29245 HOWELL POINT RD, Trappe, MD 21673

• 4 beds |
• 5 baths |
• 6,000 sqft

Property Description

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.

Listing Status:

Active

Data Last Updated:

February 15, 2026 at 7:16AM

Listing Office:

Holiday Real Estate : 4105247700

Listing Agent:

Jay Phillips : 4107268631

MLS ID:

MDTA2012732

Interior

• General: Bathroom - Walk-In ShowerBreakfast AreaBuilt-InsButlers PantryCrown MoldingsFloor Plan - TraditionalKitchen - GourmetKitchen - IslandPrimary Bedroom - Bay FrontRecessed LightingWalk-in Closet(s)WainscottingWood FloorsWine Storage
• Flooring: HardwoodHeated
• A/C: Central A/CGeothermal
• Heating: CentralGeo-thermal
• Fireplace: BrickMantel(s)WoodFireplaceFireplaces: 4
• Disability Feature: 36"+ wide Halls

Exterior

• General: Above GradeBelow Grade
• Style: CoastalColonial

Construction

• Roofing: Metal
• General: Brick VeneerCement SidingFrameHardiPlank TypeStick Built2BlockCrawl Space

Location

• Originating MLS: BRIGHT_MAIN
• School District: TALBOT COUNTY PUBLIC SCHOOLS
• County: TALBOT-MD

Lot

• Zoning: A12103129691
• View: BayWater

Utilities

• Water: Private
• Sewer: Private Septic Tank

Financial

• Source: BRIGHT_MAIN