15,756

Caroline, MD Homes

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  • /2

    $59,000 Pending

    • Land
    • 2.11 Acres
    • $27,962 per Acre

    lot 6 Harmony Woods Dr, Preston, MD 21655

    Barbara Nichols Results Realty Inc.

    lot 6 Harmony Woods Dr, Preston, MD 21655
  • /46

    $219,000 Sold Feb 13, 2025

    • 1,868 Sq Ft
    • $117/SF
    • 32 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1916

    111 Riverton Ave, Denton, MD 21629

    The heavy lifting has already been done in this adorable, cozy, 1900's Victorian! Brand new mini split units with room for expansion, and a completely refurbished foundation & gutter system, this home is ready to make it your own! This home features an open floor plan downstairs with hardwood flooring, a low maintenance backyard, 2 larger bedrooms & one small bedroom would make a great office,

    Megan Rosendale Rosendale Realty

    111 Riverton Ave, Denton, MD 21629
    • /79

      Est $751,344 Not Listed For Sale

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

      24534 Choptank Blvd, Denton, MD 21629

      24534 Choptank Blvd, Denton, MD 21629
  • /33

    $289,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft

    6101 Bethlehem Rd, Preston, MD 21655

    Charming 3-bedroom, 1-bathroom home on 1.3 acres with room to grow! This well-maintained, one-family-owned property features recent upgrades throughout, including a new roof (2024), hot water heater (2023), new appliances and countertops (2024), fresh paint (2024), new fencing (2024), and a brand-new septic system. The oversized 2-car garage offers ample storage or workspace. The primary bedroom

    Katie Moore Coldwell Banker Chesapeake Real Estate Company

    6101 Bethlehem Rd, Preston, MD 21655
  • /83

    $305,000 Sold Feb 13, 2025

    • 2,276 Sq Ft
    • $134/SF
    • 68 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1900

    22040 Main St, Hillsboro, MD 21641

    Welcome to this Grand Victorian home resting on 3 lots for a total of .76 acres with mature planting and ample storage, including 2 outbuildings one a small horse barn with stall and a storage shed with workshop area and a large garage/shop area. This grand home offers large rooms with high ceilings and all the expected original features: beautiful hardwood floors, original pocket doors,

    Roger Boyce Chesapeake Real Estate Associates, LLC

    22040 Main St, Hillsboro, MD 21641
    • /45

      Est $392,707 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,668 Sq Ft

      202 N Central Ave, Ridgely, MD 21660

      202 N Central Ave, Ridgely, MD 21660
  • /52

    $344,900 Coming Soon

    • 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
  • /59

    $389,900 Sold Feb 13, 2025

    • 1,744 Sq Ft
    • $224/SF
    • 200 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1900

    15885 Meeks Rd, Goldsboro, MD 21636

    Improved price!! Country charmer -located on just under 2 acres this property is an Eastern Shore dream! Situated among tranquil fields with a pond, this farmhouse boast refinished hard wood floors, updated baths, wonderful country kitchen, primary bedroom with walk in closet, and tons of storage space. Mudroom area with built ins , dining room with raised panels, and a pellet stove in the

    Valerie Brown Charles C. Powell, Inc. Realtors

    15885 Meeks Rd, Goldsboro, MD 21636
    • /44

      Est $432,658 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,252 Sq Ft

      18 Lister Ln, Ridgely, MD 21660

      18 Lister Ln, Ridgely, MD 21660
  • /54

    $499,500 Coming Soon

    • 4 Beds
    • 3 Baths
    • 1,900 Sq Ft

    11575 Maplewood Dr, Ridgely, MD 21660

    Giving you another opportunity to buy in this community but this time with an inground pool, tiki hut and more! Homes in this community do not come on very often, so lets grab it while we can. A popular model built by Mike's Custom Homes featuring 3 bedrooms, and 2 baths on the main floor and a bedroom/den on the second floor also with a full bath and walk in closet. Located in the covenant

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    11575 Maplewood Dr, Ridgely, MD 21660
  • /44

    $329,900 Sold Feb 13, 2025

    • 2,000 Sq Ft
    • $165/SF
    • 251 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1957

    618 Liberty Rd, Federalsburg, MD 21632

    New Price! This beautifully maintained brick rancher is located close to all Mid Shore locations. Park like yard.The home features 3 generous bedrooms (2 have their own attached baths) and an additional 1/2 bathroom ("The Library"). Large living room with hardwood floors, fireplace and lots of windows. The family room/den is finished in gorgeous wood that you can not find today. Eat in

    Valerie Brown Charles C. Powell, Inc. Realtors

    618 Liberty Rd, Federalsburg, MD 21632
    • /15

      Est $337,318 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft

      23592 Henry Rd, Ridgely, MD 21660

      23592 Henry Rd, Ridgely, MD 21660
  • /2

    $465,000 Coming Soon

    • 4 Beds
    • 4 Baths
    • 3,408 Sq Ft

    135 Walnut St, Ridgely, MD 21660

    Welcome to this Grande Home in Lister Estates. This home offer Three Full Levels of living space. Main floor features the Owners Primary with En Suite and two closets. 2 additional bedrooms and full bath. Dining Room or Office, Large open kitchen overlooks Great Room and added Morning Room for additional dining or needed space. Exterior backyard offers deck for entertaining and area for garden

    Roger Boyce Chesapeake Real Estate Associates, LLC

    135 Walnut St, Ridgely, MD 21660
  • /73

    $650,000 Sold Feb 13, 2025

    • 2,226 Sq Ft
    • $292/SF
    • 229 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1970

    20810 Frazier Point Ln, Preston, MD 21655

    ASSUMABLE VA LOAN! GREAT OPPORTUNITY TO OWN AT A LOWER RATE! Welcome to this meticulously renovated 3 bedroom 2.5 bath fully furnished craftsman-style home, where timeless charm meets modern luxury. Nestled on over 5 well landscaped and pristine acres, this idyllic setting invites you to embrace the beauty of nature. Traveling down your private drive, a sense of serenity washes. Approaching

    Barbara McCaffrey Redfin Corp

    20810 Frazier Point Ln, Preston, MD 21655
    • /69

      Est $422,911 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,644 Sq Ft

      1130 Osprey Ln, Denton, MD 21629

      1130 Osprey Ln, Denton, MD 21629
  • /2

    $399,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 2,267 Sq Ft

    306 S 2nd St, Denton, MD 21629

    Welcome to 306 S 2nd St, a lovingly restored colonial farmhouse style home on a private lane in a great neighborhood. Situated on a large in-town lot, the home features gleaming hardwood floors, new carpeting, and well-maintained gardens. From roof to basement, nearly everything in this home has been updated or upgraded. New architectural shingles were replaced, and the basement received new

    Jana Meredith Meredith Fine Properties

    306 S 2nd St, Denton, MD 21629
  • /25

    $420,000 Sold Feb 11, 2025

    • 1,280 Sq Ft
    • $328/SF
    • 93 Days On Market
    • Studio
    • Built 1880

    403 Gay St, Denton, MD 21629

    INVESTMENT OPPORTUNITY! 2 duplexes being sold together, 401 Gay St and 403 Gay St. All 4 units have recently signed one year leases in place. Rental licenses and MDE Lead Paint certificates are current.2 one bedroom units and 2 two bedroom units.

    Andrew Beaven Wright Real Estate

    403 Gay St, Denton, MD 21629
    • /28

      Est $181,362 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft

      321 S University Ave, Federalsburg, MD 21632

      321 S University Ave, Federalsburg, MD 21632
  • /2

    $329,900 Coming Soon

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

    407 Wood Duck Dr, Greensboro, MD 21639

    COMING SOON in Caroline Farms! This beautiful home will be hitting the market soon. Stay tuned for more photos and details!

    Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
  • /20

    $194,000 Sold Feb 07, 2025

    • 1,008 Sq Ft
    • $192/SF
    • 72 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    313 Holt St, Federalsburg, MD 21632

    Welcome home to 313 Holt Street located in a quiet section of Federalsburg Maryland. This is a move-in ready home with new windows, new carpet and has been freshly painted inside.

    Joseph Hawkins Hawkins Real Estate Company

    313 Holt St, Federalsburg, MD 21632
    • /19

      Est $385,902 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft

      11458 Reed Cir, Ridgely, MD 21660

      11458 Reed Cir, Ridgely, MD 21660
  • /2

    $385,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    106 Lednum Ave, Preston, MD 21655

    Eric Haro The Parker Group

    106 Lednum Ave, Preston, MD 21655
  • /112

    $1,450,000 Sold Feb 07, 2025

    • 2,864 Sq Ft
    • $506/SF
    • 36 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    18870 Crown Stone Rd, Marydel, MD 21649

    INTRODUCING BELLO SUENO HORSE FARM. This 95.4+- acre mixed use farm has 55+- acres tillable, 31+- acres of timber, with the remainder containing the improvements and equine features. The tillable acreage has been used to grown small grain. The timber is a mix of hardwoods and pine, and has only been lightly hunted. There are no conservation easements, nor is it in ag preservation. Additionally,

    Benjamin Alder The Land Group

    18870 Crown Stone Rd, Marydel, MD 21649
    • /15

      Est $60,899 Not Listed For Sale

      27515 Anthony Mill Rd, Denton, MD 21629

      27515 Anthony Mill Rd, Denton, MD 21629
  • /44

    $419,900 Under Contract

    • 3 Beds
    • 3 Baths
    • 1,884 Sq Ft

    14267 Cherry Ln, Queen Anne, MD 21657

    Enjoy peaceful rural living in this beautifully crafted home on over 2 wooded acres. Features include exposed wood beams, hardwood floors, a cozy wood stove, stunning stone fireplace, country kitchen, and clawfoot soaking tub. Relax on the large front porch or back deck surrounded by nature. Includes a spacious detached garage/workshop, new roof, and freshly painted exterior. Don’t miss the

    Rick Parreco RE/MAX Executive

    14267 Cherry Ln, Queen Anne, MD 21657
  • /25

    $350,000 Sold Feb 06, 2025

    • 1,512 Sq Ft
    • $231/SF
    • 65 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1902

    407 Maryland Ave, Ridgely, MD 21660

    Welcome to this completely remodeled Farmhouse style home located in the heart of Ridgely, Maryland. This one of a kind property features 4 bedrooms and 2 full bathrooms, a brand new kitchen with Quartz countertops and stainless steel appliances, fully remodeled bathrooms, electric fireplace, new LVP flooring throughout the house, brand new HVAC system, newly installed architectural shingles and

    Eric Haro The Parker Group

    407 Maryland Ave, Ridgely, MD 21660
    • /26

      Est $295,354 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft

      26680 Marydel Rd, Marydel, MD 21649

      26680 Marydel Rd, Marydel, MD 21649
  • /31

    $215,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,091 Sq Ft

    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
  • /48

    $265,900 Sold Feb 04, 2025

    • 3,076 Sq Ft
    • $86/SF
    • 272 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1900

    213 N Main St, Federalsburg, MD 21632

    Federalsburg - imagine the possibilities! Situated on the banks of Marshyhope Creek with water rights and rights to build a dock, this home offers waterfront living at a very affordable price. Great place to catch rockfish! Colonial home with updated eat-in kitchen with granite counter tops, 4 bedrooms, cool back stairs, expandable attic, wood burning fireplace, large living room and dining

    Valerie Brown Charles C. Powell, Inc. Realtors

    213 N Main St, Federalsburg, MD 21632
    • /34

      Est $224,292 Not Listed For Sale

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

      1403 Blue Heron Dr, Denton, MD 21629

      1403 Blue Heron Dr, Denton, MD 21629
  • /81

    $314,900 Under Contract

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

    3995 American Corner Rd, Federalsburg, MD 21632

    Freshly redone and updated 1890 farmhouse with 3 bedroom, 2.5 baths. Spacious kitchen with new stainless appliances. First floor primary bedroom with walk-in closet and private bath.This house is ready for you to move in and make it your own with your furniture and decorations. There is a large screened room on the back of the house to enjoy the outdoors and have room for your crab feasts or

    Earl Sheats Long & Foster Real Estate, Inc.

    3995 American Corner Rd, Federalsburg, MD 21632
  • /38

    $145,000 Sold Jan 31, 2025

    • 1,024 Sq Ft
    • $142/SF
    • 60 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1974

    204 Horsey St, Greensboro, MD 21639

    Motivated Sellers – No Ground Rent or Land Lease!! This beautifully updated 3-bedroom, 1.5-bathroom mobile home with a bonus room addition is located in the heart of Greensboro, directly across from Ober Park! It features numerous upgrades, including fresh paint, new lighting, new countertops, new duct work, new insulation, new water vapor barrier, and new flooring throughout. The kitchen is

    Heather Branham The Parker Group

    204 Horsey St, Greensboro, MD 21639
    • /47

      Est $466,104 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,526 Sq Ft

      5577 Harmony Woods Dr, Preston, MD 21655

      5577 Harmony Woods Dr, Preston, MD 21655
  • /26

    $280,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,055 Sq Ft

    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
  • /18

    $285,000 Sold Jan 31, 2025

    • 1,376 Sq Ft
    • $207/SF
    • 35 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1946

    26220 Auction Rd, Federalsburg, MD 21632

    All brick bungalow on nearly 1 acre featuring 3 bedrooms, 1.5 bathrooms, large loft, fireplace and huge 3 car garage. Includes adjacent 5.34 acre parcel with approved perc. (Legal Description: 5.34 AC L-4 W/S RT 313 NW of Federalsburg).

    Peter Stark Benson & Mangold, LLC

    26220 Auction Rd, Federalsburg, MD 21632
    • /23

      Est $267,626 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,462 Sq Ft

      318 N School St, Greensboro, MD 21639

      318 N School St, Greensboro, MD 21639
  • /29

    $238,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,568 Sq Ft

    306 Railroad Ave, Goldsboro, MD 21636

    Charming Modern Farmhouse fully renovated with Spacious Backyard and country views.Welcome to your dream home! This beautifully renovated 2-story farmhouse blends classic charm with modern updates. Nestled on a generous lot with peaceful farmland views, privacy, and stylish living.Property Features:3 Bedrooms | 1 Full BathroomGorgeous curb appeal with fresh

    Brett Schrader Taylor Properties

    306 Railroad Ave, Goldsboro, MD 21636
  • /8

    $470,000 Sold Jan 30, 2025

    • 1,560 Sq Ft
    • $301/SF
    • 127 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1965

    23209 Gilpin Point Rd, Preston, MD 21655

    Perfect waterfront retreat for hunters and nature lovers! Views of the 485’ water frontage from living room as well as creek views from kitchen. Enjoy everything the Shore has to offer with this home. Fully renovated and remodeled one level cottage offering gorgeous water and sunset views. Great waterfowl hunting and fishing potential in front and back of property. Property also offers 100 foot

    rachael harrison Coldwell Banker Realty

    23209 Gilpin Point Rd, Preston, MD 21655
    • /18

      Est $299,994 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,584 Sq Ft

      4664 Cedar Place, Preston, MD 21655

      4664 Cedar Place, Preston, MD 21655
  • /39

    $399,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft

    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

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