Representing the best Nantucket real estate and rentals since 1931

Welcome to 39 Orange Street, a masterclass in architectural ingenuity where stunning renovation seamlessly blends historic charm with modern luxury. This sun-drenched in-town lovingly cared for & maintained home showcases the elegance of a historic stately captain's home combined with the desired amenities of today's discerning buyers. With 7 bedrooms and 8.5 bathrooms in the Main House, along with a one-bedroom guest Cottage, this significant property is prominently situated on an oversized lot at the corner of Orange St. and Plumb Lane. Offering approximately 6,000 square feet of living space in the Main House and 460 square feet in the Private Cottage. The craftsmanship and attention to detail throughout the home are remarkable, with high ceilings, exquisite moldings, antique pine original floors, multiple fireplaces and a wine cellar among the features that add to its allure. The finished basement provides additional space for recreation or relaxation. Located in Nantucket's highly sought after Historic District, this property offers off-street parking and substantial room to grow with remaining ground cover. Its coveted location on upper Orange Street provides both privacy and proximity to downtown Nantucket - an opportunity that won't last.

Fabulous beach house with sweeping, uninterrupted ocean vistas. Immerse yourself with the best sunsets on the East Coast from the upper and lower wrap-around decks. This spacious home features an inviting open-concept living area, complete with three generously sized bedrooms, three full baths, and a private office with deck access and captivating ocean panoramas. Convenient one-car garage. Experience coastal living, where every sunset is a masterpiece.

Private Cliff compound surrounded by nature. Filled with natural light, the open concept floor plan and mature landscaping blend the outside with the inside seamlessly integrating multiple living areas and the well appointed kitchen. The thoughtfully designed outdoor space with pool, fire pit, outdoor kitchen and dining area make this the perfect spot for entertaining. The fully equipped two bedroom cottage rewards the property by acting as an additional entertaining space and pool cabana. There is a second shelled driveway off Pilgrim road with access to the over-sized garage.

This smartly renovated and designer decorated cottage lives large with 2 bedrooms, 2.5 bathrooms, 2 living areas, a fireplace, washer/dryer, and two parking spaces. Beautifully landscaped private yard and patio with outdoor dining, fire-pit and Adirondack chairs, and outdoor shower. Located a short distance to Town, the supermarket, and the beach. Successful rental history with >$85k gross annual rental income in 2022 and 2023.

Enjoy the sense of leaving the world behind as you turn down Bosworth Road, a private dirt road flanked by high brush that transports you to your happy place. Park in the white clamshell driveway and open the wooden gate to a brick path that leads you to the large covered porch. An open floor plan welcomes you into the living room with a wood burning fireplace and first floor water views of the Atlantic Ocean. A large kitchen island will be the gathering place for family and friends and a large dining room table is begging for lobster bakes in the summer and Thanksgiving dinners in the fall. Strong water views from nearly every window ensures a constant reminder that you’re home at the beach.

Well maintained 4 bedroom home on attractive corner lot, a stones throw from public walking trails and park. Nice open layout on 1st floor, including spacious kitchen and large deck off living room. 1 bedroom suite w full bath in the lower level w separate access directly to driveway. Additional ground cover left for possible expansion. Tenants in residence until 3/31/24. Sellers require a 2023 closing.

This five-bedroom home is located off Cliff on a private shell lane and boasts easy access to nearby Steps Beach and Town. The home enjoys an upscale casual feeling with open living areas on three floors. The finishes and details, including shiplap walls and beamed ceilings, help make this an exceptional property. The outdoor deck and terrace adjacent to the pool and hot tub offer additional living space in the summer months. The property was rented in 2023 and generated excellent revenue. Offered fully furnished. The seller requires a 2024 closing.

The well maintained two story home is situated on an expansive fenced parcel, in a desirable Naushop location, featuring Maine Post and Beam ceilings and soring vaulted entry and dining areas. The open first floor layout affords many opportunities for adaption to one's personalized lifestyles. Beautiful pine floors extend from front to rear entry, thru French doors and the bright, sunny 2018 expansion, Master Suite with private living area, to the deck and oversized backyard. The kitchen has stainless steel Frigidaire and Bosch Appliances, and a spacious adjacent pantry. The front living area enjoys a working brick fireplace and provides a versatile array of additional possible use. Adding to the properties unique attributes is the large laundry/mud room with outdoor access. Throughout the home are ample closets, in addition to the 4.5' high insulated crawl space and outdoor shed.