15,800

Caroline, MD Homes

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  • /22

    $369,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,746 Sq Ft

    25432 Piney Branch Ln, Denton, MD 21629

    Beautiful country rancher sitting on private 1.16 +- acre lot with mature landscaping. The property features 3 bedrooms, 2 bathrooms, large kitchen, family room, and attached 2 car garage. A bright screened in porch off the back of the home leads to a spacious yard and additional storage shed. Single level with modern amenities, just minutes to downtown Denton shopping and restaurants!

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 494-2377

    25432 Piney Branch Ln, Denton, MD 21629
  • /16

    $465 - $1,290 per month

    Riverwoods at Denton

    1 - 3 Beds

    101 Quinn Cir, Denton, MD 21629

    Riverwoods at Denton is an affordable housing community featuring newly renovated existing apartments and 36 apartment homes. All of the apartments offer the latest Green energy-saving and conserving features and include a modern kitchen, with abundant cabinetry as well as dishwasher, disposal and microwave. Handicap accessible apartments are also available.Riverwoods at Denton features a 1,500

    101 Quinn Cir, Denton, MD 21629
  • /7

    $240,000 Sold Aug 29, 2025

    • 736 Sq Ft
    • $326/SF
    • 0 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1949

    4539 Houston Branch Rd, Federalsburg, MD 21632

    Complete rehab house, metal roof, new kitcen, new windows bounus room in attic

    Barbara Nichols Results Realty Inc.

    4539 Houston Branch Rd, Federalsburg, MD 21632
    • /10

      Est $648,869 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft

      Unlisted Address

      Unlisted Address
  • /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

    (443) 232-1392

    23296 Wilder Way, Denton, MD 21629
  • /18

    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • House for Rent

    104 Roe St, Greensboro, MD 21639

    Located in the heart of Greensboro, this recently remodeled, three bedroom, 2 bath home is the perfect place to call home! Front porch, rear deck, driveway and a nice-sized yard for enjoying the outdoors.Minimum credit score of 650 for all adults residing at the property and pets are on a case-by case basis.

    Nora Turner Long & Foster Real Estate, Inc.

    104 Roe St, Greensboro, MD 21639
  • /99

    $420,000 Sold Aug 29, 2025

    • 3,734 Sq Ft
    • $112/SF
    • 16 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1930

    208 Bloomingdale Ave, Federalsburg, MD 21632

    **Discover Your Dream Retreat: A Stunning 3-Bedroom Rancher with Unmatched Amenities!**Welcome to your private sanctuary, where elegance meets endless possibilities! This remarkable 3-bedroom, 2.5-bath rancher is nestled on an expansive lot, featuring a beautifully brick-fenced yard, a finished basement, a detached 2-car garage, and even a stable/barn. With an entertainment room complete

    Blaine Williamson McClain-Williamson Realty, LLC

    208 Bloomingdale Ave, Federalsburg, MD 21632
    • /23

      Est $321,912 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      323 Mallard Dr, Greensboro, MD 21639

      323 Mallard Dr, Greensboro, MD 21639
  • /93

    $520,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,372 Sq Ft

    13800 Cedar Ln, Greensboro, MD 21639

    Discover Your Dream Farm! This incredible 18-acre property, currently perfect for horses, offers endless possibilities for your agricultural pursuits, hobby farm or a serene country lifestyle. This lovely home features a fireplace and gorgeous honey-toned hardwood floors throughout and an abundance of natural light. The 2BR/1BA cottage is self-sufficient and quaint with an open concept floor

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 698-4178

    13800 Cedar Ln, Greensboro, MD 21639
  • /10

    $1,165 - $1,415 per month

    Sunset Hargraves Ridgely

    1 - 3 Beds

    502 Sunset Blvd, Ridgely, MD 21660

    Welcome to Sunset Hargraves Ridgely, where newly renovated affordable apartment homes meet the charm of Maryland’s Eastern Shore. Located in the heart of Ridgely, our spacious 1, 2, and 3-bedroom apartments feature brand-new kitchens, energy-efficient appliances, luxury vinyl plank flooring, new windows, and more. Community-wide upgrades include new roofing, gutters, and refreshed breezeways,

    502 Sunset Blvd, Ridgely, MD 21660
  • /31

    $350,000 Sold Aug 27, 2025

    • 1,772 Sq Ft
    • $198/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 2010

    1109 Trice Meadows Cir, Denton, MD 21629

    Welcome to 1109 Trice Meadows Circle — a beautifully refreshed and move-in-ready 3-bedroom, 2-bath rancher nestled in the desirable Trice Meadows community in charming Denton, Maryland. This thoughtfully updated home offers a perfect blend of comfort, style, and convenience, making it an ideal choice for anyone looking to settle into a peaceful neighborhood setting with modern features already in

    Laura Anderson Coldwell Banker Realty

    1109 Trice Meadows Cir, Denton, MD 21629
    • /30

      Est $307,740 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft

      319 Mallard Dr, Greensboro, MD 21639

      319 Mallard Dr, Greensboro, MD 21639
  • /44

    $370,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft

    3590 Choptank Rd, Preston, MD 21655

    The ULTIMATE DREAM HOME ALERT! Are you tired of feeling like you're stuck in a never-ending cycle of home repairs and renovations? Well, buckle up, friend, because this stunning three-bedroom, two-bath rancher is about to become your happy place!Imagine waking up every morning in a beautiful, meticulously cared-for home, surrounded by lush greenery on a half-acre lot that's just begging

    Agent Photo

    Dawn O'Day

    Samson Properties

    (410) 291-1022

    3590 Choptank Rd, Preston, MD 21655
  • /28

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 2,688 Sq Ft
    • House for Rent

    22721 Marsh Creek Rd, Preston, MD 21655

    Enjoy the unique charm of country living in this spacious 4-bedroom, 2-bathroom Sears Farmhouse. Situated on one acre, this farmhouse offers picturesque views of an active farm. This home has classic farmhouse feel featuring generous rooms filled with natural light. The main level includes a large living room, a family room, kitchen, sunroom and a full bath. This house radiates vintage charm with

    Lisa Lynch Keller Williams Realty

    22721 Marsh Creek Rd, Preston, MD 21655
  • /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
    • /19

      Est $207,260 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      206 Maple Ave, Ridgely, MD 21660

      206 Maple Ave, Ridgely, MD 21660
  • /10

    $620,000

    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Great Apartment Building investment opportunity, updated, and ready to go! The building includes three 2-bedroom, 1-bath units and one 3-bedroom, 1-bath unit — all with private entrances and separately metered utilities. A furnished office space adds additional potential for on-site management or rental income.Recent upgrades include: New well (less than a year old) with a 20-year warranty,

    Agent Photo

    Sharon Daugherty

    Keller Williams Realty Delmarva

    (410) 881-8824

    310 Main St, Marydel, MD 21649
  • /8

    $1,300 per month

    • 1 - 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    106 W Railroad Ave Unit 2B, Ridgely, MD 21660

    Welcome to this unique, 2Br/1 Bath apartment located in the heart of the charming town of Ridgely, MD. This rental offers a perfect blend of comfort, practicality, and town charm.Among the property's key features is a spacious open layout that makes the 1000 square foot space feel expansive and comfortable. Large windows welcome an abundance of natural light, enhancing the town views and

    106 W Railroad Ave Unit 2B, 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
    • /10

      Est $408,024 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      1101 Trice Meadows Cir, Denton, MD 21629

      1101 Trice Meadows Cir, Denton, MD 21629
  • /31

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft

    406 N Academy St, Greensboro, MD 21639

    Back on the market- Buyer couldn’t perform. Don’t miss the second chance! Charming 3-bedroom, 2-bath ranch with endless potential! This home boasts an open-concept design,featuring an eat-in kitchen and a bright sunroom overlooking the backyard. A full basement offers plenty ofspace to customize however you wish. Fresh updates include brand-new luxury vinyl plank flooringthroughout,

    Agent Photo

    Predaricka Mendez-Lopez

    Realty One Group Performance, LLC

    (667) 247-8578

    406 N Academy St, Greensboro, MD 21639
  • /38

    $2,575 per month

    • 3 Beds
    • 3 Baths
    • 3,316 Sq Ft
    • House for Rent

    25369 Harpers Branch Dr, Denton, MD 21629

    Privacy abounds at this rustic 3 bed 3 bath waterfront home. Home features cathedral ceiling in the living room, wood laminate floors, large bedrooms 1 with fireplace , 1 with woodstove and kitchenette. A 3 season room with hot-tub and water views ad to the relaxing experience of living at this home. Tenant has access and use of shed and 1 bay garage on the left of the main garage.

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    25369 Harpers Branch Dr, Denton, MD 21629
  • /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
    • /15

      Est $408,691 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      204 Briarwood Cir, Denton, MD 21629

      204 Briarwood Cir, Denton, MD 21629
  • /71

    $500,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    Mortgage savings may be available for buyers of this home.Discover the perfect blend of comfort, versatility, and investment potential in this completely remodeled 1,986 sq ft home set on 17.36 acres. Every detail has been thoughtfully upgraded—from new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /9

    $1,200 per month

    • 1 - 2 Beds
    • 1 Bath
    • 100 Sq Ft
    • Condo for Rent

    10 Maryland Ave Unit 4, Ridgely, MD 21660

    Large second floor 1 br, 1 bath apartment kitchen and bathroom, central heat and air, walking distance to park and downtown, no smoking, no pets, a Security deposit approved application, first months required for move in.1200 per month plus Gas and electric, water/sewer,

    10 Maryland Ave Unit 4, Ridgely, MD 21660
  • /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
    • /23

      Not Listed For Sale

      • Studio
      • 3,200 Sq Ft

      5 Park Ave, Ridgely, MD 21660

      5 Park Ave, Ridgely, MD 21660
  • /54

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Why wait months to build when you can start enjoying this meticulously built, and finely crafted contemporary farmhouse home right now? Situated on an .85 acre lot in the established community of Ashworth, this 2023 built, 3,168 square foot, 4 bedroom, 2.5 bath home contemporary farmhouse-style home blends rustic charm with contemporary elegance. The exterior features classic white siding,

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /21

    $2,250 per month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    139 Riverwalk Terrace, Federalsburg, MD 21632

    Brand New Endunit 3 Bedroom 2.5 bath townhome in the heart of Federalsburg. The lower level is bright and spacious with a dining area, kitchen with stainless steel appliances and great room that leads to Deck overlooking the river. The upper levels features 3 bedrooms, 2 full baths and in unit washer and dryer. This Riverside community features nature trails along Marshyhope Creek and over the

    Theresa Deminne O'Brien Realty ERA Powered

    139 Riverwalk Terrace, Federalsburg, MD 21632
  • /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
    • /21

      Est $209,598 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      613 Denton Rd, Federalsburg, MD 21632

      613 Denton Rd, Federalsburg, MD 21632
  • /3

    $99,000

    • Land
    • 1.00 Acre
    • $99,000 per Acre

    0 Holly Rd Unit 24208711, Ridgely, MD 21660

    Own 1 Acre of Vacant Land in Caroline County, Maryland. This property offers 1 acre of vacant residential and agricultural land, featuring 250 feet of road frontage and access via the peaceful Holly Road. With a tranquil rural setting, this versatile property provides privacy, space, and zoning that supports both farming and single-family development. Property Highlights:Location:

    Community Lands

    0 Holly Rd Unit 24208711, Ridgely, MD 21660
  • /2

    $670 - $1,454 per month

    Riverview Gardens

    1 - 4 Beds

    500 High St, Denton, MD 21629

    500 High St, 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
    • /3

      Est $64,000 Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      510 Lincoln St, Denton, MD 21629
  • /144

    $1,449,000

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    24512 Marblehead Rd, Ridgely, MD 21660

    This 99-acre wooded farm offers a well-rounded mix of equestrian, hunting, and homesteading features. Lovely 2 bedroom, 3 bath home, built in 2004, includes vaulted ceilings, a brick hearth propane fireplace with remote, hardwood flooring, and a fully conditioned crawlspace. A wrap-around front porch overlooks the horse pasture and garden, and the rear enclosed screen porch opens to a large brick

    Mike Arajakis

    24512 Marblehead Rd, Ridgely, MD 21660
  • /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
  • /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
    • /16

      Est $152,444 Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632

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