Pending
Sale Pending at 21939 Sherwood Landing Rd, Sherwood, MD 21665 | MLS# MDTA2014838 | Listing updated on 2026-08-28
Photo 1 of Sale Pending at 21939 Sherwood Landing Rd, Sherwood, MD 21665 | MLS# MDTA2014838 | Listing updated on 2026-08-28
Photo 2 of Sale Pending at 21939 Sherwood Landing Rd, Sherwood, MD 21665 | MLS# MDTA2014838 | Listing updated on 2026-08-28
Photo 3 of Sale Pending at 21939 Sherwood Landing Rd, Sherwood, MD 21665 | MLS# MDTA2014838 | Listing updated on 2026-08-28
Photo 4 of Sale Pending at 21939 Sherwood Landing Rd, Sherwood, MD 21665 | MLS# MDTA2014838 | Listing updated on 2026-08-28
57+
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Street View

$718,000

Monthly Est:$3,574

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,696sqft

21939 Sherwood Landing Rd, Sherwood, MD 21665

$3,574/moEst:

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  • 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 Bright MLS-NJ

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Talbot Md County

  • City

    Sherwood

  • 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

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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

DateEventPrice

08/28/2026

Source: mls_logoBright MLS-NJ #MDTA2014838

Listed for Sale

$718,000

$423/sqft

08/28/2026

Source: mls_logoBright MLS-NJ #MDTA2014838

Pending

$718,000

$423/sqft

08/22/2026

Source: mls_logoBright MLS-NJ #MDTA2014838

Coming Soon

$718,000

$423/sqft

Nearby Homes

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