Current Real Estate Roundup - November 20, 2025

This week’s Current Real Estate Roundup includes property transfers from November 13^th, 2025 to November 20^th, 2025. It is led by the sale of a Derrymore Road property for over $9 million, an Orange Street property for over $8 million, and an Easton Street property for over $7.5 million.

12 Derrymore Road for $9,550,000 from The 12 Derrymore Realty Trust to ACK PACK LLC. The property is .22 acres, a dwelling, and a Land Bank fee of $191,000 was paid. The assessed value of the property is $1,847,200.

Property Description: "Nantucket traditional on the outside meets modern luxury on the inside in this fantastic new build, by Robert Alves of Island Construction LLC, offering a six-bedroom main home, two-bedroom cottage with a garage in the sought-after Cliff area of Nantucket Island, a short distance from North Shore beaches and the historic downtown Nantucket. This home offers spacious, airy living spaces with a stunning neutral color palette. A sparkling new swimming pool (somewhat rare in this zoning), surrounded by lush landscaping and privacy fencing, complete with an outdoor shower and auto cover."

13 Orange Street for $8,025,000 from 13 Orange Street LLC to Galena East LLC. The property is .14 acres, a dwelling, and a Land Bank fee of $160,500 was paid. The assessed value of the property is $2,500,058.

Property Description: "13 Orange Street is a rare in-town opportunity that blends historic character with modern comfort. Meticulously maintained with historic details preserved, the home offers three finished levels plus a versatile basement, a rare oversized yard, expansion potential, and two off-street parking spaces, creating an ideal layout. The heart of the home is a sunlit kitchen that opens through French doors to a large patio and one of the deepest, most private yards you’ll find in town. Multiple living areas, both formal and casual, provide space for every occasion. A roofwalk crowns the residence, capturing sweeping views of the harbor and town. With two-car off-street parking and additional ground coverage available for a garage, this property offers a level of potential rarely seen in this location. Rich in history, beautifully updated, and offering unmatched outdoor space in the heart of town, 13 Orange Street is a timeless Nantucket home—and an extraordinary opportunity for today’s market."

45 Easton Street for $7,800,000 from Harold Brothers Realty LLC ton 45 Easton Street LLC. The property is .11 acres, a dwelling, and a Land Bank fee of $156,000 was paid. The assessed value of the property is $5,763,600.

Property Description: "Situated in stunning Brant Point, this idyllic area boasts picturesque harbor views and is conveniently located across from the iconic White Elephant and next to downtown Nantucket. Both the main house and adjacent cottage are beautifully renovated blending classic Nantucket charm with modern design. The main house is four bedrooms with en-suite baths plus mudroom and powder room and a surprise sleeping nook with full bath. The first level features an open floor plan flooded with sunlight. A comfortable living room with ample seating orients around a fireplace and flows into a spacious dining area – creating a seamless space for entertaining. The kitchen acts as the central gathering area with bright, White Rino marble countertops, a large eat-in center island, fully equipped bar and top-of-the-line appliances. Open shelving and tiled accent walls add character and a touch of color. A deck is accessed off the kitchen with seating that flows down to a bluestone patio for additional outdoor entertaining. The 'Love Shack' guest house is ideal for company overflow with a one-bedroom, beautiful ensuite bath and a quaint yet modern cottage kitchen with eat-in island and open seating area."

17 Cannonbury Lane for $6,350,000 from 17 Cannonbury Lane LLC to Salty Shoals LLC. The property is .46 acres, a dwelling, and a Land Bank fee of $127,000 was paid. The assessed value of the property is $1,914,600.

Property Description: "Living the Nantucket summer lifestyle, from the proximity to Pebble beach and ’Sconset Village to the perfect blend of classic coastal design with modern amenities. The compound consists of six-bedroom main house with three finished levels, plus a guest suite and poolside cabana, offers both luxury and versatility. There is great seamless indoor-outdoor living, especially with the outdoor features like the large pool, bluestone patio, built-in grill and gas fire pit. Included in this new construction compound is deeded beach access and exclusive use of the clubhouse, gym, and cutting garden."

12 North Pasture Lane for $6,300,000 from Elizabeth Harvey and Douglas Firstenberg, Trustees to David M. Boyce and Alexander M. Boyce, Trustees of 12 North Pasture Realty Trust. The property is 2.75 acres, a dwelling, and a Land Bank fee of $126,000 was paid. The assessed value of the property is $5,287,000.

Property Description: "Perched at a high elevation, this beautiful setting includes a main house and guest house. It is bordered by conservation land to the north, ensuring both protected views and privacy. A long driveway gently leads to the highest point of the lot, where the main house is perfectly positioned to capture 180-degree views of the harbor, the Nantucket skyline to the west, and Great Point Light to the east. Just a few miles from town, the location offers easy access to the bike path loop that runs to Sconset Village."

2 Shore Road for $5,300,000 from John McDonough and Stephanie McDonough to 2 Shore Nantucket LLC. The property is .13 acres, a dwelling, and a Land Bank fee of $106,000 was paid. The assessed value of the property is $3,705,700.

Property Description: "A truly rare opportunity to own a harbor-view property with unmatched development potential — 2 Shore Rd lot is 11,484 feet, 50 percent ground cover by right for five years from purchase (grandfathered from CN conversion). That equates to 5,742 square feet of buildable ground cover — a scope nearly impossible to find this close to Town, with direct harbor views. The property currently includes: Main Home 1894 square feet on the ground and  garage structure 384 square feet on the ground. Total existing ground cover of just 2,278 square feet, leaving 3,464 square feet available — ideal for a substantial new residence or addition.

"Enjoy panoramic views over Nantucket Harbor, the Town Pier, Francis Street Beach, and kayak launch. Just a quarter mile from Main Street on a private street, this site offers walk-to-town convenience with a rare combination of scale, zoning flexibility, and scenery. With Great Harbor Yacht Club to the east and the soon-to-be removed Senior Center adjacent, this parcel sits in a rapidly enhancing view corridor. Surrounded by 14 properties now owned by the Town or Land Bank, the future of this location is primed for open space and long-term view protection.

"Whether you're envisioning a stunning new harbor-view home or strategic development in a high-demand area, 2 Shore Road delivers rare scale, flexibility, and investment potential in the heart of Nantucket."

31 Western Avenue for $4,500,000 from 31 Western Avenue LLC to ACK Nightingale LLC. The property is .69 acres, a dwelling, and a Land Bank fee of $90,000 was paid. The assessed value of the property is $3,668,000.

You can read more about the former Surfside Lifesaving Station and Star of the Sea Youth Hostel on Western Avenue being sold earlier this week - marking a new chapter in what has been a tumultuous half-decade for the historic property - here.

12 Longwood Drive for $3,675,000 from Slade Realty Trust to Anne Herrmann, John Magnusson, and Olivia Magnusson. The property is 2.75 acres, a dwelling, and a Land Bank fee of $49,500 was paid. The assessed value of the property is $3,046,600.

Property Description: "Minutes away from the Nantucket Golf Club, and including two complete homes. 12 Longwood Drive is a magical property surrounded by manicured lawns and mature natural vegetation. The long winding driveway passes the two bedroom guest cottage before continuing down a slight grade to the expansive four bedroom main house site. The main house has an open floor plan with a cathedral ceiling living room, connected to a long hallway, creating privacy for the bedrooms. At the end of the hallway is the TV room. Two outdoor decks, a fire pit, and an apple orchard that produces different varieties, as well as a fruit-bearing pear tree, add to the special ambience of this property. A private path leads to the milestone bicycle path and easy access to Sconset Village. Across Milestone road are hundreds of acres of conservation land, cranberry bogs and miles of trails to walk or bike. Multiple locations available for a pool and a pool cabana or tennis court."

8 Grey Lady Lane for $3,300,000 from Michael White Trust to Matthew Fleissner Sr. The property is .13 acres, a dwelling, and a Land Bank fee of $66,000 was paid. The assessed value of the property is $3,308,900.

Property Description: "Welcome to the epitome of modern living at Grey Lady Lane. This meticulously crafted five bedroom, five bath new construction home boasts three floors of exquisite living space, offering the perfect blend of style, comfort, and convenience. Located in a charming community of just 12 homes, residents will enjoy exclusive access to a sparkling community pool and cabana, creating the perfect setting for relaxation and entertainment. Situated just a stone's throw away from the renowned Miacomet Golf Course, Bartlett Farm, Ladies Beach, and the scenic bike path, this home is a true haven for outdoor enthusiasts and nature lovers. Indulge in the freshest seafood from the nearby fish market, savor craft beers at the local brewery, or simply unwind in your private backyard oasis. This stunning home is being sold fully furnished, ensuring a seamless transition into island living. Don't miss this rare opportunity to own a piece of paradise at Grey Lady Lane – where every day feels like a vacation."

5 Chester Street for $3,182,500 from Chester Smiley LLC to 5 Chester ACK LLC. The property is .10 acres, a dwelling, and a Land Bank fee of $63,650 was paid. The assessed value of the property is $2,500,058.

Property Description: "Antique house located in the Residential Old Historic District of Town with four+ bedrooms and three and one half baths. Historic details intact, six fireplaces, raised panelling, original doors and wide pine floors throughout. Patio, off-street parking, large easily accessed shed and potential for expansion on spacious third floor. Excellent location, close to all that Town has to offer. New cedar roof, interior and exterior painting and oil tanks."

2 The Grove for $3,150,000 from Anne M. Aumais to 2 The Grove LLC. The property is .26 acres, a dwelling, and a Land Bank fee of $63,000 was paid. The assessed value of the property is $2,334,000.

Property Description: "Set at the end of a quiet lane in Fisher’s Landing, this property is a complete package offering privacy, convenience, and versatility. Overlooking a conservation park and surrounded by a greenbelt of permanently protected land, the setting provides both natural beauty and lasting value. The main house features three bedrooms along with a recently added bonus room and thoughtful upgrades, including new appliances and European oak floors. At the rear of the property, an oversized two-car garage is topped with a spacious one bedroom apartment, ideal for guests or rental income. Two additional outbuildings provide flexible use for storage, office, or studio space. Ownership in Fisher’s Landing includes access to two tennis courts, boat storage, and water access at Warren’s Landing, plus a beach path to 40th Pole. The location offers excellent proximity to the Wave shuttle, Madaket bike path, and Madaket Harbor, while still only four miles from town. Beach access points are nearby, including North Shore beaches, Madaket beaches, Hither Creek, Jackson Point, and the Walter Barrett public pier. The community also abuts the Linda Loring Nature Foundation with its extensive walking trails. Enjoy the serenity and relaxed atmosphere of Nantucket’s West End with all the benefits of Fisher’s Landing."

17 New Street (Siasconset) for $3,150,000 from Summer Shelter LLC to Siasconset LLC. The property is .19 acres, a dwelling, and a Land Bank fee of $63,000 was paid. The assessed value of the property is $2,190,800.

Property Description: "Nestled in the heart of ’Sconset, this charming and spacious property features two fully renovated cottages and an additional fun shed offering a great opportunity to enjoy the perfect Nantucket retreat. Set on an oversized lot, this serene summer compound blends modern comfort with timeless character. The main house offers two bedrooms and two full bathrooms, highlighted by vaulted ceilings and classic shiplap detailing, creating a light and airy ambiance. The adjacent cottage adds flexibility with two additional bedrooms, two full bathrooms, a full secondary kitchen, and an open-concept living area ideal for guests or entertaining. Tucked at the rear of the property, the fun shed provides a versatile space; Perfect as a home office, bunk room, potting shed, rod room, love shACK or creative studio. With air conditioning, updated amenities, and the rare advantage of additional ground cover for potential expansion, this turn-key property is ready to enjoy now and offers exciting opportunities for the future."

6 Dovekie Court for $2,188,000 from Kelly M. Gallagher and Colleen E. Gallagher to Mathew Talcoff and Ruby Chan. The property is .13 acres, a dwelling, and a Land Bank fee of $43,760 was paid. The assessed value of the property is $1,939,300.

Property Description: "Spacious and sun-filled five bedroom, three and one half bathroom home is privately tucked away in the corner of a cul-de-sac in the charming Naushop neighborhood. With a flowing open floor plan and thoughtfully designed spaces, this property offers the perfect blend of comfort, functionality, and classic Nantucket charm. This home gives you access to beautifully maintained amenities, including tennis courts, pickleball courts, a swimming pool and a playground. Centrally located and just a short distance from Town and south shore beaches."

1 Daffodil Lane (50 percent interest transferred) for $588,000 from One Daffodil Lane to One Daffodil LLC. The property is 1.84 acres, vacant land, and a Land Bank fee of $11,760 was paid. The assessed value of the property is N/A.