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21939 Sherwood Landing Rd, 
Sherwood, MD 21665

$718,000


3

Beds


2

Baths


1,696

Sq Ft


Single Family

Pending

Listed by

James M. Baldwin

, 

Andrea G Griffin

Compass, (410) 886-7342

Last updated:

October 19, 2026, 08:20 AM

MLS#

MDTA2014838

Source:

BRIGHTMLS

About This Home

21939 Sherwood Landing Rd

OPEN HOUSE CANCELED. Homes like these rarely come along in Talbot County: a totally updated cottage with a beautiful in-ground saltwater swimming pool and every update imaginable – all less than 300 feet from the Sherwood Landing pier, where you might launch your kayak, take a morning swim, or even dock your boat for the season. You’ll enjoy greeting neighbors on sunny mornings and cool afternoon naps on the lovely screened porch. Just inside, you’ll find a beautiful living room with so many original early 1900’s details, including an antiqued farmhouse staircase, hardwood floors, and a beautiful mantle and fireplace (propane-fired but easily converted back to wood). There is also a cozy family room that can easily be used as a first-floor bedroom, a powder room, a laundry closet, and a gorgeous kitchen fully remodeled in 2019. The kitchen features a large center island hub, granite counters, new cabinetry, and replaced appliances, including a gas cooking range, plus an enlarged Pella bay window above the sink that offers sunny views of the backyard and pool. Just off the kitchen is a dining area with banquette seating and a neat wet bar, easily accessed through replaced Pella sliders to the expansive rear deck. This home is built for entertaining! Upstairs, you will be pleased to find 3 nicely proportioned bedrooms, all with hardwood flooring and two of which have views over Harris Creek’s Waterhole Cove. A full bath features more original detailing along with a jetted bathtub. A small basement with an encapsulated crawl space houses many of the home’s systems, including the water heater, a sump pump, and a zoned hybrid fuel heat pump (2023) with oil-fired backup. A second heat pump (2010) in the attic services the top floor. While the interior of this home offers so much charm and character, along with every thoughtful amenity possible, the real star of the show is the fenced rear yard. The sellers have invested years of sweat equity into creating a beautifully landscaped backyard oasis complete with a kidney-shaped saltwater concrete pool with travertine decking. The gardens burst all season with hydrangea, verbena, hibiscus, crepe myrtle, and many native perennials. The large deck offers multiple dining and entertaining areas for summer cookouts and crab feasts. Bonus! A single bay garage provides ample storage for all your bikes, boats, tools, and yard and pool equipment. A full list of updates and upgrades is available, including but not limited to: 50 year architectural shingle roof (2025), front porch (2025), heat pump (2023), blown in hardpack insulation (2018), chimney liners and flue (2021), whole house water treatment system (2021), oil tank (2021), kitchen (2019) and over $35,000 of landscaping and hardscaping. The list goes on and on. Life in Talbot County's quaint Village of Sherwood doesn't get much better than this. You’ll be nestled solidly on the banks of Waterhole Cove on the Harris Creek and in the heart of this small community of approximately 20 turn-of-the-Century homes. An 8-minute drive from Saint Michaels, Sherwood is known for its friendly, caring neighbors, beautiful sunrises, community pier enjoyed by residents, and a wonderful 4th of July celebration.

Home Facts

Single Family

2 Baths

3 Bedrooms

Built in 1905

Subdivision & Development:

SHERWOOD

Price Summary

718,000

$423 per Sq. Ft.

MLS #:

MDTA2014838

Last Updated:

October 19, 2026, 08:20 AM

Added:

1 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

1

Interior

Living Area:

1,696 Sq. Ft.


Structure

Structure

Architectural Style:

Coastal, Cottage

Building Area:

1,696 Sq. Ft.

Year Built:

1905


Lot

Lot Size (Sq. Ft):

12,632


Finances & Disclosures

Finances

Price:

$718,000

Price per Sq. Ft:

$423 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.

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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.