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 $386K
Lowest Price $4
Highest Price $11.6M
Total Listings 686
Avg. Days On Market 89
Avg. Price/SQFT $197

Property Types (active listings)

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Coming Soon
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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Coming Soon
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
15395 Oakland Rd, Goldsboro

$355,000

15395 Oakland Rd, Goldsboro, MD, 21636

3 2 0

Chesapeake Real Estate Associates, LLC

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New
1111 Whistling Pine Rd, Denton

$409,000

1111 Whistling Pine Rd, Denton, MD, 21629

4 2 1

Benson & Mangold, LLC 4108226665

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New
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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New
507 N Caroline St, Denton

$410,000

507 N Caroline St, 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 3012525515

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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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Lot 4 River Rd, Greensboro

$147,000

Lot 4 River Rd, Greensboro, MD, 21639

0 0 0

Taylor Properties

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0 Houston Branch Rd, Federalsburg

$55,000

0 Houston Branch Rd, Federalsburg, MD, 21632

0 0 0

Taylor Properties

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2821 Meadowbrook Rd, Federalsburg

$65,000

↓ $10,000

2821 Meadowbrook Rd, Federalsburg, MD, 21632

0 0 0

LPT Realty, LLC

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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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27286 Willin Ln, Federalsburg

$59,900

↓ $100

27286 Willin Ln, Federalsburg, MD, 21632

0 0 0

Harlan C. Williams Co.

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Brooklyn Ave, Federalsburg

$39,950

Brooklyn Ave, Federalsburg, MD, 21632

0 0 0

Marshy Hope Realty LLC 410-754-7000

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