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Property Description

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.

Overview

Property Status
Sold
Date Sold
October 1, 2025
Lot Size
3.55 Acres
MLS ID
MDTA2011594
Property Type
Residential
Year Built
1986

Features & Amenities

Architecture Styles
Post Beam, Colonial, Dutch
View Description
Bay, Water
Stories
2
Garage Spaces
2.0
Water Source
Well
Roof
Asphalt, Shingle, Architectural Shingle
Lot Features
Cul-de-sac, Landscaping, Front Yard, Level, No Thru Street, Rear Yard, Side Yard(s)
Parking
Attached Garage
Heat Type
Heat Pump(s), Baseboard - Electric
Air Conditioning
Central A/C, Heat Pump(s)
Appliances
Exhaust Fan, Refrigerator, Washer, Dryer
Other 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
Sewer
On Site Septic, Septic of BR
Substructure
Crawl Space, Permanent, Concrete Perimeter
Disability Features
Grab Bars Mod, Level Entry - Main
Other Exterior Features
Exterior Lighting, Flood Lights, Sidewalks
High School
ST. MICHAELS
Sales Price
$1,175,000
Real Estate Tax
$9,590/yr
Zoning
W2

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9190 Pennywhistle Dr

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