# 645 S Orleans Road, Orleans, MA 02653

> **TL;DR:** 7bd/7ba single family, $2,700,000 ($761/sqft), built 1945, 3,548 sqft.
> Waterfront, View. Est. $14,441/mo. Listed 540 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $2,700,000 |
| Price/sqft | $761 |
| Bedrooms | 7 |
| Bathrooms | 6 full, 1 half |
| Square Feet | 3,548 |
| Year Built | 1945 |
| Lot Size | 10,890 sqft (0.25 acres) |
| Stories | 2 |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 540 |

## Why This Home Stands Out

- **Waterfront** - Waterfront location listed
- **Views** - Harbor

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $13,653 |
| Estimated Insurance | $788 |
| **Total** | **$14,441** |

## Key Amenities

- Waterfront
- View

## Property Highlights

- Built in 1945
- 0.25 acre lot
- 2 stories
- Waterfront

## Description

### Agent Description
For the first time in generations, this landmark Pleasant Bay compound--anchored by the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, ''Topside'' offers 5 bedrooms and 4.5 baths with timeless coastal character and spaces designed for gathering, while the ''Boathouse'' sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity!

## Location

- **Address:** 645 S Orleans Road, Orleans, MA 02653
- **County:** Barnstable
- **Coordinates:** 41.732431, -69.991148
- **Google Maps:** https://www.google.com/maps?q=41.732431,-69.991148

## Listing Agent

- **Name:** Guthrie Schofield Group
- **Brokerage:** Robert Paul Properties, Inc.
- **Broker Phone:** (508) 863-4663
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/645-S-Orleans-Rd_Orleans_MA_02653_M33989-55093?f=listhub&s=CCIAORMA&m=22502226&c=propsimple)

## Photos

![645 S Orleans Road - Photo 1](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3241063089r.jpg)

![645 S Orleans Road - Photo 2](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1374467017r.jpg)

![645 S Orleans Road - Photo 3](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3281458558r.jpg)

![645 S Orleans Road - Photo 4](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3471277975r.jpg)

![645 S Orleans Road - Photo 5](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f4168137747r.jpg)

![645 S Orleans Road - Photo 6](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f888118080r.jpg)

![645 S Orleans Road - Photo 7](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2201416177r.jpg)

![645 S Orleans Road - Photo 8](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1991145528r.jpg)

![645 S Orleans Road - Photo 9](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3999360128r.jpg)

![645 S Orleans Road - Photo 10](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1461627942r.jpg)

![645 S Orleans Road - Photo 11](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2283144210r.jpg)

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![645 S Orleans Road - Photo 19](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2871124971r.jpg)

![645 S Orleans Road - Photo 20](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2747163763r.jpg)

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![645 S Orleans Road - Photo 22](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f440923239r.jpg)

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![645 S Orleans Road - Photo 27](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3844207237r.jpg)

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![645 S Orleans Road - Photo 29](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2794562571r.jpg)

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![645 S Orleans Road - Photo 32](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f144038103r.jpg)

![645 S Orleans Road - Photo 33](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1143189206r.jpg)

![645 S Orleans Road - Photo 34](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1634633402r.jpg)

![645 S Orleans Road - Photo 35](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3207106043r.jpg)

![645 S Orleans Road - Photo 36](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f4136965688r.jpg)

![645 S Orleans Road - Photo 37](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2591319592r.jpg)

![645 S Orleans Road - Photo 38](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2785851356r.jpg)

![645 S Orleans Road - Photo 39](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3440514506r.jpg)

![645 S Orleans Road - Photo 40](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3261045494r.jpg)

![645 S Orleans Road - Photo 41](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f81128072r.jpg)

![645 S Orleans Road - Photo 42](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f335530807r.jpg)

![645 S Orleans Road - Photo 43](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1941494338r.jpg)

![645 S Orleans Road - Photo 44](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2041277398r.jpg)

![645 S Orleans Road - Photo 45](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f430312407r.jpg)

![645 S Orleans Road - Photo 46](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1129360387r.jpg)

![645 S Orleans Road - Photo 47](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3741359383r.jpg)

![645 S Orleans Road - Photo 48](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f211931034r.jpg)

![645 S Orleans Road - Photo 49](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1842676364r.jpg)

![645 S Orleans Road - Photo 50](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2050870172r.jpg)

![645 S Orleans Road - Photo 51](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1844128586r.jpg)

![645 S Orleans Road - Photo 52](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1405369411r.jpg)

![645 S Orleans Road - Photo 53](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3314020735r.jpg)

![645 S Orleans Road - Photo 54](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f428268671r.jpg)

![645 S Orleans Road - Photo 55](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f1902193477r.jpg)

![645 S Orleans Road - Photo 56](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f3084135135r.jpg)

![645 S Orleans Road - Photo 57](http://lh.rdcpix.com/0886c19a3625b388827775f9caad7016l-f2908211499r.jpg)

---

**MLS#:** 22502226 | **Updated:** 2026-10-31
**Source:** listhub

*Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://staging.propertysimple.ai/listing/645-s-orleans-road-orleans-ma-02653-2c35b9a224aa4ce88e30a3e133fe61f8)

---

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