Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
5 Beds
5 Baths
2,617 sqft

$1,495,000

370 Main Street, South Dennis MA, 02660

Price per sqft$571.26
Built in1840
Property size2,617 sqft
Property typeResidential

Overview

Active

Listed Jul 24, 2026

Updated 5h ago

Meticulously restored circa-1840 Sea Captain's home in the heart of the South Dennis Historic District. Landmark property offers 5 BRs and 4.5 BAs, including 2 first-floor en suite BRs that provide exceptional flexibility & convenience. Versatile floor plan is equally well suited for a private residence, multigenerational living, seasonal retreat, or hospitality use. Extensively renovated & improved over the past 2 decades, the home features a luxury chef's kitchen w/ premium appliances & custom cabinetry, updated baths, modernized systems, mini-split heating & cooling, new roof, restored interiors, & exceptional craftsmanship throughout. Historic details including wide-board floors, exposed beams, fireplaces, built-ins, & an antique brick oven blend seamlessly w/ modern comforts. Beautifully landscaped grounds feature a covered porch, brick terrace, mature gardens, & a distinctive seashell driveway. For nearly 20 years, the property was operated as a successful bed & breakfast w/ an international clientele, & remains an actively licensed B&B property. Prime location near Bass River, beaches, marinas, golf, dining, shopping, conservation & the Cape Cod Rail Trail The spacious chef's kitchen has been recently & extensively renovated with upscale finishes, top line appliances, crisp white cabinetry, and thoughtful planning (including two sinks!) This is a home designed for gathering -- the kind of place where large families, grandchildren, and summer visitors naturally come together. There is room for everyone, yet the home still feels warm, intimate, and welcoming. Outdoors, life slows down. The covered side porch overlooks a brick terrace, perennial gardens, & the wooded beauty of its shady hollow. Whether enjoying morning coffee, hosting summer gatherings, or simply listening to birdsong drifting through the trees, the setting feels remarkably peaceful & private. Lovingly restored and extensively improved over the past two decades, the property combines historic integrity with modern comfort. Significant recent updates include a beautifully renovated kitchen, new roof, comprehensive interior & exterior painting, updated systems, mini-split heating and cooling, renovated interior spaces, new porches, exterior improvements, & artistic landscaping. Just minutes from beaches, boating, the bike trail, restaurants, shops, & conservation land, this exceptional South Dennis property offers the very best of Cape Cod living. Located above the flood zone and close to Bass River, Nantucket Sound beaches, Cape Cod Bay beaches, bike trail, dining, shopping, and marinas, this is a rare opportunity to own one of South Dennis Village's landmark properties.

$9,946/mo

Est. mortgage payment based on a $1,495,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
22602581

Interior Features

Bedrooms
5
Bathrooms
5
Fireplace
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.88 Acres

Other Property Details

Taxes
$3,678
Tax Frequency
Annually

Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Fran I Schofield

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Cape Island Estates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 10/11/2026. Neither the listing broker nor Cape Island Estates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.

Copyright© 2026 Cape Cod and Islands Multiple Listing Service, Inc. All rights reserved.

Powered by Luxury Presence