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Pending
    • $1,550,000

    322 S 2nd St, Denton, MD 21629

    5beds
    4,853sqft
    : 
    $9,993/mo
    Get pre-qualified
    Single Family Residence
    Built in 2006
    2.44 Acres Lot
    $1,442,100 Zestimate®
    $319/sqft
    $-- HOA

    What's special

    Waterfront estateBoat liftHand-laid stone stepsFull showerBrand-new trex deckCold plungeVoice-command sauna
    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.
    91 days
    |
    1,106
    |
    47
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Liz Osborn 443-699-2689,

    Coldwell Banker Realty 4102638686

    Source: Bright MLS,MLS#: MDCM2006964MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      • Main level bathrooms: 3
      • Main level bedrooms: 2
      Basement
      • Area: 0
      Heating
      • Heat Pump, Electric
      Cooling
      • Other, Electric
      Appliances
      • Included: Microwave, Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Exhaust Fan, Extra Refrigerator/Freezer, Ice Maker, Oven/Range - Gas, Range Hood, Six Burner Stove, Refrigerator, Washer, Tankless Water Heater, Water Heater
      • Laundry: Main Level
      Features
      • Attic, Other, Sauna, Recessed Lighting, Primary Bedroom - Bay Front, Pantry, Kitchen Island, Kitchen - Gourmet, Formal/Separate Dining Room, Open Floorplan, Family Room Off Kitchen, Entry Level Bedroom, Crown Molding, Ceiling Fan(s), Butlers Pantry, Soaking Tub
      • Flooring: Hardwood, Carpet
      • Has basement: No
      • Has fireplace: No
      Interior area
      • Total structure area: 4,853
      • Total interior livable area: 4,853 sqft
      • Finished area above ground: 4,853
      • Finished area below ground: 0
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Garage Faces Side, Garage Faces Front, Garage Door Opener, Inside Entrance, Oversized, Asphalt, Circular Driveway, Driveway, Private, Attached
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: Grip-Accessible Features, Accessible Entrance, Roll-in Shower
      Features
      • Levels: Three
      • Stories: 3
      • Exterior features: Extensive Hardscape, Lighting, Rain Gutters
      • Pool features: None
      • Has spa: Yes
      • Spa features: Private
      • Has view: Yes
      • View description: River, Scenic Vista, Water, Park/Greenbelt
      • Has water view: Yes
      • Water view: River,Water
      • Waterfront features: Private Dock Site, River, Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard
      • Body of water: Choptank River
      • Frontage length: Water Frontage Ft: 268
      Lot
      • Size: 2.44 Acres
      • Dimensions: 185.00 x
      • Features: Level, Premium, Private, Stream/Creek
      Details
      • Additional structures: Above Grade, Below Grade
      • Parcel number: 0603021041
      • Zoning: SR
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Coastal,Colonial
      • Property subtype: Single Family Residence
      Materials
      • HardiPlank Type
      • Foundation: Crawl Space
      • Roof: Architectural Shingle
      Condition
      • Excellent
      • New construction: No
      • Year built: 2006
      • Major remodel year: 2016

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Propane

      Community & HOA

      Community
      • Security: Exterior Cameras, Monitored, Motion Detectors, Security System
      • Subdivision: Downtown Denton
      HOA
      • Has HOA: No
      Location
      • Region: Denton
      • Municipality: Denton

      Financial & listing details

      • Price per square foot: $319/sqft
      • Tax assessed value: $986,367
      • Annual tax amount: $16,148
      • Date on market: 5/26/2026
      • Listing agreement: Exclusive Agency
      • Ownership: Fee Simple

        Estimated market value

        $1,442,100

        $1.37M - $1.51M

        $4,101/mo

        Price history

        DateEventPrice
        8/21/2026Pending sale$1,550,000$319/sqft
        Source: Bright MLS #MDCM2006964 Report a problem
        5/27/2026Listed for sale$1,550,000+174.3%$319/sqft
        Source: Bright MLS #MDCM2006964 Report a problem
        5/23/2016Sold$565,000-5.7%$116/sqft
        Source: Public Record Report a problem
        4/27/2016Pending sale$599,000$123/sqft
        Source: Long & Foster Real Estate, Inc. #CM9599752 Report a problem
        3/18/2016Listed for sale$599,000$123/sqft
        Source: Long & Foster Real Estate, Inc. #CM9599752 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$11,049 -22.4%$954,400 +15.5%
        2024$14,233 +16.3%$826,567 +18.3%
        2023$12,242 +21%$698,733 +22.4%
        2022$10,116 -0.7%$570,900 +0.4%
        2021$10,188 -0.1%$568,533 +0.4%
        2020$10,202 +0.4%$566,167 +0.4%
        2019$10,160 +76.3%$563,800
        2018$5,762 -7.7%$563,800
        2017$6,241 $563,800 -6%
        2016-- $599,800
        2015-- $599,800
        2014-- $599,800 -14%
        2013-- $697,800
        2012-- $697,800
        2011-- $697,800 -13.4%
        2010-- $805,540 +8%
        2009-- $745,686 +8.7%
        2008-- $685,833 +9.6%
        2007-- $625,980 +256.8%
        2006-- $175,450 -44%
        2005-- $313,466 +30.3%
        2004-- $240,650
        2003-- $240,650
        2002-- $240,650 -3.4%
        2001-- $249,100
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 21629

        Getting around

        48 / 100
        Car-Dependent
        37 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Caroline County Public Schools

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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