7 Beds /
6.5 Baths
/ 3,548 SqFt
For the first time in generations, this extraordinary Pleasant Bay compound–featuring the iconic ”Topside” main residence and the charming two-bedr…
4 Beds /
3 Baths
/ 2,544 SqFt
Tucked away in one of the area’s most coveted in-town waterfront settings, this exceptional property offers the perfect blend of privacy, convenience,…
5 Beds /
5 Baths
/ 4,091 SqFt
Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding land…
3 Beds /
2.5 Baths
/ 1,956 SqFt
A waterfront gem, where your back yard meets the water’s edge in Orleans’ coveted Briar Springs neighborhood, is 63 Briar Spring offering three levels…
3 Beds /
3.5 Baths
/ 2,892 SqFt
Enjoy the best of Cape Cod summer living at this inviting Orleans getaway, just a 5-minute walk to a private beach and dock on Little Pleasant Bay. Th…
4 Beds /
3 Baths
/ 2,759 SqFt
Tucked behind the famous ”Hedges of East Orleans,” this coastal retreat offers privacy, history, and seaside charm. Nestled in one of the area’s mos…
7 Beds /
8 Baths
/ 3,234 SqFt
Now’s your chance to own one of East Orleans’ most iconic properties!Once home to the beloved Kadee’s Lobster & Clam Bar, a bustling fish market, a we…
6 Beds /
6.5 Baths
/ 3,843 SqFt
Selling as one unit: 3 parcels of improved land in the center of Orleans, Village Center District. The property consists of #88: a 2-bedroom one bath …
5 Beds /
3 Baths
/ 3,397 SqFt
Discover this spacious 5-bedroom, 3-bath Orleans home perfectly located at the end of a quiet cul-de-sac with direct access to Harvey’s Pond. This pro…
3 Beds /
3 Baths
/ 2,432 SqFt
Exceptional craftsmanship, forward-thinking efficiency, & a premier Orleans location come together just 1/2 mile from Pleasant Bay. Built by renowned …
3 Beds /
2.5 Baths
/ 2,841 SqFt
Lush lawns and hydrangeas flanking a winding seashell driveway create a storybook entrance to a peaceful Cape Cod estate tucked away on 1.57 acres. We…
4 Beds /
2 Baths
/ 1,825 SqFt
Rarely available, this renovated 2023 four-bedroom home is tucked away on a quiet road shared by just six properties, offering a rare blend of privacy…
The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service. All properties are subject to prior sale, changes, or withdrawal.
This site was last updated Jul 01-2026 17:31:05.