322 S 2nd Street, Denton, MD 21629 - Photo 1

1/1

$1,500,000

Sold
Closed
Single Family
5 Beds
4 Full Baths
1 Partial Bath
4,853 Sq. Ft.
3 Car Garage

1/1

Property 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.

Full Property Details

Full Property Details for 322 S 2nd St

General

Sold For: $1,500,000
Taxes: $16,148 (2025)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDCM2006964
Added to Site: 138 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

Architectural Style: Coastal, Colonial
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
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 4853

Disclosures and Reports

Ownership: Fee Simple

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Meet the listing agent

— 322 S 2nd St —

Liz Osborn

Email Me

(443) 699-2689 mobile
(410) 263-8686 office

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Schools

Schools serving 322 S 2nd St

School District:Caroline County Public Schools, Denton, MD

Name	Grades	Distance
Denton Elementary School 303 Sharp Road, Denton, MD 21629	PK-5	0.8 mi
Lockerman Middle School 410 Lockerman Street, Denton, MD 21629	6-8	0.8 mi
North Caroline High School 10990 River Road, Ridgely, MD 21660	9-12	1.9 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

Date

Details

Price

Change

Source

9/18/2026

Sold

$1,500,000

-3.23%

MLS

5/26/2026

Listed

$1,550,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

105 Parkland Rd, Greensboro, MD 21639 - Photo 1

Just Listed

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Single Family
Active
Updated 5 days ago

4
Beds
2
Total Baths
1,460
Sq. Ft.

Listed by D.R. Horton Realty of Virginia, LLC, Justin K Wood

307 Mallard Dr, Greensboro, MD 21639 - Photo 1

Just Listed

$250,000

307 Mallard Dr Greensboro, MD 21639

Single Family
Active
Updated 2 days ago

3
Beds
3
Total Baths
1,836
Sq. Ft.

Listed by Brokers Realty Group, LLC, John A Fifer

11518 Woodwinds Ct, Cordova, MD 21625 - Photo 1

Just Listed

$549,000

11518 Woodwinds Ct Cordova, MD 21625

Single Family
Active
Updated 1 day ago

4
Beds
3
Total Baths
2,293
Sq. Ft.

Listed by Meredith Fine Properties, Traci L Jordan

29 Harlequin Loop, Bridgeville, DE 19933 - Photo 1

Just Listed

$340,000

29 Harlequin Loop Bridgeville, DE 19933

Single Family
Active
Updated 5 days ago

2
Beds
2
Total Baths
1,975
Sq. Ft.

Listed by Active Adults Realty, AUDREY HAMMOND

11509 Reed Cir, Ridgely, MD 21660 - Photo 1

11509 Reed Cir Ridgely, MD 21660

Single Family
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,392
Sq. Ft.

Listed by Keller Williams Realty, Samantha Kay Jackson

13166 Oakland Rd, Ridgely, MD 21660 - Photo 1

Price Reduced

-$20,000 (-4.82%)

$395,000

13166 Oakland Rd Ridgely, MD 21660

Farm Single-Family
Active
Updated 2 days ago

3
Beds
2
Total Baths
3,112
Sq. Ft.

Listed by The Land Group, BRIAN MORRIS

11592 Holly Rd, Ridgely, MD 21660 - Photo 1

Price Reduced

-$20,000 (-3.33%)

$580,000

11592 Holly Rd Ridgely, MD 21660

Single Family
Active
Updated 1 day ago

6
Beds
4
Total Baths
3,592
Sq. Ft.

Listed by Samson Properties, Jarnell Preston Foster

24882 Riverview Way, Ridgely, MD 21660 - Photo 1

Price Reduced

-$29,100 (-6.78%)

$399,900

24882 Riverview Way Ridgely, MD 21660

Single Family
Active
Updated 5 days ago

3
Beds
3
Total Baths
1,542
Sq. Ft.

Listed by Benson & Mangold, LLC, Edwin M Matthews

12633 Connelly Rd, Cordova, MD 21625 - Photo 1

Sold

$1,723,750

12633 Connelly Rd Cordova, MD 21625

Farm Single-Family
Closed

3
Beds
2
Total Baths
2,076
Sq. Ft.

Listed by Benson & Mangold, LLC, Coard A Benson
Sold by Meredith Fine Properties, Shawn Moore

322 S 2nd Street, Denton, MD 21629 (MLS# MDCM2006964) is a Single Family property that was sold at $1,500,000 on September 18, 2026. This property was 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.

322 S 2nd St Denton, MD 21629