
Land with Home for Sale in Denton, Maryland
322 S 2nd St, Denton, MD 21629
Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore - with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built in 2006 and extensively renovated in 2016, this 5-bed, 4.5-bath home has been meticulously maintained - nothing to do but move in. Two private primary suites on the main level each offer a serene river view retreat, ideal for multi-generational living or hosting guests in style. Three additional bedrooms upstairs provide room to spread out. Soaring 9-ft ceilings, hardwood floors with a dark walnut finish, maple paneling, and a custom Hagerstown Kitchens kitchen set the tone for quality throughout. Entertain on the brand-new Trex deck (2025) or unwind on the screened porch with spectacular western sunsets - and those views are yours forever. The land across the river is a protected Resource Conservation Area. All major systems are in excellent condition and maintained on yearly service contracts: three Carrier variable-speed HVAC units, dual Rinnai tankless water heaters, closed-cell foam insulation, and Hardie Board siding. The private dock features 8 ft MLW, a boat lift, and dedicated kayak dock with water, 240V power, and security cameras - accessed via hand-laid stone steps. Ospreys, Eagles, Herons, and Owls are regular visitors. A dedicated wellness room with river view includes a voice-command sauna, cold plunge, full shower, and workout space. The 3-bay epoxy-floored garage with LED lighting offers abundant storage for all your gear. A short walk to historic downtown Denton - an Eastern Shore best-kept secret with Eden Town Brewery, award-winning Caroline's Restaurant, Clayton Farms, and Shore Gourmet and the Chesapeake Culinary Center. Easton, St. Michaels, and Oxford are less than 30 minutes away, while Annapolis, Ocean City, Rehoboth Beach, Assateague, and Chincoteague are all within roughly an hour. You're already in the heart of it all.
Location
- Street address
- 322 S 2nd St
- County
- Caroline County
- Zip code
- 21629
- Community
- Downtown Denton
- School district
- Caroline County Public Schools
- Elevation
- 32 feet
Property details
- Acreage
- 2.44 acres
- MLS #
- TREND MDCM2006964
- Posted
Property taxes
- Recent
- $16,148
Parcels
- 0603021041
Details and features
Listing
- Type
- Residential
- Franchise
- Coldwell Banker Real Estate
Lot
- Waterfront
- Navigable Water, Waterfront
Exterior
- Parking Spaces
- 3
- Parking
- Driveway, Garage-Attached
Structure
- Heating
- Heat Pump
- Materials
- Hardi Plank Type
Interior
- Rooms
- Bathroom x 5, Bedroom x 5, Dining Room, Family Room
- Appliances
- Built-In Microwave, Dishwasher, Disposal, Dryer-Front Loading, Energy Efficient Appliances, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Oven/Range-Gas, Range Hood, Refrigerator, Six Burner Stove, Washer-Front Loading, Water Heater-Tankless
- Features
- Attic, Bathroom-Soaking Tub, Butlers Pantry, Carpet, Ceiling Fan(s), Crown Moldings, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan-Open, Formal/Separate Dining Room, Kitchen-Gourmet, Kitchen-Island, Pantry, Primary Bedroom-Bay Front, Recessed Lighting, Sauna
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| May 27, 2026 | New listing | $1,550,000 | — | TREND |






















































































