370 Main Street Dennis — Photo 1 of 41
Recent Drop: $74,000
$1,495,000
Investment Analysis — 370 Main Street
Dennis, MA 02660 — South Dennis
Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 5-bedroom in 02660 carries an estimated $3,330/mo in gross rent — about a 1.79% cap rate and $26,692/yr in estimated NOI at the $1,495,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
4.5
SqFt
2,617
Style
Single Family
Built
1840
Meticulously restored 1840 Sea Captain's home in the heart of the South Dennis Historic District. This landmark property offers 5 BRs & 4.5BAs, 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. Renovated to the studs & extensively improved over the past 2 decades, the home features a luxury chef's kitchen w/ 2 sinks, 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. 20-year history as successful B&B, currently licensed.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,617 sq ft principal dwelling). Lot size: 38,332 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Range • Dishwasher • Microwave • Refrigerator • Freezer • Washer • Dryer
Neighborhood
Shopping • Park • Walk/Jog Trails • Golf • Medical Facility • Bike Path
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl FirstVaulted Ceiling(s), Closet/Cabinets - Custom Built, Flooring - Wood, High Speed Internet Hookup
Dining Room
Lvl FirstExterior Access, High Speed Internet Hookup
Kitchen
Lvl Main,FirstBeamed Ceilings, Flooring - Wood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Cabinets - Upgraded, Country Kitchen, Exterior Access, High Speed Internet Hookup, Recessed Lighting, Stainless Steel Appliances, Storage, Gas Stove
Family Room
Lvl SecondWalk-In Closet(s), Flooring - Wood, High Speed Internet Hookup
Primary Bedroom
Lvl FirstBathroom - Full, Closet, Flooring - Wood
Bedroom 2
Lvl FirstBedroom 3
Lvl SecondBathroom - Full, Closet, Flooring - Wood, High Speed Internet Hookup
Bedroom 4
Lvl SecondBathroom - Full, Closet, Flooring - Wood, High Speed Internet Hookup
Bedroom 5
Lvl SecondBathroom - 1/4, Walk-In Closet(s), Flooring - Wood, High Speed Internet Hookup
Bathroom 1
Lvl FirstBathroom 2
Lvl FirstBathroom 3
Lvl FirstProperty History
$1,495,000
Was $1,569,000
Sep 1, 2026
MLS® 73541329
$1,569,000
Jun 24, 2026
MLS® 73541329
Listing Agent: Frances Schofield
Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties
MLS® Number: 73541329
