322 S 2nd St
Denton, MD 21629
5 Beds
4.5 Baths
4,853 sqft (on 2.44 acres)
5 Beds
4.5 Baths
4,853 sqft
(on 2.44 acres)
Local Information
- Map ViewExplore the area around 322 S 2nd St.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
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.
Home Highlights
Parking
3 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$319
Listed
49 days ago
Home Details for 322 S 2nd St
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Interior Details Number of Rooms: 1Types of Rooms: Basement |
Beds & Baths Number of Bedrooms: 5Main Level Bedrooms: 2Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1Number of Bathrooms (main level): 3 |
Dimensions and Layout Living Area: 4853 Square Feet |
Appliances & Utilities Utilities: PropaneAppliances: 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 HeaterDishwasherDisposalDryerLaundry: Main LevelMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Other,ElectricHas HeatingHeating Fuel: Heat Pump |
Fireplace & Spa Spa: PrivateNo FireplaceHas a Spa |
Windows, Doors, Floors & Walls Flooring: Hardwood, Carpet |
Levels, Entrance, & Accessibility Stories: 3Levels: ThreeAccessibility: Grip-Accessible Features, Accessible Entrance, Roll-in ShowerFloors: Hardwood, Carpet |
View Has a ViewView: River, Scenic Vista, Water, Park/Greenbelt |
Security Security: Exterior Cameras, Monitored, Motion Detectors, Security System |
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Exterior Home Features Roof: Architectural ShingleOther Structures: Above Grade, Below GradeExterior: Extensive Hardscape, Lighting, Rain GuttersFoundation: Crawl SpaceNo Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Garage Faces Side,Garage Faces Front,Garage Door Opener,Inside Entrance,Oversized,Asphalt,Circular Driveway,Driveway,Private,Attached |
Pool Pool: None |
Frontage WaterfrontWaterfront: Private Dock Site, River, Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/WakeboardOn Waterfront |
Water & Sewer Sewer: Public SewerWater Body: Choptank River |
Farm & Range Frontage Length: Water Frontage Ft: 268Not Allowed to Raise Horses |
Finished Area Finished Area (above surface): 4853 Square Feet |
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Days on Market: 49 |
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Year Built Year Built: 2006Year Renovated: 2016 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Coastal,Colonial |
Building Construction Materials: HardiPlank TypeNot a New ConstructionNo Additional Parcels |
Property Information Condition: ExcellentParcel Number: 0603021041 |
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Price List Price: $1,550,000Price Per Sqft: $319 |
Status Change & Dates Possession Timing: 0-30 Days CD |
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MLS Status: ACTIVE |
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Direction & Address City: DENTONCommunity: Downtown Denton |
School Information Elementary School District: Caroline County Public SchoolsJr High / Middle School District: Caroline County Public SchoolsHigh School District: Caroline County Public Schools |
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Listing Agent Listing ID: MDCM2006964 |
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Building Area Building Area: 4853 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 2.44 Acres |
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Special Conditions: Standard |
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Listing Agreement Type: Exclusive Agency |
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Business Information Ownership: Fee Simple |
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Mls Number: MDCM2006964Municipality: DentonWater ViewWater View: River, WaterAbove Grade Unfinished Area: 4853 |
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Source Internet Consumer Comment: YSource Internet Automated Valuation Display: YSource Internet Entire Listing Display: YSource Internet Address Display: Y |
Last check for updates: about 3 hours ago
Listing courtesy of Liz Osborn, (443) 699-2689
Coldwell Banker Realty, (410) 263-8686
Co-Listing Agent: Rachel Holmes, (202) 258-3055
Coldwell Banker Realty, (410) 263-8686
Source: Bright MLS, MLS#MDCM2006964
Also Listed on Bright MLS.
Market trends in Denton
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
52
7MoM
Price History for 322 S 2nd St
| Date | Price | Event | Source |
|---|---|---|---|
| 05/27/2026 | $1,550,000 | Listed For Sale | Bright MLS #MDCM2006964 |
| 05/23/2016 | $565,000 | Sold | N/A |
| 04/27/2016 | $599,000 | Pending | Agent Provided |
| 03/18/2016 | $599,000 | Listed For Sale | Agent Provided |
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New Listings near 322 S 2nd St
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,049 |
| Assessment | $954,400 |
Home facts updated by county records
Comparable Sales for 322 S 2nd St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.09 | Single-Family Home | $399,000 | 09/26/25 | 5 | 2.5 | 2,267 | |
0.21 | Single-Family Home | $359,000 | 10/14/25 | 4 | 1.5 | 2,974 | |
0.15 | Single-Family Home | $500,000 | 05/20/26 | 3 | 2 | 1,616 | |
0.42 | Single-Family Home | $340,000 | 12/05/25 | 3 | 2 | 1,764 | |
0.28 | Single-Family Home | $255,000 | 10/22/25 | 4 | 1.5 | 2,406 | |
0.33 | Single-Family Home | $299,000 | 03/05/26 | 3 | 2 | 1,232 | |
0.55 | Single-Family Home | $325,000 | 10/06/25 | 3 | 2.5 | 2,508 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALE0.28 ACRESColdwell Banker Chesapeake Real Estate Company
Assigned Schools
These are the assigned schools for 322 S 2nd St.
- Denton Elementary School
- PK-5
- Public
- 596 Students
5/10GreatSchools RatingParent Rating AverageDenton Elementary School has gone don hill over the years especially the 2013-2014 school year. My daughter has been hurt several times and no call from the nurse. The principals don't bother resolving issues between students and teachers and parents even when requesting to have students removed from a classroom before the school year begins to stop a problem before it begins. Teachers refuse to answer questions when my child raises their hand for help. A class size of 54 students is to large for my child to learn and when I requested for her to be moved the principals over looked it and turned their backs. Teacher only allow their favorite students parents on field trips and to bring things in for class parties. No communication what so ever. Very unorganized.Parent Review12y ago - North Caroline High School
- 9-12
- Public
- 1238 Students
4/10GreatSchools RatingParent Rating AverageThis school is awful. The staff bullies students just as much as the students. The "resource officers" talk about the female students and stare at them. The whole school should be shut down and redone.Parent Review5y ago - Lockerman Middle School
- 6-8
- Public
- 827 Students
4/10GreatSchools RatingParent Rating AverageHorrible school, do not recommend. People will bully you over the most stupid reasons, teachers are disrespectful, and the school food has mold. Very dirty school as well.Student Review4mo ago 
Check out schools near 322 S 2nd St.
What Locals Say about Denton
At least 28 Trulia users voted on each feature.
87 % Say parking is easy
86 % Say yards are well-kept
84 % Say car is needed
79 % Say there's holiday spirit
78 % Say it's dog friendly
72 % Say they plan to stay for at least 5 years
71 % Say kids play outside
68 % Say it's quiet
66 % Say people would walk alone at night
63 % Say neighbors are friendly
58 % Say there are sidewalks
57 % Say streets are well-lit
55 % Say there are community events
53 % Say it's walkable to restaurants
48 % Say there's wildlife
42 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Liz Osborn, Coldwell Banker Realty, (410) 263-8686
Agent Phone: (443) 699-2689
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Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc. Click here for more information
322 S 2nd St, Denton, MD 21629 is a 5 bedroom, 5 bathroom, 4,853 sqft single-family home built in 2006. This property is currently available for sale and was listed by Bright MLS on May 27, 2026. The MLS # for this home is MLS# MDCM2006964.