29 Jessies Landing
Chatham, MA · $3,699,900
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29 Jessies Landing

Chatham, MA 02633
$3,699,900
4 days on market · Listed Apr 28, 2026
Data refreshed Apr 28, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
3
Baths
4.5
Sq Ft
4,565
Acres
0.46
Year Built
2026
$ / Sq Ft
$810
Days on Market
4

Investment Snapshot

Monthly Carrying
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Cash Flow / yr
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Cash-on-Cash
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Cash Required
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Projected Revenue / yr
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Avg Daily Rate
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Occupancy
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STR Range (P50)
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Location & Nearby

Map of 29 Jessies Landing, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Dogfish Taco Co
    0.15 mi
  • B
    🍽️ Asian Paradise
    0.18 mi
  • C
    🍽️ Larry's PX
    0.20 mi
  • D
    🍽️ Mom & Pops Burgers
    0.22 mi
  • E
    🍽️ Chatham Moods Cafe and Grill
    0.26 mi
  • F
    🍽️ Kream N' Kone - Chatham
    0.34 mi
  • G
    🌲 Valley Farm Conservation Area
    0.35 mi
  • H
    🍽️ Mac's Chatham Fish & Lobster
    0.55 mi

About this property

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.

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📋 Chatham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Chatham
Listed by Doug Grattan, Christie's International Real Estate Atlantic Brokerage