$499,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,756sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
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12384 River Rd, RIDGELY, MD 21660 
Dover Bridge Rd, PRESTON, MD 21655
Price Drop: $35K
5820 Bell Creek Rd, PRESTON, MD 21655
15078 Drapers Ml Rd, GREENSBORO, MD 21639
3D Tour
13099 Ridgely Rd, GREENSBORO, MD 216393D Tour
11473 Holly Rd, RIDGELY, MD 21660 
12484 Greensboro Rd, GREENSBORO, MD 21639
24749 Woods Dr, DENTON, MD 21629
11289 Gregg Rd, DENTON, MD 21629
104 Riverton Ave, DENTON, MD 21629
22889 Hog Creek Rd, PRESTON, MD 21655
11421 Maplewood Dr, RIDGELY, MD 21660
7 Lister Ln, RIDGELY, MD 21660
1233 Painted Fern Rd, DENTON, MD 21629
23629 Willow Pond Rd, DENTON, MD 21629
20915 Dover Bridge Rd, PRESTON, MD 216553D Tour
23255 Magnolia Hills Rd, DENTON, MD 21629 
22408 Hog Creek Rd, PRESTON, MD 21655
14418 Poplar St, GOLDSBORO, MD 21636
River Rd, RIDGELY, MD 216603D Tour
25699 Auction Rd, FEDERALSBURG, MD 21632 3D Tour
New Construction
13926 S Quail Ct, GREENSBORO, MD 21639 
25485 Hignutt Rd, DENTON, MD 216293D TourNew Construction
S Quail Ct, GREENSBORO, MD 21639 3D Tour
11509 Reed Cir, RIDGELY, MD 21660 
1101 Trice Meadows Cir, DENTON, MD 216293D Tour
109 Walnut St, RIDGELY, MD 21660 
11231 River Rd, RIDGELY, MD 21660
1709 Cattail Commons Wy, DENTON, MD 21629
304 Tidewater Cir, PRESTON, MD 21655
507 N Caroline St, DENTON, MD 216293D Tour
23491 Brunkhorst Rd E, PRESTON, MD 21655 
1503 Cattail Cmns Way, DENTON, MD 21629
24882 Riverview Way, RIDGELY, MD 21660
14990 Greensboro Rd, GOLDSBORO, MD 21636
15204 Jarrell Rd, GOLDSBORO, MD 21636Price Drop: $14K3D Tour
1111 Whistling Pine Rd, DENTON, MD 21629 
13166 Oakland Rd, RIDGELY, MD 21660
12658 Oakland, RIDGELY, MD 21660
320 N Main St, GREENSBORO, MD 21639
7392 Todds Wharf Rd, PRESTON, MD 21655
506 Central Ave, RIDGELY, MD 21660
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Homes for Sale Under 500K in Caroline Md County, MD
215 Homes for Sale
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$499,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 63.16acres lot
Sale Pending
Benson & Mangold, Llc
Price Drop: $35K$490,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,292sqft
Land for sale
Exp Realty, Llc
$489,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,584sqft
Single family home for sale
Benson & Mangold, Llc.
3D Tour$485,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,856sqft
Sale Pending
Caprika Realty
3D Tour$479,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,248sqft
Single family home for sale
Re/Max Executive
$475,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,858sqft
Sale Pending
Chesapeake Real Estate Associates, Llc
$469,900
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,550sqft
Single family home for sale
Benson & Mangold, Llc
$469,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 2,320sqft
Sale Pending
Benson & Mangold, Llc.
$467,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,318sqft
Single family home for sale
Long & Foster Real Estate, Inc.
$465,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,872sqft
Single family home for sale
Coldwell Banker Chesapeake Real Estate Company
$465,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,840sqft
Single family home for sale
Wilson Realty & Staging Llc
$464,000
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 3,040sqft
Single family home for sale
Brenton Realty Group
$459,500
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 4,222sqft
Single family home for sale
Exit Sunshine Realty
$450,000
Bedrooms: 1Bd
Bathrooms: 3Ba
Area: 1,596sqft
Single family home for sale
Long & Foster Real Estate, Inc.
$447,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,904sqft
Single family home for sale
The Agency Dc
3D Tour$445,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,004sqft
Sale Pending
Long & Foster Real Estate, Inc.
$444,900
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 2,667sqft
Sale Pending
Benson & Mangold, Llc
$444,500
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,848sqft
Single family home for sale
Chesapeake Real Estate Associates, Llc
$440,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 44.74acres lot
Sale Pending
Wright Real Estate
3D Tour$440,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,986sqft
Sale Pending
Benson & Mangold, Llc
3D TourNew Construction$435,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,802sqft
Single family home for sale
Cr Realty
$435,000
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,720sqft
Single family home for sale
Taylor Properties
3D TourNew Construction$434,500
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,802sqft
Single family home for sale
Cr Realty
3D Tour$419,990
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,392sqft
Single family home for sale
Keller Williams Realty
$419,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,256sqft
Single family home for sale
Long & Foster Real Estate, Inc.
3D Tour$419,000
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 2,250sqft
Single family home for sale
Coldwell Banker Realty
$419,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,600sqft
Single family home for sale
Brenton Realty Group
$415,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,492sqft
Single family home for sale
Benson & Mangold, Llc
$414,499
Bedrooms: 6Bds
Bathrooms: 3Ba
Area: 2,934sqft
Single family home for sale
Samson Properties
$410,000
Bedrooms: --Bds
Bathrooms: --Ba
Area: 4.52acres lot
Land for sale
Brenton Realty Group
3D Tour$399,999
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,280sqft
Sale Pending
Coldwell Banker Realty
$399,999
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,036sqft
Single family home for sale
Douglas Realty Llc
$399,900
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,542sqft
Single family home for sale
Benson & Mangold, Llc
$399,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,016sqft
Sale Pending
Wright Real Estate
$399,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,424sqft
Sale Pending
Monument Sotheby'S International Realty
Price Drop: $14K3D Tour$395,000
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,117sqft
Single family home for sale
Benson & Mangold, Llc
$395,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,408sqft
Land for sale
The Land Group
$395,000
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,692sqft
Single family home for sale
Rosendale Realty
$389,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,816sqft
Single family home for sale
Clark & Co Realty, Llc
$385,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,300sqft
Single family home for sale
Long & Foster Real Estate, Inc.
$385,000
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,370sqft
Single family home for sale
Taylor Properties
Showing 1 - 42 of 215 homes for sale in Caroline Md County, MD
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Based on information from Bright MLS through Oct 29, 2026, 2:15 PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
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