21

Caroline County MD Homes for Sale with Pool

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  • /63

    $399,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    7392 Todds Wharf Rd, Preston, MD 21655
  • /37

    $325,000

    • 5 Beds
    • 2.5 Baths
    • 2,232 Sq Ft

    2792 Meadowbrook Rd, Federalsburg, MD 21632

    Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits on a beautiful .46-acre lot.The upper level features three bedrooms, including a primary bedroom with its own private bath. The living room offers an open feel and an opportunity to create an even more unique space with the potential for an upper balcony. The

    Agent Photo

    Kate Lewis

    Keller Williams Realty

    2792 Meadowbrook Rd, Federalsburg, MD 21632
  • /32

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

    Michael Shipley Benson & Mangold, LLC.

    28402 Liden School Rd, Denton, MD 21629
  • /58

    $620,000

    • 4 Beds
    • 2.5 Baths
    • 2,704 Sq Ft

    16881 Heritage Hills Ln, Henderson, MD 21640

    Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property.Built in 2005, the home offers

    Kaitlyn Collins Benson & Mangold, LLC

    16881 Heritage Hills Ln, Henderson, MD 21640
  • /89

    $649,900

    • 3 Beds
    • 3 Baths
    • 2,343 Sq Ft

    7737 Westerly Dr, Preston, MD 21655

    **Thoughtfully Renovated & Move-In Ready**Welcome to a beautifully renovated home offering 3 bedrooms plus a flexible bonus space with potential for a 4th bedroom in the water front community of Two Johns. Extensively updated from top to bottom, this home offers a fresh, modern feel while maintaining a warm and inviting atmosphere.As you enter, you’ll immediately notice the

    Amy Endzel Keller Williams Select Realtors of Annapolis

    7737 Westerly Dr, Preston, MD 21655
  • /80

    $419,000

    • 5 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    109 Walnut St, Ridgely, MD 21660

    If you've been dreaming of peaceful country living without giving up the convenience of town, this beautifully maintained Colonial in the desirable Lister Estates community may be exactly what you've been waiting for. Enjoy the feeling of space and privacy while still being close to a quaint town square, local shopping, churches, schools, parks, and major commuter routes.From the moment

    Camille Bullard Coldwell Banker Realty

    109 Walnut St, Ridgely, MD 21660
  • /39

    $336,900

    Open Sat 10:30AM - 12:30PM $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft

    504 Main St, Goldsboro, MD 21636

    Welcome to this turn-key, eco-friendly rancher offering single-level living and a modern, open layout. Step inside to a fluid floor plan featuring striking dark wood-look laminate flooring throughout. The spacious living room features a designer green accent wall and flows seamlessly into the country kitchen and dining combination. The kitchen boasts sleek white cabinetry, stainless steel

    Dustin Parker The Parker Group

    504 Main St, Goldsboro, MD 21636
  • /50

    $624,000

    Coming Soon Sep 14
    • 4 Beds
    • 3.5 Baths
    • 2,289 Sq Ft

    10903 Holt Ct, Denton, MD 21629

    Welcome to 10930 Holt Court in the Hackett's Garden community in Denton/Hillsboro Maryland. This beautiful 4 bedroom, 3.5 bath home is resting on a 1.69 acre manicured lot at the very end of the cul-de-sac is awaiting it's next owner. As you arrive at this home, you'll immediately notice the care and pride that the current owners have in this home, The large just resurfaced driveway leading to

    Edward Beres RE/MAX Executive

    10903 Holt Ct, Denton, MD 21629
  • /61

    $569,900

    • 3 Beds
    • 2.5 Baths
    • 2,769 Sq Ft

    7884 Laurel Ln, Denton, MD 21629

    Offered for the first time, this custom-built home is nestled on 2 private acres in the highly sought-after water access community of Forest Landing, conveniently located between historic downtown Denton and Easton. Beautifully updated and move-in ready, this property offers 3 bedrooms, 2.5 baths, and a finished bonus room, providing flexible space for a home office, gym, playroom, or guest

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    7884 Laurel Ln, Denton, MD 21629
  • /72

    $499,990

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    22845 Peaviner Rd, Ridgely, MD 21660

    Welcome to your own private retreat! Situated on 4 peaceful acres, this well-maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality.Inside, you'll find a spacious and inviting floor plan with generous living areas, an updated kitchen, and plenty of room for family and guests. Step outside to the enormous rear deck, an ideal space for

    Chris Rosendale CR Realty

    22845 Peaviner Rd, Ridgely, MD 21660
  • /50

    $595,000

    • 5 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /47

    $755,000

    • 3 Beds
    • 2 Baths
    • 2,504 Sq Ft

    3769 Bradley Rd, Federalsburg, MD 21632

    This is your farmette dream come true! This beautiful 3 bed, 2 full bath home is situated on 6+ acres of partially fenced in land, has a barn with a tack room, a large screened-in back porch, a 2 car garage and an in-ground saltwater pool. The barn features 3 stalls, a hay loft with elevator, washroom, a tack room with a closet and shelves for storage. The water to the barn is sourced from a 290

    Sarah Robins Coldwell Banker Realty

    3769 Bradley Rd, Federalsburg, MD 21632
  • /70

    $359,900

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Welcome to this charming ranch-style home, where classic character meets modern comfort. This spacious residence features three inviting bedrooms and two full bathrooms, providing plenty of room for both everyday living and relaxation. The beautifully renovated kitchen and bathrooms, along with fresh interior and exterior paint, give the home a bright, updated, and welcoming feel.The home

    neveela gondal Keller Williams Realty Central-Delaware

    412 N Main St, Greensboro, MD 21639
  • /48

    $600,000

    • 6 Beds
    • 3.5 Baths
    • 3,592 Sq Ft

    11592 Holly Rd, Ridgely, MD 21660

    Welcome to 11592 Holly Road in Ridgely, MD! This spacious 6-bedroom, 3.5-bath home offers plenty of room inside and out, with a flexible layout to fit a variety of needs.Inside, you'll find a bright kitchen with premium appliances, a comfortable living room with a gas fireplace, and a primary suite featuring a separate sitting area and attached office. The home also includes an in-law

    Jarnell Foster Samson Properties

    11592 Holly Rd, Ridgely, MD 21660
  • /59

    $1,250,000

    $250K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    New price improvement! Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /74

    $599,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,938 Sq Ft

    23130 Sparks Rd, Ridgely, MD 21660

    Robert Walker McClain-Williamson Realty, LLC

    23130 Sparks Rd, Ridgely, MD 21660
  • /38

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 2,552 Sq Ft

    4 N Maryland Ave, Ridgely, MD 21660

    Welcome to 4 N Maryland Ave in Ridgely! This spacious 4-bedroom, 2.5-bath home offers 2,552 square feet of living space on approximately 0.21 acres. The home features a two-story layout, fireplace, open and enclosed porch areas, and a private pool—perfect for relaxing and entertaining. Conveniently located in the Town of Ridgely, this property offers plenty of space and potential to make it your

    Heather Brummell Keller Williams Realty

    4 N Maryland Ave, Ridgely, MD 21660
  • /16

    $230,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    ***NEWLY ADJUSTED PRICE***Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenience 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 updated with fresh paint, new appliances and more to ensure it's move-in

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • /37

    $385,000

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    5716 Bethlehem Rd, Preston, MD 21655

    Space, flexibility and over an acre to call your own — welcome to 5716 Bethlehem Road! Set on 1.14 acres in Preston, this spacious one-level home offers 4 bedrooms, 2 full bathrooms, a separate den/flex room and a floor plan with room to spread out.Step inside and you'll find bright, generously sized living spaces and plenty of possibilities. The owner's suite is tucked away with its own

    Catelin Schwarz NextHome Envision

    5716 Bethlehem Rd, Preston, MD 21655
  • /66

    $995,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    5315 Smithville Rd, Federalsburg, MD 21632

    Nestled in a farm like setting, this exquisite ranch-style home offers a luxurious lifestyle on a sprawling 40.64+/-acre lot, seamlessly blending elegance with nature. The property boasts modern comforts throughout its 1,568+/- sq. ft. of meticulously designed space. Step inside to discover an inviting interior adorned with rich hardwood and plush carpet flooring. The traditional floor plan

    Bill Wieland Benson & Mangold, LLC

    5315 Smithville Rd, Federalsburg, MD 21632
  • /55

    $340,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    306 Caroline Ave, Ridgely, MD 21660

    Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    306 Caroline Ave, Ridgely, MD 21660
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