18
$235,000
3 bd · 2 ba · 1,292 sqft
29499 Laurwayn Dr, Trappe, MD
Nora Turner · Long & Foster Real Estate, Inc.
Est. $70,411/moGet pre-qualified$1,833/sqft · 254 days on Realty
4
Beds
5
Baths
6,000
Sqft
1890
Built
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 agent
Jay Phillips
Courtesy of Holiday Real Estate
(410) 726-8631
Bright MLS · Listing MDTA2012732
Range $726,995 – $844,779 · as of July 14, 2026
ATTOM automated valuation model · 6 published estimates over 6.5 years · shaded band is the model's own published low-to-high range
Highest reading $1,250,593 in April 2026; lowest $308,104 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$2,200,000
Estimated monthly payment
$70,411/mo
Loan amount $8,800,000. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
School ratings (A+ to F) from HJN community data.
White Marsh Elementary School
PK-5 · Regular · Talbot County Public Schools
289 students · 12.7:1 student–teacher
Sandy Hill Elementary School
PK-5 · Regular · Dorchester County Public Schools
393 students · 11.9:1 student–teacher
Judith P. Hoyer Early Childhood Center
PK-5 · Alternative/Other · Dorchester County Public Schools
Within 2 miles of this home: 7 parks and green spaces.
Place data from OpenStreetMap.
Holmes Creek
Reeds Creek
Crosidore Creek
Porpoise Creek
Harrison Circle Play Area
Harrison Circle Playground
Harrison Circle Pond
Bright MLSThis content last refreshed on 2026-10-03 11:50:28 UTC. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
18
$235,000
3 bd · 2 ba · 1,292 sqft
29499 Laurwayn Dr, Trappe, MD
Nora Turner · Long & Foster Real Estate, Inc.
Price Reduced64$459,990
3 bd · 2 ba · 2,523 sqft
1553 Lake Tahoe Dr, Trappe, MD
Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC
Price Reduced72$479,990
3 bd · 2 ba · 2,137 sqft
1549 Lake Tahoe Dr, Trappe, MD
Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC
Price Reduced101$2,695,000
4 bd · 5 ba · 3,589 sqft
4440 Baildon Rd, Trappe, MD
Janet R Larson · Benson & Mangold, LLC
132$1,500,000
4 bd · 3 ba · 2,900 sqft
31720 Ayres Dr, Trappe, MD
Mary C McGuinness · Weichert, REALTORS
Price Reduced47$499,900
4 bd · 2 ba · 2,142 sqft
3853 Rumsey Dr, Trappe, MD
Bryan D Wieland · Benson & Mangold, LLC




