Current Real Estate Roundup - December 18, 2025

This week’s Current Real Estate Roundup includes nearly two dozen property transfers from December 11^th, 2025 to December 18^th, 2025. It is led by the sale of a Fintry Lane property for $10 million, three Polpis Road properties for a combined value of over $8.5 million, and a Surfside Road property for just under $8 million.

4 Fintry Lane for $10,000,000 from Keith Wallace to 4 Fintry Lane Realty Trust. The property is 1.84 acres, a dwelling, and a Land Bank fee of $200,000 was paid. The assessed value of the property is $7,894,900.

Property Description: "Welcome to Dionis seclusion - Set on 1.84 acres and enveloped by over 700 acres of pristine conservation land, this exceptional eight-bedroom estate in Dionis offers rare privacy and sweeping sunset vistas. The thoughtfully designed six-bedroom main house features expansive indoor and outdoor living spaces ideal for entertaining or relaxing in complete seclusion. A separate two-bedroom garage apartment provides comfortable accommodations for guests or extended family. A true sanctuary just moments from town and the beach."

238-240 Polpis Road for $8,565,000 from Michael J. O. Mara to 240 Polpis LLC. The property is 7.26 acres, a dwelling, and a Land Bank fee of $171,300 was paid. The assessed value of the property is $9,601,300.

Property Description: "It's the good life. Serenity and privacy await on shore and on the water. This gracious four-bedroom, four and one half bath harborfront home in Polpis is located on 7.2-acres with a two car garage and a 260-foot pier including a title float for the tie-up of two boats. The property is surrounded by 1000+ acres of conservation lands. This is truly a boaters' dream as it is one of 15 licensed, privately-owned docks on the island. Imagine, from your dock to one of the Yacht Clubs, the Angler's Club or the Town Pier within fifteen minutes. On your boat ride back, pull out your fishing pole, drop in a line and reel in a Striped Bass or tie up at The Wauwinet for lunch. The tastefully designed interior rooms are spacious, light-filled and take full advantage of the spectacular views. This truly unique waterfront property must be seen to be appreciated."

115 Surfside Road for $7,950,000 from Peter Miller and Rose Miller to One Fifteen Surfside LLC. The property is .96 acres, a dwelling, and a Land Bank fee of $159,000 was paid. The assessed value of the property is $6,893,500.

Property Description: "Spacious, stylish, and steps from Surfside Beach, this thoughtfully designed home offers expansive landscaped grounds with a pool, hot tub, and a separate cabana featuring a loft—ideal for guests or added entertaining space. Inside, large windows throughout flood the home with natural light and offer uninterrupted views of the pool and surrounding gardens. The main living room impresses with a vaulted ceiling, clerestory windows, and a dry-stacked stone fireplace. A true gourmet kitchen is the centerpiece, built for serious cooking and seamless entertaining. Spread across three levels, the home includes two primary suites—one conveniently located on the main floor—plus a lower-level media and game room. Every room is well proportioned, with quality materials and finishes throughout. The layout is both functional and elegant, with an effortless flow between indoor and outdoor living areas. A rare combination of space, quality, and location."

27 Cato Lane for $7,850,000 from Cato LLC to Cato Rental LLC. The property is .51 acres, a dwelling, and a Land Bank fee of $157,000 was paid. The assessed value of the property is $2,686,800.

Property Description: "It’s official - the wait is over. This unparalleled expansive Nantucket property offers everything you’ve been dreaming of: three newly constructed dwellings, six private ensuite bedrooms, two bunk rooms, a separate studio, and sun-drenched interiors throughout, all centered around a sparkling southern-facing 16' x 40' pool on a beautifully landscaped half-acre in coveted South of Town. With effortless access to downtown, Cisco, and Miacomet’s beaches and amenities, this property delivers the perfect blend of luxury, convenience, and room to roam. Whether entertaining family and friends or planning future additions like a sports court, the possibilities are endless. Designed by acclaimed local architect Chip Webster and built with impeccable craftsmanship by a respected builder in Wellesley, MA, every detail reflects quality and sophistication. Move in immediately - don’t miss this opportunity to claim a truly exceptional, newly constructed Nantucket residence."

1 Chester Street for $7,400,000 from One Chester LLC fka One Chester Smiley LLC to One Chester Realty Trust. The property is .12 acres, a dwelling, and a Land Bank fee of $148,000 was paid. The assessed value of the property is $4,087,900.

Property Description: "One Chester Street is an exceptional residence that perfectly blends historic charm with modern luxury. Situated at the edge of Nantucket's historic district where the Cliff area meets Brant Point, this home offers a prime location that provides easy access to the best of island living. This 18th-century ship captain’s home has been meticulously restored, preserving its original details, including five working fireplaces, while integrating contemporary amenities for today's lifestyle. Sold fully furnished with interior design by The Nantucket Looms, the home boasts four levels of living space, with six bedrooms and five and a half baths, it comfortably accommodates large groups, offering ample room for relaxation and privacy. The spacious open kitchen features the original 6' walk-in fireplace, breakfast area, adjoining a bright family/TV room that opens directly onto the rear deck, patio, and garden. The formal dining room features a beautiful lacquered finish.

"The outdoor space is equally impressive, with a unique artist-built gazebo and fire pit—a perfect spot for evening gatherings. The home’s renovations are top of the line, including all new plumbing, electrical, and HVAC systems, with high-end finishes throughout. The lower level is dedicated to entertainment, with a fully equipped game room including a combination ping pong/pool table, three TVs, a separate seating area, and a kitchenette. For quieter moments, the third-floor guest suite provides access to the roof walk with panoramic views of Nantucket Sound and Harbor, making it a wonderful spot to unwind. One Chester Street is the perfect combination of historic elegance and modern comfort. Approximately 350+/-sf remaining ground cover for an addition or a garage."

32A and 32B West Chester Street for $4,500,000 from Mary Marshall to 32 West Chester ACK LLC. The property is .27 acres, a dwelling, and a Land Bank fee of $90,000 was paid. The assessed value of the property is $4,088,200.

Property Description: "Incredible opportunity on West Chester Street. Two oversized lots (total of 12,632 square feet in the Residential Old Historical district) with an existing three bedroom 1918 Arts and Crafts style home and a newer, 2007 one bedroom cottage that offers a world of possibility! The main house features many original details and lovely woodwork and built-ins. The cottage was built by Main Street Construction and is charming and light-filled. The setting features mature landscaping and is extremely private. Future expansion possible on both lots. Wonderful compound living in the heart of Town. Ideally located on the corner of Wesco Place with convenient access to the Lily Pond Conservation property, the Oldest House/Coffin Park, Something Natural, Steps Beach, Brant Point, and of course, Town. This property has been loved by this current family for over fifty years and is awaiting its next steward."

25 Nobadeer Avenue Lot 1 for $4,500,000 from Rockland Trust Company, Successor Trustee of C’Scape II Realty Trust to Seven Dials Nantucket LLC. The property is 1.15 acres, a dwelling, and a Land Bank fee of $90,000 was paid. The assessed value of the property is $2,459,800.

Property Description: "A rare offering in one of Surfside’s most coveted locations, this newly created 30,000 square foot lot (in progress) provides the foundation for a true Nantucket compound. With R-20 zoning permitting 12.5 percent ground coverage, there is ample room for a main residence, pool, and cottage, subject to approvals. Plans for a 4-bedroom I/A septic system are in progress by the seller. A modest two-bedroom, one-bath cottage is currently sited on the property and could be repurposed as a guest house or pool cabana. From this property, enjoy a barefoot stroll to Surfside Beach and the potential for second-floor water views."

6 Gingy Lane for $4,422,888 from Sarah B. Minella, Amy M. Albrecht, and Joseph P. Minella to The Merry B., LLC. The property is .12 acres, a dwelling, and a Land Bank fee of $88,458 was paid. The assessed value of the property is $4,451,400.

Property Description: "Custom built five bedroom, five and one half bathroom home on highly sought after Gingy Lane moments to Town and north shore beaches offers the perfect blend of modern luxury and timeless island charm. The light filled open plan naturally flows to side deck and patio. Versatile layout that offers the lower level as a separate 'apartment' or an extension of the house. Gorgeous built-ins and millwork throughout."

5 Okorwaw Avenue for $4,000,000 from 5 Okorwaw Avenue LLC to Nancy and George Dugdale. The property is 2.76 acres, a dwelling, and a Land Bank fee of $80,000 was paid. The assessed value of the property is $3,768,900.

35 Sankaty Road for $3,600,000 from Charles Pastore to Isaac Wheeler and Sarah Wheeler. The property is .45 acres, a dwelling, and a Land Bank fee of $72,000 was paid. The assessed value of the property is $2,049,100.

Property Description: "This is a rare double lot offering in Sconset. Beautiful tree-lined 20,000 square foot parcel in the SR-10 zone. Charming three-bedroom cottage w mini split ACs. Fantastic development potential minutes from Sconset Village. Walk or bike to shops, restaurants and the Sconset Casino. Enjoy property as-is or plan your dream home."

3 Grey Lady Lane for $3,500,000 from Michael Crowe and Kerridan Crowe to 3 Grey Lady Lane LLC. The property is .12 acres, a dwelling, and a Land Bank fee of $70,000 was paid. The assessed value of the property is $2,532,200.

Property Description: "This beautifully crafted home at 3 Grey Lady Lane blends refined coastal architecture with the relaxed sophistication of Nantucket living. Set in a serene pocket in the island’s Miacomet area, the property offers a bright, open floor plan with airy interiors, natural textures, and generous windows that capture the island’s signature light and brings the exterior inside. With a community pool shared by only eleven homes, it's as if the pool is your own without the upkeep that comes with one. Just moments from Miacomet Golf Course, it’s ideal for golf enthusiasts seeking quick access to one of Nantucket’s premier 18-hole courses. The home is also close to Ladies Beach, a local favorite known for its wide sandy shoreline and rolling surf, and just a short distance from the beloved farm stands and food trucks along Hummock Pond Road—perfect for grabbing fresh produce, flowers, baked goods, or a ready-made meal after a morning swim or round of golf. Altogether, this location combines upscale coastal comfort with the best of Nantucket’s outdoor and culinary lifestyle."

6 Gay Street for $3,202,500 from Kales Family 2022 Revocable Trust to Dunmoor LLC. The property is .09 acres, a dwelling, and a Land Bank fee of $64,050 was paid. The assessed value of the property is $3,571,700.

Property Description: "Tucked away on a quiet side street just moments from the heart of downtown Nantucket, this well maintained four-bedroom, three-bath Federal style home blends historic charm with modern comfort. Sunlight pours through numerous windows and glass doors, creating a seamless indoor-outdoor connection to the deck and stone patio. Six fireplaces, original wood floors, and preserved architectural details speak to its rich history, while central air conditioning and off-street parking provide contemporary convenience. A true gem in an unbeatable location."

161 Orange Street for $3,100,000 from Sharon L. Bassett and George H. Bassett, Jr., Trustees of the Sharon L. Bassett Revocable Trust to 161 Orange Street LLC. The property is .26 acres, a dwelling, and a Land Bank fee of $62,000 was paid. The assessed value of the property is $2,049,500.

Property Description: "Situated on a highly visible 11,325 square foot corner lot within the CMI Zoning district (5,000 square foot zoning), this property enjoys a prime location directly across the road from more than 15 acres of harbor front Land Bank conservation land. It comprises of a charming three-bedroom main residence with an attached two-car garage, alongside a one-bedroom guest house that has been lovingly cared for and occupied year-round. The property offers a range of residential and commercial possibilities. Move in and enjoy it as-is, or explore development opportunities to take full advantage of its mixed-use zoning. The property also allows, with a special permit, an exception to the standard building height—presenting a unique chance to capture the scenic views of Nantucket Harbor."

17 Milk Street for $2,850,000 from Manioucha Krishnamurti to 17 Milk Street Nominee Trust. The property is .08 acres, a dwelling, and a Land Bank fee of $57,000 was paid. The assessed value of the property is $1,827,400.

Property Description: "Ideally located just moments from the heart of downtown, 17 Milk Street blends timeless Nantucket charm with modern updates. This classic in-town residence features a beautifully renovated kitchen and updated bathrooms, along with newly installed wood flooring that enhances its warm and inviting interior. Step inside to a bright and comfortable entry. To the right of the front door is a cozy living room, perfect for relaxing or entertaining. To the left, the first-floor primary suite offers desirable flexibility for guests or convenient single-level living. The dining room flows seamlessly into the modernized kitchen, appointed with contemporary finishes that complement the home’s historic character. Beyond, a stunning living room with vaulted ceilings, a gas fireplace, and French doors opens directly to the private backyard and patio—ideal for alfresco dining and summer evenings under the stars. Upstairs, two spacious bedrooms and a recently refreshed bathroom provide a peaceful retreat for family or guests. With its prime location, thoughtful improvements, and quintessential island style, this property presents an exceptional opportunity for year-round living, a seasonal getaway, or an investment with strong rental potential."

16 Atlantic Avenue for $2,340,000 from 16 Atlantic Avenue LLC to Nantucket 16 Atlantic Avenue LLC. The property is .12 acres, a dwelling, and a Land Bank fee of $46,800 was paid. The assessed value of the property is $2,045,100.

Property Description: "Welcome to 16 Atlantic Avenue, ideally sited moments from Nantucket’s cobblestoned historic district, schools, the windmill, and mid-island conveniences. This versatile property features two mirror-image, separately metered residences, each with two bedrooms, a full kitchen, designated outdoor spaces, and off-street parking. Whether you're an investor seeking steady rental income, a homeowner interested in living on one side and renting the other, or looking to expand with the remaining ground coverage available, this rare offering presents a multitude of possibilities. Its prime location and flexible layout make it an appealing opportunity for a wide range of buyers."

19 Honeysuckle Drive for $2,294,250 from Nantucket Property Owner LLC to Reagan Driscoll Real Estate Holdings LLC. The property is .09 acres, a dwelling, and a Land Bank fee of $45,885 was paid. The assessed value of the property is $1,427,800.

Property Description: "Nantucket's best kept secret. This is a rare opportunity to own a new home in the heart of Nantucket, only two miles from town and offering easy access to the best Nantucket beaches. This neighborhood will consist of 36 single family homes, a community clubhouse called "The Landing" featuring an outdoor California Kitchen, Putting Green, Gathering Room with large screen tv and retractable walls for indoor outdoor enjoyment, Fitness Center with a Peleton, Treadmill and weights, Heated Pool and lounging areas, fire pit. The new ACK home design delivery 2025, with high end appliances and finishes throughout, three bedrooms, three and one half bathrooms, finished great room in lower level with additional full bathroom."

9 Huntington Street for $1,700,000 from Boston Trust Lending LLC to Tom Nevers Investment LLC. The property is .18 acres, a dwelling, and a Land Bank fee of $34,000 was paid. The assessed value of the property is $1,643,900.

167R Orange Street for $1,220,000 from Daniel T. Mooney and Anna S. Mooney to 167R LLC. The property’s acreage is .28 acres, vacant land, and a Land Bank fee of $24,400 was paid. The assessed value of the property is $1,976,200.

1 McGarvey’s Way for $1,195,000 from Jessie M. Brescher, Trustee of One McGarveys Way Realty Trust to 1 McGarveys Way LLC. The property is .13 acres, a dwelling, and a Land Bank fee of $23,900 was paid. The assessed value of the property is $1,565,700.

2-4-6-8 Orchid Place & Beach Grass Road & Iris Place & 1-3-5-7 Clover Place (8.824% LLC Membership Interest In Sandplain Realty LLC) for $1,095,502 from Steven P. Rosenthal, Trustee of the Arthur J. Epstein 2015 Revocable Trust to Richmond Meadows One ACK LLC. The property is over seven acres, a multi-family, and a Land Bank fee of $21,910 was paid. The assessed value of the property is N/A.

14 Easy Street, West Unit for $1,095,000 from 14 Easy Street LLC to Cascabelles Dos LLC. The property’s acreage is N/A, a condominium, and a Land Bank fee of $21,900 was paid. The assessed value of the property is N/A.

55 Washington Street (50%) for $875,000 from Jeremy Chase Barlow to Deneige Barlow Nash. The property is .06 acres, a dwelling, and a Land Bank fee of $17,500 was paid. The assessed value of the property is $2,868,600.

2-4-6-8 Orchid Place & Beach Grass Road & Iris Place & 1-3-5-7 Clover Place (2.571% LLC membership interest in Eel Point RE Group LLC) for $375,518 from Steven P. Rosenthal, Trustee of the Arthur J. Epstein 2015 Revocable Trust to Richmond Meadows One ACK LLC. The properties combined are over seven acres, multi-family, and a Land Bank fee of $7,510 was paid. The assessed value of the property is N/A.