New Real Estate Listings: Week Ending Friday, September 25, 2026

Welcome to 1D Freedom Square a bright and airy second-floor condo, conveniently located in mid-island and featuring two bedrooms and one full bath. The open living space is enhanced by high, beamed ceilings and distinctive bow windows tucked into each side of the eaves, creating a light-filled and spacious feel. The updated kitchen is equipped with a 5-burner range, double oven and handsome backsplash. A spacious full bath includes a tub/shower and convenient stackable laundry. Enjoy low-maintenance condo living just moments from mid-island shopping, restaurants, and everyday conveniences. A wonderful opportunity to enjoy the island lifestyle without the upkeep of a larger property.

Ideally located just a short distance from downtown and harbor beach access, this thoughtfully designed home offers a flexible floor plan in a prime Nantucket location. With four bedrooms, two full and one half baths across three finished levels, the property provides comfortable and versatile living spaces, including a peek of the harbor from the second floor. Well suited for year-round living, a Nantucket retreat, or investment opportunity, the home is conveniently located near Town, the harbor, beaches, restaurants, shops, and island amenities, offering a wonderful opportunity to enjoy the best of Nantucket living.

The Hill House, set on one of Nantucket’s most prominent residential streets, presents a rare opportunity to reimagine a classic Brant Point property in an exceptional location. The seven-bedroom residence enjoys views toward Nantucket Harbor and an enviable address on coveted Hulbert Avenue. The three-story home retains the character of a classic Nantucket summer house, with original architectural details, a covered wraparound porch, generous proportions, and water views from many of its rooms. A widow’s walk crowns the house, offering an unusually high vantage point with sweeping 360-degree views across Nantucket Harbor, Town, and Brant Point. The property also features yard space, oversized enclosed outdoor shower, and off-street parking. With immediate appeal as a traditional summer home, The Hill House also offers a compelling opportunity for thoughtful renovation. Surrounded by some of Nantucket’s most distinguished properties, 34 Hulbert Avenue brings together a coveted location, generous scale, remarkable views, and exceptional potential.

Tucked into Surfside and bordering more than 20 acres of Land Bank conservation land, this post-and-beam home offers flexibility. Either move in and update it as-is, or reimagine the property entirely. The lot spans just under half an acre, with 1,387 sq. ft. of allowable ground cover total. The existing home uses 1,061 sq. ft., leaving 326 sq. ft. of room to expand the existing home or build an Accessory Dwelling Unit. Purchased as a land sale, the site supports a new home with three levels of living space. Town sewer and water are both available at the street, giving a buyer considerable flexibility in how they move forward. Property is being sold as-is.

There’s something wonderfully uncomplicated about this classic Cape-style home. With four bedrooms, two full baths, and a big, sunny yard, it’s the kind of house that invites you to come for the summer and never leave. Comfortable, welcoming, and genuinely charming, it has all the ingredients for an easy Nantucket life.

The first-floor primary bedroom, conveniently located near the full bath, is ideal for those who prefer single-level living. The generously sized kitchen is well appointed with LG stainless steel appliances and a large pantry. Upstairs, three more bedrooms surround a second full bath. One of the bedrooms is large enough to serve as a second primary, game room, or flexible gathering space.

The large yard gives you plenty of room for lawn games, cookouts or gardening. The central location is especially convenient, with Nantucket Elementary School right across the street. The bike path is at your fingertips, and the Wave is just as convenient. Head one way and you’re downtown in no time; go the other and you’ll quickly find yourself at Miacomet or Surfside Beach.

Whether you’re looking for a year-round home, summer getaway, or staff housing, this home offers wonderful flexibility. Move right in and enjoy it as is, or bring your own sense of island style and make it yours. It’s a sweet Nantucket house in a very convenient location!

Look no further! Nashaquisset’s latest offering is a true 4-bedroom, 4.5-bathroom jewel box, completely renovated inside and out with an exceptional level of detail and thoughtful design. No space was overlooked in creating this stunning Nantucket home, where every room has been carefully considered, resulting in a sophisticated yet effortlessly inviting retreat. Richly refinished wood flooring spans both levels, adding warmth and character throughout. Tucked away in an idyllic storybook setting, this gem is perfectly positioned in one of the island’s most convenient and sought-after locations, offering the best of Nashaquisset living just south of Town. Ideally situated approximately 1.5 miles from Nantucket Town, Cisco Beach, and Surfside Beach, the location makes it easy to enjoy all that the island has to offer. Enjoy a true club-like lifestyle with Nashaquisset’s heated community pool, Har-Tru tennis courts, professional management, and beautifully maintained landscaping—all designed to make island living effortless. Don’t let this one pass you by!

Town & Country. The one you’ve been waiting for has arrived.
Singular in its setting, scale, and design, 141 Main Street is unlike anything else on Nantucket. A grand approach from Upper Main Street introduces the celebrated George C. Gardner House, an elegant 1835 Greek Revival and one of the island’s most treasured historic residences. Meticulously preserved in keeping with its architectural significance, the property brings together historic grace, thoughtful design, and gracious modern living.
Extraordinary natural light fills every level of the main residence, while beautifully conceived living spaces create an effortless, open flow among the kitchen, dining, family, and sitting rooms, all extending naturally to the gardens and grounds. Four en suite bedrooms enjoy individual access to the pool, while the exceptional separation of space provides privacy for family and guests. The primary living space encompasses the entire third floor and is distinguished by a sensational outdoor living room with expansive decking overlooking the pool, gardens, and privately owned open space beyond. A private primary suite and office or sitting room complete this remarkable retreat.
Believed to have been Nantucket’s first pool, it was reoriented on the grounds by the current owners and now sits perfectly at the back of the property. Easily accessible from both the main residence and the separate three-bedroom guest cottage, the pool and surrounding grounds create an exceptional setting for outdoor living and entertaining.
Set on more than half an acre with mature gardens, a private courtyard, pool, and guest cottage, the estate offers the scale and seclusion of a country property in the heart of Town. A stroll down Main Street’s cobblestones leads to Nantucket’s celebrated restaurants, boutiques, galleries, museums, waterfront, and enduring island culture.
It is impossible to compare 141 Main Street to anything else on the island. Its setting, provenance, privacy, and pristine condition place it in a category of its own—the ultimate expression of gracious in-Town living and your own private island resort in downtown Nantucket.

Charming and full of Nantucket character, 29 Milk Street is a sunny four-bedroom antique conveniently located at the edge of Town. Thoughtfully updated while retaining the warmth and character of an older island home, the property offers a comfortable blend of traditional details and modern living. The open first-floor layout features a vaulted kitchen and dining area, inviting living spaces, and a first-floor primary suite. Three additional bedrooms are located on the second floor. Outside, a spacious backyard, mature landscaping, shelled driveway, garage/outbuilding, patio, and outdoor shower complete this inviting in-Town property.

Beautifully appointed and thoughtfully designed, this 4-bedroom, 3.5-bathroom residence in Beach Plum Village offers a welcoming blend of coastal style, comfortable living spaces, and inviting outdoor areas. The open-concept main level features oak flooring, white shiplap-style walls, and a seamless flow between the living, dining, and kitchen areas.

The well-equipped kitchen includes generous cabinetry, a spacious center island, a Wolf stove, a 36-inch Sub-Zero refrigerator, and a Sharp Insight Pro microwave—creating an ideal setting for everyday living and entertaining. Additional living space provides flexibility, while the home’s warm natural finishes and carefully considered details create a polished yet relaxed island atmosphere.

The full unfinished basement offers valuable potential for future expansion and could be transformed into a media room, private gym, recreation space, home office, or additional gathering area.

Outside, recent plantings enhance the property’s natural screening and create a greater sense of privacy. The beautifully landscaped grounds feature mature plantings, a spacious lawn, brick patio, outdoor seating areas, and a fire-pit gathering space—providing inviting opportunities to enjoy Nantucket’s seasons.

Located within the desirable Beach Plum community, the property offers the amenities and atmosphere of a private club without having to leave the neighborhood. Residents and guests enjoy access to a community swimming pool, clubhouse, tennis courts, fitness facilities, bocce, playground, and beautifully maintained common areas. Conveniently situated near island bike paths and South Shore beaches, this property presents an exceptional opportunity to enjoy the comfort of a private residence with the added benefits of a well-appointed residential community.