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$1,550,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,853 Sq. Ft.
  • 3 Car Garage
  • Updated 1 day ago

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Open House: 1:00 PM - 3:00 PM

Saturday 5/30 1:00 PM - 3:00 PM

322 S 2nd Street,Denton, MD 21629

322 S 2nd StreetDentonMD21629

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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.

Full Property Details for 322 S 2nd St

General

  • Price: $1,550,000
  • Taxes: $16,148 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDCM2006964
  • Updated: 5/27/2026
  • Added to Site: 2 day(s) ago

Interior

  • 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
  • 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
  • Flooring: Hardwood, Carpet

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 3
  • Main - Full Baths: 2
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 3
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Spa: Yes
  • Spa Description: Private
  • Security/Safety: Exterior Cameras, Monitored, Motion Detectors, Security System, Surveillance Sys

Exterior

  • Exterior Features: Extensive Hardscape, Exterior Lighting, Gutter System

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 3
  • Parking Features: Asphalt Driveway, Circular Driveway, Paved Driveway, Private
  • Parking Type: Attached Garage
  • Garage Description: Garage - Side Entry, Garage - Front Entry, Garage Door Opener, Inside Access, Oversized

Location

  • Municipality: Denton
  • County: CAROLINE
  • Subdivision: DOWNTOWN DENTON
  • Driving Directions: Route 404
  • Location Details: River
  • City Limits: Yes

School Information

  • School District: Caroline County Public Schools

Heating & Cooling

  • Cooling Type: Other
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Propane

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 0 Feet
  • Utility Description: Propane

Structural Information

  • Structure Type: Detached
  • Construction: HardiPlank Type
  • Foundation: Crawl Space
  • Roof: Architectural Shingle
  • Stories Description: Main, Upper 1
  • Square Feet: 4,853
  • Sq. Ft. Source: Assessor
  • Living Area: 4,853 Sq. Ft.
  • Finished Above Grnd: 4,853 Sq. Ft.
  • Year Built: 2006
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Property View: River, Scenic Vista, Water, Park/Greenbelt
  • Lot Size (Acres): 2.44
  • Lot Size (Sq. Ft.): 106,286
  • Lot Size Source: Assessor
  • Lot Dimensions: 185.00 x
  • Zoning: SR
  • Lot Description: Level, Premium, Private, Stream/Creek

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard
  • Water Front Type: River
  • Water Front Name: Choptank River
  • Dock/Slip Conveys: Yes
  • Docks: 1

Financial Considerations

  • Price Per Sq. Ft.: $319.39
  • Assessment Year: 2026
  • City/TownTax: $6,299
  • City/TownTax Freq: Annually
  • County Tax: $9,849
  • County Tax Freq: Annually
  • Tax w/Assessment: $986,367
  • Tax Amount: $16,148
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 4853

Disclosures and Reports

  • Ownership: Fee Simple
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 322 S 2nd St —

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NMLS#: 1598647

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Be ready to buy your new home!

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NMLS#: 1598647

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Schools serving 322 S 2nd St

School District:Caroline County Public Schools, Denton, MD
NameGradesDistance
Denton Elementary School
303 Sharp Road, Denton, MD 21629
PK-50.8 mi
Lockerman Middle School
410 Lockerman Street, Denton, MD 21629
6-80.8 mi
North Caroline High School
10990 River Road, Ridgely, MD 21660
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 322 S 2nd St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/26/2026
Listed
$1,550,000
174.34%
MLS
5/16/2016
Sold
$565,000
—
Public Record
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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 322 S 2nd St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$10,452
—
$954,400
15%
2023
$10,452
—
$826,567
18%
2023
$10,452
3%
$698,733
22%
2022
$10,116
62%
$570,900
—
2017
$6,241
-39%
$568,533
—
2021
$10,202
—
$566,167
—
2020
$10,160
1%
$563,800
—
2019
$10,103
1%
$563,800
—
2018
$9,991
-5%
$563,800
-6%
2017
$10,508
1%
$599,800
—
2016
$10,449
1%
$599,800
—
2015
$10,329
-11%
$599,800
-14%
2014
$11,667
—
$697,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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322 S 2nd Street, Denton, MD 21629 (MLS# MDCM2006964) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 322 S 2nd Street is currently listed for $1,550,000 and was received on May 26, 2026. This property is listed by Liz Osborn from our Annapolis Church Circle Office.Want to learn more about 322 S 2nd Street? Do you have questions about finding other Single Family real estate for sale in Denton? You can browse all Denton real estate or contact a Coldwell Banker agent to request more information.

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