301 Whidah Road
Chatham, MA · $12,950,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

301 Whidah Road

Chatham, MA 02650
$12,950,000
20 days on market · Listed Mar 19, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
5
Baths
6.5
Sq Ft
7,259
Acres
2.18
Year Built
2020
$ / Sq Ft
$1,784
Days on Market
20

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$69,217
Cash Flow / yr
$-685,698
Cash-on-Cash
-18.9%
Cash Required
$3,626,000
Projected Revenue / yr
$252,305
Avg Daily Rate
$1,234
Occupancy
56%
STR Range (P50)
$184,677
🟢 LOW RISK — Registration required with town clerk. No current caps.
STR revenue range: $115,770$256,160

Location & Nearby

Map of 301 Whidah Road, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🚴 Old Colony Rail Trail - Chatham End
    0.76 mi
  • B
    Ryder's Cove Boatyard
    0.77 mi
  • C
    🚤 Ryder's Cove Landing
    0.81 mi
  • D
    🍽️ Cape Cod Coffee @ Chatham Perk
    0.91 mi
  • E
    🍽️ Elwood's Raw Bars
    0.91 mi
  • F
    🍽️ Chatham Sunrise
    1.03 mi
  • G
    Eastward Ho! Country Club
    1.29 mi
  • H
    Chatham Yacht Club
    1.35 mi

About this property

Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha's Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool area. The main living spaces balance comfort and sophistication with warm wood floors, curated finishes, and multiple gathering areas, including a lower level with a glass-enclosed wine room, custom bar, game area, and media lounge. The kitchen features sleek cabinetry, open shelving, and picture windows overlooking the landscape, while bedrooms serve as private retreats complemented by spa-quality baths. Outside, panoramic water views unfold as a private stairway leads to the shoreline. A detached two-car garage with a guest suite above adds flexibility, completing this exceptional offering.

📋 Chatham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Chatham
Listed by Paul E. Grover, Berkshire Hathaway HomeServices Robert Paul Properties