4 Bedroom Nantucket Home for Sale: 5B Chuck Hollow Road | Congdon
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road
5B Chuck Hollow Road

5B Chuck Hollow Road


Year Built


Lot Size (SF)


Land Assessed


Bldg. Assessed


Property Details

Beds: 4

First Floor Bedrooms: 0

Baths: 2

Half Baths: 1

Tom Nevers East! Long winding driveway leads to a four bedroom two and one half bath two story gambrel style house situated on a 1.1 acre lot with incredible privacy. Nicely landscaped irrigated grounds.  Enjoy gorgeous Nantucket sunsets and star gazing from the beach sand fire pit area. Room for a pool in the secluded backyard. Be sure to see the GIS Plans in the Document section...privacy assured! Solid vacation/investment property! Being sold fully furnished and equipped! Great rental potential! Property is located approximately 1.5 miles from the quaint village of Siasconset and in close proximity to the Wave shuttle stop on Milestone Road. All Tom Nevers East property owners pay $400 annual road maintenance fee. Membership in seasonal association tennis courts (optional $250/annually) available for owners and their guests. 6 bedroom Title V Certified shared septic system in place. Property owner is a licensed Massachusetts Real Estate Broker.




Yes full (unfinished).

First Floor

Open living room with raised old brick hearth and beautiful Bordeaux Vermont Castings wood stove for chilly evenings by the fire.  Dining room with french door access to westerly facing brick patio.  Great working kitchen with butcher block breakfast bar, large pantry, and desk work area.  Separate tiled laundry room.  Powder room. Game room/family room leading to covered porch with outside shower. Incredibly private backyard with hot tub and beach sand fire pit.

Second Floor

Master bedroom with full private ensuite bath and walk-in closet.  Three additional guest bedrooms with hallway access to full bath. Linen/clothes storage closet. Large luggage closet.

Third Floor

Attic (unfinished)

Other Structures

Storage shed (8' X 12')

Second Dwelling

Charming and private 2 bedroom, 1 1/2 bath guest cottage with oil heat, loft, back deck, outside shower and full unfinished basement.

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Interior Amenities

Lead Paint
Wood & carpet
Vermont Castings Wood Stove
Whirlpool Duet
Whirpool Duet Propane
GE Double Oven Propane

Exterior/Construction Info



Water Frontage


Water Views


Other Views



Poured Concrete

Easement Description

Driveway and septic easements granted to 5A Chuck Hollow Rd.

Listing Office/Agent


Rick Donnellan


Grey Lady Properties

Link ID


Tom Nevers

Tom Nevers is a lovely area of the island situated south of Milestone Road between Madequecham and Sconset. It was named after a Native American whose name was shortened to Tom Never, thus the area was called Tom Never’s Head, as he was hired by British settlers to man a whale lookout station in the mid 1700s. Fast forwarding to the 1950s, the United States Navy built a facility on an old World War II bombing range on the coastal area of Tom Nevers. It also held as a bomb shelter for President John F. Kennedy in the event that a nuclear attack occurred while he was at home in Hyannisport. Currently the bunker is still intact and houses the Nantucket Hunting Association. The area around the bunker is home to softball fields, a skating rink, and hosts an annual carnival and demolition derby.

Tom Nevers is also home to beautiful south shore beaches and is a favorite spot to fish for striped bass and bluefish in the summertime. Homeowners and renters enjoy peaceful neighborhoods that have the best of both worlds – the beach is just down the road, yet they are only a few short miles to town.