Waterfront home with spectacular sunsets by Seaside Vacations & Sales

Ninety-five feet of private Chincoteague Bay shoreline. That's what's waiting in your backyard at Lookout on Main — along with a dock, a ladder, two kayaks, a canoe, crab pots, and front-row seats to the most spectacular sunsets on the island.

Set on South Main Street in one of Chincoteague's most coveted locations, this beautifully renovated 5-bedroom home is the kind of place families return to year after year. Floor-to-ceiling windows and soaring ceilings flood the living space with panoramic bay views, while the massive screened porch stretching across the back of the home was made for crab feasts, late-night conversations, and breezy summer evenings. After sunset, gather around the fire pit in Adirondack chairs and watch the stars come out over the water.

Inside, the home was designed for relaxing together without ever feeling crowded. The main living area offers sweeping water views from nearly every seat, comfortable gathering spaces, and fast WiFi if you need to check in with the outside world. Just off the living room, the entertainment room features a 70-inch TV with Blu-ray player and sound bar — perfect for movie nights after long beach days.

The open kitchen and dining area overlook the bay and are fully stocked for everything from pancake breakfasts to seafood dinners with the day’s catch. Prefer to leave the cooking to someone else Main Street’s restaurants, ice cream shops, and local favorites — including J&B Subs — are all just a short stroll away.

Lookout on Main comfortably sleeps up to 10 guests across five bedrooms. Upstairs, the private primary suite features a king bed, waterfront balcony, and incredible bay views — the perfect spot for morning coffee or stargazing before bed.

Downstairs, a second family room gives everyone space to spread out. Bedroom 2 features a queen bed, Bedroom 3 has a twin bunk bed, Bedroom 4 offers two twin beds, and Bedroom 5 includes a twin-over-full pyramid bunk that kids are sure to claim first.

But the real magic of Lookout on Main happens outside. Spend your days kayaking from the backyard, crabbing off the dock, playing yard games on the waterfront lawn, or simply watching herons and egrets drift along the shoreline. End the evening with a glass of wine as the sun melts into the bay and the sky turns shades of orange and pink you won’t quite believe are real.

This is the kind of Chincoteague vacation people talk about all year long.

Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. We do NOT rent to party groups, high school groups, or bachelor-type parties.

Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.