15,673

Caroline County, MD Homes

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  • /2

    $20,000

    • Land
    • 0.70 Acre
    • $28,571 per Acre

    Parcel 210 Dover Bridge Rd, Preston, MD 21655

    Unimproved lot on Dover Bridge Rd. No perc on the property currently. Close to Easton and Preston. Partially cleared, seller offering to clear remaining tree stumps.

    Katie Stecklair Cross Street Realtors LLC

    Parcel 210 Dover Bridge Rd, Preston, MD 21655
  • /44

    $390,000 Sold Jul 31, 2025

    • 1,228 Sq Ft
    • $318/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2014

    10803 Greensboro Rd, Denton, MD 21629

    Pride in Ownership! Amazingly maintained rancher offering one-level living with open floor plan. Chill on your front porch looking out on the fields that make this area so special. Or relax on the new huge back deck while you grill or pick crabs with family and friends. This quiet setting is removed from the hustle and bustle of daily life, yet close to highway access points to DE and the Bay

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    10803 Greensboro Rd, Denton, MD 21629
    • /31

      Est $541,919 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,200 Sq Ft

      5132 Clark Canning House Rd, Federalsburg, MD 21632

      5132 Clark Canning House Rd, Federalsburg, MD 21632
  • /6

    $279,000

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD Situated on a large double lot with mature landscaping. Don’t miss this beautifully renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of Choptank. Every inch of this home has been thoughtfully updated from top to bottom, blending modern finishes with classic Eastern Shore charm.Currently tenant-occupied and

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /31

    $250,000 Sold Jul 30, 2025

    • 1,344 Sq Ft
    • $186/SF
    • 11 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1946

    21344 Tanyard Rd, Preston, MD 21655

    Classic Charm Meets Modern Comfort on the Eastern ShoreWelcome to 21344 Tanyard Road—a spacious 4-bedroom, 2-bath single-family home nestled on a private, tree-lined 1⁄2-acre lot in Preston, MD. Just 5 miles from Easton and Route 50, this inviting property offers the perfect blend of peace, privacy, and proximity to everyday conveniences.Step inside to find gleaming hardwood

    Charlotte Savoy The KW Collective

    21344 Tanyard Rd, Preston, MD 21655
    • /20

      Est $272,330 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,440 Sq Ft

      306 N Academy St, Greensboro, MD 21639

      306 N Academy St, Greensboro, MD 21639
  • /13

    $190,000

    • Land
    • 16 Acres
    • $11,614 per Acre

    0 Oakland Rd, Ridgely, MD

    Discover a unique opportunity to own two adjacent parcels on Oakland Road in beautiful Caroline County. This offering includes 16.36-acres identified as Tax Map 0009, Parcel 103, Grid 0023....Note there is an Additional Separate Parcel that is adjacent with 1.0 acres, listed in MLS: MDCM2006238 for sale, identified as Tax Map 0009, Parcel 63, Grid 0023.....Together, these properties provide ample

    Sandra Gendleman Long & Foster Real Estate, Inc.

    0 Oakland Rd, Ridgely, MD
  • /58

    $345,000 Sold Jul 30, 2025

    • 1,984 Sq Ft
    • $174/SF
    • 91 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2005

    510 Pintail St, Greensboro, MD 21639

    Do not miss your chance to own this 5-bedroom, 2.5 bath Colonial home with attached garage located in the "Small-Town, Big Heart" city of Greensboro! The gourmet kitchen includes stainless steel appliances, a stylish backsplash, granite countertops, and a pantry. The kitchen/dining room opens to the family room, giving you a great open space to entertain and enjoy family time! The back deck is

    Jon Fleming Weichert Realtors - Blue Ribbon

    510 Pintail St, Greensboro, MD 21639
    • /52

      Est $498,972 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft

      23741 Solitude Dr, Henderson, MD 21640

      23741 Solitude Dr, Henderson, MD 21640
  • /8

    $25,000

    • Land
    • 1.00 Acre
    • $25,000 per Acre

    0 Oakland Rd, Ridgely, MD

    Discover a unique opportunity to own two adjacent parcels on Oakland Road in beautiful Caroline County. This offering includes 1.0-acre identified as Tax Map 0009, Parcel 63, Grid 0023....Note there is an Additional Separate Parcel that is adjacent with 16.36 acres, listed in MLS: MDCM2006238 for sale, identified as Tax Map 0009, Parcel 103, Grid 0023.....Together, these properties provide ample

    Sandra Gendleman Long & Foster Real Estate, Inc.

    0 Oakland Rd, Ridgely, MD
  • /31

    $225,000 Sold Jul 25, 2025

    • 1,091 Sq Ft
    • $206/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1994

    3427 Holland Dr, Federalsburg, MD 21632

    Welcome to 3427 Holland Dr, a cute home at the end of a cul-de-sac. This 3-bedroom 1-bathroom home is priced to sell! Highlights include a recently installed water heater (2021), a new dishwasher, stove, and refrigerator (2023-24), hardwood floors, and a spacious fenced-in backyard. The home needs carpet in 2 bedrooms and minor drywall repairs. A fresh coat of paint would go a long way. The

    Matthew Olson EXP Realty, LLC

    3427 Holland Dr, Federalsburg, MD 21632
    • /23

      Est $405,745 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,682 Sq Ft

      14011 Cantor Ct, Queen Anne, MD 21657

      14011 Cantor Ct, Queen Anne, MD 21657
  • /5

    $199,000

    • Land
    • 6 Acres
    • $30,853 per Acre

    Lot 1 Dover Bridge Rd, Preston, MD 21655

    The perfect setting for your dream home on this 6.446-acre perc-approved buildable lot, ideally located between Preston and Easton. Offering both space and convenience, this property combines the tranquility of country living with easy access to nearby towns, shopping, dining, and commuter routes. With plenty of room for your vision—whether that’s a custom residence, hobby farm, or private

    Alicia Gannon Dulin Benson & Mangold, LLC

    Lot 1 Dover Bridge Rd, Preston, MD 21655
  • /57

    $405,000 Sold Jul 25, 2025

    • 2,994 Sq Ft
    • $135/SF
    • 20 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    1208 Painted Fern Rd, Denton, MD 21629

    BEST VALUE IN THE SOUGHT AFTER COMMUNITY OF SAVANNAH OVERLOOK! This pristine 2006 built, 4 bedroom, 2.5 bath updated colonial is situated on a .25 lot and offers newly installed privacy fence, pemium 50-year architectural roofing system installed 2022 (transferable warranty included), brand new laundry appliances, 2024, new carpeting throughout, 2024, contemporary lighting upgrades interior

    Barbara McCaffrey Redfin Corp

    1208 Painted Fern Rd, Denton, MD 21629
    • /26

      Est $286,193 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft

      13274 Greensboro Rd, Greensboro, MD 21639

      13274 Greensboro Rd, Greensboro, MD 21639
  • /34

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    158 Wright St, Preston, MD 21655
  • /56

    $400,000 Sold Jul 25, 2025

    • 2,500 Sq Ft
    • $160/SF
    • 73 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1984

    18089 Templeville Rd, Marydel, MD 21649

    Welcome to 18089 Templeville Road, a 4-bedroom, 2-bath rancher set on nearly half an acre of wide-open land, with pond and pole barn to max it all out—offering the space you want and the flexibility you need.This home delivers a classic layout with a large living room, separate dining space, and a generously sized kitchen ready for your vision. With a split-bedroom floor plan, the primary

    Phil Gerdes Real Broker, LLC - Annapolis

    18089 Templeville Rd, Marydel, MD 21649
    • /12

      Est $186,758 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,446 Sq Ft

      522 Denton Rd, Federalsburg, MD 21632

      522 Denton Rd, Federalsburg, MD 21632
  • /13

    $350,000

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft

    4516 Frazier Neck Rd, Preston, MD 21655

    Property OverviewNestled in the rural heart of Caroline County, this 40± acre farmette offers the perfect blend of agricultural ground, wooded acreage, and a modest country home—all just minutes from Preston and the Choptank River. Whether you're seeking a recreational retreat, a starter farm, or a homestead to build on, Frazier Neck Farmette delivers natural beauty, income potential, and

    Benjamin Alder The Land Group

    4516 Frazier Neck Rd, Preston, MD 21655
  • /31

    $290,000 Sold Jul 25, 2025

    • 1,265 Sq Ft
    • $229/SF
    • 102 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    278 Wood Duck Dr, Greensboro, MD 21639

    NEW PRICE and THE SELLER IS OFFERING A 1% INTEREST RATE BUY DOWN which could save you $200 a month on your mortgage! No HOA restrictions or monthly fees or extra community closing costs. This stunning newly built home is completed and a must see brought to you by Lomaxx Custom Homes! 278 Wood Duck Drive features 3 bedrooms and 2 beautifully designed bathrooms. From the moment you step inside,

    Crystal Smith RE/MAX Executive

    278 Wood Duck Dr, Greensboro, MD 21639
    • /6

      Est $284,766 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft

      105 Chamber St, Preston, MD 21655

      105 Chamber St, Preston, MD 21655
  • /3

    $104,900

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft

    9709 Foy Rd, Denton, MD 21629

    Priced To Sell Fast! Investor Alert! Renovate & Resell, Buy and Hold or Tear Down and Develop. Major Rehab Needed, City Will Require Permits. Per the City Lot Can be Split into 3 Parcels. 1.72 Acres Total. 3 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Hardwood Floors, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and

    Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
  • /31

    $280,000 Sold Jul 24, 2025

    • 1,456 Sq Ft
    • $192/SF
    • 120 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    5059 Gina Ln, Federalsburg, MD 21632

    PRICE IMPROVEMENT! Three bedroom and two bath rancher in a quiet rural setting on over 1 acre. New roof, appliances, flooring, and paint. Nice family room with a stone fireplace off the eat-in kitchen. Call to schedule your showing today.

    Andrew Beaven Wright Real Estate

    5059 Gina Ln, Federalsburg, MD 21632
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft

      22510 Ash Blvd, Preston, MD 21655

      22510 Ash Blvd, Preston, MD 21655
  • /13

    $240,000

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft

    1202 Blue Heron Dr, Denton, MD 21629

    WELCOME HOME!!! 1753 SQ FT OF COMFORT...... 3 FLOORS, 3 SPACIOUS BEDROOMS, 3 BATHROOMS, WHITE WOOD CABINETS, MARBLE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LUXURY VINYL FLOORING DOWNSTAIRS, FULLY CARPETED UPSTAIRS, LAUNDRY ROOM, PANTRY AND MORE. CORNER LOT/ QUICK ENTRY & EXIT/ PLAYGROUND/ POOL / CLUBHOUSE/ PET FRIENDLY NEIGHBORHOOD/ HOA / CLOSE DRIVE TO SCHOOLS, STORES, OCEAN CITY,

    SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
  • /24

    $349,900 Sold Jul 23, 2025

    • 1,200 Sq Ft
    • $292/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    5540 American Corner Rd, Federalsburg, MD 21632

    Escape to your own slice of paradise with this stunning new construction country home, set on 3.279 acres of serene land just outside Denton in rural Federalsburg, Maryland. Step inside the spacious 1,200-square-foot haven and discover a bright, open main level, where a sleek, modern kitchen with quartz countertops, white Kraftmaid cabinetry, and Frigidaire Gallery appliances makes cooking a joy

    David Moore RE/MAX Executive

    5540 American Corner Rd, Federalsburg, MD 21632
    • /17

      Est $447,072 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      3498 Pepper Rd, Federalsburg, MD 21632

      3498 Pepper Rd, Federalsburg, MD 21632
  • /72

    $285,000

    • 2 Beds
    • 2 Baths
    • 2,048 Sq Ft

    115 Maple Ave, Goldsboro, MD 21636

    Step into this beautifully renovated Victorian home, nestled on a generous .55-acre lot. This 2048 sqft gem blends timeless architectural charm with contemporary updates, offering a perfect blend of classic style and modern comfort.The home features three spacious bedrooms on the second floor, complemented by two full bathrooms—one on each level. The freshly painted interior, along with

    Phill Whitby Long & Foster Real Estate, Inc.

    115 Maple Ave, Goldsboro, MD 21636
  • /18

    $425,000 Sold Jul 23, 2025

    • 3,482 Sq Ft
    • $122/SF
    • 78 Days On Market
    • Studio
    • Built 1890

    8 N 2nd St, Denton, MD 21629

    Price Improvement! Historic District in Downtown Denton. The Downes House consists of four apartments and a commercial office. Fourth unit was most recently occupied by Caroline County Chamber of Commerce but contains a kitchen with full bath and can be utilized as a commercial office or an apartment ( flex space ). Most recent fully occupied yearly gross income was $57,000.Replacement windows

    Andrew Beaven Wright Real Estate

    8 N 2nd St, Denton, MD 21629
    • /26

      Est $215,049 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,184 Sq Ft

      304 N School St, Greensboro, MD 21639

      304 N School St, Greensboro, MD 21639
  • /21

    $269,000

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft

    529 N 6th St, Denton, MD 21629

    Welcome to this beautifully maintained 3 bedroom, 1 bath home that blends classic character with modern updates. Inside, you’ll find original hardwood floors that add warmth and charm throughout the living space.Enjoy a spacious backyard perfect for entertaining or relaxing, plus a brand new oversized back deck completed in 2025, ideal for outdoor gatherings. The home also features new

    Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
  • /48

    $460,000 Sold Jul 22, 2025

    • 2,131 Sq Ft
    • $216/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2003

    14462 Poplar St, Goldsboro, MD 21636

    First time on the market. Become one with nature at this very private location close to the town of Greensboro.This property sits on 5.87 acres and backs up to an embankment looking over the head of the Choptank river.This well maintained three bedroom, two and a half bath home is in great condition and move in ready. An open floor plan in the kitchen to living room with vaulted

    Peter Mellor Wright Real Estate

    14462 Poplar St, Goldsboro, MD 21636
    • /32

      Est $180,763 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,548 Sq Ft

      28012 Bloomery Rd, Federalsburg, MD 21632

      28012 Bloomery Rd, Federalsburg, MD 21632
  • /60

    $724,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This home is on one acre with an additional 15.77 acres - possibly one additional acre in deed. This home says "home from the time you drive up the drive and into this gorgeous rancher with comfort written all over." The kitchen has all stainless steel appliances and a large pantry. Large Island with cabinetry as well as seating for meals or snacks or just relaxing in the kitchen. The pellet

    Bonnie Duley Long & Foster Real Estate, Inc.

    28402 Liden School Rd, Denton, MD 21629
  • /49

    $565,000 Sold Jul 22, 2025

    • 2,379 Sq Ft
    • $237/SF
    • 41 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2010

    15185 Day Rd, Goldsboro, MD 21636

    Are you dreaming of a peaceful escape to the countryside? Well, Imagine owning a beautiful and spacious home nestled on nearly three acres of serene land. This private retreat is surrounded by mature trees, creating a peaceful haven teeming with lots of wildlife. This well-maintained, open-floor rancher offers 3 bedrooms and 2.5 baths plus a den and office that could easily function as a fourth

    Karen Clark Clark & Co Realty, LLC

    15185 Day Rd, Goldsboro, MD 21636
    • /15

      Est $201,688 Not Listed For Sale

      • Studio
      • 1,608 Sq Ft

      23904 Bridgetown Rd, Goldsboro, MD 21636

      23904 Bridgetown Rd, Goldsboro, MD 21636
  • /20

    $199,900

    • 3 Beds
    • 1 Bath
    • 1,904 Sq Ft

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill across from the Tuckahoe Creek with some winter views of the water. --the park across the street has a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be;, and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living room to the right and then the dining room

    Bonnie Duley Long & Foster Real Estate, Inc.

    21948 Main St, Hillsboro, MD 21641
  • /30

    $390,000 Sold Jul 21, 2025

    • 2,475 Sq Ft
    • $158/SF
    • 21 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2021

    333 Morning Glory Dr, Denton, MD 21629

    Stunning 4-Bedroom Single Family Home with Bonus Room & Modern Touches!Welcome to your dream home! Built in 2021, this beautifully maintained three-story single family home offers 2,475 sq. ft. of stylish living space designed for comfort, function, and entertaining.Step inside to discover a bright open floor plan featuring a spacious kitchen with granite countertops, a beautiful

    Danny Martin Keller Williams Flagship

    333 Morning Glory Dr, Denton, MD 21629
    • /33

      Est $282,778 Not Listed For Sale

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

      1901 Blue Heron Dr, Denton, MD 21629

      1901 Blue Heron Dr, Denton, MD 21629
  • /44

    $225,000

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft

    148 Main St, Preston, MD 21655

    Welcome to this timeless 1880 Federal style House, where historic charm meets thoughtful modern updates. Situated on a serene and spacious lot dotted with beautiful mature fruit trees, this 4 bedroom, 2 bath home offers approximately 2800 sq ft of character-filled space. Many renovations have already been completed- preserving original architectural details while adding essential modern

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    148 Main St, Preston, MD 21655

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