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…
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 /
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…
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 …
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…
4 Beds /
3.5 Baths
/ 2,817 SqFt
Set at the peaceful end of a cul-de-sac and bordered by 9.5 acres of conservation land, this Cape Cod retreat offers rare privacy and serenity, with P…
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 17:59:35.