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!”
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!”
Property Details
Price:
$1,650,000
MLS #:
22600861
Status:
Active
Beds:
2
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
westchatham
Listed Date:
Mar 20, 2026
Finished Sq Ft:
1,810
Total Sq Ft:
1,810
Lot Size:
21,780 sqft / 0.50 acres (approx)
Year Built:
1997
See this Listing
Schools
School District:
Monomoy
Interior
Appliances
Dishwasher, Security System, Refrigerator, Electric Range, Gas Water Heater
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Flooring
Wood, Carpet, Tile
Heating
Hot Water
Exterior
Architectural Style
Cape Cod, Contemporary
Construction Materials
Clapboard, Shingle Siding
Exterior Features
Garden
Parking Spots
2
Roof
Asphalt
Financial
HOA Includes
Professional Property Management
Tax Year
2026
Taxes
$3,400
Map
Community
- Address39 Jedidiah Way Chatham MA
- CityChatham
- CountyBarnstable
- Zip Code02633
Market Summary
Current real estate data for Single Family in Chatham as of Mar 23, 2026
48
Single Family Listed
121
Avg DOM
1,102
Avg $ / SqFt
$3,467,446
Avg List Price
Property Summary
- 39 Jedidiah Way Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $1,650,000 and features 2 beds, 2 baths, and has approximately 1,810 square feet of living space, and was originally constructed in 1997. The current price per square foot is $912. The average price per square foot for Single Family listings in Chatham is $1,102. The average listing price for Single Family in Chatham is $3,467,446. To schedule a showing of MLS#22600861 at 39 Jedidiah Way in Chatham, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.
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