Coldwell Banker Home Page
Local Realty Service Provided By: Coldwell Banker Flanagan Realty
Property view
Listing view 2
Listing view 3

4440 Baildon Rd, 
Trappe, MD 21673

$2,895,000


4

Beds


5

Baths


3,589

Sq Ft


Single Family

Active

Listed by

Janet R Larson

Benson & Mangold, LLC., (410) 745-0415, info@bensonandmangold.com

Last updated:

July 14, 2026, 03:50 AM

MLS#

MDTA2014482

Source:

BRIGHTMLS

About This Home

4440 Baildon Rd

With sweeping sunset views, this picturesque estate—perfectly sited on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—schools of fish, abundant waterfowl, and diverse wildlife—making this an ideal Eastern Shore retreat.

Home Facts

Single Family

5 Baths

4 Bedrooms

Built in 1968

Price Summary

2,895,000

$806 per Sq. Ft.

MLS #:

MDTA2014482

Last Updated:

July 14, 2026, 03:50 AM

Added:

2 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

3

Interior

Living Area:

3,589 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

3,589 Sq. Ft.

Year Built:

1968


Lot

Lot Size (Sq. Ft):

138,520


Finances & Disclosures

Finances

Price:

$2,895,000

Price per Sq. Ft:

$806 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.