Current Real Estate Roundup - September 25, 2025

This week’s Current Real Estate Roundup includes property transfers from September 18^th, 2025 to September 25^th, 2025. It is led by the sale of a Main Street property for $14.5 million, a White Elephant Way property for over $7.5 million, a Pilgrim Road property for over $6.5 million, and a New Lane property for over $5 million.

126 Main Street for $10,000,000 from K22S LLC to Casino Partners LLC. 126R Main Street was also sold for $4,500,000 from the same seller to the same buyer for a combined transaction of $14.5 million. The properties combined are .26 acres, it is a dwelling, and a combined total of $290,000 in Land Bank fees were paid. The assessed value of the two properties combined is $4,500,800.

Property Description: "A once in a lifetime opportunity to own a bespoke, custom compound on historic Main Street Nantucket built by renowned design/build firm, The Stahl Group. Over the course of three years, three generations of luxury designers and builders came together to reimagine an historic home, situated on a rare double lot on upper Main Street. With the utmost attention to detail and high end craftsmanship, 126 Main Street is a true passion project that is ready for its next steward. A total of five en suite bedrooms and en suite sleeping loft provide plenty of space to entertain family and friends or enjoy true multigenerational family living. Every detail imaginable has been thought of, including and especially in the kitchen where a Lacanche range and hood, hand selected in Burgundy, offer a stunning focal point. The wet bar and butler's pantry lend themselves to beautiful entertaining reminiscent of the most high end homes, only to be outdone by the custom mahogany wine cellar. Generous and gracious living, dining, and entertaining spaces offer many options for an elegant, in town Nantucket life.

"A full lower level with two exterior access points offers its own self sufficient guest suite comprising two en suite bedrooms, kitchenette, living, dining, outdoor shower, powder room, and laundry suite. Multiple dining and entertaining spaces flow into the oversized garden and rear lot, which can be fully customized to suit your needs. With approved hardscaping and landscaping plans, as well as HDC approval to build a custom 3000sf guest house, the rear lot can be crafted into the perfect complement to elevate your lifestyle. The possibilities are endless to put the finishing touches on an in town Nantucket dream home."

2 White Elephant Way for $7,600,000 from White Elephant Hotel Residencies LLC to 2 White Elephant Way LLC. The property is .12 acres, a dwelling, and a Land Bank fee of $152,000 was paid. The assessed value of the property is N/A.

Property Description: "Welcome to 2 White Elephant Way, a stunning corner lot home in one of Nantucket's most coveted in-town locations. As one of the first two homes offered by this prestigious company, the property boasts a prime spot just across from Lola 41 restaurant, providing effortless access to the town's vibrant shops and restaurants. With a design that beautifully marries modern luxury and Nantucket charm, the home features a wrap-around porch perfect for leisurely watching the world go by. Inside, it includes four bedrooms and four and a half bathrooms, all within an open-plan living space ideal for entertaining family and friends."

17 Pilgrim Road for $6,825,000 from Two Pilgrims LLC to 17 Pilgrim Road LLC. The property is .33 acres, a dwelling, and a Land Bank fee of $136,500 was paid. The assessed value of the property is $1,636,900.

Property Description: "Welcome to Cliff living at its finest. 17 Pilgrim is a rare opportunity to own a brand new home on a fabulous oversized property within walking distance to Town, north shore beaches and the Westmoor Club. Hanley Development has partnered with Sophie Metz Design to create a magnificent 7,600+ square foot compound featuring a 6 bedroom main house with a garage, 2 bedroom guest house and a pool/spa. The spacious main house has over 5,800 square feet of finished living space with an attached garage and fully finished basement. The two-story guest house offers an additional 1,826 square feet of finished area with downstairs living space including full kitchen and two bedrooms upstairs. All bedrooms in both main and guest house are en-suite. The outdoor living is highlighted by the 16 x 30 pool with raised spa, outdoor kitchen and dining and a covered patio with fireplace off of the guest house. Construction is underway with completion scheduled for fall of 2026. Buyers now would have the ability to customize finishes or sit back and await full turnkey delivery of their dream home on the Cliff. Recorded sale is for land only, accompanied by separate $7 million construction contract."

10 New Lane for $5,300,000 from Sheila K. Gargano, Trustee of Sheila K. Gargano 2018 Trust to Brian Gruber and Nancy A. Gruber. The property is .46 acres, a dwelling, and a Land Bank fee of $106,000 was paid. The assessed value of the property is $2,632,600.

Property Description: “'Winds Aloft'  has five bedrooms, four baths, a private pool, and a two-car garage with a guest suite. Tucked away on a peaceful and generously sized 20,000 square foot lot, 'Winds Aloft' is an exceptional Nantucket residence that blends timeless design with effortless coastal living. The sun-drenched, open-concept main house features three bedrooms plus a flexible den space, and gracious layout designed for both comfort and entertaining. Expansive windows frame picturesque views of the beautifully landscaped yard, lush gardens, and a private swimming pool, creating a seamless connection between indoor and outdoor living. Perfect for hosting guests or working remotely, the detached two-car garage includes a fully equipped one-bedroom guest suite above—offering flexible space for extended family, visitors, or a private office retreat. Located in R-1 zoning, this oversized parcel allows for 30 percent ground cover, leaving generous square footage for future expansion or a potential subdivision (with appropriate approvals). Just .8 miles from the center of downtown Nantucket and with easy access to bike paths and Nantucket’s pristine beaches, 'Winds Aloft' offers exceptional lifestyle and investment potential. Whether as a personal retreat or a high-performing rental, this distinctive property presents a rare opportunity to enjoy — and grow into — one of the island’s most desirable locations."

13 Derrymore Road for $4,700,000 from Raymond J. Marocco to LFP III LLC. The property is .11 acres, a dwelling, and a Land Bank fee of $94,000 was paid. The assessed value of the property is $4,087,300.

Property Description: “Ideally located in the sought-after Cliff neighborhood, this turnkey five bedroom home is just moments from North Shore beaches, The Westmoor Club, Something Natural, and downtown Nantucket. Offered fully furnished, the property features three levels of living space, a first floor primary suite, two inviting living areas, and ensuite guest bedrooms — making it the perfect island retreat."

1 Brier Patch Road for $3,375,000 from Katherine M. Nichols and Joseph C. Huber to 1 Brier Patch Road LLC. The property is .58 acres, a dwelling, and a Land Bank fee of $67,500 was paid. The assessed value of the property is $3,721,900

Property Description: “Welcome to this spectacular private retreat on the edge of Quidnet Village. This attractive home offers four spacious bedrooms, three and one half baths, and two cozy fireplaces within an open floor plan. The interior is thoughtfully designed with two primary suites—one conveniently located on the main floor and another on the second floor. Multiple common rooms provide ample space for relaxation and entertainment indoors. Enjoy the naturally landscaped outdoor areas, featuring a large wisteria-covered front porch, a pergola-shaded rear patio, and an expansive backyard perfect for outdoor activities. There's ample room for a pool and cabana, the possibilities for customization are endless. The large open full basement offers great potential for additional living space or storage. The property is a true sanctuary, abutting over 40 acres of NCF conservation land, ensuring privacy and a connection to nature."

38 Monohansett Road for $3,200,000 from 38 Monohansett LLC to Judith Brownell. The property is 1.84 acres, a dwelling, and a Land Bank fee of $64,000 was paid. The assessed value of the property is $4,626,500.

Property Description: "Six bedrooms, six full baths of new construction in Surfside on over 1.8 acres with a pool, wraparound porch and close proximity to south shore beaches. Open floor plan with gas fireplace, high end appliances, center island and french doors leading out to the pool area. Three floors of finished living space with shiplap walls and custom built ins. A 18' x 36' pool with bluestone patio and large yard help to complete this offering. There is approximately 1500 square feet of ground cover remaining and HDC approved plans for a cabana/outdoor kitchen to be added adjacent to the pool."

1 Gully Road for $2,795,000 from David A. Jackson and Cynthia M. Jackson to Sunshine Daydreams LLC. The property is .07 acres, a dwelling, and a Land Bank fee of $55,900 was paid. The assessed value of the property is $1,371,800.

Property Description: "Just a short stroll to the beach and nestled in the heart of Sconset, this charming three bedroom, two bathroom home is the perfect blend of Nantucket character and coastal ease. The generous second floor primary suite boasts ocean views, an ensuite bath, and vaulted ceilings framed by the home’s classic gambrel roofline. A cozy gas fireplace anchors the second-floor living space, ideal for relaxing after a day by the sea. A large picture window perfectly frames the iconic Sconset Bridge leading down to the beach, bringing the seaside beauty inside. The first floor features a large, updated kitchen, a fun bunk room, and a flexible bonus space perfect for a home office or extra guests. Step outside to a darling seaside deck—perfect for dining al fresco while listening to the sound of the ocean. Offered fully furnished and turnkey this coastal getaway designed for effortless beachside living awaits. Pine floors run throughout, and the home is outfitted with air conditioning, a 2019 roof, and an on-demand tankless water heater for efficiency, and self-watering flower boxes with automated irrigation."

137 Surfside Road for $2,600,000 from Reardon John J. & Susan K Trust – 2019 Reardon Family Living Trust to DSM Surfside LLC. The property is .63 acres, a dwelling, and a Land Bank fee of $52,000 was paid. The assessed value of the property is $1,947,400.

Property Description: "If your ideal island summer includes the sound of the surf, starlit nights, easy access to Nantucket's favorite ocean beach, and a bike path leading to town, then 137 Surfside Road is the perfect match. Ideally located just a half mile from Surfside Beach and two miles from downtown Main Street, this home blends beachside serenity with island convenience. Located on a peaceful lane shared by only five other homes it offers a quiet retreat while keeping you effortlessly connected. With the Surfside Road bike path and The Wave bus route just outside your door, getting to town, the beach, and other island destinations couldn’t be easier. Set on a spacious half-acre lot, the home features a total of four bedrooms: three bedrooms and three baths in the main house, plus a studio and bathroom above the attached garage. Zoning allows for an in-ground pool so whether you're looking for a vacation escape or a year-round home, 137 Surfside Road puts you just moments from the ocean while keeping you connected to all that Nantucket has to offer. Whether you're looking to restore or reimagine, this property presents a rare opportunity to create something truly special."

50 Burnell Street, Lot 35 for $2,250,000 from Costa’s Avalon LLC to Jordan Brice Tamchin and Sarah Tamchin. The property’s acreage is N/A, vacant land, and a Land Bank fee of $45,000 was paid. The assessed value of the property is N/A.

8R Union Street for $1,800,000 from Middle Child LLC to Okay Okay House LLC. The property’s acreage is N/A, a dwelling, and a Land Bank fee of $36,000 was paid. The assessed value of the property is $1,345,900.

8 Cato Lane/35 Vesper Lane (Lot Two On Subdivision Plan) for $1,625,000 from Lynn, Marie Medeiros, Trustee of William A. Medeiros Trust 2003 to Cato Lane PropCo LLC. The property is .17 acres, a dwelling, and a Land Bank fee of $32,500 was paid. The assessed value of the property is $484,000.

3B Yawkey Way Unit 2 for $1,425,000 from Chad Jeremy Gingras to Three Yawkey Way LLC. The property’s acreage is N/A, a condominium, and a Land Bank fee of $28,500 was paid. The assessed value of the property is $1,111,900.

35 Vesper Lane (Lot 3 on Subdivision Plan) for $849,999 from William A. Medeiros Trust to Alfred T. Sanford. The property is .34 acres, a dwelling, and a Land Bank fee of $17,000 was paid. The assessed value of the property is $1,897,900.