15,673

Caroline County, MD Homes

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  • /66

    $484,999

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    2570 Guard Rd, Federalsburg, MD 21632

    Welcome to this 3-bedroom, 2-bathroom home nestled on more than Eight acres of land, offering the perfect blend of comfort, space, and opportunity. The main level features a practical layout with three bedrooms, two full baths, and a warm, inviting living space. Upstairs, you’ll find an unfinished second story, a blank slate ideal for adding extra bedrooms, a bonus room, or a private retreat

    Thomas Burdett Keller Williams Realty

    2570 Guard Rd, Federalsburg, MD 21632
  • /2

    $1,000 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    107 W Central Ave, Federalsburg, MD 21632

    Property Id: 2106426This spacious one bedroom apartment has lots of updates and is ready to move in.

    107 W Central Ave, Federalsburg, MD 21632
  • /18

    $169,900 Sold Aug 27, 2025

    • 700 Sq Ft
    • $243/SF
    • 31 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    601 Cedar Ln, Greensboro, MD 21639

    Nice location out of town on 4 Acres, Carport/Canopy, 2 Bedrooms, one bath house, close to town, nice enclosed porch, large front and back yard, two outbuildings, horseshoe driveway

    Diane Wenk Wright Real Estate

    601 Cedar Ln, Greensboro, MD 21639
    • /3

      Est $64,000 Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      510 Lincoln St, Denton, MD 21629
  • /25

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    2828 Guard Rd, Federalsburg, MD 21632

    Welcome to 2828 Guard Rd in beautiful Federalsburg! If you are looking for peace and serenity and you like to stargaze this property is for you. With the convenience of being within 45 minutes to the eastern shore beaches and parks, 2828 Guard rd offers 1.4 acres of beautiful land surrounded by fields. As you enter the home you will be greeted with open living dining and kitchen . The large

    Alicia Guinn RE/MAX Executive

    2828 Guard Rd, Federalsburg, MD 21632
  • /2

    $2,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,664 Sq Ft
    • House for Rent

    14500 Cherry Ln, Ridgely, MD 21660

    Enjoy the unique charm of country living in this spacious home set on 1.5 acres. The main level features a primary bedroom with full bath, a large living room, and an oversized kitchen with dining area. You’ll also find a convenient half bath, a generous laundry room, and a massive great room/game room complete with a pool table - perfect for entertaining.Upstairs offers two additional large

    Penny Hollis Keller Williams Select Realtors of Annapolis

    14500 Cherry Ln, Ridgely, MD 21660
  • /26

    $280,000 Sold Aug 25, 2025

    • 1,055 Sq Ft
    • $265/SF
    • 7 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1973

    104 S 8th St, Denton, MD 21629

    Welcome to your modern retreat in the heart of Denton!104 S 8th Street is more than just a home — it's a lifestyle! This cozy and stylish rancher sits on an impressive .44-acre lot inside town limits, offering the perfect blend of privacy, charm, and convenience. Whether you’re starting out, downsizing, or simply looking for a place that just feels right, this one checks all the

    Tony Letizia VRA Realty

    104 S 8th St, Denton, MD 21629
    • /16

      Est $152,444 Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632
  • /25

    $380,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    25291 Calvert Dr, Greensboro, MD 21639

    Welcome to Passapae Landing community, where peace, privacy, and comfort come together! This beautiful maintained 3-bedroom, 2-full bathroom ranch style home offers 1,344 sq ft of easy, single level living on nearly 1/2-acre lot-and its ready for you to move right in! Step inside to a bright, inviting layout perfect for both everyday living and entertaining. the spacious living area flows

    Erene Katris Coldwell Banker Realty

    25291 Calvert Dr, Greensboro, MD 21639
  • /15

    $80,000 Sold Aug 22, 2025

    • 1,593 Sq Ft
    • $50/SF
    • 92 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1890

    307 Caroline Ave, Ridgely, MD 21660

    Spacious three bedroom colonial style single family home with huge and private backyard. Three large bedrooms on upper level. Huge rear addition. Let this former beauty shine again.

    Klaus Breitsameter RE/MAX Realty Group

    307 Caroline Ave, Ridgely, MD 21660
    • /13

      Not Listed For Sale

      • Studio
      • 2,184 Sq Ft

      712 Gay St, Denton, MD 21629

      712 Gay St, Denton, MD 21629
  • /28

    $314,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    113 Chambers St, Preston, MD 21655

    Welcome to the quiet quaint town of Preston, MD, just outside of Easton and a short drive to the Famous Suicide Bridge Restaurant! This will not last long! Schedule your showing today!This 3 bedroom two bathroom rancher sits on .42 acres that is fenced in! Rear deck, large detached garage that is temperature controlled, plumbing, electric and plenty of space to park your car and still

    Amy Betts Coldwell Banker Realty

    113 Chambers St, Preston, MD 21655
  • /15

    $265,000 Sold Aug 20, 2025

    • 1,120 Sq Ft
    • $237/SF
    • 23 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1990

    3181 Gallagher Rd, Preston, MD 21655

    Price Improvement! 3 bedroom, 2 bath rancher sitting on 2 acres just outside of Preston. Conveniently located approximately 15 minutes from Easton. This home has a new roof, new heat pump, new kitchen, new flooring, new fixtures and has been freshly painted. Call to schedule your showing today as this one will not last.

    Andrew Beaven Wright Real Estate

    3181 Gallagher Rd, Preston, MD 21655
    • /24

      Est $337,178 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft

      5 Seward Rd, Ridgely, MD 21660

      5 Seward Rd, Ridgely, MD 21660
  • /40

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    13070 Ridgely Rd, Greensboro, MD 21639

    Enjoy peaceful country living in this charming 3-bedroom, 2-bath rancher set on 2.5 acres backing to open farmland. The home welcomes you with a comfortable living room featuring a cozy gas fireplace and a separate dining space just off the kitchen. The kitchen offers newer appliances and opens to an enclosed sun room—a versatile space perfect for an office, playroom, art studio, or home

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    13070 Ridgely Rd, Greensboro, MD 21639
  • /32

    $227,500 Sold Aug 20, 2025

    • 1,816 Sq Ft
    • $125/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    1303 Blue Heron Dr, Denton, MD 21629

    Charming 3-Bedroom Townhouse with Modern Updates & Low HOA!Welcome to this spacious and beautifully maintained 3-bedroom, 2.5-bath townhouse offering 1,816 sq ft of comfortable living space. Recent upgrades include new carpet, fresh paint, updated light fixtures, and new flooring in the kitchen and primary bathroom—making this home move-in ready!The main level features an

    Justin Pokrywka Meredith Fine Properties

    1303 Blue Heron Dr, Denton, MD 21629
    • /5

      Est $84,667 Not Listed For Sale

      328 E Central Ave, Federalsburg, MD 21632

      328 E Central Ave, Federalsburg, MD 21632
  • /40

    $395,000

    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    1111 Trice Meadows Cir, Denton, MD 21629

    Welcome to 1111 Trice Meadows Circle in Denton, MD!This charming 4-bedroom, 2-bath detached single-family home offers comfort, style, and convenience in the sought-after Trice Meadows community. Featuring an open and inviting floor plan, this home is perfect for both everyday living and entertaining.The spacious living room flows seamlessly into a modern kitchen, complete with ample

    LaTanya Drayton United Real Estate Premier

    1111 Trice Meadows Cir, Denton, MD 21629
  • /30

    $340,000 Sold Aug 20, 2025

    • 2,000 Sq Ft
    • $170/SF
    • 64 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2015

    123 Briarwood Cir, Denton, MD 21629

    Get ready to fall in love with this charming Cape Cod, built in 2015 and beautifully maintained. Nestled on a peaceful street in the heart of Denton, this 3-bedroom, 2.5-bath home offers 2,000+ square feet of bright, comfortable living space.From the moment you arrive, you’ll notice the inviting curb appeal and classic Cape Cod character. Step inside to discover a spacious main level with

    Lou Chirgott Core Maryland Real Estate LLC

    123 Briarwood Cir, Denton, MD 21629
    • /5

      Est $39,921 Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      26302 Sennett Rd, Denton, MD 21629
  • /8

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • /39

    $399,000 Sold Aug 19, 2025

    • 2,780 Sq Ft
    • $144/SF
    • 19 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1993

    8912 Osterman Ct, Denton, MD 21629

    Coming Soon. Great Mid Shore Location convenient to anywhere not he Delmarva. Great home for larger Family with a spacious fenced back yard, sweet little Patio house and extra driveway for Outdoor Rv or boating storage. All Bedrooms and 3 Full baths up, Laundry Center up with Large Master containing Walk in Closet and 4pc Master Bath. Lovely mature landscaping in front and located on

    Nanci Gardner Meredith Fine Properties

    8912 Osterman Ct, Denton, MD 21629
    • /79

      Est $606,472 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      13056 Hog Lot Rd, Ridgely, MD 21660

      13056 Hog Lot Rd, Ridgely, MD 21660
  • /52

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    7881 Dyer Rd, Denton, MD 21629

    Country location - 3BR, 2BA Home on Private 1± Acre Lot!This beautifully maintained home offers comfort, updates, and space both inside and out. Enjoy peace of mind with recent upgrades including a new well, septic system, HVAC, roof, and driveway. The home features gleaming wood floors, a bright, updated kitchen and bathrooms, and flexible living spaces – potential for a first-floor

    Valerie Brown Charles C. Powell, Inc. Realtors

    7881 Dyer Rd, Denton, MD 21629
  • /2

    $258,000 Sold Aug 18, 2025

    • 1,326 Sq Ft
    • $195/SF
    • 1 Day On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1953

    318 S 5th Ave, Denton, MD 21629

    This home is spruced up on the inside and new siding on the outside. Owner estimates to complete it by late June or July. One car garage for extra storage. Close to all amenities.

    Barbara Beaudet Brenton Realty Group

    318 S 5th Ave, Denton, MD 21629
    • /23

      Est $309,666 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      106 Noble Ave, Preston, MD 21655

      106 Noble Ave, Preston, MD 21655
  • /15

    $445,000

    • 5 Beds
    • 2.5 Baths
    • 2,692 Sq Ft

    5 Lister Ln, Ridgely, MD 21660

    Lister Estates = Excellent Location!! Lovely 5 Bedroom 2.5 Bath Home in very sought after Lister Estates. Roof 2 years old and HVAC system only 5 years old. High ceilings and partially open main floor plan with a warm and sunny bump-out breakfast nook, Kitchen and Family Room along with Powder room, and a separate Dinning and Sitting room area. The upper floor boasts a Huge primary bedroom

    Connie Mahaney Schwartz Realty, Inc.

    5 Lister Ln, Ridgely, MD 21660
  • /2

    $286,990 Sold Aug 15, 2025

    • 1,460 Sq Ft
    • $197/SF
    • 7 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2025

    110 Parkland Rd, Greensboro, MD 21639

    Discover 110 Parkland Road, a new home in our newest community Kinnamon Meadows in Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home.The

    Kathleen Cassidy D R Horton Realty of Virginia LLC

    110 Parkland Rd, Greensboro, MD 21639
    • /17

      Est $277,131 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft

      104 Noble Ave, Preston, MD 21655

      104 Noble Ave, Preston, MD 21655
  • /37

    $369,000

    • 2 Beds
    • 1 Bath
    • 1,234 Sq Ft

    6238 Bethlehem Rd, Preston, MD 21655

    Endless Possibilities Await!Discover the perfect blend of residential comfort and commercial potential with this unique property on .75 acres, ideally located between Easton and DentonThe 2 Bedroom/1Bathroom home offers a charming layout featuring a living room, dining room, family room, office, breakfast nook, and a screened in porch for relaxing evenings.On the commercial

    Amy Betts Coldwell Banker Realty

    6238 Bethlehem Rd, Preston, MD 21655
  • /33

    $1,050,000 Sold Aug 15, 2025

    • 2,748 Sq Ft
    • $382/SF
    • 162 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1954

    21498 Dover Bridge Rd, Preston, MD 21655

    Beautiful country setting on 30 acres with a 3 bedroom, 3 bathroom ranch home, two large shops [30x400 & 50x100] and three income-producing poultry houses.

    SCOTT REAGAN CALLAWAY FARNELL AND MOORE

    21498 Dover Bridge Rd, Preston, MD 21655
    • /60

      Est $365,026 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,088 Sq Ft

      240 Main St, Preston, MD 21655

      240 Main St, Preston, MD 21655
  • /49

    $425,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    8556 Tuckahoe Rd, Denton, MD 21629

    Don’t miss this incredible buy it won’t last much longer , Come take a Peek at Your New Home ,you’ll be glad you did ,next summer when your swimming, Bbq’ing and enjoying your fire pit with family and friends..This home is the lowest priced home in the area with over an acre of property , gorgeous inground pool and with extensive hardscape . USDA ELIGIBLE -"LOW TO NO DOWN" PAYMENT

    Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
  • /13

    $225,000 Sold Aug 15, 2025

    • 3,731 Sq Ft
    • $60/SF
    • 148 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1890

    505 Market St, Denton, MD 21629

    This home is located in Down town Denton close to and within walking distance to most everything. The home has lots of potential to be and easily transformable to a Duplex or with having so much space and a full attic, maybe even additional units. Live in one unit and rent the other. Lots of Possibilities . This home is sold in an as is condition and Seller has found their home of choice and

    Barbara Beaudet Brenton Realty Group

    505 Market St, Denton, MD 21629
    • /14

      Est $363,765 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft

      111 Fooks Ave, Preston, MD 21655

      111 Fooks Ave, Preston, MD 21655
  • /35

    $335,000

    • 4 Beds
    • 2 Baths
    • 1,326 Sq Ft

    1203 Tuckahoe Ct, Denton, MD 21629

    Take a look at this charming 4 BR 2 Bath Cape Cod. Many improvements have been done to make this place your sweet dream. The kitchen has all new cabinets with a new gas range and Corian countertops and the living room has new vinyl flooring. The kitchen and the dining area overlook the new contracted deck that leads to the large backyard with 2 sheds, 1 being new (2023), along with new

    Stephen Brown Iron Valley Real Estate Ocean City

    1203 Tuckahoe Ct, Denton, MD 21629
  • /13

    $260,000 Sold Aug 13, 2025

    • 1,539 Sq Ft
    • $169/SF
    • 120 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1955

    306 Sunrise Ave, Ridgely, MD 21660

    YOU'RE IN LUCK! THIS HOUSE IS BACK ON THE MARKET! This charming four-bedroom, 2 full bathroom home is priced to sell immediately. It is move-in ready and waiting for you. The house and 2 utility sheds sit on a corner lot in the beautiful friendly town of Ridgely, Maryland. It features off-street parking in the front and the rear as well as on-street parking. There is dual heat with a heat

    Wanda Hampton Clark & Co Realty, LLC

    306 Sunrise Ave, Ridgely, MD 21660
    • /38

      Est $259,603 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,314 Sq Ft

      113 Noble Ave, Preston, MD 21655

      113 Noble Ave, Preston, MD 21655
  • /25

    $329,900

    • 4 Beds
    • 2.5 Baths
    • 1,624 Sq Ft

    407 Wood Duck Dr, Greensboro, MD 21639

    Welcome to 407 Wood Duck Drive, a charming two-story colonial in the highly desirable Caroline Farms community of Greensboro, Maryland. This 4-bedroom, 2.5-bath home offers a perfect blend of style, comfort, and convenience, with no HOA. Step inside to find hardwood flooring, beautiful matching countertops, and stainless steel appliances. The spacious kitchen offers room for a table and opens

    Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
  • /10

    $100,000 Sold Aug 12, 2025

    • 1,423 Sq Ft
    • $70/SF
    • 61 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1900

    103 Reliance Ave, Federalsburg, MD 21632

    A diamond in the rough that you can make your own. Charming 1423 Sq Ft. Colonial home on Reliance Ave in Federalsburg with open views overlooking the river. Needing some TLC, spacious bedrooms, 1.5 baths, front porch, large driveway for parking and 2 car detached garage (with electric). A large loft room above with outdside stairs. Thoughtful details throughout. Partially renovated, replacement

    rachael harrison Coldwell Banker Realty

    103 Reliance Ave, Federalsburg, MD 21632

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