Trappe Homes with Coastal Style

Welcome to Trappe, Maryland – a hidden gem nestled in Talbot County, where the charm of small-town living meets the allure of coastal elegance. With its picturesque landscapes and rich history, Trappe offers a serene escape for those seeking a peaceful lifestyle while remaining close to the vibrant communities of the Eastern Shore.

Trappe is known for its friendly atmosphere and tight-knit community, making it an ideal place for families and retirees alike. The town is steeped in history, with beautifully preserved architecture that tells the story of its past. As you stroll through the streets, you’ll be captivated by the quaint shops, delightful eateries, and the warmth of the locals.

One of the standout features of Trappe is its stunning homes, many of which showcase a coastal style that perfectly complements the surrounding natural beauty. Imagine waking up in a beautifully designed home that reflects the soothing colors of the Chesapeake Bay, with airy open spaces, large windows, and outdoor living areas that invite you to enjoy the gentle breezes and breathtaking sunsets. Whether you’re looking for a charming cottage or a spacious family home, Trappe offers a variety of options that embody the essence of coastal living.

With easy access to the waterfront, residents can enjoy boating, fishing, and exploring the nearby beaches. Trappe is also conveniently located within a short drive to Easton and St. Michaels, where you can indulge in fine dining, boutique shopping, and cultural experiences.

Discover the coastal charm of Trappe, Maryland, and find your dream home in this idyllic town where every day feels like a vacation.

$11,000,000

4 Beds ⋅ 5 Baths

Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700

Trappe Homes with Coastal Style

Newest Trappe Homes with Coastal Style