65 & 75 Deer Path Way
Wellfleet, MA · $2,400,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

65 & 75 Deer Path Way

Wellfleet, MA 02667
$2,400,000
7 days on market · Listed Apr 1, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
5
Baths
4.5
Sq Ft
4,209
Acres
2.48
Year Built
1987
$ / Sq Ft
$570
Days on Market
7

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$13,098
Cash Flow / yr
$-77,224
Cash-on-Cash
-11.5%
Cash Required
$672,000
Projected Revenue / yr
$113,825
Avg Daily Rate
$725
Occupancy
43%
STR Range (P50)
$82,809
🟢 LOW RISK — Registration required.
STR revenue range: $54,612$115,730

Location & Nearby

Map of 65 & 75 Deer Path Way, Wellfleet MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ The Flying Fish
    0.90 mi
  • B
    🍽️ Box Lunch
    0.91 mi
  • C
    🍦 Gelato Joy Cafe
    0.93 mi
  • D
    🍽️ Moby Dick's Restaurant
    0.98 mi
  • E
    🍽️ Pizza Spinello
    1.05 mi
  • F
    🍽️ Winslow's Tavern
    1.06 mi
  • G
    🛒 Hatch's Fish & Produce
    1.08 mi
  • H
    🍽️ Chequessett Club
    1.18 mi

About this property

Discover a timeless piece of livable art. It is a masterclass in organic design by architect Robert Kennedy and builder Eric Winslow. Set on 2.48 wooded acres bordering the estuaries of Herring River (Cape Cod National Seashore), this estate offers ultimate privacy. Kennedy's signature integration of architecture and custom furnishings begins at the boardwalk entrance and continues throughout the home.The interior features connected separation, using a central chimney, open balconies, and elevation changes to define spaces while maintaining an airy flow. Multiple curving perches offer intimate views of the wild Wellfleet landscape. While social areas are open, the bedrooms are distinctly private. The property also includes a 400 sq. ft. studio loft with a kitchenette above the two-car garage, plus a separate structure housing an artist's studio (also with kitchenette) and a once-functional indoor pool. This home is the pinnacle of Outer Cape privacy and architectural intent, perfect for the discerning visionary.

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📋 Wellfleet Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Wellfleet
Listed by The Cape House Team, William Raveis Real Estate & Home Services