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. 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 Primary Bedroomwith 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
Interior Features
Pantry, Interior Balcony, HU Cable TV
Main Level Bathrooms
1
Exterior
Architectural Style
Cape Cod, Contemporary
Attached Garage YN
1
Construction Materials
Clapboard, Shingle Siding
Exterior Features
Garden
Fencing
Partial
Garage Spaces
1
Lot Features
Bike Path, Cape Cod Rail Trail, Conservation Area, Wooded, Cul-De-Sac, North of Route 28
Open Parking YN
1
Parking Spots
2
Parking Total
2
Patio And Porch Features
Deck, Porch
Roof
Asphalt
Stories
2
Window Features
Skylight(s), Skylight
Financial
HOA Includes
Professional Property Management
Tax Year
2026
Taxes
$3,400
Map
Community
- Address39 Jedidiah Way Chatham MA
- CityChatham
- CountyBarnstable
- Zip Code02633
Subdivisions in Chatham
Market Summary
Current real estate data for Single Family in Chatham as of May 13, 2026
74
Single Family Listed
90
Avg DOM
1,027
Avg $ / SqFt
$3,259,651
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 $1,027. The average listing price for Single Family in Chatham is $3,259,651. 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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39 Jedidiah Way
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