waters of Nantucket Harbor and a short drive from the cobblestone streets of Nantucket Town, this rare offering marries countryside calm with coastal refinement. With approximately 2,000 square feet of ground cover remaining, the possibilities for expansion are plentiful.
62 Nobadeer Avenue
Surfside
$4,400,000
Days on Market:
Bed: 4 Bath: 4
A rare opportunity to build your dream beach house on Nantucket’s highly sought-after south shore. This .69-acre parcel comes with approved architectural plans by renowned Workshop/APD, providing a shovel-ready path to creating a custom compound with a main house, guest house, garage, and pool. Located just moments from iconic Nobadeer Beach, 62 Nobadeer Avenue offers sweeping ocean views, breathtaking sunsets, and the sound of surf as your backdrop. Zoned R-20 with 3,750 sq. ft. of allowable ground cover (and additional potential for expansion with further permitting), this site offers generous flexibility for design. Enjoy the best of coastal living with sea breezes, beach access, and proximity to all that Surfside has to offer.
24 Flintlock Road
Tom Nevers
$9,750,000
Days on Market: 59
Bed: 10 Bath: 10
Nestled on an expansive 2.45-acre parcel adjoining pristine Nantucket Land Bank conservation land, 24 Flintlock Road offers a private and tranquil retreat for discerning families. The homes on this thoughtfully curated estate create a charming family compound, featuring a generously appointed six-bedroom main residence, complemented by a delightful three-bedroom guest cottage, a stylish pool house, and a garage thoughtfully integrated with a private studio apartment.
Step into a meticulously designed outdoor haven—a true summer oasis ideal for relaxation and entertaining. Enjoy leisurely days beside the striking 20′ x 36′ heated Gunite pool, accented with elegant bluestone surrounds, or relax in the pool cabana, which seamlessly blends inviting indoor and outdoor living spaces. The compound also features a covered outdoor living room with a vaulted ceiling and impressive oversized fireplace, a fully equipped outdoor kitchen and bar with seating for eight, and multiple seating areas throughout the grounds. Whether hosting large gatherings or seeking a peaceful retreat, this exceptional property offers the perfect environment for memorable Nantucket summers.
Beyond the lush landscaping and carefully tended gardens, this property offers abundant space to expand amenities, including room for a private tennis court. Expertly styled by renowned interior designer Trisha Wynn Designs, the property is presented fully furnished and turnkey-ready, ensuring immediate enjoyment and comfort.
With its rare blend of spacious luxury, privacy, and versatility, 24 Flintlock Road is the ideal setting for creating cherished Nantucket memories or leveraging its exceptional rental potential, commanding impressive weekly six-figure rates during selective seasonal periods. Video Tour: https://player.vimeo.com/video/1107763165?byline=0&title=0&owner=0&name=0&logos=0&profile=0&profilepicture=0&vimeologo=0&portrait=0
36 West Chester Street
Town
$7,300,000
Days on Market: 134
Bed: 5 Bath: 5
Anchored between Main Street and Steps Beach, this extraordinary home captures the essence of refined coastal living. Five private ensuite bedrooms provide luxurious comfort for family and guests, while the chef’s kitchen and adjoining dining room invite gatherings both large and intimate. The sun-soaked, south-facing deck extends the living space into a private, landscaped yard, where views of the Lily Pond Conservancy and the town’s iconic church steeples create a remarkable setting in the heart of Town. With three finished floors of living space and quality craftsmanship throughout, 36 West Chester Street is graceful Nantucket living.
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