Swaying Pines, Expansive Modern Estate with Main & Guest House on 3 Wooded Acres

Welcome to Swaying Pines, a serene architectural retreat tucked away on an expansive wooded lot at the end of a magical private dirt road in East Orleans. Designed by a graduate of the Harvard Graduate School of Design in the mid-1960s, this original modern home is a striking example of thoughtful, era-defining architecture. The main house was built in the late 1960s, with a complementary guest house added in the 1980s, and together they create a harmonious compound connected by adjoining decks and a network of outdoor living spaces. The design intentionally optimizes natural light, cross-ventilation, and a seamless indoor/outdoor flow, allowing the home to feel fully immersed in its woodland surroundings.

This ethereal oasis offers a rare sense of privacy and tranquility, alive with birdsong and local wildlife, yet ideally positioned for enjoying Cape Cod’s waterways. Residents and guests of Mayflower Point enjoy access to a small private beach on Pilgrim Lake, a peaceful freshwater retreat that is far less crowded than the public access points. Two additional private saltwater landings on Kent’s Bay and the Namequoit River provide exceptional opportunities for kayaking, paddleboarding, and exploring Pleasant Bay. After a day on the water or at the beach, rinse off in the outdoor shower — there’s nothing quite like warm water under the open sky.

Arriving at the property, the home appears to rise organically into the tree canopy, blending effortlessly with the landscape. Inside, sliding glass doors flood the living spaces with natural light and open onto sun-drenched decks, while vaulted ceilings enhance the airy, open feel. The home’s modern design is complemented by multi-colored lighting and a charming collection of vintage board games from the 1970s and 1980s, adding personality and a nostalgic touch. The well-equipped kitchen flows into multiple dining areas, offering several options for indoor and outdoor meals — perfect for casual breakfasts, family dinners, or al fresco evenings under the trees. Sleeping accommodations are thoughtfully spread across the main house and guest house, featuring king, queen, and twin options, along with 3.5 baths. The guest house also includes a walk-in closet, providing added comfort and convenience for longer stays or extended families.

Swaying Pines is perfectly situated to enjoy the very best of Cape Cod. Skaket Beach on Cape Cod Bay and Nauset Beach on the Atlantic Ocean are each just three miles away, offering miles of sand, surf, and unforgettable sunsets. Nearby Kent’s Point features scenic, dog-friendly hiking trails, while Orleans town center — just over two miles away — offers charming shops, restaurants, and everyday conveniences. Chatham is eight miles away for additional exploration. Whether you’re drawn by the home’s iconic architecture, the private water access, or the peaceful woodland setting, Swaying Pines delivers a rare blend of design, comfort, adventure, and serenity.

Layout of Bedrooms & Bathrooms:

Main House
Bedroom #1 - Queen bed
Bedroom #2 - Queen bed
Bedroom #3 - Two twin beds

Bathroom #1 - Full bathroom with a tub and shower
Bathroom #2 - Full bathroom with a tub and shower

Guest House
Bedroom #1 - King bed
Bedroom #2 - Two twin beds

Bathroom #1 - Half bath
Bathroom #2 - Full bathroom with a tub and shower

**This home provides linens and bath towels. Please remember to bring your own beach towels!**
**This is a dog friendly home. Please inform Nauset Rental if you plan to bring your pup along so we can send you screening questions.**
Amenities
Hospitality Amenities:
Hangers
Iron and Ironing Board
Hair Dryer
Washer and Dryer
Fans

Kitchen Amenities:
Blender
Toaster
Microwave
Cutting Board and Knives
Dishes
Glasses and Utensils
Lobster Pot
Dishwasher
Pots and Pans
Cooking Utensils
Regular Drip Coffee Maker
French Press
Refrigerator
Stove or Range Top
Dish Towels
Wine and/or Bottle Opener

Entertainment Amenities:
Standard TV
WiFi - High Speed
Books and Games
Bluetooth Speaker
Radio

Outdoor Amenities:
Gas Grill
Charcoal Grill
Outdoor Dining Table with Umbrella
Lounge Chairs
Adirondack Chairs
Deck
Hammock
Outdoor Shower - Partially Enclosed or Open Air

Beach Gear:
Boogie Boards
Beach Chairs
Cooler
Standup Paddleboard