# 299 Main Street, South Dennis, MA 02660

> **TL;DR:** 5bd/5ba single family, $8,550,000 ($1471/sqft), built 1953, 5,814 sqft.
> Pool, Fireplace, Waterfront, View. Est. $37,050/mo. Listed 164 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $8,550,000 |
| Price/sqft | $1471 |
| Bedrooms | 5 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 5,814 |
| Year Built | 1953 |
| Lot Size | 222,592 sqft (5.11 acres) |
| Stories | 2 |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 164 |

## Why This Home Stands Out

- **Pool** - Private pool
- **Waterfront** - Direct water access
- **Views** - River
- **Hardwood Floors** - Throughout the home

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $37,050 |
| **Total** | **$37,050** |

## Key Amenities

- Pool
- Fireplace
- Waterfront
- View
- Hardwood
- A/C

## Property Highlights

- Built in 1953
- 5.11 acre lot
- 2 stories
- 7 parking spaces
- Private pool
- Fireplace

## Description

### Agent Description
A truly remarkable Bass River estate, set on an extraordinary 5.11 acres of private waterfront. This stunning property is the epitome of Cape Cod elegance, where timeless character meets thoughtful modern luxury. Lovingly restored to honor its original charm, the home has been impeccably updated throughout while preserving the architectural details that make it so special. At the heart of the residence is a grand, state of the art kitchen, designed for both everyday living and elegant entertaining. Spanning over five acres, the grounds create a rare private riverfront oasis, complete with a private dock offering direct access to the Bass River leading to the ocean. Outdoor living is elevated with a resort-style pool and gazebo, the perfect setting to unwind and take in unforgettable sunset views. For the equestrian enthusiasts there is a stable. With five generously sized bedrooms, this exceptional home offers space and comfort for family and guests alike. A property of this scale, setting, and craftsmanship is rarely available truly one of a kind and not to be missed.

## Location

- **Address:** 299 Main Street, South Dennis, MA 02660
- **County:** Barnstable
- **Coordinates:** 41.680614, -70.158604
- **Google Maps:** https://www.google.com/maps?q=41.680614,-70.158604

## Virtual Tour & Media

- **Video Tour:** https://player.vimeo.com/video/1154698885?h=75cf682d26

## Listing Agent

- **Name:** Tori Harrison Farr
- **Brokerage:** Sotheby's International Realty, Inc.
- **Phone:** 5084557288
- **Email:** tori.harrison@sothebyshomes.com

## Primary Photo

![299 Main Street - Primary Photo](http://lh.rdcpix.com/208d4f12ce964add79ae2ca720ecc560l-f1128291856r.jpg)

*95 total photos available on [listing page](https://www.propertysimple.com/listing/299-main-street-south-dennis-ma-02660-22600117)*

---

**MLS#:** 22600117 | **Updated:** 2026-06-24
**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://www.propertysimple.com/listing/299-main-street-south-dennis-ma-02660-22600117)

---

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