Elegant family home off upper Main Street

Elegant Nantucket Retreat – Main House & Guest Cottage Near Town with use of Nantucket Club Facilities Included

This beautifully appointed 5-bedroom home with an optional 2-bedroom guest cottage offers the perfect blend of classic Nantucket charm and modern luxury. Located on Woodbury Lane, just off Upper Main Street, the property is within an easy stroll of Nantucket’s shops, restaurants, and harbor.

Main House Highlights

Grand Entryway: A graceful curved staircase, marble floors, and settee welcome you into the home.
Spacious Living Areas: Gather in the inviting living room with fireplace, enjoy meals in the elegant dining room (seating for 8–10) with fireplace, or relax in the sunlit family room with plush seating and a third fireplace.
Chef’s Kitchen: Custom cabinetry, quartz countertops, SubZero fridge, Wolf 6-burner range, Miele dishwasher, and island seating for 3 make cooking and entertaining a delight.
Outdoor Living: French doors from the family and dining rooms open to a bluestone patio with Weber grill and fire pit lounge for 4, beyond which is a teak dining table seating 8 and two sun loungers. A private garden with an expansive lawn is perfect for croquet, badminton, or soaking up a Nantucket sunset.
Bedrooms & Baths

Primary Suite: King bed, fireplace, custom storage, and a spa-like en-suite with BainUltra soaking tub, double vanity, and walk-in shower.
Guest Rooms: Two queen bedrooms (each with fireplace and reading nook) share a newly-renovated full bath.
Third Floor: Two additional bedrooms (twin and twin/trundle) with a shared newly-renovated full bath.
Extras: Sun-filled upstairs sitting area, fully stocked linens, and a first floor laundry room with high-performance washer/dryer.
Outdoor Amenities

Outdoor shower and dressing area with beach rinse station.
Croquet, badminton, and horseshoes provided.
Six beach chairs, umbrellas, coolers, and beach toys included.
Two sun loungers for private garden relaxation.

Guest Cottage (Optional – $3,000/week) (Remains vacant if not rented by family renting the house)

Perfect for extended family or guests, this charming 2-bedroom cottage accommodates 4 and features:

First-floor bedroom with full-size bed.
Second-floor living/dining area with kitchenette, dining for 4, loveseat, chairs, and twin/trundle.
Full bath with shower.

Why Guests Love It:

Walk to town in minutes, return to luxurious comforts, gather for evenings around the fire pit, and enjoy games on the lawn or sunsets in the private garden. This home is ideal for families and friends seeking both convenience and relaxation in Nantucket’s most desirable setting. Use of Nantucket Club fitness center, pools and hot tub by 6 adults is included. Also included is availability of the Nantucket Club's Children's Program.

Please note: A signed rental agreement is required to finalize your reservation. Even if your booking request is accepted through VRBO, it is not fully confirmed until the rental agreement has been reviewed and signed. Instructions to complete the agreement will be provided immediately after booking
The Town of Nantucket or simply “Town” as many call it, is the epicenter of life on the island. Situated on the north side of the island around Nantucket Harbor, Town offers both natural beauty and historical charm. In the early 1800s, Nantucket was the whaling capital of the world. While the wharves and many structures in the commercial district were lost in the Great Fire of 1846, some still stand today and are thoughtfully preserved and accessible to the general public. Whether it is through tours of Nineteenth Century whaling captains’ homes, events at churches or the Athenaeum Library, or a visit to a museum, Town is steeped in history. Have you ever heard of Maria Mitchell, renowned astronomer and professor? How about Herman Melville’s Moby Dick? Surely you’ve read Nathaniel Philbrick’s In the Heart of the Sea, or seen the Hollywood blockbuster of the same name. Interestingly, Benjamin Franklin and Macy’s Department Store both have roots to Nantucket as well.

Restaurants, Shopping & Galleries

Along with historical charm, downtown Nantucket today is chock full of restaurants, shops, and galleries. A true gastronome’s paradise, Town offers all types of cuisine and levels of sophistication from A to Z. Whether you’re looking for Classic French, New American, Global, or something casual for the kids, you’re covered. In between meals, check out one of the many boutiques or art galleries as you stroll up and down narrow, beautifully landscaped cobblestoned streets. In the evening, there are many options for entertainment – whether it’s live music in a relaxed environment, or singing and dancing the night away in a swanky, lively spot.

Boating & Fishing

There are many active pursuits in Town, as well. Being located on the harbor, there are kayak, sailboat, and stand-up paddle board rentals. Take a walk down to Straight Wharf and reserve a sport-fishing charter or spend a day on a boat catching bass, bluefish, bonito, and maybe even see a few dolphins, whales, or sharks! There is also a Critter Cruise available for the kids.

Beaches & Biking

The Brant Point and Cliff areas are next to Town and offer several options for sunbathing at one of the north shore beaches. Also most of the bike paths are accessible from Town, making the rest of the island just a bike ride away!

Pets - allowed


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