322 S 2ND STREETDENTON, MD 21629

Single Family · 5 Beds · 4 Full Baths · 1 Half Bath · 4,853 Sq. ft. | 2.44 Acres
$1,550,000 ACTIVE

322 S 2ND STREET Overview

Time on Site:
34 days
Visits:
9

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.

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322 S 2ND STREET Facts & Features

  • Type Single Family
  • Sq. ft. 4,853
  • Price/Sq.ft. $319
  • Lot 2.44 Acres

Details

General

Association/HOA

  • Association: No
  • Condo/Coop Association: No

Listing Information

  • Real Estate Owned: No
  • Short Sale: No

Building Information

  • New Construction: No
  • Pool: No Pool
  • Total SQFT: 4853
  • Year Built: 2006

Location/Region

  • Country: US
  • County: CAROLINE
  • County Or Parish: CAROLINE
  • In City Limits: Yes
  • Subdivision Name: DOWNTOWN DENTON

Parking Information

  • Total Parking Spaces: 3
  • Type of Parking: Attached Garage

Tax Information

  • City/Town Tax: 6299.00
  • City/Town Tax Payment Frequency: Annually
  • County Tax: 9849.00
  • County Tax Payment Frequency: Annually
  • Tax Annual Amount: $16,148.00
  • Tax Assessed Value: 986367.00
  • Tax Year: 2025

General Information

  • Property Condition: Excellent
  • Property Type: Residential
  • School District Name: CAROLINE COUNTY PUBLIC SCHOOLS
  • Senior Community: No
  • Special Listing Conditions: Standard
  • Vacation Rental: No
  • Year Assessed: 2026
  • Zoning: SR

Interior

Building Information

  • Building Winterized: No
  • Cooling Fuel: Electric
  • Heating Fuel: Electric

Parking Information

  • Garage Features: Garage - Side Entry,Garage - Front Entry,Garage Door Opener,Inside Access,Oversized
  • Garage Spaces: 3.00
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 4
  • Bathrooms Full Main Level: 2
  • Bathrooms Half: 1
  • Bathrooms Half Main Level: 1
  • Bathrooms Total: 5
  • Bedrooms Total: 5

Building Exterior/Construction

  • Structure Type: Detached

Building Interior

  • Above Grade Finished Area: 4853
  • Above Grade Finished Area Source: Assessor
  • Above Grade Finished Area Units: Square Feet
  • Below Grade Finished Area: 0
  • Below Grade Finished Area Source: Assessor
  • Below Grade Finished Area Units: Square Feet
  • Central Air: No
  • Hot Water: Propane
  • Laundry Type: Main Floor

General Information

  • Accessibility Features: Grab Bars Mod,Level Entry - Main,Roll-in Shower
  • 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
  • Basement: No
  • Cooling: Other
  • Fireplace: No
  • Flooring: Hardwood, Carpet
  • Foundation Details: Crawl Space
  • Interior Features: 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
  • Levels: 3
  • Living Area: 4853
  • Living Area Source: Assessor
  • Main Level Bathrooms: 3.00
  • Main Level Bedrooms: 2
  • Security Features: Exterior Cameras,Monitored,Motion Detectors,Security System,Surveillance Sys
  • Spa Features: Private
  • Spa: Yes

Exterior

Parking Information

  • Parking Features: Asphalt Driveway, Circular Driveway, Paved Driveway, Private

Lot Information

  • Additional Parcels: No
  • Lot Dimensions Source: Assessor
  • Lot Features: Level, Premium, Private, Stream/Creek
  • Lot Size Acres: 2.44
  • Lot Size Dimensions: 185.00 x
  • Lot Size Source: Assessor
  • Lot Size Square Feet: 106286.00
  • Lot Size Units: Square Feet
  • Water Source: Public

Waterfront/View

  • View: River, Scenic Vista, Water, Park/Greenbelt
  • Water Body Name: Choptank River
  • Water Body Type: River
  • Water Oriented: Yes
  • Water View: Yes
  • Waterfront Features: Private Dock Site
  • Waterfront: Yes

Building Exterior/Construction

  • Architectural Style: Coastal, Colonial
  • Construction Materials: HardiPlank Type
  • Dock Type and Features: Hoist/Lift Electric,Material - Treated Lumber,Pier (Perpendicular),Other
  • Docks Count: 1
  • Roof: Architectural Shingle

General Information

  • Exterior Features: Extensive Hardscape, Exterior Lighting, Gutter System
  • Horse: No
  • Other Structures: Above Grade,Below Grade
  • Sewer: Public Sewer
  • Utilities: Propane
  • Water Access Features: Boat - Powered,Canoe/Kayak,Fishing Allowed,Personal Watercraft (PWC),Private Access,Sail,Swimming Allowed,Waterski/Wakeboard
  • Water Access: Yes

322 S 2ND STREET Neighborhood

Community

21629 (DENTON) Demographics

40
Median Age
111
Population Density (per sq. mile)
32%
College Educated
$65,625
Estimated Median Income
2,592
Estimated Total Home Owners
727
Estimated Total Renters
78% / 22%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

322 S 2ND STREET Monthly Cost

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$
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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

322 S 2ND STREET Market Data

Based on the last 30 days in this zip code

$470,670
Average List Price
$215
Average Price per Square Foot
7
Properties Sold
110
Average Days on Market
57
Properties for Sale
Calculations provided by Reliance Network

322 S 2ND STREET History

Date Event Value Agent
5/26/2026Source: BRIGHT MLS Added to Database
May 26, 2026
12/3/2024Source: BRIGHT MLS Added to Database
August 12, 2021
Listing provided courtesy of Coldwell Banker Realty- MLS# MDCM2006964MLS ProviderContact Information: [email protected] - 4102638686