15

Caroline County MD Homes for Sale with Pool

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  • 23296 Wilder Way, Denton, MD 21629
    23296 Wilder Way, Denton, MD 21629
    23296 Wilder Way, Denton, MD 21629
    /102

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 376-8486

    23296 Wilder Way, Denton, MD 21629
  • 12820 Porters Landing Rd, Greensboro, MD 21639
    12820 Porters Landing Rd, Greensboro, MD 21639
    12820 Porters Landing Rd, Greensboro, MD 21639
    /72

    $720,000

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft

    12820 Porters Landing Rd, Greensboro, MD 21639

    The Ultimate Secluded Waterfront Retreat! Privately positioned along the Choptank River, this 12.43 acre waterfront property is surrounded by mature trees, open sky, and abundant natural beauty. The mostly wooded landscape offers privacy and tranquility, creating a peaceful escape that feels worlds away yet remains connected to the charm of Maryland’s Eastern Shore. Outdoor amenities elevate the

    Agent Photo

    Penny Hollis

    Keller Williams Select Realtors of Annapolis

    (410) 834-0596

    12820 Porters Landing Rd, Greensboro, MD 21639
  • 28402 Liden School Rd, Denton, MD 21629
    28402 Liden School Rd, Denton, MD 21629
    28402 Liden School Rd, Denton, MD 21629
    /60

    $699,000

    • 3 Beds
    • 2 Baths

    28402 Liden School Rd, Denton, MD 21629

    Private serene living at its finest! This 15.77 acres is included with one-acre parcel with the rancher on it for a total of 16.77 acres according to tax records. This property has it all -- gorgeous rancher with 3 BR and 2 full baths; large pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood if buyer desires to do so; two large walk-in closets in primary

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 421-7747

    28402 Liden School Rd, Denton, MD 21629
  • 4757 Long Swamp Rd, Federalsburg, MD 21632
    4757 Long Swamp Rd, Federalsburg, MD 21632
    4757 Long Swamp Rd, Federalsburg, MD 21632
    /47

    $693,000

    • 4 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    4757 Long Swamp Rd, Federalsburg, MD 21632

    Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, Federalsburg, MD 21632
  • 11142 Log Cabin Rd, Denton, MD 21629
    11142 Log Cabin Rd, Denton, MD 21629
    11142 Log Cabin Rd, Denton, MD 21629
    /55

    $675,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11142 Log Cabin Rd, Denton, MD 21629

    Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

    Courtney Gallagher Keller Williams Realty Central-Delaware

    11142 Log Cabin Rd, Denton, MD 21629
  • 320 N Main St, Greensboro, MD 21639
    320 N Main St, Greensboro, MD 21639
    320 N Main St, Greensboro, MD 21639
    /40

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    320 N Main St, Greensboro, MD 21639

    Welcome to 320 N Main St in the quaint town of Greensboro, where you'll find a home that invites you to kick off your shoes and stay a while. This residence sits on a half-acre lot and features three bedrooms and 2.5 baths, offering an ideal balance of space, comfort, and style. The beautifully updated kitchen is ready for all your culinary adventures, boasting a five-burner gas range, stainless

    Karen Clark Clark & Co Realty, LLC

    320 N Main St, Greensboro, MD 21639
  • 4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    /127

    $2,999,000

    • 8 Beds
    • 16 Baths
    • 9,364 Sq Ft

    4218 Harmony Rd, Preston, MD 21655

    A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • 22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    /51

    $495,000

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Enjoy peace and space on two tranquil country acres with no deed restrictions adjacent to open farmland. The deep backyard features a large vinyl-fenced area ideal for kids and pets, an above-ground pool with deck perfect for summer fun, additional fenced space for farm animals (pets), and even a shooting mound for those interested. This lovely home offers 2,667 Square feet (estimated)

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • 12 N Maple Ave, Ridgely, MD 21660
    12 N Maple Ave, Ridgely, MD 21660
    12 N Maple Ave, Ridgely, MD 21660
    /23

    $290,000 Open Sat 10AM - 12PM

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    12 N Maple Ave, Ridgely, MD 21660

    Seller has to find home of choice. Welcome home to this charming 2-bedroom, 1-bath gem nestled in a quiet, established neighborhood. Perfect for first-time buyers, downsizers, or anyone looking for comfortable, low-maintenance living, this home offers both warmth and functionality. Step inside to find beautiful new wood flooring flowing through the living room, kitchen, and hallway, creating a

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    12 N Maple Ave, Ridgely, MD 21660
  • 315 Morning Glory Dr, Denton, MD 21629
    315 Morning Glory Dr, Denton, MD 21629
    315 Morning Glory Dr, Denton, MD 21629
    /40

    $409,000

    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    315 Morning Glory Dr, Denton, MD 21629

    From the moment you step inside, this gorgeous Colonial immediately feels like home. Thoughtfully designed with a 5-foot bump-out extension and a highly desirable open floor plan, the layout offers both space and functionality for everyday living and entertaining. The living room is filled with natural light thanks to an added third window, creating a bright and inviting atmosphere that carries

    Crystal Smith RE/MAX Executive

    315 Morning Glory Dr, Denton, MD 21629
  • 412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    /43

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into a living-dining area anchored by a cozy wood-burning fireplace, the versatile bonus room/office and the entertainment-ready basement with a

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • 1907 Blue Heron Dr, Denton, MD 21629
    1907 Blue Heron Dr, Denton, MD 21629
    1907 Blue Heron Dr, Denton, MD 21629
    /30

    $309,000

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1907 Blue Heron Dr, Denton, MD 21629

    Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family room on the main floor. A few easy steps to the second floor brings you to a beautiful open kitchen, dining, and living room. The third floor

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    1907 Blue Heron Dr, Denton, MD 21629
  • 1204 Blue Heron Dr, Denton, MD 21629
    1204 Blue Heron Dr, Denton, MD 21629
    1204 Blue Heron Dr, Denton, MD 21629
    /16

    $245,000

    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenince and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been thoughtfully updated with fresh paint, new appliances and more to ensure it's move-in ready for you.

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • 13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    /99

    $1,099,000

    • 6 Beds
    • 3.5 Baths
    • 3,704 Sq Ft

    13539 Hokum Dr, Greensboro, MD 21639

    A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining!Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces,

    Vincent Payne Realty Navigator

    13539 Hokum Dr, Greensboro, MD 21639
  • 1404 Blue Heron Dr, Denton, MD 21629
    1404 Blue Heron Dr, Denton, MD 21629
    1404 Blue Heron Dr, Denton, MD 21629
    /26

    $232,000

    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1404 Blue Heron Dr, Denton, MD 21629

    Rehab in 2025/2026. 3 story Townhome with Xtra Large Primary Bedroom with Walk in Closet and Private Bathroom. 2 other Large Bedrooms with Spacius closets. Kitchen with all new Cabinets and Granite Countertops. New flooring thru-out entire Townhome. Whole House painted. All three Bathrooms updatd with new Tile, Vanities, Bathtubs and fixtures! You will not be disappointed.!!!Located within

    Kathleen Brenton Brenton Realty Group

    1404 Blue Heron Dr, Denton, MD 21629
Maryland Caroline County

Homes for Sale with Pool in Caroline County, MD

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