Current Real Estate Roundup - October 9, 2025

This week’s Current Real Estate Roundup includes property transfers from October 2^nd, 2025 to October 9^th, 2025. It is led by the sale of a Sherburne Way property for over $37 million, a Pleasant Street property for over $15 million, and a North Swift Rock Road property for over $10 million.

3 Sherburne Way for $37,750,000 from Cliffside 2 LLC to Sarah F. Alger, as Trustee of 3 Sherburne Way Nominee Trust. The property is 1.97 acres, a dwelling, and a Land Bank fee of $755,000 was paid. The assessed value of the property is $26,477,600.

You can read the full story on this Sherburne Way sale here.

15 Pleasant Street for $15,450,000 from Cavu Pleasant LLC to 15 Pleasant LLC. The property is .24 acres, a dwelling, and a Land Bank fee of $309,000 was paid. The assessed value of the property is $5,505,200.

Property Description: "Built circa 1800, this original Obed Macy homestead has undergone a meticulous restoration and has been finished to the highest level. Set on an oversized 10,000+ square foot lot among grand homes in the Old Historic District, it’s just moments from Main Street with easy access out of Town."

7 North Swift Rock Road for $10,800,000 from Coulon Realty Nominee Trust to 7 North Swift Road LLC. The property is 2.56 acres, a dwelling, and a Land Bank fee of $216,000 was paid. The assessed value of the property is $8,885,400.

Property Description: "Dionis estate, Great Summer Home for entertaining. Conveniently located within minutes to The Westmoor Club, this rare opportunity to acquire an oversized property, situated on over 2.5 acres of land, and located directly across the street from Nantucket Sound. 7 North Swift Rock is a custom built three bedroom, three full bath and two half bath home featuring spacious rooms that include a great room, living room, kitchen, and dining area. The expansive second floor water views are exceptional. This amazing property has and additional 1400 + square feet of expansion possibilities."

3 Tautemo Way for $7,875,000 from Jonathan A. Jacoby and Suzanne L. Jacoby to Three Tautemo Way Realty Trust. The property is .46 acres, a dwelling, and a Land Bank fee of $157,500 was paid. The assessed value of the property is $4,579,200.

Jonathan Jacoby made national headlines after a lawsuit was filed by his neighbor, Patricia Belford, in June, accusing him of trespassing into their yard at 1 Tautemo Way earlier this year and cutting down a stand of 50-year-old trees in order to create an ocean view for himself from the abutting property at 3 Tautemo Way. Jacoby then subsequently listed his property for sale for nearly $10 million while touting its “sweeping ocean views” in the property description. You can read the full story on this sale here.

13 Cliff Road for $6,000,000 from Barbara O. De Zalduondo II and Lucille De Zalduondo Briance to Lucky Fluke LLC. The property is .45 acres, a dwelling, and a Land Bank fee of $120,000 was paid. The assessed value of the property is $5,129,825.

Property Description: "This early 20th-century home, dubbed 'the Fluke' due to its whale-tail footprint, has been loved and enjoyed as a year-round and summer retreat by multiple generations of the same family for over fifty years. It is beautifully nestled on a large lot amongst grand homes on coveted Cliff Road. With surprising spaces for entertaining and for quiet retreat, the property enjoys an elevated perch over Brant Point that provides wide views and fresh breezes towards Nantucket Sound. The generous lot affords a front lawn with parking and additional expansion options.. The cliffside includes protected lands that guarantee open views for generations to come. This special location is a five-minute walk from Main Street, a short bike ride to the Westmoor Club, and calm water North Shore Beaches."

69 Orange Street for $4,800,000 from Judith F. Lee to Edward Scott Roe and Marion Roe. The property is .12 acres, a dwelling, and a Land Bank fee of $96,000 was paid. The assessed value of the property is $3,588,500.

Property Description: "This beautifully restored and well-maintained federal-style home from the 1830s, located on historic Orange Street, offers a perfect blend of antique charm and modern comforts. It's an ideal property for someone who values both historical character and contemporary upgrades. The home features three finished levels of living space with four bedrooms and four-and-a-half baths. Additionally, it boasts meticulously cared-for gardens, stone walls and a patio area for seating, offering both functional living space and outdoor enjoyment. The home is complete with historic details such as six working fireplaces, uncommonly high ceilings, classic mortgage button in newel post and NHC designated exterior plaque."

3 Chatham Road for $3,575,000 from 3 Chatham Road LLC to Haley Buonaiuto and David Buonaiuto. The property is .44 acres, a dwelling, and a Land Bank fee of $71,500 was paid. The assessed value of the property is $3,888,500.

Property Description: "This four bedroom, four and one half bath home is situated in Monomoy, one of Nantucket's most sought after neighborhoods. Ample room to add a cottage, and garage. Potential for pool. The property features an attractive well maintained home with harbor views. Near to harbor and beach access for fishing, clamming, scalloping and boating. The modern open kitchen and casual dining area is light and bright, as is the great room which features a fireplace and formal dining. The open floor plan is perfect for entertaining. Enjoy the harbor view from the primary bedroom suite, privately located on the third floor. There is an additional primary bedroom on the first floor. A large second floor deck offers beautiful sunsets over the harbor and town. Approximately 490 square feet of ground cover remaining."

5 Hollister Road for $3,192,500 from 5 Hollister Road Trust to Brian Michael Majczak and Tracy Majczak. The property is .46 acres, a dwelling, and a Land Bank fee of $63,850 was paid. The assessed value of the property is $2,150,600.

Property Description: "A tranquil retreat awaits you. This multi-level, light and bright home features views of the Atlantic Ocean and Sankaty Lighthouse. Nestled just off Old Tom Nevers Road, the white shell driveway at the end of Hollister Road takes you to the main house as well as the garage. Enter through the kitchen and dining area, walk a few stairs to the spacious living room with its cathedral ceiling, abundant windows to showcase the ocean views, a fireplace, and access to the wrap-around deck. Bedrooms are situated on the lower levels. An oversized garage has a large studio dwelling on the second floor with a large deck. Beach access is 0.3 miles from the home. Potential for pool needs verification. This turn-key property is a gem."

8 Polliwog Pond Road for $2,900,000 from Henry McNamara and Laura McNamara to Amanda Woods and Daniel S. Ashdon. The property is .18 acres, a dwelling, and a Land Bank fee of $58,000 was paid. The assessed value of the property is $2,077,400.

Property Description: "Welcome to 8 Polliwog Pond Road tucked behind tall hedges and perfectly situated on a tranquil street conveniently located near Town, Surfside, and Cisco. This beautifully renovated Nantucket home offers three finished floors of thoughtfully designed living space, featuring four spacious bedrooms, four full baths, plus a comfortable den ideal for extra guests—all enhanced by central air conditioning for ultimate comfort. The newly remodeled kitchen is an absolute dream, showcasing gorgeous marble countertops, an elegant apron sink, and premium appliances seamlessly integrated behind custom cabinetry, creating a clean and sophisticated aesthetic. The inviting living room exudes authentic Nantucket charm with its tasteful shiplap-covered walls, providing a warm and cozy ambiance. Outside, lush grassy front and private decking off the backyard offers plenty of room to relax or entertain. Enjoy summertime BBQs on the expansive backyard deck, or host delightful al fresco dinners in the charming flagstone side yard. Completing this home's appeal is the serene primary suite, offering a restful retreat after a day exploring all that Nantucket has to offer. Experience the best of island living at 8 Polliwog Pond Road—your perfect Nantucket getaway awaits."

12 Beach Grass Road for $2,754,000 from Nantucket Property Owner LLC to Alpha Wave Trust. The property is .09 acres, a dwelling, and a Land Bank fee of $55,080 was paid. The assessed value of the property is N/A.

17 Lyons Lane for $2,365,000 from BJM2 LLC to QBW LLC. The property is 1.55 acres, a dwelling, and a Land Bank fee of $47,300 was paid. The assessed value of the property is $1,067,800.

2 Olivers Way (portion) for $2,300,000 from La Barca Realty Trust to Tanner E. Powell and Meriwether M. Powell. The property is .46 acres, a dwelling, and a Land Bank fee of $46,000 was paid. The assessed value of the property is N/A.

181 Polpis Road for $2,150,000 from Rebecca A. Mack, Trustee of 181 Polpis Road Realty Trust to 181 Polpis Nominee Trust. The property is 1.95 acres, a dwelling, and a Land Bank fee of $43,000 was paid. The assessed value of the property is $2,252,900.

50 Burnell Street, Lot 36 for $1,925,000 from Costa’s Avalon LLC to Nantucket Peanut LLC. The property’s acreage is N/A, a dwelling, and a Land Bank fee of $38,500 was paid. The assessed value of the property is N/A.

40A Union Street for $1,900,000 from Pickering Properties ACK LLC to Susan M. Lagarce. The property’s acreage is N/A, a condominium, and a Land Bank fee of $38,000 was paid. The assessed value of the property is $1,897,100.

13 Spring Street Unit 2 for $1,900,000 from Pearce Properties ACK LLC to 13 Spring Street Condo LLC. The property’s acreage is N/A, it is a condominium, and a Land Bank fee of $38,000 was paid. The assessed value of the property is $1,532,800.

11 First Way & Cow Pond for $1,880,000 from Alan S.W. Reed, Trustee of the Crow Pasture Trust to Matthew C. Anderson. The property is a combined 1.80 acres, a dwelling, and a Land Bank fee of $37,600 was paid. The combined assessed values of the two properties is $1,698,600.

Lot 1185 on Land Court Plan 16514-167 for $1,440,000 from Lynn McLaughlin to MIYC LLC. The property is .22 acres, a dwelling, and a Land Bank fee of $28,800 was paid. The assessed value of the property is N/A.