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$1,175,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 3,315 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 9190 Pennywhistle Dr

General

  • Sold For: $1,175,000
  • Taxes: $9,590 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2011594
  • Added to Site: 155 day(s) ago

Interior

  • Rooms/Areas: Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Foyer, Breakfast Room, Laundry, Loft, Primary Bathroom, Full Bath, Screened Porch
  • Interior Features: Bathroom - Tub Shower, Breakfast Area, Carpet, Combination Kitchen/Living, Dining Area, Exposed Beams, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Floor Plan - Traditional, Kitchen - Table Space, Skylight(s), Walk-in Closet(s), Window Treatments, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Exhaust Fan, Refrigerator, Washer, Dryer
  • Flooring: Ceramic Tile, Engineered Wood, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 2
  • Primary Bathroom: Primary Bathroom, Main

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 3
  • Bedrooms Main & Up: 1
  • Primary Bedroom: Primary Bedroom - Walk-In Closet(s), Main
  • Bedroom 1: Bedroom 2 - Flooring - Carpet, Upper 1
  • Bedroom 2: Bedroom 3 - Ceiling Fan(s), Flooring - Carpet, Upper 1
  • Bedroom 3: Bedroom 4, Upper 1

Other Rooms

  • Foyer/Entry: Foyer, Main
  • Family Room: Family Room - Breakfast Room, Cathedral/Vaulted Ceiling, Fireplace - Wood Burning, Main
  • Sitting Room: Sitting Room - Balcony Access, Upper 1
  • Kitchen: Kitchen - Flooring - HardWood, Island, Pantry, Main
  • Dining Room: Dining Room - Flooring - HardWood, Formal Dining Room, Main
  • Breakfast Room: Breakfast Room, Main
  • Loft: Loft - Cathedral/Vaulted Ceiling, Flooring - Engineered Wood, Upper 1
  • Laundry: Main
  • 3 Season Porch: Screened Porch, Main

Exterior

  • Exterior Features: Exterior Lighting, Flood Lights, Sidewalks

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Attached Garage
  • Garage Description: Garage - Side Entry, Garage Door Opener, Inside Access, Oversized, Additional Storage Area

Location

  • County: Talbot
  • Development Name: McDaniel
  • Subdivision: McDaniel
  • Cross Streets: McDaniel Farm Lane
  • Driving Directions: Rt 33 through St. Michaels, left on Macks Lane, continue straight on McDaniel Farm Lane, left on Pennywhistle Drive, house at end of the street, sign posted.
  • Location Details: Bayside

School Information

  • School District: Talbot County Public Schools
  • High School: St. Michaels

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Baseboard - Electric
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: On Site Septic, Septic < # of BR
  • Water: Well

Structural Information

  • Architectural Info: Post & Beam, Colonial, Dutch
  • Architectural Style: Post & Beam, Colonial, Dutch
  • Structure Type: Detached
  • Builder: Monroe - Thurmond
  • Construction: Frame, Brick, Concrete
  • Foundation: Crawl Space, Permanent, Concrete Perimeter
  • Roof: Asphalt, Shingle, Architectural Shingle
  • Walls/Ceilings: 9'+ Ceilings, Beamed Ceilings, Brick, Dry Wall, Other,
  • Stories/Levels: 2
  • Stories Description: Main, Upper 1
  • Square Feet: 3,315
  • Sq. Ft. Source: Estimated
  • Living Area: 3,315 Sq. Ft.
  • Year Built: 1986
  • Year Built Source: Estimated

Lot Features

  • Property View: Bay, Water
  • Lot Size (Acres): 3.55
  • Lot Size (Sq. Ft.): 154,638
  • Lot Size Source: Estimated
  • Street/Road Desc.: Black Top
  • Lot Features: Cul-de-sac, Landscaping, Front Yard, Level, No Thru Street, Rear Yard, SideYard(s)
  • Zoning: W2
  • Lot Description: Cul-de-sac, Landscaping, Front Yard, Level, No Thru Street, Rear Yard, SideYard(s)

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, Personal Watercraft (PWC), Sail, Swimming Allowed
  • Water Front Type: Creek
  • Dock/Slip Conveys: Yes
  • Docks: 1

Financial Considerations

  • Price Per Sq. Ft.: $376.77
  • Assessment Year: 2025
  • County Tax: $9,590
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,094,700
  • Tax Amount: $9,590
  • Tax Year: 2024
  • Terms: Standard Sale

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 6

Listed by Benson & Mangold, LLC, Kimberly J Crouch and George Howard Real Estate Inc., George Howard
Sold by Keller Williams Realty, LEE MARLAND

Listing agents

— 9190 Pennywhistle Dr —

  • Kimberly J Crouch

    Benson & Mangold, LLC

  • George Howard

    George Howard Real Estate Inc.

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 9190 Pennywhistle Dr

School District:Talbot County Public Schools
NameGradesDistance
Tilghman Elementary School
21374 Foster Ave, Tilghman Island, MD 21671
K-66.8 mi
St. Michaels Middle/High School
200 Seymour Avenue, Saint Michaels, MD 21663
7-123.9 mi
Easton High School
723 Mecklenburg Avenue, Easton, MD 21601
9-1212.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 9190 Pennywhistle Dr

Date
Details
Price
Change
Source
10/01/2025
Sold
$1,175,000
-5.92%
MLS
8/14/2025
Listed
$1,249,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Benson & Mangold, LLC, Kimberly J Crouch and George Howard Real Estate Inc., George Howard
Sold by Keller Williams Realty, LEE MARLAND

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9190 Pennywhistle Drive, McDaniel, MD 21647 (MLS# MDTA2011594) is a Single Family property that was sold at $1,175,000 on October 01, 2025. Want to learn more about 9190 Pennywhistle Drive? Do you have questions about finding other Single Family real estate for sale in McDaniel? You can browse all McDaniel real estate or contact a Coldwell Banker agent to request more information.