2079 Head Of The Bay Road

Taxes: $34,868.72 (2026)

About this home

Nestled on 1.85 acres along Pleasant Bay, this extraordinary waterfront estate offers refined craftsmanship, comfort, and sweeping water views. The home features a striking post-and-beam addition with soaring ceilings and walls of glass framing views of the bay and Eastward Ho! Golf Course. Designed for relaxed living and entertaining, the kitchen boasts a dramatic vaulted ceiling, custom cabinetry, and seamless flow to dining and living areas. French doors and oversized windows open to expansive decks and porches, ideal for enjoying the scenery. With over 5,500 sq ft of living space, the home includes spacious bedrooms, inviting gathering areas, and a spectacular primary suite. An additional 2-car garage with a former caretaker's cottage attached provides endless possibilities. Set among mature trees with a private path to the shore, this rare coastal retreat is minutes from Wequassett Resort, Chatham Village, and all the natural beauty and recreation the area has to offer.

Property details

Sewer

On-Site

Style

Cape

Water

City/Town Water

Cooling

Individual

Heating

Electric Baseboard, Individual

Type

Detached

Flooring

Hardwood

Road type

Public, Paved

Waterfront

Bay, Harbor

Master Bath

Yes

Roof

Membrane

Garage

Attached

Lot

Paved Drive, Gentle Slope, Scenic View(s)

Parking

Paved Driveway

Basement

Partially Finished, Interior Access

Exterior

Porch, Deck, Deck - Wood

Waterview Features

Bay