15,677

Caroline County, MD Homes

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  • /55

    $950,000

    • 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
  • /18

    $195,000 Sold Jun 27, 2025

    • 1,200 Sq Ft
    • $162/SF
    • 33 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1880

    7 S 7th St, Denton, MD 21629

    Coming Soon. This 2-bedroom home sits on an oversized corner lot that is walking distance to downtown shops and restaurants. Home has had roof replaced within last 8 years and windows were updated as well. Original Hardwood floors in Living room and dining room. Attached laundry room and small garage/shop area could be converted into a first floor Primary. Bathroom has been updated with double

    Roger Boyce Chesapeake Real Estate Associates, LLC

    7 S 7th St, Denton, MD 21629
    • /22

      Est $368,365 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,654 Sq Ft

      110 S 8th St, Denton, MD 21629

      110 S 8th St, Denton, MD 21629
  • /6

    $199,900

    • Land
    • 4.00 Acres
    • $49,975 per Acre

    12316 Ridgely Rd, Ridgely, MD 21660

    BUILD YOUR DREAM HOME IN HISTORIC RIDGELY, MARYLANDNestled just outside the charming town of Ridgeley, this expansive 4-acre parcel offers a unique opportunity to create your custom retreat amidst the rich tapestry of Maryland's Eastern Shore. Ridgeley, often referred to as the ' Dream City', was meticulously planned in 1867 during the post -Civil War railroad boom. Though the grand vision of a

    Gary Lucks Keller Williams Realty

    12316 Ridgely Rd, Ridgely, MD 21660
  • /34

    $386,000 Sold Jun 27, 2025

    • 2,064 Sq Ft
    • $187/SF
    • 48 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    306 Kerr Ave, Denton, MD 21629

    Looking for a spacious and private family home with easy access to everything you need? Look no further than this stunning 4 bedroom, 2.5 bathroom home nestled in the heart of Denton, Maryland. The home sits on a very private lot (almost a half acre) so you have the feel of living in the country but the conveniences of living in town. Come check this great home out today!

    Justin Pokrywka Meredith Fine Properties

    306 Kerr Ave, Denton, MD 21629
    • /30

      Est $406,753 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft

      1606 Cattail Commons Way, Denton, MD 21629

      1606 Cattail Commons Way, Denton, MD 21629
  • /4

    $345,000

    • Studio
    • 2,260 Sq Ft

    517 W Sunset Ave, Greensboro, MD 21639

    Three unit apartment building. Two 1bedroom apartments, one 2 bedroom. Fully leased with positive income to support expense and debt service

    Randy Staats Benson & Mangold, LLC

    517 W Sunset Ave, Greensboro, MD 21639
  • /8

    $329,000 Sold Jun 23, 2025

    • 1,568 Sq Ft
    • $210/SF
    • 0 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1994

    17840 Cool Spring Rd, Marydel, MD 21649

    Welcome to the Country! Rancher featuring 4 bedrooms and 2 full bathrooms, living area with brick wood fireplace. Consists of two parcels (202 & 203) totaling approx. 9.04 acres. Oversized garage with loft area. Separate 2 car garage with shop area. Needs some TLC but can be brought back to life and enjoy the peaceful Eastern Shore Living.

    Amanda Morgan Brenton Realty Group

    17840 Cool Spring Rd, Marydel, MD 21649
    • /18

      Est $409,194 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,505 Sq Ft

      1308 Trice Meadows Cir, Denton, MD 21629

      1308 Trice Meadows Cir, Denton, MD 21629
  • /54

    $250,000

    • 4 Beds
    • 1.5 Baths
    • 2,406 Sq Ft

    108 S 2nd St, Denton, MD 21629

    Historic charm meets endless potential in this spacious corner-lot home in the heart of downtown Denton—formerly home to the beloved local flower shop! With 4 bedrooms and 1.5 bathrooms, this well-maintained property offers incredible space, character, and small-town walkability.From the welcoming front porch to the large family room that opens to an oversized deck, this home is perfect

    Crystal Smith RE/MAX Executive

    108 S 2nd St, Denton, MD 21629
  • /39

    $907,650 Sold Jun 23, 2025

    • 3,648 Sq Ft
    • $249/SF
    • 12 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1974

    21710 Marsh Creek Rd, Preston, MD 21655

    This 20.2 acre farm includes a second parcel of 49.99 acres that is all woods. Fenced in for horses, cattle or sheep with a pole shed for protection , hay and equipment storage. A two story home with 4 bedrooms and 3 baths. Also an apartment above the garage for an additional bed and bath. More pictures to come. Not available to be shown until April 21, 2025

    Ed Quidas Long & Foster Real Estate, Inc.

    21710 Marsh Creek Rd, Preston, MD 21655
    • /24

      Est $435,768 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,880 Sq Ft

      23116 Gilpin Point Rd, Preston, MD 21655

      23116 Gilpin Point Rd, Preston, MD 21655
  • /25

    $259,000

    • Studio
    • 1,820 Sq Ft

    207 Gay St, Denton, MD 21629

    Price Improvement! Great investment. Perfect opportunity for an investor or owner-occupied duplex as first floor unit generates $1100/month and second floor unit is currently vacant.Conveniently located, multi-family in Downtown Denton with the Denton Police Department directly across the street.Vinyl siding, replacement windows, ductless mini split HVAC and off-street parking in the rear.

    Andrew Beaven Wright Real Estate

    207 Gay St, Denton, MD 21629
  • /55

    $390,000 Sold Jun 20, 2025

    • 2,646 Sq Ft
    • $147/SF
    • 37 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2021

    305 Morning Glory Dr, Denton, MD 21629

    Welcome home to The Gardens! One of Dentons' newest communities offering gorgeous homes close to town amenities and shopping! 305 Morning Glory Drive is the 2021 Somerset model and was carefully chosen to include all the builders' upgrades that were available! This home showcases a generous 2,646 sq.ft. of beautifully finished living space that you will enjoy for years to come. At the front of

    Cornelia Fallon Coldwell Banker Waterman Realty

    305 Morning Glory Dr, Denton, MD 21629
    • /27

      Est $394,511 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,184 Sq Ft

      6 W Liberty St, Ridgely, MD 21660

      6 W Liberty St, Ridgely, MD 21660
  • /10

    $195,000

    • Land
    • 15 Acres
    • $13,338 per Acre

    12837 Ridgely Rd, Greensboro, MD 21639

    14.62 acres of privacy, nature, and waterfront access. This wooded recreational lot offers — a serene wooded 14.62 acre escape surrounded by the Choptank River.This vacant property is perfect for hunting, camping, kayaking, and outdoor enjoyment. The woods offer access for hiking, exploring, and wildlife watching — including deer, turkeys, and geese. This lot is not perc approved and has no

    Melissa Tippett TTR Sotheby's International Realty

    12837 Ridgely Rd, Greensboro, MD 21639
  • /30

    $222,200 Sold Jun 20, 2025

    • 2,052 Sq Ft
    • $108/SF
    • 191 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1940

    312 W Central Ave, Federalsburg, MD 21632

    Very well kept 2 bedroom, 1 1/2 bath Cape Cod. Family room with a nice brick fireplace that's currently set up with gas logs. Three season porch with gas heater. Stone driveway leading to a one car garage. This property is being sold as part of an estate.

    Diane Wenk Wright Real Estate

    312 W Central Ave, Federalsburg, MD 21632
    • /29

      Est $302,850 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,568 Sq Ft

      217 Briarwood Cir, Denton, MD 21629

      217 Briarwood Cir, Denton, MD 21629
  • /31

    $290,000

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

    202 Maryland Ave, Ridgely, MD 21660

    INCREDIBLE VALUE! Looking for a well maintained and move-in ready home with no HOA?! Look no further - this home is just awaiting your personal touch, and you can move in with peace of mind with the one-year home warranty the sellers are offering to the new buyer! Situated on a corner lot, 202 Maryland Avenue comes with a large back yard - perfect for entertaining, gardening, or turning into your

    Mikeshia Wilson Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
  • /15

    $315,000 Sold Jun 19, 2025

    • 1,638 Sq Ft
    • $192/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    11891 Central Ave, Ridgely, MD 21660

    3 bedroom, 2 bath rancher on 12.5+/- acres. This property is being sold AS/IS and is part of an estate.Owners have no information on this property. Full basement, screened porch at rear, backs to woods. The small garage is in poor condition.

    Andrew Beaven Wright Real Estate

    11891 Central Ave, Ridgely, MD 21660
    • /48

      Est $577,311 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,074 Sq Ft

      24668 Tribbett Cir, Ridgely, MD 21660

      24668 Tribbett Cir, Ridgely, MD 21660
  • /24

    $153,000

    • Land
    • 3.00 Acres
    • $51,000 per Acre

    0 Asbury Dr, Denton, MD 21629

    Discover your ideal homesite in the scenic Asbury on the Choptank community, where peaceful living meets convenient access. This expansive 3-acre lot is perc approved for a three-bedroom septic system.Within this sought-after community, residents enjoy well-maintained roads, a private nature trail, and exclusive access to a community deepwater dock on the Choptank River. Ideal for boating

    Coard Benson Benson & Mangold, LLC

    0 Asbury Dr, Denton, MD 21629
  • /22

    $225,000 Sold Jun 18, 2025

    • 1,056 Sq Ft
    • $213/SF
    • 31 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1972

    203 Bernard Ave, Federalsburg, MD 21632

    Federalsburg - cute house in a quiet neighborhood. 3 bedroom, 1 bath home with large eat-in kitchen and utility room. New roof and new appliances are an added bonus. Great location near the ball field and all mid shore locations. Nice yard!

    Valerie Brown Charles C. Powell, Inc. Realtors

    203 Bernard Ave, Federalsburg, MD 21632
    • /4

      Est $442,975 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      10961 Greensboro Rd, Denton, MD 21629

      10961 Greensboro Rd, Denton, MD 21629
  • /7

    $58,900

    • Land
    • 0.58 Acre
    • $101,552 per Acre

    205 New St, Goldsboro, MD 21636

    Currently home on the lot. DO NOT ENTER. Value in the land. This 0.57-acre corner lot in Goldsboro offers a great opportunity for new construction. Property is ready to be tapped into Town of Greensboro's Sewage. Existing well on site, (condition unknown, not hooked up) Current home allows per Planning and Zoning no Excise tax on next build. Permits for new construction to be applied through

    Roger Boyce Chesapeake Real Estate Associates, LLC

    205 New St, Goldsboro, MD 21636
  • /71

    $380,000 Sold Jun 18, 2025

    • 2,413 Sq Ft
    • $157/SF
    • 107 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    411 Main St, Marydel, MD 21649

    Welcome to 411 Main St! This stunning Victorian home one of a kind offering 4 spacious bedrooms and 2 baths with over 2400 sqft of living space. This house has been lovingly maintained and updated by long term owners, offering amazing original character. Home draws you in with a porch swing and a stunning wrap around porch with made with teak wood- wood that is strong, durable, and virtually

    Yuliana Goldin-Dunn Patterson-Schwartz-Middletown

    411 Main St, Marydel, MD 21649
    • /27

      Est $162,060 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft

      308 Park Ave, Federalsburg, MD 21632

      308 Park Ave, Federalsburg, MD 21632
  • /4

    $169,500

    • Land
    • 10 Acres
    • $16,314 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc tested for a 3-bedroom home. The woods are a great habitat for deer and turkey and other wildlife. This lovely lot is all ready for the new owner to apply for home construction as the buyer has had the survey completed with the SRA noted on it so lots of the necessary paperwork is complete. So come see and come buy and

    Bonnie Duley Long & Foster Real Estate, Inc.

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /40

    $325,000 Sold Jun 17, 2025

    • 2,704 Sq Ft
    • $120/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    21968 Main St, Hillsboro, MD 21641

    Come take a look at this well maintained four bedroom and two full bath farmhouse. It boasts an upgraded kitchen with stainless steel appliances and granite counter tops. There is a breakfast nook right off the kitchen allowing a great spot to have breakfast in the mornings. The large formal dining room boasts bamboo hardwood floors that stretch into the spacious living room. Let's not forget

    Ross Hunsberger Coldwell Banker Realty

    21968 Main St, Hillsboro, MD 21641
    • /3

      Est $480,435 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      12141 Greensboro Rd, Greensboro, MD 21639

      12141 Greensboro Rd, Greensboro, MD 21639
  • /35

    $615,000

    • 3 Beds
    • 2 Baths
    • 1,651 Sq Ft

    12459 Kibler Rd, Greensboro, MD 21639

    Outstanding small farm property on quiet country road! This spacious home features 3 bedrooms and two baths, kitchen with new stainless steel appliances, breakfast bar and dining area. The large living room with wood floors over look the expansive front yard and opens to the front porch where you can enjoy your morning coffee. In the rear of the home there is a large family room that offers a

    Marcia Rostien Long & Foster Real Estate, Inc.

    12459 Kibler Rd, Greensboro, MD 21639
  • /52

    $715,000 Sold Jun 16, 2025

    • 3,854 Sq Ft
    • $186/SF
    • 21 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2000

    17435 Melville Rd, Henderson, MD 21640

    Welcome to 17435 Melville Road! Nestled on 21.5 picturesque acres in Henderson, Maryland, this sprawling home boasts 5 spacious bedrooms and 4 bathrooms. The exterior of this property features landscaped grounds, fenced pastures perfect for equestrian enthusiasts, and a 3-car garage equipped with a lift and an air compressor—ideal for car aficionados. Additionally, the property has leased solar

    Brody Sergent Northrop Realty

    17435 Melville Rd, Henderson, MD 21640
    • /22

      Est $262,042 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,350 Sq Ft

      350 Deep Shore Rd, Denton, MD 21629

      350 Deep Shore Rd, Denton, MD 21629
  • /30

    $385,000

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

    313 S 3rd St, Denton, MD 21629

    Meticulously Maintained & Move In Ready!! Many recent Improvements to this 3 bedroom, 2 bath, Open floor plan rancher with Large Yard, Deck, Multiple Organically prepped Gardens (including an asparagus) ready for your harvest this summer, Covered Porch, Pool with Decking, Oversized 2 Car Garage. Top is off with a large bonus room ready to make it your own! Plenty of off street parking. Close

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    313 S 3rd St, Denton, MD 21629
  • /20

    $350,000 Sold Jun 13, 2025

    • 1,736 Sq Ft
    • $202/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    23807 Westbridge Dr, Henderson, MD 21640

    Welcome to the charming neighborhood of Westbridge, where this delightful 3-bedroom, 2-bathroom rancher invites you to experience comfort and style in a serene setting! Step inside and discover an open kitchen and dining area, perfect for gatherings and everyday meals. The cozy living space, complete with a warm wood stove and stunning built-in bookshelves, creates an inviting atmosphere you’ll

    Amanda Morgan Brenton Realty Group

    23807 Westbridge Dr, Henderson, MD 21640
    • /27

      Est $260,378 Not Listed For Sale

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

      319 Kerr Ave, Denton, MD 21629

      319 Kerr Ave, Denton, MD 21629
  • /71

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft

    8816 Dorothy Ln, Denton, MD 21629

    Nestled on over six acres of pristine land with direct access to the Choptank River, this contemporary waterfront estate offers the ultimate in Eastern Shore luxury living. Designed to impress, the home features four spacious bedrooms, three and a half baths, and soaring cathedral ceilings that crown a dramatic two-story living room with floor-to-ceiling windows—flooding the home with natural

    Dustin Parker The Parker Group

    8816 Dorothy Ln, Denton, MD 21629
  • /15

    $315,000 Sold Jun 13, 2025

    • 1,680 Sq Ft
    • $188/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1910

    8888 Harmony Rd, Denton, MD 21629

    Charming 3BR/2BA Ranch Style Home– Priced to Sell!Nestled in a wooded setting just off Denton’s Route 404, this 3-bedroom, 2-bath home offers peace and privacy with modern updates throughout. Enjoy serene views from the expansive 28’ rear deck, perfect for outdoor relaxing or entertaining. Interior features include hardwood floors, a bright dining room, and a cozy living room with sliders leading

    Preda Mendez-Lopez Realty One Group Performance, LLC

    8888 Harmony Rd, Denton, MD 21629
    • /19

      Est $286,839 Not Listed For Sale

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

      111 Maple Ave, Goldsboro, MD 21636

      111 Maple Ave, Goldsboro, MD 21636
  • /28

    $349,000

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

    208 Oriole Ave, Ridgely, MD 21660

    Come see this Beautiful well maintained Ranch home in the heart of Ridgely. The house is a block away from the local park. The house has had many upgrades including an addition in 2020. New siding in 2020. New deck after 2020. New windows in 2017. There are solar panels on the roof. Spacious back yard with a patio. Many other upgrades to come and see.

    Rachel Penska Long & Foster Real Estate, Inc.

    208 Oriole Ave, Ridgely, MD 21660

Showing Results 241 - 280, Page 7 of 18

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