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TJ Willoughby
REALTOR®
(410) 259-7983
Office: (410) 814-2400
  • 322 S 2nd Street, Denton, MD 21629 Main Photo

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New to the Market
BEDS5 BATHS4 full 1 partial SQUARE FEET4,853 MLS#MDCM2006964
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONDOWNTOWN DENTON SCHOOLCAROLINE COUNTY PUBLIC SCHOOLS

Property Description

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.

322 S 2nd Street | MLS# MDCM2006964

This single family home located at 322 S 2nd Street, Denton, MD 21629 is currently listed for sale with an asking price of $1,550,000. This property was built in 2006 and has 5 bedrooms and 4 full and 1 partial baths with 4853 sq. ft. S 2nd Street is located in the DOWNTOWN DENTON subdivision within the CAROLINE COUNTY PUBLIC SCHOOLS school district. Search DOWNTOWN DENTON real estate on tjwilloughby.homesale.com today.

Upcoming Open Houses

Open House Saturday May 30th, 1:00pm - 3:00pm

Property Features

Property Type: Residential - Single Family
Fuel Type: Electric
Garage: 3
Heating: Heat Pump(s)
Home Style: 10000001216
Lot Size: 2.44 Acres
Roof Type: Architectural Shingle
Stories: 3.0
Taxes: $16,148
Year Built: 2006

Feature Descriptions

Accessibility: Grab Bars Mod, Level Entry - Main, Roll-in Shower
Additional Structures: Above Grade, Below Grade
Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer - Front Loading, Energy Efficient Appliances, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Oven/Range - Gas, Range Hood, Six Burner Stove, Refrigerator, Washer - Front Loading, Water Heater - Tankless
Exterior: Extensive Hardscape, Exterior Lighting, Gutter System
Exterior: HardiPlank Type
Flooring: Hardwood, Carpet
Interior: Attic, Other, Sauna, Recessed Lighting, Primary Bedroom - Bay Front, Pantry, Kitchen - Island, Kitchen - Gourmet, Formal/Separate Dining Room, Floor Plan - Open, Family Room Off Kitchen, Entry Level Bedroom, Crown Moldings, Ceiling Fan(s), Carpet, Butlers Pantry, Bathroom - Soaking Tub
Lake Name: Choptank River
Location: River
Lot: Level, Premium, Private, Stream/Creek
Lot Dimensions: 2.44 Acre(S)
Municipality: Denton
Parking Features: Asphalt Driveway, Circular Driveway, Paved Driveway, Private
Parking Notes: 3 Total Parking Spaces
Sewer: Public Sewer
Special View Info: River, Scenic Vista, Water, Park/Greenbelt
SQFT Above Finished: 4853
SQFT Total Finished: 4853
Structure Type: Detached
Total Garage/Parking Spaces: 3
Utilities: Propane
Water: Public
Water Access: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard
Waterfront: Private Dock Site

Local Schools

School District: CAROLINE COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Realty
Agency Phone: 4102638686

Shown By

Agent Name: TJ Willoughby
Agent Phone: (410) 259-7983
Agency Title: Berkshire Hathaway HomeServices Homesale Realty

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Estimated Payment

$ 5,247.38 per month $3,449.63 Principal & Interest $1,345.67 Property Tax $452.08 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/27/2026. The listing information on this page last changed on 05/27/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 05/27/2026 12:03:38 AM EST) or Bright MLS (last updated Tue 05/26/2026 11:57:44 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agent License Information: 
Licensed in Maryland
TJ Willoughby 

3500 Boston Street, Baltimore, MD 21224
410-814-2400

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