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A real estate and business search guide for Oceancity Directions provided by the real estate brokerage of Realty Directions. All rights reserved. All information provided is deemed reliable, but is not guaranteed and should be independently verified.

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty Directions participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than Realty Directions contain detailed information including the name of the listing brokers. copyright BRIGHT, All Rights Reserved. Information Deemed Reliable But Not Guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Data last updated:

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    MD,CAROLINE - 1550000
    MDCM2006964

    For Sale: 322 S 2ND ST, DENTON, MD, 21629

    • 5
      Beds
    • 4.1
      Bath
    • $1,550,000
      Price
    • 4853 Sq. ftLiving Area
    1. Home
    2. Real Estate
    3. Caroline
    4. Denton
    5. 21629
    6. 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.

    • Status: Active
    • MLS #: MDCM2006964
    • Days On Market: 54
    • Taxes: $16148 / 2025
    • Property Type: Residential
    • Year Built: 2006
    • Lot Size: 2.44 / 106286
    • InteriorFeatures: 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
    • Courtesy of: Coldwell Banker Realty

    Property Information

    • Accessibility Features: Grab Bars Mod, Level Entry - Main, Roll-in Shower
    • New Construction: No
    • Roof: Architectural Shingle
    • Structure Design Type: Detached
    • Style: CoastalColonial
    • Levels: 3
    • Property Condition: Excellent

    Community

    • County: CAROLINE-MD
    • City: DENTON
    • Zip: 21629
    • Subdivision: DOWNTOWN DENTON

    School

    • School District: CAROLINE COUNTY PUBLIC SCHOOLS
    • Elementary School: -
    • Middle School: -
    • High School: -

    Amenities

    • Property: Residential
    • MLS: ACTIVE-BRIGHT
    • Acres: 2.44
    • Status: Active
    • Basement: No
    • Year Built: 2006
    • Lot SQFT: 106286
    • Lot Size Units: Square Feet
    • Structure Design Type: Detached
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    Map

    322 S 2ND ST, DENTON, MD, 21629

    Contact Agent

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