39 Jedidiah Way
Chatham, MA · $1,650,000
Zillow ↗
📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

39 Jedidiah Way

Chatham, MA 02633
$1,650,000
19 days on market · Listed Mar 20, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
View on Zillow ↗
Type
SF
Beds
2
Baths
2
Sq Ft
1,810
Acres
0.5
Year Built
1997
$ / Sq Ft
$912
Days on Market
19

Investment Snapshot

🟢 LOW RISK
Monthly Carrying
$8,819
Cash Flow / yr
$-63,817
Cash-on-Cash
-13.8%
Cash Required
$462,000
Projected Revenue / yr
$64,780
Avg Daily Rate
$306
Occupancy
58%
STR Range (P50)
$48,918
🟢 LOW RISK — Registration required with town clerk. No current caps.
STR revenue range: $33,204$65,836

Location & Nearby

Map of 39 Jedidiah Way, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🐕 Chatham Dog Park
    0.31 mi
  • B
    🌲 Sam Ryder Conservation Area
    0.33 mi
  • C
    🌲 George Ryder Forest
    0.69 mi
  • D
    🍽️ Kream N' Kone - Chatham
    0.78 mi
  • E
    🐟 Goose Pond Beach
    0.81 mi
  • F
    🍽️ Hangar B Eatery
    0.85 mi
  • G
    🚴 Old Colony Rail Trail
    0.85 mi
  • H
    🍽️ Chatham Moods Cafe and Grill
    0.86 mi

About this property

39 Jedidiah Way, has been gently utilized by the same family for the past 29 years, serving as a reliable summer retreat. Situated on a .5-acre elevated lot overlooking a wooded cul-de-sac, this property boasts direct access to the Old Colony Rail Trail, a unique feature among current Chatham offerings. Enjoy the convenience of being just 1 mile from Nantucket Sound Beaches or capitalize on the 25 miles of paved trails stretching from Chatham to Wellfleet. This prime location is ideal for couples or families seeking an active on-the go lifestyle. After exploring Chatham & Cape Cod, return to the serene ambiance of a park-like setting. The property showcases an open floor plan, complemented by a vaulted living room featuring a wood-burning fireplace and a dining area with sliders leading to the deck & private backyard. Additional features include a kitchen equipped w/island, pantry, & pull-out shelves, as well as a first-floor bedroom with a full bath and laundry facilities situated across the hall. The second floor, accessible via a spacious oak staircase, features a loft currently utilized as a family room and an ensuite master with seating area & large walk-in closet. Key amenities include oak, tile, and carpet flooring, central air conditioning, town water, and a well for irrigation purposes, as well as an unfinished lower level with interior access. You are likely searching for a vacation home, permanent residence, or potentially a combination of both over time. Your intended use of the home significantly influences your priorities in a property. I recognize the importance of personalizing your space to reflect your individual tastes and lifestyle. The property at 39 Jedidiah Way provides a canvas for your personal touches. Many of the photos were taken during the Blizzard of '26 and serve as a testament that our "Summer Homes Look Great in the Winter Too!"

Similar listings in Chatham

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