99 Uncle Alberts Drive Extension
Chatham, MA · $5,495,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

99 Uncle Alberts Drive Extension

Chatham, MA 02633
$5,495,000
244 days on market · Listed Mar 20, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
2
Baths
2.5
Sq Ft
1,850
Acres
1.44
Year Built
2004
$ / Sq Ft
$2,970
Days on Market
244

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$29,371
Cash Flow / yr
$-317,304
Cash-on-Cash
-20.6%
Cash Required
$1,538,600
Projected Revenue / yr
$79,315
Avg Daily Rate
$410
Occupancy
53%
STR Range (P50)
$58,696
🟢 LOW RISK — Registration required with town clerk. No current caps.
STR revenue range: $39,733$80,523

Location & Nearby

Map of 99 Uncle Alberts Drive Extension, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🚤 Oyster Pond Furlong Town Landing
    0.45 mi
  • B
    🌲 Rolf E. Sylvan Gardens
    0.48 mi
  • C
    🍽️ Pates Restaurant
    0.49 mi
  • D
    🍽️ Mac's Chatham Fish & Lobster
    0.49 mi
  • E
    🛒 Chatham Village Market
    0.50 mi
  • F
    🍽️ Del Mar Bar & Bistro
    0.51 mi
  • G
    🍽️ Codo Mexican Kitchen
    0.53 mi
  • H
    🍽️ Chatham Cheese Co
    0.56 mi

About this property

Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes. Combining timeless Cape Cod charm with a vision for the future, 99 Uncle Alberts Dr is a one-of-a-kind offering on the waterfront, perfect for those seeking privacy & a truly iconic Chatham location.

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📋 Chatham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Chatham
Listed by Shane K Masaschi, Compass