SEE ALL PHOTOS

For Sale

645 S Orleans

645 S Orleans, Orleans, MA 02653

$3,950,000

For the first time in generations, this extraordinary Pleasant Bay compound--featuring the iconic "Topside" main residence and the charming two-bedroom "Boathouse"--is offered as a rare legacy estate. With a deep-water dock, moorings, and direct bay access, it delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. "Topside" offers 5 bedrooms and 4.5 baths with timeless coastal charm and inviting gathering spaces. The "Boathouse," perched just above the shoreline, features 2 bedrooms, 1 bath, and a private deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn complete the experience. With strong rental history and exceptional potential for personalization or expansion, this lifestyle property invites multigenerational enjoyment, investment, or retreat--an iconic opportunity in one of Cape Cod's most storied settings.

7
beds

7
baths

3,549 Sq.Ft. LIVING AREA

10,890 Sq.Ft. lot

Features & Amenities

Interior

total bedrooms7
Total bathrooms7
full bathrooms6
half bathroom1

Area & Lot

Status For Sale
Living Area3,549 Sq.Ft.
Lot Area10,890 Sq.Ft.
MLS® ID73373131
TypeResidential
YEAR BUILT1930
Architecture StylesAntique
Water FrontageWaterfront, Beach Front, Ocean, Bay, Harbor, Dock/Mooring, Frontage, Deep Water Access, Direct Access, Private, Beach Access, Bay, Harbor, Direct Access, Frontage, 0 to 1/10 Mile To Beach
View DescriptionScenic View(s)

Exterior

water SourcePublic
HEAT TYPEBaseboard
AIR CONDITIONINGWindow Unit(s)
sewerPrivate Sewer
SubstructureBlock

Financial

Sales Price$3,950,000
Real Estate Tax $9,500/yr
Zoning 96-23-0

Schedule a Showing

We would love to show you this beautiful property. Select your preferred date and time below. We will contact you shortly to confirm your appointment.

In Person

Via Video Chat

Schedule a Showing

We would love to show you this beautiful property. Select your preferred date and time below. We will contact you shortly to confirm your appointment.

By providing Guthrie Schofield Group your contact information, you acknowledge and agree to our Privacy Policy and consent to receiving marketing communications, including through automated calls, texts, and emails, some of which may use artificial or prerecorded voices. This consent isn’t necessary for purchasing any products or services and you may opt out at any time. To opt out from texts, you can reply, ‘stop’ at any time. To opt out from emails, you can click on the unsubscribe link in the emails. Message and data rates may apply.

Middle Name

Thank you for your interest in 645 S Orleans, Orleans, MA 02653. We are reviewing your request and will be in touch shortly!

Change time

Mortgage Calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

$0,000 Your Payment

Search Homes For Sale By Community

Cape Cod Homes For Sale

Chatham Homes For Sale

Harwich Homes For Sale

Brewster Homes For Sale

Orleans Homes For Sale

Barnstable Homes For Sale

Osterville Homes For Sale

Cotuit Homes For Sale

Falmouth Homes For Sale

Exclusive Listings

Be in Touch

TONY GUTHRIE

Phone

(508) 246-3236

[email protected]

ALFRED SCHOFIELD

Phone

774-487-8554

[email protected]

Address

499 Main Street Chatham MA 02633

Send a Message

Middle Name

Name

Phone

Message

By providing Tony Guthrie and Alfred Schofield your contact information, you acknowledge and agree to our Privacy Policy and consent to receiving marketing communications, including through automated calls, texts, and emails, some of which may use artificial or prerecorded voices. This consent isn’t necessary for purchasing any products or services and you may opt out at any time. To opt out from texts, you can reply, ‘stop’ at any time. To opt out from emails, you can click on the unsubscribe link in the emails. Message and data rates may apply.