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Sold for $1,500,000
  • $1,500,000

    322 S 2nd St, Denton, MD 21629

    5beds
    4,853sqft
    Single Family Residence
    Built in 2006
    2.44 Acres Lot
    $1,499,900 Zestimate®
    $309/sqft
    $3,654 Estimated rent

    Home value

    $1,499,900

    Estimated sales range

    Not available

    $3,654/mo

    Zestimate® history
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    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Liz Osborn 443-699-2689,

    Coldwell Banker Realty

    Bought with:

    Steven Parker

    L C Parker Real Estate

    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

    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: $309/sqft
    • Tax assessed value: $986,367
    • Annual tax amount: $16,148
    • Date on market: 5/26/2026
    • Listing agreement: Exclusive Agency
    • Ownership: Fee Simple

    Price history

    DateEventPrice
    9/18/2026Sold$1,500,000-3.2%$309/sqft
    Source: Bright MLS #MDCM2006964 Report a problem
    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

    Neighborhood: 21629

    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.

    Sell for more on Zillow
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    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $1,499,900
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    +$29,998
    With Zillow Showcase(estimated)
    $1,529,898