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.
Pending
$718,000
21939 Sherwood Landing Rd, Sherwood, MD 21665
3beds
1,696sqft
Single Family Residence
Built in 1905
0.29 Acres Lot
$718,900 Zestimate®
$423/sqft
$-- HOA
What's special
Fenced rear yardBeautifully landscaped backyard oasisAntiqued farmhouse staircaseHardwood floorsLovely screened porchCozy family roomGranite counters
- 65 days
- 31
- 0
Zillow last checked:
Listing updated:
Listed by:
James M. Baldwin 443-255-2502,
Compass (410) 886-7342,
Listing Team: The Baldwin & Griffin Group Of Compass, Co-Listing Team: The Baldwin & Griffin Group Of Compass,Co-Listing Agent: Andrea G Griffin 410-591-9183,
Compass
Source: Bright MLS,MLS#: MDTA2014838
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Basement, Primary Bathroom, Half Bath
Primary bedroom
- Features: Flooring - HardWood
- Level: Upper
Bedroom 2
- Features: Flooring - HardWood
- Level: Upper
Bedroom 3
- Features: Flooring - HardWood
- Level: Upper
Primary bathroom
- Features: Bathroom - Jetted Tub
- Level: Upper
Basement
- Features: Basement - Unfinished
- Level: Lower
Dining room
- Features: Breakfast Room, Wet Bar, Window Treatments
- Level: Main
Family room
- Features: Flooring - HardWood, Fireplace - Gas, Fireplace - Wood Burning
- Level: Main
Half bath
- Level: Main
Kitchen
- Features: Flooring - HardWood, Granite Counters, Dining Area, Kitchen Island, Lighting - Ceiling, Kitchen - Propane Cooking
- Level: Main
Living room
- Features: Flooring - HardWood
- Level: Main
Screened porch
- Level: Main
Heating
- Central, Forced Air, Heat Pump, Programmable Thermostat, Radiator, Zoned, Electric, Oil
Cooling
- Central Air, Electric
Appliances
- Included: Electric Water Heater
Features
- Floor Plan - Traditional, Kitchen Island, Family Room Off Kitchen, Beamed Ceilings, Dry Wall, Plaster Walls
- Flooring: Ceramic Tile, Hardwood
- Basement: Drainage System,Exterior Entry,Concrete,Sump Pump,Unfinished
- Number of fireplaces: 1
Interior area
- Total structure area: 1,696
- Total interior livable area: 1,696 sqft
- Finished area above ground: 1,696
- Finished area below ground: 0
Property
Parking
- Total spaces: 4
- Parking features: Storage, Garage Faces Front, Inside Entrance, Parking Space Conveys, Private, Shared Driveway, Driveway, Detached, Off Street
- Garage spaces: 1
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Porch, Screened, Screened Porch
- Exterior features: Outdoor Shower, Storage
- Has private pool: Yes
- Pool features: In Ground, Private
- Fencing: Full
- Has view: Yes
- View description: Water, Bay
- Has water view: Yes
- Water view: Water,Bay
- Waterfront features: Bayblock, Canoe/Kayak, Fishing Allowed, Public Access, Swimming Allowed, Bay
- Body of water: Harris Creek
Lot
- Size: 0.29 Acres
- Features: Backs to Trees, Front Yard, Landscaped, Level, No Thru Street, Open Lot, Rear Yard, Rural, Poolside
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2105188067
- Zoning: RESIDENTIAL
- Zoning description: Rural residential -Talbot County Village
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Coastal,Cottage
- Property subtype: Single Family Residence
Materials
- Wood Siding, Blown-In Insulation
- Foundation: Crawl Space, Brick/Mortar
- Roof: Architectural Shingle
Condition
- Excellent
- New construction: No
- Year built: 1905
Utilities & green energy
- Sewer: Septic Exists
- Water: Public
Community & HOA
Community
- Subdivision: Sherwood
HOA
- Has HOA: No
Location
- Region: Sherwood
Financial & listing details
- Price per square foot: $423/sqft
- Tax assessed value: $316,667
- Annual tax amount: $2,827
- Date on market: 8/28/2026
- Listing agreement: Exclusive Right To Sell
- Inclusions: Parking Included In Listprice, parking Included In Saleprice
- Ownership: Fee Simple
Estimated market value
$718,900
$683,000 - $755,000
$2,486/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/28/2026 | Pending sale | $718,000$423/sqft |
Source: | ||
| 8/28/2026 | Listed for sale | $718,000+52.8%$423/sqft |
Source: | ||
| 9/8/2009 | Sold | $470,000-14.4%$277/sqft |
Source: Public Record Report a problem | ||
| 5/2/2009 | Listed for sale | $549,000-7.7%$324/sqft |
Source: Lacaze Meredith Real Estate #TA6788157 Report a problem | ||
| 7/21/2008 | Price change | $595,000-7.8%$351/sqft |
Source: Lacaze Meredith Real Estate #TA6788157 Report a problem | ||
| 6/18/2008 | Listed for sale | $645,000+145.7%$380/sqft |
Source: Lacaze Meredith Real Estate #TA6788157 Report a problem | ||
| 9/30/2005 | Sold | $262,500$155/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2026 | $2,588 +1.9% | $316,667 +2.5% |
| 2025 | $2,540 -4.5% | $308,900 +4.9% |
| 2024 | $2,659 +11% | $294,500 +5.1% |
| 2023 | $2,396 +13.6% | $280,100 +5.4% |
| 2022 | $2,110 +6% | $265,700 |
| 2021 | $1,991 | $265,700 |
| 2020 | $1,991 -4.9% | $265,700 -4.9% |
| 2019 | $2,093 +4.3% | $279,300 |
| 2018 | $2,006 +5.2% | $279,300 |
| 2017 | $1,907 -11.6% | $279,300 -14.4% |
| 2016 | $2,157 | $326,300 |
| 2015 | $2,157 +8.6% | $326,300 |
| 2014 | $1,987 | $326,300 -15.3% |
| 2013 | -- | $385,100 +4.5% |
| 2012 | -- | $368,687 +4.7% |
| 2011 | -- | $352,273 +4.9% |
| 2010 | -- | $335,860 +12% |
| 2009 | -- | $299,866 +13.6% |
| 2008 | -- | $263,873 +15.8% |
| 2007 | -- | $227,880 +14.9% |
| 2006 | -- | $198,362 +17.5% |
| 2005 | -- | $168,846 +21.2% |
| 2004 | -- | $139,330 +11.7% |
| 2003 | -- | $124,752 +13.2% |
| 2002 | -- | $110,176 +15.2% |
| 2001 | -- | $95,600 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 21665
Nearby schools
Schools provided by the listing agent
- Elementary: Tilghman
- Middle: St. Michaels
- High: St. Michaels
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.




