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Greensboro, MD, 21639 • 21639 • Caroline County
$269/sqft
-$29,900 since Mar 12, 2026
Down payment assistance available
3Beds
2Baths
2,676Sqft
12.4 acLot
1989Built
On the Choptank River
Private Dock Site, Private Access, River
Water Views
Water
Cape Cod Style
Built 1989 · 37 years of history
None Available
21639
1 Fireplace
Cozy heat source
Special Features
Above Grade · Below Grade
Private Pool
Private
2-Car Garage
Garage Faces Front · Garage Door Opener · Storage · Gravel · Driveway · Attached
This home is getting attention
Listed 81 days ago · 1,849 views · 90 saves
Demand and pricing signals for this listing
1,849 views
People checking out this listing
90 saves
Buyers have saved this home
81 days on market
Established listing
$269/sqft
Price per square foot
This home ranks in the top 50% of listings most likely to go under contract soon, based on market activity and demand signals.
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Single Family · Built 1989
The Ultimate Secluded Waterfront Retreat! Privately positioned along the Choptank River, this 12.43 acre waterfront property is surrounded by mature trees, open sky, and abundant natural beauty. The mostly wooded landscape offers privacy and tranquility, creating a peaceful escape that feels worlds away yet remains connected to the charm of Maryland’s Eastern Shore. Outdoor amenities elevate the waterfront lifestyle. A private pier extends into the Choptank River, offering excellent fishing and direct water access. A stunning in-ground pool overlooks the river and is framed by multiple outdoor living spaces, including two decks - one accessed from the primary bedroom with tranquil water views and a welcoming front porch, perfectly positioned for observing deer, turkey, bald eagles, and other wildlife in their natural habitat. The property also features numerous garden areas, a detached workshop/shed, and a stream winding through the wooded acreage enhancing the sense of seclusion and natural charm. Wildlife is abundant, making this an exceptional property for hunters, nature lovers, or anyone seeking a peaceful waterfront setting. Move-in Ready - This lovingly cared for and well-maintained two-story home offers peace of mind with major updates already completed, including a new architectural shingle roof (2019), new HVAC system (2018), new garage doors (2020), and a new pool liner and cover (2022). The home features a main level with three bedrooms and two full bathrooms, complemented by a spacious open floor plan ideal for both everyday living and entertaining. The main level Primary Suite boasts new carpet, a spacious ensuite bath with a large walk-in shower, separate jetted tub, and French doors overlooking the river and leading to a private deck and pool area. A country-style kitchen anchors the home and flows seamlessly into the inviting family room, where a wood stove creates warmth and ambiance. A generously sized laundry room connects to the oversized attached garage, providing both function and convenience. Upstairs, a large finished bonus room, previously used as a private theater, offers flexible living space, while an additional finished room over the garage provides an ideal setting for a home office, studio, or guest retreat. Schedule a visit today to experience the charm and tranquility of this exceptional waterfront property!
Standout features identified
Our analysis highlights oversized attached garage, generously sized laundry room, and surrounded by mature trees as key attractions of this home.
Based on current rates
Est. 6.02% rate · 30yr fixed · $576,000 loan
Full calculator →Key facts and listing details
12 categories of property features
12 rooms detailed
Primary Bedroom
MainBedroom2
MainBedroom3
MainBathroom2
MainBonus Room
UpperDen
MainMarket data and value estimates
3 schools rated nearby
Greensboro, MD, 21639
5 events
25 years of records
Local context around this listing
Greensboro, MD • Caroline County
Nearby cities
Nearby zip codes
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