20 Jessies Landing Chatham MA 02633 MLS #22600591

20 Jessies Landing
Chatham, MA, 02633
$3,299,900
4 Beds
3.5 Baths
2,940 SqFt
0.47 Acres
$3,299,900
20 Jessies Landing
Chatham, MA, 02633
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Open House Mar 07, 2026
11:00 – 01:00
Welcome to this beautifully crafted residence in Jessie’s Landing, an exclusive Eastward Companies development, ideally located just a short walk to Harding’s Beach. Set on nearly a half-acre and outside the flood zone, this thoughtfully designed home offers the perfect blend of Cape Cod charm, modern comfort, and peace of mind. The open floor plan is ideal for everyday living and entertaining, featuring an oversized chef’s kitchen with a large center island, a dining area, and an inviting living room with a gas fireplace. The main-level primary suite offers a walk-in closet and an elegant bath, along with the convenience of a first-floor laundry. The second level includes two spacious bedrooms, a full bath, and a separate bonus room perfect for guests, a home office, or media space. Outdoor living is exceptional, with an expanded paver patio, custom pergola, mature landscaping, and professionally designed landscape lighting. Additional highlights include a full-house generator, central vacuum, security system with cameras, Hunter Douglas window treatments, and an expansive unfinished basement offering excellent storage and future potential. With its private setting, timeless curb appeal, and turnkey condition, this home offers a rare opportunity to enjoy the very best of Cape Cod living close to beaches, town landing, and local amenities.

Property Details

Price:
$3,299,900
MLS #:
22600591
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Jessie’s Landing
Listed Date:
Mar 2, 2026
Finished Sq Ft:
2,940
Total Sq Ft:
2,940
Lot Size:
20,534 sqft / 0.47 acres (approx)
Year Built:
2017
Cape CodJessie’s LandingMonomoy

Schools

School District:
Monomoy

Interior

Appliances
Cooktop, Washer, Range Hood, Refrigerator, Gas Range, Microwave, Electric Dryer, Dishwasher, Gas Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Hardwood, Tile
Laundry Features
Recessed Lighting, First Floor

Exterior

Architectural Style
Cape Cod
Association Amenities
Common Area, Road Maintenance
Construction Materials
Shingle Siding
Exterior Features
Outdoor Shower
Other Structures
Other
Parking Spots
6
Roof
Asphalt, Pitched

Financial

HOA Fee
$1,000
HOA Frequency
Annually
Tax Year
2025
Taxes
$6,580
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Map

Current real estate data for Single Family in Chatham as of Mar 04, 2026
38
Single Family Listed
131
Avg DOM
1,138
Avg $ / SqFt
$3,467,276
Avg List Price

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Property Summary

    Located in the Jessie’s Landing subdivision, 20 Jessies Landing Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $3,299,900 and features 4 beds, 4 baths, and has approximately 2,940 square feet of living space, and was originally constructed in 2017. The current price per square foot is $1,122. The average price per square foot for Single Family listings in Chatham is $1,138. The average listing price for Single Family in Chatham is $3,467,276. To schedule a showing of MLS#22600591 at 20 Jessies Landing in Chatham, MA, contact your Rover IDX%2C LLC agent at 800 BOB-REALTY.
20 Jessies Landing
Chatham, MA