Stay at Windward Point

Summary:

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality.



✓ Direct waterfront setting with panoramic harbor views from nearly every room

✓ Seawall path wrapping the property with steps and ladders into the Atlantic

✓ Tidal beach that appears just outside the home

✓ Renovated open-concept living with vaulted ceilings, exposed beams, and stone fireplace

✓ Expansive deck, waterfront lawn and outdoor dining



See more photos, videos, and local recommendations on IG @staycapeann



The Space:

Set at the water’s edge on a quiet point in East Gloucester, this extraordinary coastal home feels almost surrounded by the sea. Expansive windows frame the harbor from nearly every room, bringing the changing tides, passing boats, and coastline into the heart of the home.



A seawall walking path wraps around the property, with stone steps and ladders leading directly into the water. At high tide, the Atlantic becomes your swimming pool. As the tide recedes, a beautiful stretch of beach appears directly in front of the home, creating an ever-changing waterfront experience throughout the day.



The renovation pairs the character of a classic Cape Ann cottage with a bright, refined interior. Vaulted ceilings, exposed wood beams, white shiplap walls, natural hardwood floors, and a dramatic stone fireplace create a setting that feels warm, polished, and distinctly coastal.



At the center of the home, the kitchen, dining area, and living room come together in one open waterfront space. Glass doors lead directly to the deck, lawn, and outdoor dining area, making it easy to move between relaxed indoor living and time beside the water.



★★★ WATERFRONT LIVING ★★★



→ Seawall Path: Walk along the water as the path wraps around the property

→ Direct Water Access: Stone steps and swim ladders lead directly into the Atlantic

→ Tidal Beach: As the tide goes out, a beautiful beach appears in front of the home

→ Swimming: Enjoy an unforgettable saltwater swimming experience just outside the door

→ Deck: Expansive waterfront deck for dining, relaxing, and taking in the harbor views

→ Outdoor Dining: Table and umbrella for meals beside the water

→ Grill: Gas grill available for easy summer dinners

→ Lawn: Landscaped waterfront lawn with room to relax and spread out

→ Garden: Mature trees, hydrangeas, coastal plantings, and Adirondack seating

→ Views: Watch the tides change, boats pass, and evening light move across the cove



Spend mornings walking the seawall, afternoons swimming from the property, and evenings gathered on the deck as the light moves across the water. Few homes offer such a direct and immersive connection to the Cape Ann coastline.



★★★ BEDROOMS AND BATHROOMS ★★★



→ Primary Suite: Spacious bedroom with water views, vaulted ceilings, direct deck access, and a beautifully finished en-suite bathroom

→ Bedroom 2: Bright waterfront bedroom with expansive windows and a built-in window seat overlooking the cove

→ Bedroom 3: Generous sleeping space with two beds, vaulted ceilings, exposed beams, water views and en-suite bathroom

→ Spa Bathroom: Soaking tub, oversized walk-in shower, vaulted ceiling, and elevated stone finishes

→ Additional Bathrooms: Beautifully renovated with walk-in showers, custom tilework, and thoughtful coastal details

→ Laundry: Full-size washer and dryer conveniently located near the bedrooms



Guest Access:

Guests will have access to the full home, waterfront deck, lawn, garden, seawall walking path, outdoor dining area, grill, laundry, tidal beach, and direct water access.



On-site parking is provided. Detailed parking, entry, and check-in instructions will be sent prior to arrival.



For guests arriving by boat, access to the dock at the neighboring property may be available by advance arrangement for an additional fee. The slip is best suited for smaller boats, while larger vessels may be accommodated at the deep-water mooring directly in front of the home.



The Neighborhood:

The home is located on Windward Point in East Gloucester, a peaceful waterfront setting surrounded by some of Cape Ann’s most beautiful coastal scenery.



Niles Beach, Rocky Neck, Eastern Point, the Back Shore, and downtown Gloucester are all nearby. Spend the day swimming, walking along the coast, visiting waterfront galleries, or enjoying fresh seafood overlooking Gloucester Harbor.



Downtown Gloucester offers restaurants, shops, museums, whale watches, fishing charters, and views of the city’s historic working waterfront. Rocky Neck is also close by, with galleries, seasonal dining, and classic harbor scenery.



Our Stay Cape Ann team lives and works locally and is always happy to share recommendations for beaches, restaurants, galleries, boating excursions, and lesser-known local favorites.



Getting Around:

A car is recommended for exploring Gloucester, Cape Ann, and the surrounding beaches.



Niles Beach, Rocky Neck, Eastern Point, the Back Shore, downtown Gloucester, Good Harbor Beach, Stage Fort Park, and Rockport are all accessible by a short drive.



The Gloucester MBTA Commuter Rail station provides service to Boston’s North Station. Rideshare availability may vary seasonally, so having a vehicle is the easiest way to explore the area.



The Stay Cape Ann team is available to help with beach access, local transportation questions, boating information, and recommendations for planning your time on Cape Ann.



Other Things to Note:

This is a direct waterfront property. Guests should use extra care around the seawall, walking path, stone steps, swim ladders, deck, tidal beach, and water access areas, especially when traveling with children.



The beach, water depth, and shoreline change significantly with the tides. Swimming and entering the water are at guests’ own risk, and children should be supervised at all times near the waterfront.



Boat access may be available by advance arrangement for an additional fee. Smaller boats may use the neighboring slip, while larger boats may be accommodated at the deep-water mooring directly in front of the property. Availability must be confirmed before arrival.



The home is located in a quiet residential neighborhood. Please remain mindful of noise, observe quiet hours, and enjoy the outdoor spaces respectfully.



No pets, smoking, or events are permitted.



Fireplace is not in use.



Traveling with little ones? A pack-and-play and high chair may be available upon request. Please let us know before arrival so we can confirm availability and have the requested items ready for your stay.



Our Stay Cape Ann team lives and works locally. If you need recommendations for beaches, restaurants, fishing charters, boating excursions, or rainy-day activities, we are happy to help.



Interaction with Guests:

We give guests privacy during their stay, but our local Stay Cape Ann team is available if anything comes up. We can be reached through the booking platform for questions, recommendations, or assistance before and during your stay.



Prior to arrival, the Stay Cape Ann team will send your check-in instructions, access information, parking details, and important property notes.