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 $385K
Lowest Price $4
Highest Price $11.6M
Total Listings 688
Avg. Days On Market 207
Avg. Price/SQFT $197

Property Types (active listings)

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Coming Soon
7922 Detour Rd, Denton

$395,000

7922 Detour Rd, Denton, MD, 21629

3 2 0

Clark & Co Realty, LLC 410-490-2183

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Coming Soon
315 Hughlett St, Preston

$399,000

315 Hughlett St, Preston, MD, 21655

5 3 1

Keller Williams Select Realtors of Annapolis 4109724000

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New
22067 Dover Bridge Rd, Preston

$99,000

22067 Dover Bridge Rd, Preston, MD, 21655

3 1 0

Benson & Mangold, LLC 4108226665

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New
233 Oldtown Rd, Goldsboro

$239,900

233 Oldtown Rd, Goldsboro, MD, 21636

3 2 0

Taylor Properties

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Coming Soon New
3395 Jefferson Pond Rd, Federalsburg

$309,900

3395 Jefferson Pond Rd, Federalsburg, MD, 21632

3 2 0

Keller Williams Realty 3023600300

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New
522 Denton Rd, Federalsburg
OPENHOUSE
  • Sunday, Oct 18th, 1:00pm - 3:00pm

$215,000

522 Denton Rd, Federalsburg, MD, 21632

4 1 0

Keller Williams Realty 3023600300

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New
11502 Greensboro Rd, Greensboro

$384,900

11502 Greensboro Rd, Greensboro, MD, 21639

3 2 0

Redfin Corp 3016586186

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New
23255 Magnolia Hills Rd, Denton
OPENHOUSE
  • Sunday, Oct 18th, 11:00am - 1:00pm

$445,000

23255 Magnolia Hills Rd, Denton, MD, 21629

3 2 0

Long & Foster Real Estate, Inc.

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New
201 E 6th St, Ridgely

$425,000

201 E 6th St, Ridgely, MD, 21660

4 3 0

Berkshire Hathaway HomeServices Homesale Realty (800) 383-3535

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Coming Soon
8275 New Bridge Rd, Denton

$379,900

8275 New Bridge Rd, Denton, MD, 21629

3 1 0

Clark & Co Realty, LLC 410-490-2183

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Coming Soon New
15395 Oakland Rd, Goldsboro

$355,000

15395 Oakland Rd, Goldsboro, MD, 21636

3 2 0

Chesapeake Real Estate Associates, LLC

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1111 Whistling Pine Rd, Denton

$409,000

1111 Whistling Pine Rd, Denton, MD, 21629

4 2 1

Benson & Mangold, LLC

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307 Mallard Dr, Greensboro

$250,000

307 Mallard Dr, Greensboro, MD, 21639

3 2 1

Brokers Realty Group, LLC 8556872765

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Under Contract
Parcel 91 Cool Spring, Marydel

$114,900

Parcel 91 Cool Spring, Marydel, MD, 21649

0 0 0

Long & Foster Real Estate, Inc.

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507 N Sixth St N, Denton

$410,000

507 N Sixth St N, Denton, MD, 21629

0 0 0

Brenton Realty Group 4104794663

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26519 3 Bridges Rd, Federalsburg

$30,000

26519 3 Bridges Rd, Federalsburg, MD, 21632

0 0 0

Smart Realty, LLC

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Lot 37 Paradise Ln, Goldsboro

$165,000

Lot 37 Paradise Ln, Goldsboro, MD, 21636

0 0 0

Long & Foster Real Estate, Inc.

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Houston Branch Rd, Federalsburg

$175,000

Houston Branch Rd, Federalsburg, MD, 21632

0 0 0

Wright Real Estate (410) 924-3111

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