Active

645 S Orleans

Orleans, MA 02653

$2,700,000 $11,383/Mo

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Overview

Bed

Bath

3,549

Sqft

0.25

Acre(Lot)

Description

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 except ional 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.

Property Details

Property Type : Residential

Price : $2,700,000

AD Id : 64661264

MLS Id : 73373131

Beds : 7

Lot Size : 0.25 Acre

Living Area Size : 3,549

Year Built : 1930

County : Barnstable

Map

What's Nearby

Nearby Areas

Features

Bathroom Information

Total Baths: 7 Full Baths: 6 Half Baths: 1

Room Information

Total Bedroom: 7
Heating & Cooling

Heating: Baseboard Cooling: Window Unit(s) Water front: Yes WaterSource: Public

Building Information

Year Built: 1930
Exterior Features

Foundation Details: Block

Lot Information

Lot Size Area: 0.25 Lot Size Units: Acres Lot Square Feet: 10,890 Lot Acres: 0.25 Waterfront: Waterfront, 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 Main Square Feet: 0.25

Property Information

Property Type: Residential Sub Type: Single Family ResidenceStyle: Antique SQ ft (Living Area): 3,549

Listing Price Information

Original Listing Price: $3950000

Tax Information

Parcel Number: 2365906 Annual Tax: $10740

Parking Information

Parking Total: 4

Location Information

Direction: On S Orleans Road, heading North, turn right. Main House is on the right of driveway.

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Nearby Home Value

Address	Estimate	Bed	Bath	Sq. Ft	Lot Size
12 Windswept Lane, Orleans, MA, 02653	$4,400,000	4	5	4,311	4,311 SqFt
27 Lovell Lane, Orleans, MA, 02653	$1,230,000	3	2	1,216	1,216 SqFt
7 Little Cove Lane, Orleans, MA, 02653	$2,895,000	5	4	4,381	4,381 SqFt
16 Carlton Rd, Orleans, MA, 02653	$1,995,000	3	4	2,691	2,691 SqFt
343 Tonset Rd, Orleans, MA, 02653	$2,595,000	6	4	4,676	4,676 SqFt
66 Tides End Ln, Orleans, MA, 02653	$4,999,000	4	3	3,867	3,867 SqFt
6-12 Snow Way, Orleans, MA, 02653	$3,860,000	4	3	3,250	3,250 SqFt
6 Snow Way, Orleans, MA, 02653	$3,860,000	4	3	3,250	3,250 SqFt
77 Towhee Lane, Orleans, MA, 02653	$9,200,000	5	7	7,372	7,372 SqFt
18 Sturbridge Dr, Orleans, MA, 02653	$850,000	3	3	2,072	2,072 SqFt

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ByOwner last updated this listing 06/13/2026 @ 21:22

MLS: 73373131 LISTED BY: Guthrie Schofield Group, Berkshire Hathaway HomeServices Robert Paul Properties 508-945-5553 SOURCE: MLS Property Information Network