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$3,699,900 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 3 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,565 Sq. Ft.
  • 0.46 Acres
  • Updated 7 days ago
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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.

Full Property Details for 29 Jessie's Lndg

General

  • Price: $3,699,900
  • HOA FEE: $83/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,337 (2026)
  • Status: Pending
  • Type: Single Family
  • Source: CCI
  • MLS ID: 22601788
  • Updated: 5/7/2026
  • Added to Site: 20 day(s) ago

Interior

  • Number of Rooms: 12
  • Interior Features: Wet Bar, Recessed Lighting, Pantry, Hookup for Cable TV
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Gas
  • Appliances: Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Microwave, Electric Dryer, Gas Water Heater
  • Flooring: Hardwood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Primary Bathroom: Private Full Bath

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Walk-In Closet(s), Recessed Lighting, Hookup for Cable TV, First
  • Bedroom 3: Second Level
  • Bedroom 4: Second Level

Other Rooms

  • Living Room: First Level
  • Kitchen: Kitchen, Upgraded Cabinets, Breakfast Nook, Kitchen Island, Private Half Bath, Recessed Lighting, First Level
  • Laundry: Recessed Lighting, Laundry Areas, First Floor

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Pool Cover, In Ground, Heated, Gunite

Exterior

  • Exterior Features: Outdoor Shower
  • Deck/Patio: Patio

Parking

  • Garage: Yes
  • Total Spaces: 4

Location

  • County: Barnstable
  • Subdivision: Jessie's Landing
  • Driving Directions: Barn Hill Road to Jessie's Landing. Home is on the left.

Community

  • Association: Yes

Heating & Cooling

  • Cooling Type: Central Air

Utilities

  • Sewer: Public Sewer
  • Water: Well

Structural Information

  • Architectural Style: Cape Cod
  • Construction: Shingle Siding
  • Exterior Const.: Shingle Siding
  • Basement Desc.: Bulkhead Access, Interior Entry, Full, Finished
  • Roof: Asphalt, Pitched
  • Stories/Levels: 3
  • Square Feet: 4,565
  • Sq. Ft. Source: Plans
  • Year Built: 2026
  • Property Condition: Actual, To Be Built, Under Construction

Lot Features

  • Lot Size (Acres): 0.46
  • Lot Size (Sq. Ft.): 20,016
  • Lot Size Source: Field Card
  • Frontage: Private Road
  • Street/Road Desc.: Paved
  • Road Maintenance: Assoc Maintained
  • Zoning: R20

Financial Considerations

  • Price Per Sq. Ft.: $810
  • Association Fee: $1,000
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $97,900
  • Land Assmt: $97,900
  • Tax Amount: $5,337
  • Tax Year: 2026

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 9D12B2

Listed by Christie's International Real Estate Atlantic Brokerage, The Grattan Group and Christie's International Real Estate Atlantic Brokerage, Doug Grattan

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Listing agents

— 29 Jessie's Lndg —

  • The Grattan Group

    Christie's International Real Estate Atlantic Brokerage

  • Doug Grattan

    Christie's International Real Estate Atlantic Brokerage

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 29 Jessie's Lndg

School District:Monomoy Regional School District
NameGradesDistance
Monomoy Regional Middle School
425 Crowell Road, Chatham, MA 02633
5-71 mi
Chatham Elementary School
147 Depot Road, Chatham, MA 02633
PK-41.5 mi
Monomoy Regional High School
75 Oak Street, Harwich, MA 02645
8-124.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 29 Jessie's Lndg Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/24/2026
Listed
$3,699,900
67.33%
MLS
12/19/2025
Sold
$2,211,100
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 29 Jessie's Lndg

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,199
3%
$633,600
6%
2024
$2,134
10%
$597,700
20%
2023
$1,932
-16%
$498,000
—
2022
$2,301
10%
$498,000
19%
2021
$2,086
27%
$418,800
24%
2018
$1,649
—
$338,600
3%
2017
$1,653
227%
$328,600
226%
2016
$506
4%
$100,700
3%
2015
$488
-2%
$97,800
—
2014
$497
—
$97,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 29 Jessie's Lndg

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Christie's International Real Estate Atlantic Brokerage, The Grattan Group and Christie's International Real Estate Atlantic Brokerage, Doug Grattan

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Listed by Ricardo Rodriguez & Associates and Chris Swem

29 Jessies Landing, Chatham, MA 02633 (MLS# 22601788) is a Single Family property with 3 bedrooms, 4 full bathrooms and 1 partial bathroom. 29 Jessies Landing is currently listed for $3,699,900 and was received on April 24, 2026. Want to learn more about 29 Jessies Landing? Do you have questions about finding other Single Family real estate for sale in Chatham? You can browse all Chatham real estate or contact a Coldwell Banker agent to request more information.

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