58 Old Chatham Road
Brewster, MA · $1,499,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

58 Old Chatham Road

Brewster, MA 02631
$1,499,000
22 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
4
Sq Ft
2,965
Acres
0.43
Year Built
2025
$ / Sq Ft
$506
Days on Market
22

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$8,276
Cash Flow / yr
$-41,134
Cash-on-Cash
-9.8%
Cash Required
$419,720
Projected Revenue / yr
$82,905
Avg Daily Rate
$406
Occupancy
56%
STR Range (P50)
$61,356
🟢 LOW RISK — Registration required. No current permit caps.
STR revenue range: $39,792$84,201

Location & Nearby

Map of 58 Old Chatham Road, Brewster MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Shark Bah
    0.50 mi
  • B
    🍽️ Linx Tavern
    0.59 mi
  • C
    Ocean Edge Golf Club
    0.61 mi
  • D
    🌲 Sheep Pond Woodlands Trail
    1.26 mi
  • E
    🍽️ Stone L'Oven Pizza Brewster
    1.27 mi
  • F
    🍽️ Picos Taco Shack
    1.31 mi
  • G
    🍽️ Cape Cod Clam
    1.33 mi
  • H
    🚴 CCRT Underpass Rd Trailhead (Brewster)
    1.38 mi

About this property

Exceptional new custom-built smart home lives large with nearly 3,000 sq. ft. of flexible living space--perfect for extended family and friends. Ideally located on a quiet cul-de-sac near Cape Cod Bay beaches, Nickerson State Park, & the Rail Trail, with a local fruit farm just across the street. The open-concept design features white oak flooring, first-floor office, second-floor study, & finished lower level with family room & bonus area--ideal for a gym or home cinema. The chef's kitchen offers Samsung smart appliances, custom cabinetry & high-end quartz countertops flowing into a bright living area and sunroom which overlook the backyard with outdoor shower & custom shed. Spa-inspired baths include heated floors & smart commodes. Five heating/cooling zones, Mitsubishi dual-fuel system, IA septic, private well for economical landscaping, & smart-home controls enhance efficiency--truly a must-see! Buyer acknowledges the Seller must comply with FIRPTA regulations in association with this sale. Upon written request from the Seller the Buyer (s) agrees to extend the closing date for a reasonable amount of time so Seller can obtain a ''Withholding Certificate'' from the IRS prior to the Closing. IA septic-yearly maintaince fee . Taxes are not accurate; check with the town.

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📋 Brewster Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Brewster
Listed by Andrea L Lousararian, William Raveis Real Estate & Home Services