$1,550,000
 $8,321 est/mo Sourced by Back At You

322 S 2nd St,DENTON, MD 21629

DENTON, MD 21629

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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.

Details

MLS #MDCM2006964
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusPending-bright
Year2006
Days On Site103
Listing Provided ByColdwell Banker Realty | Elizabeth A Osborn

Features

Bed(s)5
Bath(s) 5 Total
SQ Feet4,853
Garage3
Story(s)3
ZoningSR
Acreage2.44
Water FrontYes
Property ViewRiver, Scenic Vista, Water, Park, Gr

Interior

CoolingOther
Heating Yes / NoYes
HeatingHeat Pump(s)
Interior FeaturesAttic, 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
AppliancesBuilt-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

Exterior

Exterior FeaturesExtensive Hardscape, Exterior Lighting, Gutter System
RoofArchitectural Shingle
Security FeaturesExterior Cameras, Monitored, Motion Detectors, Security System, Surveillance Sys
Construction MaterialsHardi Plank Type
Foundation DetailsCrawl Space
Lot FeaturesLevel, Premium, Private, Stream/Creek

Parking

Garage Yes / NoYes
Parking FeaturesAsphalt Driveway, Circular Driveway, Paved Driveway, Private

Utilities

UtilitiesPropane

Taxes

Tax Annual Amount16148

Area Information

StateMD
CountyCAROLINE MD
CityDENTON
Zip Code21629
AreaCAROLINE MD
Community NameDOWNTOWN DENTON
School DistrictCAROLINE COUNTY PUBLIC SCHOOLS
Listing VS Median (in DOWNTOWN DENTON)
Price:
$1,550,000
low | high
Med:
$1,550,000
50% of Average
sqft:
4,853
low | high
Med:
4,853
50% of Average
$ / sqft:
$319
low | high
Med:
$319
50% of Average
On site:
103
low | high
Med:
103
100% of Average
Sourced by Back At You

Market Activity 21629

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Learn More About This Property

StateMD
CountyCAROLINE MD
CityDENTON
Zip Code21629
AreaCAROLINE MD
Community NameDOWNTOWN DENTON
School DistrictCAROLINE COUNTY PUBLIC SCHOOLS
Listing VS Median (in DOWNTOWN DENTON)
Price:
$1,550,000
low | high
Med:
$1,550,000
50% of Average
sqft:
4,853
low | high
Med:
4,853
50% of Average
$ / sqft:
$319
low | high
Med:
$319
50% of Average
On site:
103
low | high
Med:
103
100% of Average
Sourced by Back At You
Listing Updated: August 30, 2026 at 6:48:26 PM PDT