645 S Road Orleans
Orleans MA $2,700,000

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...

27 S Road Orleans
Orleans MA $2,500,000

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,...

22 Winslow Drive
Orleans MA $2,150,000

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...

63 Briar Spring Road
Orleans MA $2,100,000

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...

16 Carlton Road
Orleans MA $1,995,000

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...

15 Mill Pond Road
Orleans MA $1,949,000

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...

216 Main Street
Orleans MA $1,900,000

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...

25 Pleasant View Drive
Orleans MA $1,750,000

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 Baywood Drive
Orleans MA $1,595,000

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 ...

588 S Road Orleans
Orleans MA $1,595,000

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...

9 Packet Landing
Orleans MA $1,549,000

4 Beds /

2.5 Baths

/ 3,036 SqFt

Come see this SPECTACULAR and beautifully updated home situated on nearly an acre in one of East Orleans' most desirable neighborhoods. Ideally locate...

9 Honeysuckle Lane
Orleans MA $1,474,000

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...