Caroline County, affectionately known as the "Green Garden County," is a picturesque rural haven nestled in Maryland's heartland. Defined by its lush landscapes and abundant waterways, including the Choptank River, Tuckahoe Creek, and Williston Lake, Caroline County offers a serene escape for outdoor enthusiasts and nature lovers.


For residents of Caroline County, embracing the great outdoors is not just a pastime—it's a way of life. Whether it's biking along scenic trails, kayaking on tranquil waterways, boating on expansive rivers, casting a line for fishing, or hiking through verdant forests, there's no shortage of outdoor adventures to be had here.


With over 8,000 acres of wildlife sanctuaries, nature preserves, parks, and campgrounds to explore, Caroline County provides endless opportunities for exploration and relaxation in nature's embrace. From birdwatching to picnicking, camping to wildlife spotting, there's something for everyone to enjoy amidst the county's natural beauty.


During the harvest season, don't miss the chance to visit the many fruit and vegetable farms and stands scattered throughout Caroline County. Bursting with fresh produce, these local farms offer a taste of the region's agricultural bounty and provide an opportunity to support local growers and producers.


History buffs will find much to discover and appreciate in Caroline County, with its rich historical connections to Frederick Douglass, Harriet Tubman, and many other notable figures. Explore historic sites, museums, and landmarks that bring the county's storied past to life and offer insight into its cultural heritage.


Whether you're seeking outdoor adventure, farm-fresh delights, or a journey through history, Caroline County invites you to experience the beauty and tranquility of rural Maryland living. With its vibrant landscapes, rich history, and warm community spirit, it's a place where nature's wonders and timeless traditions converge to create a truly unforgettable experience.


Caroline County, MD

Located on Maryland’s Eastern Shore, Caroline County, MD offers a blend of rural charm, historic small towns, and scenic landscapes. Known for its agricultural roots, outdoor recreation, and close-knit communities, the county features attractions like the Choptank River, Tuckahoe State Park, and the charming towns of Denton, Federalsburg, and Ridgely. With affordable real estate, easy access to major highways, and proximity to Delaware beaches, Caroline County is a hidden gem for homebuyers seeking tranquility, investors, and nature enthusiasts alike.

Real Estate Statistics

Average Price $393K
Lowest Price $4
Highest Price $11.6M
Total Listings 691
Avg. Days On Market 87
Avg. Price/SQFT $200

Property Types (active listings)

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Under Contract
10280 Log Cabin Rd, Denton

$319,900

10280 Log Cabin Rd, Denton, MD, 21629

3 2 0

Brenton Realty Group 4104794663

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27944 Possum Hill Rd, Federalsburg

$199,900

27944 Possum Hill Rd, Federalsburg, MD, 21632

2 1 0

Coldwell Banker Realty khylah.settle@cbmove.com

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New
101 S University Ave, Federalsburg

$99,000

101 S University Ave, Federalsburg, MD, 21632

3 1 1

Coldwell Banker Realty 4105434545

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Coming Soon
8851 New Bridge Rd, Denton

$955,000

8851 New Bridge Rd, Denton, MD, 21629

3 2 1

Meredith Fine Properties 4108226272

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New
6140 Laurel Grove Rd, Denton

$170,000

6140 Laurel Grove Rd, Denton, MD, 21629

2 1 0

Compass 3022029855

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New
304 Tidewater Cir, Preston

$429,499

304 Tidewater Cir, Preston, MD, 21655

6 2 1

Samson Properties 3018500255

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New
707 W Sunset Ave, Greensboro

$130,000

707 W Sunset Ave, Greensboro, MD, 21639

0 0 0

The Land Group (410) 934-3478

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New
13166 Oakland Rd, Ridgely

$435,000

13166 Oakland Rd, Ridgely, MD, 21660

3 2 0

The Land Group (410) 934-3478

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New
4471 Harmony Rd, Preston

$109,000

4471 Harmony Rd, Preston, MD, 21655

3 1 0

XRealty.NET LLC

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New
21579 Tanyard Rd, Preston

$225,000

21579 Tanyard Rd, Preston, MD, 21655

4 2 0

Benson & Mangold, LLC 4108226665

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Coming Soon
22733 Squire Ln, Queen Anne

$575,000

22733 Squire Ln, Queen Anne, MD, 21657

4 2 1

Long & Foster Real Estate, Inc.

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412 N Main St, Greensboro

$359,900

412 N Main St, Greensboro, MD, 21639

3 2 0

Clark & Co Realty, LLC 410-490-2183

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New
325 Carter Ave, Denton

$259,900

325 Carter Ave, Denton, MD, 21629

2 1 0

Brenton Realty Group 4104794663

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309 N Main St, Greensboro

$279,900

309 N Main St, Greensboro, MD, 21639

3 1 1

Benson & Mangold, LLC (410) 822-1415

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New
22845 Peaviner Rd, Ridgely

$524,500

22845 Peaviner Rd, Ridgely, MD, 21660

4 2 1

CR Realty 4104900460

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New
27286 Willin Ln, Federalsburg

$60,000

27286 Willin Ln, Federalsburg, MD, 21632

0 0 0

Harlan C. Williams Co.

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23118 Tuckahoe Springs Dr, Denton
OPENHOUSE
  • Saturday, Aug 15th, 11:00am - 1:00pm

$465,000

23118 Tuckahoe Springs Dr, Denton, MD, 21629

3 2 0

Brenton Realty Group 4104794663

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212 Apple Ln, Preston

$295,000

212 Apple Ln, Preston, MD, 21655

3 2 0

Keller Williams Realty 3028467839

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