15,754

Caroline, MD Homes

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  • /5

    $247,000

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft

    116 Maple Ave, Preston, MD 21655

    Small town location and close to SO many amenities - enjoy the best of both worlds! Great location in town and just around the corner from stores, restaurants, elementary school and more. Water access isn't too far away (about 5 minutes, if that!). The seller has done many updates since purchasing 3 years ago -- all new appliances, windows, front door, landscaping, refreshed painting throughout

    Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
  • /38

    $355,000 Sold Jun 06, 2025

    • 1,952 Sq Ft
    • $182/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    508 Teal Cir, Greensboro, MD 21639

    Welcome to this spacious well loved 3 bedroom, 2.5 bathroom colonial nestled on a peaceful cul-de-sac in the sought after neighborhood of Caroline Farms. The home offers a welcoming front porch, perfect to decorate for all the seasons. A large inviting light filled living room that seamlessly flows into the dining area and kitchen, making it ideal for gatherings. Upstairs comes complete with a

    Karen Clark Clark & Co Realty, LLC

    508 Teal Cir, Greensboro, MD 21639
    • /38

      Est $474,052 Not Listed For Sale

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

      25938 Beauchamp Branch Rd, Denton, MD 21629

      25938 Beauchamp Branch Rd, Denton, MD 21629
  • /51

    $589,900

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    Two Tranquil Country Acres with no restrictions, backs to open farmland. Deep Back Yard includes an above ground pool with a deck for your summer enjoyment, large vinyl fenced area for pets and kids, more fenced area for farm animals (pets) and includes a shooting mound should that be of interest. This lovely home Boasts 2,667 Sq. Ft. of Family Space with new LVP flooring though out the main

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • /121

    $835,000 Sold Jun 06, 2025

    • 5,328 Sq Ft
    • $157/SF
    • 47 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 2012

    22879 Stevenson Rd, Ridgely, MD 21660

    Welcome to 22879 Stevenson Road, Ridgely, MD – a private oasis nestled down a winding country lane. This exquisite residence, adorned with elegant Hardie board siding, captivates from the moment you arrive with its inviting front porch and meticulous attention to detail.Step inside to discover the grandeur of a spacious 5,328 +/- square-foot home, where gorgeous bamboo hardwood floors and rich,

    Chris Rosendale CR Realty

    22879 Stevenson Rd, Ridgely, MD 21660
    • /21

      Est $332,333 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      22354 Hillsboro Rd, Denton, MD 21629

      22354 Hillsboro Rd, Denton, MD 21629
  • /12

    $125,000

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    529 Oldtown Rd, Goldsboro, MD 21636

    1900 Brick home that is solid but needs rehab done inside. Nice hardwood floors. Owner had started renovation. For the price could be a great home for your family. Large in town lot with several outbuildings for storage, hobbies or garage. Wooded behind home for privacy in town. Convenient to Delaware, Denton, Centreville and all in between.

    Barbara Wallace Long & Foster Real Estate, Inc.

    529 Oldtown Rd, Goldsboro, MD 21636
  • /41

    $382,000 Sold Jun 06, 2025

    • 1,664 Sq Ft
    • $230/SF
    • 254 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2022

    106 Morning Glory Dr, Denton, MD 21629

    Don't miss this great opportunity to own a beautiful 1 story home in excellent condition and less than 2 years old. This home features 3 bedrooms, 2 bathrooms, numerous amenities including custom upgrades of granite countertops, LVT flooring, large kitchen with island, walk-in pantry, it's all open to the living room and sunroom/dining. The primary bedroom is spacious with private

    Daniel Foster Long & Foster Real Estate, Inc.

    106 Morning Glory Dr, Denton, MD 21629
    • /20

      Est $419,987 Not Listed For Sale

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

      25699 Auction Rd, Federalsburg, MD 21632

      25699 Auction Rd, Federalsburg, MD 21632
  • /55

    $975,000

    • 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
  • /24

    $199,000 Sold Jun 05, 2025

    • 1,304 Sq Ft
    • $153/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1910

    311 S 4th St, Denton, MD 21629

    Nice In-Town 3 bed 1 bath. Home has Large Eat-in Kitchen, Family Room, Living Room, 3 Bedrooms and Full Bath on Second Floor. Some Recent Upgrades! Spacious Yard with mature Trees and Shed. Home has a beautiful side porch for entertaining! Very private Back yard! Enjoy Downtown living with Parks, Restaurants, Shopping, Boating and Fishing access to the Choptank River. Within less than 30 miles

    Kathleen Brenton Brenton Realty Group

    311 S 4th St, Denton, MD 21629
    • /33

      Est $420,984 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft

      24565 Holsinger Ln, Ridgely, MD 21660

      24565 Holsinger Ln, Ridgely, MD 21660
  • /83

    $995,500

    • 4 Beds
    • 3 Baths
    • 2,119 Sq Ft

    23274 Holly Park Dr, Preston, MD 21655

    Experience Waterfront Living Like Never Before on the Choptank River! Welcome to “One Sweet World", where breathtaking sunsets and expansive sky views await you just 50 feet from the river’s edge. This extraordinary waterfront retreat features a beautifully designed 2-bedroom, 2-bathroom main house, complemented by a cozy 2-bedroom, 1-bathroom guest house and a separate guest room/tackle room

    Rick Parreco RE/MAX Executive

    23274 Holly Park Dr, Preston, MD 21655
  • /6

    $309,900 Sold Jun 05, 2025

    • 1,344 Sq Ft
    • $231/SF
    • 39 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    3449 Jefferson Pond Rd, Federalsburg, MD 21632

    To be completed May 2025. You will be touring 3457 Jefferson Pond Rd, as model. Welcome to 3457 Jefferson Pond Road in the charming Jefferson Run community of Federalsburg, MD! This stunning new construction home features 3 spacious bedrooms and 2 modern bathrooms, designed with both style and function in mind. The kitchen boasts elegant granite countertops and brand-new appliances, perfect for

    Amy Herr RE/MAX Advantage Realty

    3449 Jefferson Pond Rd, Federalsburg, MD 21632
    • /14

      Est $349,352 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,044 Sq Ft

      25465 Hill Rd, Greensboro, MD 21639

      25465 Hill Rd, Greensboro, MD 21639
  • /106

    $580,000

    • 4 Beds
    • 3 Baths
    • 3,039 Sq Ft

    8534 Briar Patch Dr, Denton, MD 21629

    Welcome to 8534 Briar Patch Drive. This very well maintained home has so much to offer. This beautifully maintained property offers four spacious bedrooms and three bathrooms, providing ample space and comfort for family living or entertaining guests. The main floor includes a foyer, living room, formal dining room, family room, living room, kitchen, sunroom, and a breakfast nook that

    Alana Taylor Worthington Realty Group, LLC

    8534 Briar Patch Dr, Denton, MD 21629
  • /52

    $230,000 Sold Jun 04, 2025

    • 1,988 Sq Ft
    • $116/SF
    • 15 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    105 Liberty Rd, Federalsburg, MD 21632

    An abundance of living space spread over two floors behind the doors of this 3BR/1BA Farm Home located on a spacious lot in the quiet neighborhood of Federalsburg. Parking is ample in the extra long and wide driveway as you make your way to the covered front porch of your forever home. Step inside to a home filled with tons of original character including hardwood floors and crown moldings.

    Brooke Tephabock VYBE Realty

    105 Liberty Rd, Federalsburg, MD 21632
    • /36

      Est $517,649 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,222 Sq Ft

      24911 Woods Dr, Denton, MD 21629

      24911 Woods Dr, 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
  • /50

    $180,000 Sold Jun 02, 2025

    • 2,886 Sq Ft
    • $62/SF
    • 84 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2006

    294 Tidewater Cir, Preston, MD 21655

    NEW ROOF was installed 03/22/2025, Warranty will transfer to buyer with purchase of the home.Looking for more space? This is the one that checks all the boxes. 5-Bedroom, 2.5-Bath Home in a wonderful community in the charming town of Preston. This open kitchen layout is amazing, truly is the heart of this home! Open to the large family room that features a cozy gas fireplace, the kitchens center

    Christina Smith Brenton Realty Group

    294 Tidewater Cir, Preston, MD 21655
    • /31

      Est $392,276 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,742 Sq Ft

      25400 Calvert Dr, Greensboro, MD 21639

      25400 Calvert Dr, Greensboro, MD 21639
  • /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
  • /2

    $32,500 Sold May 30, 2025

    • Land
    • 0.31 Acre
    • $104,839 per Acre
    • 11 Days On Market

    11441 Ridgely Rd, Hillsboro, MD 21641

    Discover a unique opportunity to own two adjacent parcels on Ridgely Road in beautiful Caroline County. This offering includes the lot at 11441 Ridgely Road along with an additional 1.4-acre lot identified as Tax Map 0021, Parcel 76, Grid 0024. Together, these properties provide ample space and potential for future use.Please note: There is currently no approved perc test on file. Buyers are

    Jarnell Foster Benson & Mangold, LLC

    11441 Ridgely Rd, Hillsboro, MD 21641
    • /36

      Est $387,173 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,144 Sq Ft

      1104 Coursey Ln, Denton, MD 21629

      1104 Coursey Ln, 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
  • /46

    $637,000 Sold May 30, 2025

    • 4,064 Sq Ft
    • $157/SF
    • 40 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1999

    24656 White Dogwood Dr, Denton, MD 21629

    This is a WOW!!! Looking for Space??? Let me present to you "24656 White Dogwood Drive". Home Features 6 Bedrooms, 3 Full & 1 Half Bath. Large Eat-in Kitchen with lots of Storage with Center Island with an adjacent Breakfast Nook. Separate Dining Room , Spacious Family Room which leads to Patio and Large level Lot. Primary Bedroom on First Floor with Super Bath to include Walk-in

    Kathleen Brenton Brenton Realty Group

    24656 White Dogwood Dr, Denton, MD 21629
    • /21

      Est $496,337 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,646 Sq Ft

      9605 Quail Run Rd, Denton, MD 21629

      9605 Quail Run Rd, Denton, MD 21629
  • /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
  • /17

    $60,000 Sold May 30, 2025

    • 1,488 Sq Ft
    • $40/SF
    • 53 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    223 Old Denton Rd, Federalsburg, MD 21632

    Attention investors! This 3-bedroom, 1-bath home in Federalsburg, MD is a fantastic opportunity to add to your portfolio. Featuring public water and sewer, this property offers a solid foundation for rental income or resale potential. Conveniently located near local amenities and just a short drive to major Eastern Shore destinations, this home is ready for your vision. Whether you're looking to

    Benjamin Smith Whitehead Real Estate Exec.

    223 Old Denton Rd, Federalsburg, MD 21632
    • /9

      Est $161,230 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,296 Sq Ft

      309 S University Ave, Federalsburg, MD 21632

      309 S University Ave, Federalsburg, MD 21632
  • /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
  • /25

    $350,000 Sold May 29, 2025

    • 1,472 Sq Ft
    • $238/SF
    • 320 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1959

    24636 Williston Rd, Denton, MD 21629

    Price Reduction!Welcome to the charming village of Williston. This 3 bedroom, 1 1/2 bath home has been lovingly maintained. Featuring central air, oak floors, replacement windows and a recently replaced roof; this home is move-in ready. With an attached garage and a detached garage/workshop you have plenty of storage and workspace. Relax or entertain on the spacious back porch overlooking a

    Andrew Beaven Wright Real Estate

    24636 Williston Rd, Denton, MD 21629
    • /58

      Est $561,015 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,988 Sq Ft

      4925 Edmondson Creek Rd, Preston, MD 21655

      4925 Edmondson Creek Rd, Preston, MD 21655
  • /31

    $290,000

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

    202 Maryland Ave, Ridgely, MD 21660

    PRICE REFRESH - 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

    Mikeshia Wilson Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
  • /11

    $209,000 Sold May 28, 2025

    • 1,474 Sq Ft
    • $142/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1974

    9359 Mike St, Denton, MD 21629

    One level Living!! 3 bed 1 Bath House in Stafford Heights. Large Family Room, Living Room , Eat-in Kitchen. Detached 1 Car Garage, Nice lot with plenty of space in the the front and back yard. Within minutes to Shopping, Restaurants, Parks & Boating and Fishing in the Choptank River. Sold AS-IS.

    Kathleen Brenton Brenton Realty Group

    9359 Mike St, Denton, MD 21629
    • /124

      Est $729,487 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,921 Sq Ft

      24754 Pealiquor Rd, Denton, MD 21629

      24754 Pealiquor Rd, Denton, MD 21629
  • /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
  • /63

    $529,900 Sold May 28, 2025

    • 2,250 Sq Ft
    • $236/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    20735 Tammuxzena Dr, Preston, MD 21655

    Welcome to this beautiful new custom-built home that features three bedrooms and two and a half bathrooms, guaranteed to make you fall in love at first glance! The theme of style and comfort shines through in the open-concept gourmet kitchen, where cooking and socializing become delightful shared experiences. With vaulted ceilings, the open floor plan creates a sense of spaciousness filled with

    Leo Kuneman Meredith Fine Properties

    20735 Tammuxzena Dr, Preston, MD 21655
    • /34

      Est $334,854 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft

      8157 Arch Dr, Denton, MD 21629

      8157 Arch Dr, Denton, MD 21629
  • /63

    $499,900

    • 3 Beds
    • 3 Baths
    • 2,645 Sq Ft

    14957 Cherry Ln, Ridgely, MD 21660

    Welcome to 14957 Cherry Ln. This property offers a pond and an in-ground pool. Large 2.5 acre lot. Home is over 2600 sq. ft. with the entire upstairs set-up as a primary suite with deck overlooking both the front and rear yard. Downstairs offer a large living area with kitchen and 2 additional bedrooms with 2 full baths. Oversized garage offer ample storage for all your toys. Pool liner was

    Eddie Matthews Benson & Mangold, LLC

    14957 Cherry Ln, Ridgely, MD 21660

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