29 Jessies Landing
Chatham, MA, 02633
$3,699,900
This exceptional new luxury residence by Eastward Companies offers the rare opportunity to enjoy a brand-new home for the summer season. Ideally situated within a desirable enclave of distinguished properties, this thoughtfully designed 4,500-square-foot home delivers the refined lifestyle today’s discerning buyers seek. Outdoor living takes center stage with a private backyard oasis featuring a heated saltwater pool, spa, automatic pool cover, and a gas fire pit–perfectly designed for effortless entertaining and relaxation. Inside, the home showcases an open and inviting floor plan enhanced by exquisite craftsmanship and high-end finishes throughout. The heart of the home is a stunning gourmet kitchen appointed with quartz countertops, a dramatic center island, and seamless flow into the great room, where a gas fireplace and coffered ceiling create a warm yet sophisticated gathering space. A sun-filled dining area overlooks the pool, while a vaulted sunroom provides an additional elegant setting for entertaining or quiet retreat. The first-floor primary suite offers comfort and privacy with a spacious walk-in closet and luxurious bath. Additional main-level highlights include a dedicated study with a gas fireplace, a powder room, and a well-appointed laundry room with custom cabinetry and sink. Upstairs, two generously sized bedrooms–one with a private en-suite bath–are complemented by an additional full bath and a versatile loft area ideal for a home office, media space, or overflow guests. Further enhancements include a partially finished lower level with a full bath, a two-car garage, professionally landscaped grounds with irrigation well, and connection to town sewer. A rare blend of timeless design, modern amenities, and an exceptional setting, this is Cape Cod living at its finest.
Current real estate data for Single Family in Chatham as of Apr 29, 2026
69
Single Family Listed
88
Avg DOM
1,033
Avg $ / SqFt
$3,326,204
Avg List Price
Property Details
Price:
$3,699,900
MLS #:
22601788
Status:
Active
Beds:
3
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Jessie’s Landing
Listed Date:
Apr 24, 2026
Finished Sq Ft:
4,565
Total Sq Ft:
4,565
Lot Size:
20,016 sqft / 0.46 acres (approx)
Year Built:
2026
Schools
School District:
Monomoy
Interior
Appliances
Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Microwave, Electric Dryer, Gas Water Heater
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Flooring
Hardwood, Tile
Interior Features
Wet Bar, Recessed Lighting, Pantry, HU Cable TV
Laundry Features
Recessed Lighting, Laundry Areas, First Floor
Main Level Bathrooms
2
Exterior
Architectural Style
Cape Cod
Association Amenities
Common Area, Road Maintenance
Attached Garage YN
1
Construction Materials
Shingle Siding
Exterior Features
Outdoor Shower
Garage Spaces
2
Lot Features
Bike Path, Medical Facility, House of Worship, Cape Cod Rail Trail, Shopping, Marina, Cleared, Level, Cul-De-Sac, South of Route 28
New Construction YN
1
Open Parking YN
1
Parking Spots
4
Parking Total
4
Patio And Porch Features
Patio
Roof
Asphalt, Pitched
Stories
3
Financial
HOA Fee
$1,000
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$5,337
Map
Contact Us
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Community
- Address29 Jessies Landing Chatham MA
- SubdivisionJessie’s Landing
- CityChatham
- CountyBarnstable
- Zip Code02633
Subdivisions in Chatham
Property Summary
- Located in the Jessie’s Landing subdivision, 29 Jessies Landing Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $3,699,900 and features 3 beds, 5 baths, and has approximately 4,565 square feet of living space, and was originally constructed in 2026. The current price per square foot is $810. The average price per square foot for Single Family listings in Chatham is $1,033. The average listing price for Single Family in Chatham is $3,326,204. To schedule a showing of MLS#22601788 at 29 Jessies Landing in Chatham, MA, contact your Nauset Management LLC. agent at 774.353.8668.
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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 Jon29 Jessies Landing
Chatham, MA



