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.
For sale
$1,550,000
322 S 2nd St, Denton, MD 21629
5beds
4,853sqft
Est.: Get pre-qualified
Single Family Residence
Built in 2006
2.44 Acres Lot
$1,501,700 Zestimate®
$319/sqft
$-- HOA
What's special
Waterfront estateBoat liftHand-laid stone stepsFull showerBrand-new trex deckCold plungeVoice-command sauna
- 7 days |
- 680 |
- 47 |
Zillow last checked:
Listing updated:
Listed by:
Liz Osborn 443-699-2689,
Coldwell Banker Realty 4102638686,
Co-Listing Agent: Rachel Holmes 202-258-3055,
Coldwell Banker Realty
Source: Bright MLS,MLS#: MDCM2006964
Tour with a local agent
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
- 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
$1,501,700
$1.43M - $1.58M
$5,371/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/27/2026 | Listed for sale | $1,550,000+174.3%$319/sqft |
Source:  Bright MLS #MDCM2006964 Report a problem | ||
| 5/23/2016 | Sold | $565,000-5.7%$116/sqft |
Source: Public Record Report a problem | ||
| 4/27/2016 | Pending sale | $599,000$123/sqft |
Source: Long & Foster Real Estate, Inc. #CM9599752 Report a problem | ||
| 3/18/2016 | Listed for sale | $599,000$123/sqft |
Source: Long & Foster Real Estate, Inc. #CM9599752 Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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 | -- | $249,100 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
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.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 21629
Nearby schools
GreatSchools rating
- 5/10Denton Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 4/10Lockerman Middle SchoolGrades: 6-8Distance: 0.8 mi
- 4/10North Caroline High SchoolGrades: 9-12Distance: 1.9 mi
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.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Maryland
- Caroline County
- Denton
- 21629
- 322 S 2nd St
Nearby cities
Nearby zip codes
Other Denton Topics
