1239 Main Street, Unit 18
Chatham, MA · $1,400,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

1239 Main Street, Unit 18

Chatham, MA 02633
$1,400,000
22 days on market · Listed Apr 8, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
Condo
Beds
3
Baths
2
Sq Ft
1,420
Year Built
1984
$ / Sq Ft
$986
Days on Market
22

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$7,482
Cash Flow / yr
$-32,940
Cash-on-Cash
-8.4%
Cash Required
$392,000
Projected Revenue / yr
$80,771
Avg Daily Rate
$481
Occupancy
46%
STR Range (P50)
$58,628
🟢 LOW RISK — Registration required with town clerk. No current caps.
STR revenue range: $39,724$82,350

Location & Nearby

Map of 1239 Main Street, Unit 18, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Mac's Chatham Fish & Lobster
    0.16 mi
  • B
    🍽️ Pates Restaurant
    0.20 mi
  • C
    🌲 Rolf E. Sylvan Gardens
    0.30 mi
  • D
    🚤 Vineyard Avenue Town Landing
    0.49 mi
  • E
    🐟 White's Pond Public Swimming Area
    0.54 mi
  • F
    Chatham Yacht Basin
    0.63 mi
  • G
    🐟 White Pond
    0.71 mi
  • H
    🍽️ Del Mar Bar & Bistro
    0.71 mi

About this property

Rarely available and exceptionally positioned within Chatham's coveted Oyster Pond condominium complex, this fully renovated, turnkey residence captures the essence of refined coastal living. Offered furnished and supported by a strong rental history, it presents a seamless opportunity for both personal enjoyment and investment. The thoughtfully designed layout includes 2 bedrooms, 2 full baths, and a flexible bonus room ideal as a third sleeping area, office, or den. Upstairs, a spacious primary accommodates a king-sized bed, while the second bedroom--currently a bunk room--offers versatility. A shared bath with in-unit laundry enhances everyday ease. On the main level, the bonus room is paired with a beautifully finished bath featuring a walk-in shower. The renovated kitchen anchors sunlit living spaces that flow effortlessly to a private outdoor seating area, overlooking expansive lawns stretching to the shoreline--an idyllic setting that defines the Oyster Pond lifestyle. Additional highlights include a garage, pool, and racquet courts, all moments to Main Street's iconic shops, dining, and waterfront.

Similar listings in Chatham

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