299 Main Street
Dennis, MA · $9,500,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

299 Main Street

Dennis, MA 02660
$9,500,000
86 days on market · DEL → ACT on Mar 17, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
View on Zillow ↗
Type
SF
Beds
5
Baths
4.5
Sq Ft
5,814
Acres
5.11
Year Built
1953
$ / Sq Ft
$1,634
Days on Market
86

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$52,621
Cash Flow / yr
$-568,208
Cash-on-Cash
-21.4%
Cash Required
$2,660,000
Projected Revenue / yr
$135,944
Avg Daily Rate
$887
Occupancy
42%
STR Range (P50)
$99,774
🟢 LOW RISK — Registration required. Annual renewal.
STR revenue range: $65,937$138,955

Location & Nearby

Map of 299 Main Street, Dennis MA with nearby beaches and points of interest
HThis property
  • A
    🌲 Fresh Pond Conservation Land
    0.74 mi
  • B
    🚴 Great Western Train Trek
    0.75 mi
  • C
    🐕 Fresh Pond Dog Park
    0.75 mi
  • D
    🌲 Indian Lands Conservation Area
    0.95 mi
  • E
    Grand Cove Yacht Club
    0.98 mi
  • F
    🍽️ Spinner Pizza & Burrito
    1.06 mi
  • G
    🍽️ Ring's Juice Bar at Ring Bros. Marketplace
    1.07 mi
  • H
    🛒 Ring Bros. Marketplace
    1.08 mi

About this property

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.

📋 Dennis Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Dennis
Listed by Tori Harrison Farr, Sotheby's International Realty,Inc.