15,754

Caroline, MD Homes

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  • /70

    $398,000 Sold Jun 27, 2025

    • 2,650 Sq Ft
    • $150/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    1110 Osprey Ln, Denton, MD 21629

    Discover this stunning contemporary four bedroom, 2.5 bath home located in a fantastic community that features a pool, tot lots and a community building that's perfect for gatherings! As you step inside, you'll be greeted by a fresh, modern design. The heart of the home is it's gorgeous kitchen, featuring a deep stainless farmhouse sink with a sprayer nozzle, ample storage space in the

    Judith Germain Benson & Mangold, LLC

    1110 Osprey Ln, Denton, MD 21629
    • /19

      Est $350,978 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft

      344 Meadow Vale Ln, Denton, MD 21629

      344 Meadow Vale Ln, Denton, MD 21629
  • /56

    $365,000

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

    135 Kerney St, Federalsburg, MD 21632

    Welcome to this well-maintained home that exudes pride in ownership with just over 2500 square feet of living space. This home boasts upgrades throughout. The kitchen features Granite countertops, stainless steel appliances large island, and a spacious pantry. Large dining room or convert to another living area. Well-appointed bedrooms and a primary with ex large walk-in closet and bathroom. As

    Roger Boyce Chesapeake Real Estate Associates, LLC

    135 Kerney St, Federalsburg, MD 21632
  • /22

    $399,900 Sold Jun 27, 2025

    • 1,816 Sq Ft
    • $220/SF
    • 2 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1991

    24771 Woods Dr, Denton, MD 21629

    Welcome to 24771 Woods Drive! This 3-bedroom, 3-bathroom single-level rancher sits on a 0.96+- acre lot with mature landscaping, offering ample space and privacy. The home features an attached 2-car garage for convenient parking and storage. Inside, hardwood floors run throughout the main living areas. The sunken living room includes vaulted ceilings and a wood-burning fireplace, creating a focal

    Brian Gearhart Benson & Mangold, LLC

    24771 Woods Dr, Denton, MD 21629
    • /13

      Est $258,987 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft

      12185 River Rd, Ridgely, MD 21660

      12185 River Rd, Ridgely, MD 21660
  • /71

    $434,500

    • 4 Beds
    • 3 Baths
    • 4,304 Sq Ft

    122 Lister Ln, Ridgely, MD 21660

    Welcome to 122 Lister Lane in the charming town of Ridgely, MD, nestled on a picturesque corner lot in the highly coveted Lister Estates community. This delightful home is a treasure trove of possibilities, catering to a diverse range of lifestyles.As you approach the property, you'll be greeted by its stunning brick facade that exudes classic elegance, complemented by a fully fenced

    Chris Rosendale CR Realty

    122 Lister Ln, Ridgely, MD 21660
  • /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
    • /36

      Est $728,723 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 4,521 Sq Ft

      24638 Tribbett Cir, Ridgely, MD 21660

      24638 Tribbett Cir, Ridgely, MD 21660
  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    1010 S 2nd Street offers in-town living WITHOUT in-town Taxes!!! This home rests at the edge of town on 1.06 acres with mature plantings. This 3-bed 2-bath home boasts hardwood, LVP, and tile floors. A fireplace insert for the pellet stove for heat, while the seller uses the Hot water baseboard as a backup. Full basement for additional entertaining or storage. Screened-in porch overlooks

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /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
    • /12

      Est $379,508 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft

      1108 Trice Meadows Cir, Denton, MD 21629

      1108 Trice Meadows Cir, Denton, MD 21629
  • /80

    $409,000

    • 5 Beds
    • 3.5 Baths
    • 2,330 Sq Ft

    13001 Beech Ln, Greensboro, MD 21639

    Your dream home is waiting for you! Nestled in the woods of Fox Grape Farms, 13001 Beech Lane features a DOUBLE LOT giving you just over an acre of land. This 5 Bedroom 3.5 Bathroom home includes, Multiple Outbuildings, Huge Yard, Income Producing Solar Panels, Primary Suite Loft with Balcony, Wood Burning Stove, Recently Remodeled Kitchen, & Wood Burning Fireplace. LVP & hardwood floors

    Megan Rosendale Rosendale Realty

    13001 Beech Ln, 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
    • /60

      Not Listed For Sale

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

      17832 Henderson Rd, Marydel, MD 21649

      17832 Henderson Rd, Marydel, MD 21649
  • /30

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    15 Ridgeway Dr, Ridgely, MD 21660

    Welcome to 15 Ridgeway Drive! Where comfort, convenience, and pride of ownership meet.This well maintained 3-bedroom, 2-bath home features an additional flex room perfect for a home office, den, or playroom. The updated kitchen features stainless steel appliances and a functional layout that opens into the living space, making it ideal for entertaining or everyday living.Step outside

    Jarnell Foster Benson & Mangold, LLC

    15 Ridgeway Dr, Ridgely, MD 21660
  • /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
    • /21

      Est $297,812 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,040 Sq Ft

      22606 Tanyard Rd, Preston, MD 21655

      22606 Tanyard Rd, Preston, MD 21655
  • /21

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    27381 Greenwood Rd, Denton, MD 21629

    Surrounded by farmland is what you will find at this spacious 3 bedroom, 2 bath home. Small fenced in area for small pets. Listen to the rain on the tin roof. Galley kitchen opens into the dining area that is open to the large living room. Primary bedroom located on the first floor with an extra-large bathroom. Upstairs bedrooms have mini split systems for heating and air. Plenty of parking

    Pamela Geib Long & Foster Real Estate, Inc.

    27381 Greenwood Rd, 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
    • /79

      Est $411,066 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,546 Sq Ft

      204 S Main St, Greensboro, MD 21639

      204 S Main St, Greensboro, MD 21639
  • /59

    $399,500

    • 3 Beds
    • 2 Baths
    • 2,378 Sq Ft

    502 N Academy St, Greensboro, MD 21639

    Welcome to 502 Academy Street, Greensboro, MD, a charming retreat that embodies the essence of cozy cottage living. This turnkey property has been meticulously cared for and spans almost 2,400 square feet of thoughtfully designed space on a beautifully landscaped lot.Inside, you'll find three inviting bedrooms, with two located on the lower level for added privacy and convenience. Each of the two

    Chris Rosendale CR Realty

    502 N Academy St, 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
    • /21

      Not Listed For Sale

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

      7071 American Corner Rd, Denton, MD 21629

      7071 American Corner Rd, Denton, MD 21629
  • /47

    $339,990

    • 4 Beds
    • 2 Baths
    • 2,774 Sq Ft

    111 Maple Ave, Greensboro, MD 21639

    SELLER OFFERING CONCESSIONS TOWARD CLOSING !!!Under contract with next home and motivated to sell !!! Welcome to your dream home, a charming farmhouse-style residence that beautifully blends historic character with modern comforts, that is situated on a 0.21 acre lot. Over $70,000 in upgrades since the home was purchased!!! The recently installed 6ft privacy, fenced back yard, brick patio and

    Betsy Brown Long & Foster Real Estate, Inc.

    111 Maple Ave, Greensboro, MD 21639
  • /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 $312,136 Not Listed For Sale

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

      6 Maple Ave, Ridgely, MD 21660

      6 Maple Ave, Ridgely, MD 21660
  • /19

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft

    1206 Trice Meadows Cir, Denton, MD 21629

    Beautiful open floor plan ranch style home in Trice Meadows . Lot backs to elementary school with trees for privacy. Lovely kitchen with granite countertops, all stainless-steel appliances including propane stove top, dishwasher, garbage disposal, built in microwave and refrigerator. The great room offers large dining area with upgraded lighting and living area with propane fireplace. The primary

    Bonnie Johnson Keller Williams Realty

    1206 Trice Meadows Cir, 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
    • /15

      Est $182,792 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,316 Sq Ft

      128 Bloomingdale Ave, Federalsburg, MD 21632

      128 Bloomingdale Ave, Federalsburg, MD 21632
  • /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
  • /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
    • /25

      Est $349,255 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,520 Sq Ft

      25095 Trunk Line Rd, Henderson, MD 21640

      25095 Trunk Line Rd, Henderson, MD 21640
  • /28

    $359,000

    • 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
  • /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
    • /31

      Est $536,595 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
  • /34

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    104 Hobbs St, Greensboro, MD 21639

    Fully Remodeled 3-Bedroom Home – Modern Comfort Meets Timeless CharmWelcome to 104 Hobbs St, where quality craftsmanship and stylish upgrades define this beautifully updated 3-bedroom, 1-bath home with 1,248 square feet of living space. Completely renovated from the studs, this home offers peace of mind with all-new electrical, plumbing systems, HVAC, roof & siding plus a fresh modern

    Brett Schrader Taylor Properties

    104 Hobbs St, 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
    • /20

      Est $274,279 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
  • /18

    $529,000

    • Land
    • 53 Acres
    • $9,979 per Acre

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649

    This ±53-acre timber property offers a blend of residential potential and quality recreational opportunity. The land features a mix of hardwood and pine stands in various age classes, with a healthy understory, topography changes, and seasonal wetland bottoms—ideal characteristics for managing whitetail deer and turkey habitat.The property consists of five separate parcels, four of which

    Benjamin Alder The Land Group

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
  • /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

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