Single family homes for sale in Caroline County, MD

Coming soon

$4,453 Closing Credit¹

$375,000

3 beds • 2 baths • 1,588 sqft

1010 S 2nd St, Denton, MD 21629

#MDCM2005908, Roger M Boyce, Listing office: Chesapeake Real Estate Associates, LLC

1 day on Rocket

$4,868 Closing Credit¹

$409,900

3 beds • 2.5 baths • 3,734 sqft

208 Bloomingdale Ave, Federalsburg, MD 21632

#MDCM2005904, Blaine L Williamson, Listing office: McClain-Williamson Realty, LLC

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204 Academy Ave, Federalsburg, MD 21632 - view of front of property

2 days on Rocket

$416 Closing Credit¹

$35,000

2 beds • 1 bath • 1,024 sqft

204 Academy Ave, Federalsburg, MD 21632

#MDCM2005896, Michael Dunn, Listing office: Keller Williams Realty Delmarva

3 days on Rocket

$3,497 Closing Credit¹

$294,500

3 beds • 2 baths • 1,902 sqft

6855 Eldorado Rd, Federalsburg, MD 21632

#MDDO2009860, Kelly Y Showell, Listing office: Benson & Mangold, LLC

Coming soon

$7,066 Closing Credit¹

$595,000

4 beds • 2.5 baths • 3,168 sqft

24766 Tribbett Cir, Ridgely, MD 21660

#MDCM2005900, Barbara A McCaffrey, Listing office: Redfin Corp

3 days on Rocket

$3,859 Closing Credit¹

$325,000

3 beds • 2 baths • 1,120 sqft

505 Maryland Ave, Ridgely, MD 21660

#MDCM2005898, Kaitlyn Cole Collins, Listing office: Benson & Mangold, LLC

Coming soon

$5,047 Closing Credit¹

$425,000

4 beds • 3.5 baths • 2,780 sqft

8912 Osterman Ct, Denton, MD 21629

#MDCM2005884, Nanci A Dumsha-Gardner, Listing office: Meredith Fine Properties

Room to negotiate?

Median List Price

$359K

Avg. Sale Time

99 Days

Based on our May 2025 Market Report.

5 days on Rocket

$1,959 Closing Credit¹

$165,000

3 beds • 1 bath • 960 sqft

4808 Webster St, Federalsburg, MD 21632

#MDDO2009818, James Joseph Sapia III, Listing office: Century 21 Downtown

6 days on Rocket

$3,313 Closing Credit¹

$279,000

3 beds • 2 baths • 1,120 sqft

3181 Gallagher Rd, Preston, MD 21655

#MDCM2005890, Andrew B Beaven, Listing office: Wright Real Estate

6 days on Rocket

$4,928 Closing Credit¹

$415,000

4 beds • 2.5 baths • 2,994 sqft

1208 Painted Fern Rd, Denton, MD 21629

#MDCM2005878, Barbara A McCaffrey, Listing office: Redfin Corp

Coming soon

$4,097 Closing Credit¹

$345,000

3 beds • 1 bath • 1,058 sqft

22329 Tanyard Rd, Preston, MD 21655

#MDCM2005822, Laura Anderson, Listing office: Coldwell Banker Realty

7 days on Rocket

$3,408 Closing Credit¹

$286,990

4 beds • 2 baths • 1,460 sqft

114 Parkland Rd, Greensboro, MD 21639

#MDCM2005872, Justin K Wood, Listing office: D.R. Horton Realty of Virginia, LLC

7 days on Rocket

$2,933 Closing Credit¹

$247,000

2 beds • 1.5 baths • 1,458 sqft

116 Maple Ave, Preston, MD 21655

#MDCM2005852, Mary L Haddaway, Listing office: Benson & Mangold, LLC

$2,078 Closing Credit¹

$175,000

3 beds • 2 baths • 1,392 sqft

529 Oldtown Rd, Goldsboro, MD 21636

#MDCM2005846, Barbara M Wallace, Listing office: Long & Foster Real Estate, Inc.

$2,969 Closing Credit¹

$250,000

4 beds • 2 baths • 1,344 sqft

21344 Tanyard Rd, Preston, MD 21655

#MDCM2005848, Charlotte Savoy, Listing office: The KW Collective

$3,741 Closing Credit¹

$315,000

3 beds • 2 baths • 1,344 sqft

3376 Jefferson Pond Rd, Federalsburg, MD 21632

#MDCM2005832, Amy Jo Herr, Listing office: RE/MAX Advantage Realty

Backup offers

$5,463 Closing Credit¹

$460,000

3 beds • 2.5 baths • 2,131 sqft

14462 Poplar St, Goldsboro, MD 21636

#MDCM2005842, Peter Schuyler Mellor, Listing office: Wright Real Estate

$10,000 Closing Credit¹

$890,000

3 beds • 3 baths • 3,334 sqft

25292 Sandy Point Rd, Greensboro, MD 21639

#MDCM2005802, Katherine M Christensen, Listing office: TTR Sotheby's International Realty

407 Wood Duck Dr, Greensboro, MD 21639 - view of miscellaneous listing collateral

Coming soon

$3,918 Closing Credit¹

$329,900

4 beds • 2.5 baths • 1,624 sqft

407 Wood Duck Dr, Greensboro, MD 21639

#MDCM2005844, Kathryn Matic, Listing office: Patterson-Schwartz - Greenville

$10,000 Closing Credit¹

$975,000

4 beds • 2.5 baths • 2,700 sqft

11142 Log Cabin Rd, Denton, MD 21629

#MDCM2005826, Courtney Gallagher, Listing office: Keller Williams Realty Central-Delaware

24887 Holsinger Ln, Ridgely, MD 21660 - view of front facade featuring covered porch and a front yard

Coming soon

$5,106 Closing Credit¹

$430,000

3 beds • 2 baths • 1,440 sqft

24887 Holsinger Ln, Ridgely, MD 21660

#MDCM2005834, Laura J Anthony, Listing office: Benson & Mangold, LLC

Coming soon

$5,344 Closing Credit¹

$450,000

4 beds • 3 baths • 4,304 sqft

122 Lister Ln, Ridgely, MD 21660

#MDCM2005812, Christopher J Rosendale III, Listing office: CR Realty

$7,422 Closing Credit¹

$625,000

3 beds • 3.5 baths • 2,667 sqft

22408 Hog Creek Rd, Preston, MD 21655

#MDCM2005830, James M Bent, Listing office: Benson & Mangold, LLC

Coming soon

$5,105 Closing Credit¹

$429,900

4 beds • 2.5 baths • 3,096 sqft

1207 Painted Fern Rd, Denton, MD 21629

#MDCM2005818, Trudie S Colvin, Listing office: Coldwell Banker Realty

Coming soon

$4,263 Closing Credit¹

$359,000

3 beds • 2 baths • 1,560 sqft

15 Ridgeway Dr, Ridgely, MD 21660

#MDCM2005814, Jarnell Preston Foster, Listing office: Benson & Mangold, LLC

$4,672 Closing Credit¹

$393,426

4 beds • 2.5 baths • 2,475 sqft

333 Morning Glory Dr, Denton, MD 21629

#MDCM2005762, Daniel W Martin, Listing office: Keller Williams Flagship

$6,888 Closing Credit¹

$580,000

4 beds • 3 baths • 3,039 sqft

8534 Briar Patch Dr, Denton, MD 21629

#MDCM2005794, Alana Coffey, Listing office: Worthington Realty Group, LLC

16932 Diggins Rd, Henderson, MD 21640 - view of front facade featuring an attached garage, a front yard, entry steps, brick siding, and metal roof

Coming soon

$3,741 Closing Credit¹

$315,000

3 beds • 1.5 baths • 1,294 sqft

16932 Diggins Rd, Henderson, MD 21640

#MDCM2005790, Karen T Clark, Listing office: Clark & Co Realty, LLC

Backup offers

$2,482 Closing Credit¹

$209,000

2 beds • 1 bath • 864 sqft

524 Denton Rd, Federalsburg, MD 21632

#MDCM2005786, Nora Turner, Listing office: Long & Foster Real Estate, Inc.

Backup offers

$9,797 Closing Credit¹

$825,000

4 beds • 2.5 baths • 2,644 sqft

25129 Adams Landing Rd, Denton, MD 21629

#MDCM2005748, Candace catherine Harman, Listing office: Long & Foster Real Estate, Inc.

Backup offers

$4,749 Closing Credit¹

$399,900

3 beds • 2 baths • 1,228 sqft

10803 Greensboro Rd, Denton, MD 21629

#MDCM2005780, Juliet P Wells, Listing office: Coldwell Banker Chesapeake Real Estate Company

Coming soon

$3,978 Closing Credit¹

$335,000

3 beds • 2.5 baths • 2,508 sqft

614 Market St, Denton, MD 21629

#MDCM2005772, Michael J Bozek, Listing office: Michael J. Bozek

$10,000 Closing Credit¹

$995,500

4 beds • 3 baths • 2,119 sqft

23274 Holly Park Dr, Preston, MD 21655

#MDCM2005766, Rick Parreco, Listing office: RE/MAX Executive

$3,206 Closing Credit¹

$270,000

4 beds • 1.5 baths • 2,406 sqft

108 S 2nd St, Denton, MD 21629

#MDCM2005744, Crystal M Smith, Listing office: RE/MAX Executive

$4,334 Closing Credit¹

$365,000

3 beds • 2 baths • 1,600 sqft

110 N School St, Greensboro, MD 21639

#MDCM2004790, Chad Jason Muse, Listing office: KD Realty Inc

$4,744 Closing Credit¹

$399,500

3 beds • 2 baths • 2,378 sqft

502 N Academy St N, Greensboro, MD 21639

#MDCM2005742, Christopher J Rosendale III, Listing office: CR Realty

$3,444 Closing Credit¹

$290,000

3 beds • 2 baths • 1,344 sqft

202 Maryland Ave, Ridgely, MD 21660

#MDCM2005722, Mikeshia Wilson, Listing office: Chesapeake Real Estate Associates, LLC

Backup offers

$3,741 Closing Credit¹

$315,000

3 beds • 2 baths • 1,680 sqft

8888 Harmony Rd, Denton, MD 21629

#MDCM2005724, Predaricka M Mendez-Lopez, Listing office: Realty One Group Performance, LLC

$5,451 Closing Credit¹

$459,000

5 beds • 3.5 baths • 2,330 sqft

13001 Beech Ln, Greensboro, MD 21639

#MDCM2005720, Megan E Rosendale, Listing office: Rosendale Realty

$6,649 Closing Credit¹

$559,900

3 beds • 2.5 baths • 2,379 sqft

15185 Day Rd, Goldsboro, MD 21636

#MDCM2005368, Karen T Clark, Listing office: Clark & Co Realty, LLC

Caroline County, MD Real Estate Market Overview

There are 105 single family homes for sale in Caroline County, MD. The following market insights reflect all property types in the Caroline County, MD real estate market. The number of homes for sale in Caroline County, MD increased by 39.8% between April 2025 and May 2025. While the average time on the market in May 2025 was 99 days, the median list price was $359,000.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Caroline County, MD

Overview

Caroline County is located in Maryland. There are roughly 32,982 residents, living in 12,103 households. The average temperature for Caroline County this time of the year is low of 61F and high of 84F. On average, Caroline County gets about 3.58 inches of precipitation in June. Most residents are home owners (71%), have a high school diploma (56%) and are single, no kids (33%).

Data provided by Home Junction

Schools near Caroline County, MD

Elementary Schools

Denton Elementary School
303 Sharp Rd
Public District PK-5
Federalsburg Elementary School
302 S University Ave
Public District PK-5
Chapel District Elementary School
11430 Cordova Rd
Public District PK-5

Middle Schools

Colonel Richardson Middle School
25390 Richardson Rd
Public District 6-8
Lockerman Middle School
410 Lockerman St
Public District 6-8

High Schools

North Caroline High School
10990 River Rd
Public District 9-12
Colonel Richardson High School
25320 Richardson Rd
Public District 9-12

Data provided by Great Schools

Single family homes for sale in Caroline County, MD

Caroline County, MD Real Estate Market Overview

What is it like to live in Caroline County, MD

Overview

Explore popular home types in Caroline County, MD

Related homes in Caroline County, MD

Schools near Caroline County, MD

Housing market reports in Caroline County

Homes for sale near Caroline County, MD

Top real estate cities in Maryland