- Overview
- Description
- Property Details
- Location
- Facts & Features
- Getting Around
- Nearby Homes





Street View
$718,000
Monthly Est:$3,574
3 Beds
- 2 Baths
1 full bath + 1 half bath
1,696sqft
21939 Sherwood Landing Rd, Sherwood, MD 21665
$718,000
$3,574/moEst:
Get Pre-Approved
Single Family Residence
Built in 1905
$-- HOA
12,632.4 sqft lot
$423/sq.ft
Description
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.
- Houzeo last checked: 12 hours ago
- Listing updated: August 28, 2026 at 4:25 pm
- Listing Provided by: James M. Baldwin (443) 255-2502 , Andrea G Griffin (410) 591-9183 | Compass (410) 886-7342
- Source: Bright MLS-NJ | MLS#: MDTA2014838

Property Details
Status
Pending
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1905
HOA Fees
-
Finished Area
1,696 sqft
Lot Size
12,632.4 sqft lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
MDTA2014838
MLS Status
PENDING-BRIGHT
Days on Market
1

Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Download App
Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 3
Bathrooms: 2
Interior
Flooring
Ceramic Tile, Hardwood
Cooling
Central A/c
Sewer
Septic Exists
Exterior Features
Outside Shower, Secure Storage
Heating
Central, Forced Air, Heat Pump(s), Heat Pump Oil Back Up, Programmable Thermostat, Radiator, Zoned
Interior Features
Floor Plan Traditional, Kitchen Island, Family Room Off Kitchen
Construction
Year Built
Year Built: 1905
Home type
Single Family Residence
Foundation Details
Crawl Space, Brick/mortar
Construction Materials
Wood Siding, Blown In Insulation
Roof
Architectural Shingle
Property Condition
Excellent
Architectural Style
Coastal, Cottage
Utilities & Energy
Basement
Drainage System, Outside Entrance, Poured Concrete, Sump Pump, Unfinished
Water Source
Public
Pool Features
In Ground
Parking Features
Parking Space Conveys, Private, Shared Driveway, Stone Driveway
Other Features
Patio And Porch Features
Deck, Porch, Screened
Subdivision Name
Sherwood
Lot Features
Backs To Trees, Front Yard, Landscaping, Level, No Thru Street, Open, Rear Yard, Rural, Poolside
Price History
| Date | Event | Price |
|---|---|---|
08/28/2026 Source: | Listed for Sale | $718,000 $423/sqft |
08/28/2026 Source: | Pending | $718,000 $423/sqft |
08/22/2026 Source: | Coming Soon | $718,000 $423/sqft |
Nearby Homes
Find Homes by Property Features in Sherwood, MD
Based on information from Bright MLS through Oct 09, 2026, 02:30PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
Advertising Broker: Joe Hawkins | Hawkins Real Estate Services




