This custom-designed post-and-beam home is filled with charm and character and perfectly sited on a 3.5± acre peninsula with coveted southern exposure. The property offers breathtaking sunrises and sunsets over the Northwest Branch of Harris Creek. Nature lovers will appreciate the abundance of wildlife from bald eagles and osprey to blue herons and more. A brick walkway leads to the welcoming facade, complete with two covered brick front porches. Step inside the two-story foyer, where exposed wood beams and an open stairwell set the tone for the craftsmanship found throughout the home. With an open floor plan and hardwood floors throughout the main living areas, the home’s design takes full advantage of its setting, offering water views from nearly every room and a serene backdrop for everyday living. The living room features a wood-burning fireplace with a brick surround, though the true focal point is the expansive water view framed by oversized windows. The spacious kitchen offers ample cabinet and counter space, an island and two breakfast bars, along with a dining area featuring a bay-window overlooking the backyard and creek beyond. A separate formal dining room is located off the kitchen ideal for hosting family and friends. The main-level primary suite boasts cathedral ceilings, its own wood-burning fireplace, a walk-in closet, a private bath and sliding glass doors leading directly to the rear deck. Additional features on the first floor include a full guest bath and a laundry/mudroom, located off the oversized two-car garage, with access to both the covered front porch and the rear deck. Upstairs, a sitting area overlooks the foyer, while double glass doors open to a balcony with sweeping water views. Three spacious guest bedrooms, a full bath and a loft complete the second floor. Enjoy southern breezes, nature and outdoor living with two expansive decks and a screened porch for enjoying the serene views. A private dock provides water access for boating, crabbing, exploring the Chesapeake Bay and surrounding rivers, kayaking, paddle boarding and direct access to all of the prime fishing spots. Located just 5 miles from historic downtown St. Michaels, you’ll enjoy the best of small-town living featuring boutique shops, waterfront dining, the Chesapeake Bay Maritime Museum, waterfront concerts, coffee shops, ice cream parlors, festivals, events and so much more. Whether as a weekend getaway or a full-time residence, this home offers a true Eastern Shore way of life—where every day feels like a vacation.
Sold for $1,175,000
$1,175,000
9190 Pennywhistle Dr, McDaniel, MD 21647
4beds
3,315sqft
Single Family Residence
Built in 1986
3.55 Acres Lot
$1,154,200 Zestimate®
$354/sqft
$3,910 Estimated rent
Home value
$1,154,200
Estimated sales range
Not available
$3,910/mo
Zestimate® history
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List your homeWhat's special
Wood-burning fireplaceBrick walkwaySouthern exposureWalk-in closetAbundance of wildlifeSitting areaPrivate bath
Zillow last checked:
Listing updated:
Listed by:
Kimberly Crouch 410-829-7062,
Benson & Mangold, LLC,
Co-Listing Agent: George Howard 301-233-3180,
George Howard Real Estate Inc.
Bought with:
LEE MARLAND, RS-0018613
Keller Williams Realty
Source: Bright MLS,MLS#: MDTA2011594
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Foyer, Breakfast Room, Laundry, Loft, Primary Bathroom, Full Bath
Primary bedroom
- Features: Walk-In Closet(s)
- Level: Main
- Area: 374 Square Feet
- Dimensions: 22 x 17
Bedroom 2
- Features: Flooring - Carpet
- Level: Upper
- Area: 270 Square Feet
- Dimensions: 18 x 15
Bedroom 3
- Features: Ceiling Fan(s), Flooring - Carpet
- Level: Upper
- Area: 195 Square Feet
- Dimensions: 15 x 13
Bedroom 4
- Level: Upper
- Area: 513 Square Feet
- Dimensions: 27 x 19
Primary bathroom
- Level: Main
- Area: 99 Square Feet
- Dimensions: 11 x 9
Breakfast room
- Level: Main
- Area: 120 Square Feet
- Dimensions: 12 x 10
Dining room
- Features: Flooring - HardWood, Formal Dining Room
- Level: Main
- Area: 143 Square Feet
- Dimensions: 13 x 11
Family room
- Features: Breakfast Room, Cathedral/Vaulted Ceiling, Fireplace - Wood Burning
- Level: Main
- Area: 390 Square Feet
- Dimensions: 26 x 15
Foyer
- Level: Main
- Area: 168 Square Feet
- Dimensions: 14 x 12
Other
- Level: Main
- Area: 40 Square Feet
- Dimensions: 8 x 5
Other
- Level: Upper
- Area: 56 Square Feet
- Dimensions: 8 x 7
Kitchen
- Features: Flooring - HardWood, Kitchen Island, Pantry
- Level: Main
- Area: 187 Square Feet
- Dimensions: 17 x 11
Laundry
- Level: Main
- Area: 56 Square Feet
- Dimensions: 8 x 7
Loft
- Features: Cathedral/Vaulted Ceiling, Flooring - Engineered Wood
- Level: Upper
- Area: 119 Square Feet
- Dimensions: 17 x 7
Screened porch
- Level: Main
- Area: 176 Square Feet
- Dimensions: 16 x 11
Sitting room
- Features: Balcony Access
- Level: Upper
- Area: 645 Square Feet
- Dimensions: 43 x 15
Heating
- Heat Pump, Baseboard, Electric
Cooling
- Central Air, Heat Pump, Electric
Appliances
- Included: Exhaust Fan, Refrigerator, Washer, Dryer, Electric Water Heater
- Laundry: Laundry Room
Features
- Bathroom - Tub Shower, Breakfast Area, Combination Kitchen/Living, Dining Area, Exposed Beams, Entry Level Bedroom, Family Room Off Kitchen, Open Floorplan, Floor Plan - Traditional, Kitchen - Table Space, Walk-In Closet(s), 9'+ Ceilings, Beamed Ceilings, Dry Wall, Vaulted Ceiling(s)
- Flooring: Ceramic Tile, Engineered Wood, Hardwood, Carpet, Wood
- Windows: Skylight(s), Window Treatments
- Has basement: No
- Number of fireplaces: 2
Interior area
- Total structure area: 3,315
- Total interior livable area: 3,315 sqft
- Finished area above ground: 3,315
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Side, Garage Door Opener, Inside Entrance, Oversized, Storage, Attached
- Attached garage spaces: 2
- Details: Garage Sqft: 672
Accessibility
- Accessibility features: Grip-Accessible Features, Accessible Entrance
Features
- Levels: Two
- Stories: 2
- Patio & porch: Screened Porch
- Exterior features: Lighting, Flood Lights, Sidewalks
- Pool features: None
- Has view: Yes
- View description: Bay, Water
- Has water view: Yes
- Water view: Bay,Water
- Waterfront features: Bayside, Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, Personal Watercraft (PWC), Sail, Swimming Allowed
- Frontage length: Water Frontage Ft: 720
Lot
- Size: 3.55 Acres
- Features: Cul-De-Sac, Landscaped, Front Yard, Level, No Thru Street, Rear Yard, SideYard(s)
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2105188903
- Zoning: W2
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Post & Beam,Colonial,Dutch
- Property subtype: Single Family Residence
Materials
- Frame, Brick, Concrete
- Foundation: Crawl Space, Permanent, Concrete Perimeter
- Roof: Asphalt,Shingle,Architectural Shingle
Condition
- New construction: No
- Year built: 1986
Details
- Builder name: Monroe - Thurmond
Utilities & green energy
- Sewer: On Site Septic, Septic < # of BR
- Water: Well
Community & HOA
Community
- Subdivision: Mcdaniel
HOA
- Has HOA: No
- Services included: None
Location
- Region: Mcdaniel
Financial & listing details
- Price per square foot: $354/sqft
- Tax assessed value: $1,094,700
- Annual tax amount: $9,590
- Date on market: 8/14/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,FHA,VA Loan,Other
- Ownership: Fee Simple
- Road surface type: Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 10/1/2025 | Sold | $1,175,000-5.9%$354/sqft |
Source:  Bright MLS #MDTA2011594 Report a problem | ||
| 8/23/2025 | Pending sale | $1,249,000$377/sqft |
Source: Bright MLS #MDTA2011594 Report a problem | ||
| 8/14/2025 | Listed for sale | $1,249,000-3.9%$377/sqft |
Source: Bright MLS #MDTA2011594 Report a problem | ||
| 8/11/2025 | Listing removed | $1,300,000$392/sqft |
Source: Bright MLS #MDTA2010632 Report a problem | ||
| 7/16/2025 | Contingent | $1,300,000$392/sqft |
Source: Bright MLS #MDTA2010632 Report a problem | ||
| 5/15/2025 | Listed for sale | $1,300,000$392/sqft |
Source: Bright MLS #MDTA2010632 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,094,700 +3.1% |
| 2024 | $9,590 +8.9% | $1,061,967 +3.2% |
| 2023 | $8,804 +11.3% | $1,029,233 +3.3% |
| 2022 | $7,912 +6.3% | $996,500 +0.3% |
| 2021 | $7,446 +0.3% | $993,900 +0.3% |
| 2020 | $7,427 +0.3% | $991,300 +0.3% |
| 2019 | $7,407 +4.3% | $988,700 |
| 2018 | $7,100 +5.2% | $988,700 |
| 2017 | $6,751 +92.2% | $988,700 -7.7% |
| 2016 | $3,512 | $1,070,900 |
| 2015 | $3,512 +7.4% | $1,070,900 |
| 2014 | $3,271 | $1,070,900 -11.7% |
| 2013 | -- | $1,212,900 |
| 2012 | -- | $1,212,900 |
| 2011 | -- | $1,212,900 -17.4% |
| 2010 | -- | $1,468,000 +12.1% |
| 2009 | -- | $1,309,536 +13.8% |
| 2008 | -- | $1,151,073 +16% |
| 2007 | -- | $992,610 +10.6% |
| 2006 | -- | $897,770 +11.8% |
| 2005 | -- | $802,930 +13.4% |
| 2004 | -- | $708,090 +8.9% |
| 2003 | -- | $650,450 +9.7% |
| 2002 | -- | $592,810 +10.8% |
| 2001 | -- | $535,170 |
Find assessor info on the county website
Neighborhood: 21647
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Nearby schools
GreatSchools rating
- 4/10Tilghman Elementary SchoolGrades: PK-5Distance: 6.9 mi
- 5/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 3.9 mi
Schools provided by the listing agent
- 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.
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- Maryland
- Talbot County
- McDaniel
- 21647
- 9190 Pennywhistle Dr
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