Orleans, MA Classified Ad Listings

40 Leilla Rich Dr. Looking for a NEWLY UPDATED (A/C, furnace and septic) resort-style compound with high-end craftsmanship AND a rare level of privacy? Welcome to 40 Leilla Rich Drive. Set on a fully-fenced lot with room for a pool, this upscale all-season property is perfect for long summer weekends, entertaining guests or simply unwinding near miles of National Seashore beaches. A dramatic va...

135 Marven Way. It's the house. It's the LOCATION. Both are spectacular! The house is a 4 bedroom, 3.5 bath Geiger-Phillips contemporary home. The location is perched high up on a bluff with commanding views of Wellfleet Harbor. Watch the harbor traffic from your living room or your expansive decks. In the evenings, after the unobstructed sunsets, you can see the harbor lights of Mac's and the ...

1937 State Highway Rte 6 Unit H. The iconic Brownies Cabins sit on approximately 1.5 acres by the fire tower on Rt 6. Enjoy a carefree summer or chill on weekends in this cozy, seasonal cottage. Enclosed outdoor shower, deck and extra storage accessed from the outside of the cottage. Good proximity to bike path, beaches, ponds, walking trails, and Town Center. Owners (not tenants) may have one ...

95 Toland Dr. Welcome to this charming Eastham retreat, ideally located just 1.3 miles from Sunken Meadow Beach. This well maintained home offers 3 bedrooms and 2 full baths, including a convenient first floor bedroom, perfect for guests or single level living while two additional bedrooms are situated on the second floor for added privacy. New roof was installed 3/28/2026 The inviting living s...

2067 Weatherly Ave. Set at the far end of Harborside Village, tucked away on a lovely, private site, you will find this 2 bedroom mobile home offering space and site for year round living in a wonderful Wellfleet location offering quick access to the bay, galleries and restaurants on the pier and easy routes to town center, Mayo Beach and Power's Landing. Harborside Village has 88 sites, and of...

18 West Rd. Independent Living at Its Finest! Enjoy carefree, maintenance-free living in this wonderful 62+ community, featuring around-the-clock concierge service and an impressive array of amenities. This spacious unit offers two generously sized bedrooms and two full bathrooms, with convenient laundry located in the guest bath. The full kitchen features beautiful Quartz countertops and a new...

Exhibiting its pleasing, simple lines in a distinct Ming style, this exquisite dining set is intricately carved in Chinese Key with longevity symbols. Completely handmade with solid rosewood by artisans in China using traditional joinery techniques. Two removable leaves for your convenience. The set comes with 4 side chairs and 2 armchairs. The dining room sets are in very good original conditi...

105 Trevor Ln. A pristine townhouse in one of Trevor Village's most desirable settings! Enjoy a peaceful view over a lush expanse of lawn from the slider and the private patio! Whether you're sipping a quiet morning coffee, enjoying your little family members/visitors as they scamper across the green grass, or unwinding during a colorful sunset over the horizon, the tranquil outdoor space will ...

99 Uncle Alberts Drive Ext. Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River and to Nantucket Sound. This exceptional offering includes a conceptua...

70 Hay Rd Unit 70. Cape Cod charm meets opportunity! This adorable Eastham cottage is the perfect place to create your own Cape Cod getaway and summer memories. Enjoy the laid-back Cape lifestyle with beautiful beaches ,boating ,dining, and all that Eastham has to offer nearby. Pets allowed! An additional 170 square foot porch can also be added onto the condo. Charming, inviting and full of pot...

2000 Bridge Rd. Built and maintained by a respected local builder for his own family, this gracious 4-bedroom, 2.5-bath Cape with 2-car garage reflects the quality of construction, materials, and details throughout. Beautiful hardwood floors complement multiple living areas, including a spacious fireplaced living room with handsome wood-paneled accent wall and a separate family room. The kitche...

15 Coventry Way. Welcome to 15 Coventry Way, a charming 3-bedroom, 1.5-bath home offering comfort, convenience, and excellent versatility. Featuring central air, new kitchen appliances, and a strong vacation rental history, this well-maintained property is ideal for year-round living, a Cape Cod getaway, or an investment opportunity. Enjoy summer days and evenings on the lovely deck, and rinse ...

310 S Orleans Rd Unit 7. Tucked away at the end of Golden Eagle Drive, this charming freestanding cottage-style condominium offers a peaceful sense of privacy. Surrounded by mature greenery, the home enjoys a quiet, welcoming atmosphere with parking for 3 vehicles. The updated kitchen features granite countertops, stainless steel appliances, tile flooring, and a convenient slider that opens to ...

10 Somerset Rd. I am pleased to present 'Sweet Home,' a custom-built residence located in the Somerset Heights East End neighborhood. This property features three private bedroom suites, each equipped with an en suite bathroom and an independent entrance. The primary suite is located on the top floor and includes a rooftop deck offering panoramic views and privacy. Notable amenities include rad...

760 Campground Rd. A generational bayfront opportunity in North Eastham: two existing structures on one elevated lot, with sweeping views across Cape Cod Bay. Set high above an established revetment wall, the property pairs a three-bedroom main house with a separate one-bedroom guest cottage. Both are authentic Cape homes with their original character intact, and they sit on two valuable footpr...

14 Harold St Apt 4E. Experience the best of Harwich Port from this sought-after first-floor retreat. This unit offers a rare opportunity to embrace a vibrant Cape Cod lifestyle, with the charm of the village just a short distance away. Inside, the space feels open and inviting. The main living area flows seamlessly to your own private screened-in porch-the perfect spot to sip morning coffee and...

91 Greenland Cir. There's a house on Greenland Circle that doesn't quite know it's on Cape Cod - or maybe it knows exactly what it is and refuses to apologize for it. From the road, it plays along with its neighbors: navy shingles, white trim, a rambling roofline tucked into the oaks and pines, among the kind of sophisticated, well-kept homes that don't usually go in for surprises.Open the fron...

310 Old Chatham Rd Unit E47. NO RENTALS Allowed (even if Zillow shows fake rental estimate) and NO YEAR ROUND LIVING in the park. OPEN May 1st-Oct.31st.//Spend all summers on Cape Cod in Dennis seasonal Old Chatham Resort! Pets ARE allowed w/restrictions. Spacious real 2-Bedroom (not a loft) 2013 fifth wheel trailer with 2 bump-outs on a rare less expensive and quiet E Rd site (backs up to wood...

36 Route 28. WEST HARWICH: Barnaby Inn (an established name and well known) has a long history going back decades. The Inn has 5 star reviews and is year round, 9 bedrooms in total, 8.5 baths and 4 fireplaces. All 6 guest rooms, 1st and 2nd floor have a private full bath, mini fridge, a window a/c, sitting area and wifi in the room. Along with 6 guest rooms, upstairs there is separate living qu...

2950 Old Kings Hwy. Hidden deep in the woods, where sunlight filters through the trees and the world feels far away, sits a rare and enchanting antique home straight out of a fairytale. Reached by winding paths and whispered directions - the kind of place where you half expect to leave a trail of breadcrumbs behind you - this magical retreat rewards those lucky enough to discover it. Abutting a...