39 Jedidiah Way
Chatham, MA, 02633
$1,650,000
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!”
Current real estate data for Single Family in Chatham as of Apr 24, 2026
66
Single Family Listed
93
Avg DOM
1,045
Avg $ / SqFt
$3,291,897
Avg List Price
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
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
Contact Us
Mortgage Calculator
Community
- Address39 Jedidiah Way Chatham MA
- CityChatham
- CountyBarnstable
- Zip Code02633
Subdivisions in Chatham
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 $1,045. The average listing price for Single Family in Chatham is $3,291,897. To schedule a showing of MLS#22600861 at 39 Jedidiah Way in Chatham, MA, contact your Nauset Management LLC. agent at 774.353.8668.
Similar Listings Nearby
As a lifelong resident of the outer Cape I was the third generation to pick up the mantel in the family construction business. In my early twenties, I called the Cape my home on weekends as I spent several years working for a variety of off-Cape commercial construction companies. My commercial site supervision resume includes two supermarkets, two HUD projects, a funeral home and a handful of steel industrial buildings as well as various restaurant and office remodels. Prior to striking out on m…
More About Jon39 Jedidiah Way
Chatham, MA



