15,698

Caroline County, MD Homes

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  • /53

    $234,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,709 Sq Ft

    1412 Blue Heron Dr, Denton, MD 21629

    Total Re-Hab END UNIT !!! Almost New Everything.! Homes features 3 Bedrooms 2.5 Baths. Open floor plan with All new Kitchen Cabinets, Countertops& Appliances! New Luxury Vinyl Flooring and completely painted thru-out Entire Home. All Three Bathrooms have been updated including Tile Showers, New Vanities, and Fixtures. Community offers, Pool, Community Center, Playgrounds, Yard Maintenance, Boat &

    Kathleen Brenton Brenton Realty Group

    1412 Blue Heron Dr, Denton, MD 21629
  • /26

    $115,000 Sold Jun 12, 2025

    17690 Melville Rd, Henderson, MD 21640

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1973

    Last Sold Summary

    • $106/SF
    • 119 Days On Market

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    17690 Melville Rd, Henderson, MD 21640
    • /54

      Est $436,477 Not Listed For Sale

      23060 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1977
      23060 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $223/SF
      • 7 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Glenn Hedgecoth Compass

  • /2

    $298,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    HELENA Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or

    D.R. Horton Builder
    103 Park Ave Unit 36203274, Greensboro, MD 21639
  • /16

    $230,000 Sold Jan 30, 2026

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629

    • Land
    • 3.4 Acres
    • $67,647 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 631 Days On Market

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    • /50

      Est $376,910 Not Listed For Sale

      315 W Sunset Ave, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 1880
      315 W Sunset Ave, Greensboro, MD 21639

      Last Sold Summary

      • 8% Above List Price
      • $145/SF
      • 31 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Jillian Luna Rosendale Realty

  • /8

    $120,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    22464 Hillsboro Rd, Denton, MD 21629

    Investment Opportunity on 2.4± Acres with Expansion Potential Discover the possibilities on this 2.4± acre property featuring a 1 bed, 1 bath home including a 3-bedroom approved septic system already in place for future expansion or new construction. The well was replaced in 2013, offering added peace of mind. A detached sub-panel is installed and ready to support future building plans, making

    Shawn Moore Meredith Fine Properties

    22464 Hillsboro Rd, Denton, MD 21629
  • /108

    $1,200,000 Sold Jan 21, 2026

    14271 Cedar Ln, Greensboro, MD 21639

    • 6 Beds
    • 3 Baths
    • 3,756 Sq Ft
    • Built 1998

    Last Sold Summary

    • $319/SF
    • 245 Days On Market

    Current Estimated Value $1,214,851

    Last Listing Agent Travis Gray Engel & Völkers Annapolis

    14271 Cedar Ln, Greensboro, MD 21639
    • /44

      Est $418,354 Not Listed For Sale

      1211 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,036 Sq Ft
      • Built 2006
      1211 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 10% Above List Price
      • $125/SF
      • 16 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /26

    $499,000

    • 4 Beds
    • 1.5 Baths
    • 2,320 Sq Ft

    11289 Gregg Rd, Denton, MD 21629

    Rare opportunity to purchase 19.1 acres with 2 dwellings, included property identified as 11285 Gregg Rd. Endless options to either rent one or have an in-law suite. It is said to have three septic systems, three electric services all on one property. Then main house which has the basement is in need of some remodeling, has 4 bedrooms and 1.1/4 baths, the remodling process has been started. The

    Kat Thompson Benson & Mangold, LLC.

    11289 Gregg Rd, Denton, MD 21629
  • /2

    $289,990 Sold Sep 25, 2025

    111 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Last Sold Summary

    • $199/SF
    • 13 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    111 Parkland Rd, Greensboro, MD 21639
    • /29

      Est $395,616 Not Listed For Sale

      1107 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,496 Sq Ft
      • Built 2005
      1107 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $155/SF
      • 24 Days On Market

      Last Sold Price $386,000

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • /99

    $1,099,000

    • 6 Beds
    • 3.5 Baths
    • 3,704 Sq Ft

    13539 Hokum Dr, Greensboro, MD 21639

    A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining!Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces,

    Vincent Payne Realty Navigator

    13539 Hokum Dr, Greensboro, MD 21639
  • /74

    $740,000 Sold Jan 20, 2026

    3485 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 3,326 Sq Ft
    • Built 2003

    Last Sold Summary

    • $222/SF
    • 5 Days On Market

    Current Estimated Value $726,462

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
    • /43

      Est $472,779 Not Listed For Sale

      16911 Heritage Hills Ln, Henderson, MD 21640

      • 4 Beds
      • 2.5 Baths
      • 2,428 Sq Ft
      • Built 2006
      16911 Heritage Hills Ln, Henderson, MD 21640

      Last Sold Summary

      • 3% Above List Price
      • $189/SF
      • 36 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Blake Hoffman Fathom Realty

  • /26

    $359,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    118 Briarwood Cir, Denton, MD 21629

    It's NOT PERFECT - BUT IT COULD BE!!! Seller selling "AS-IS" "WHERE-IS" *Priced at least 40K Under Market!!! Add your own finishing touches to make this one yours... or just bask in the possible equity!!! One of the few in this subdivision with a BASEMENT!!! Seller just added NEW CARPET!! NEW PAINT!" Did I mention the walk-in closet?? How about the 3-piece rough-in in the basement? (Finish the

    Robert Brendel RE/MAX Components

    118 Briarwood Cir, Denton, MD 21629
  • /52

    $390,000 Sold Oct 23, 2025

    8556 Tuckahoe Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2001

    Last Sold Summary

    • $290/SF
    • 42 Days On Market

    Current Estimated Value $387,963

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
    • /26

      Est $272,444 Not Listed For Sale

      310 W Central Ave, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,359 Sq Ft
      • Built 1941
      310 W Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 2% Above List Price
      • $196/SF
      • 4 Days On Market

      Last Sold Price $266,000

      Last Listing Agent Debbie McQuaid TTR Sotheby's International Realty

  • /2

    $175,000

    • Land
    • 18.51 Acres
    • $9,454 per Acre

    0 Houston Branch Rd Unit MDCM2006924, Federalsburg, MD 21632

    These parcels are being sold as part of an estate. Three contiguous parcels with a total of 18.51 acres. Parcel 2 received Preliminary Perc Approval April 2015.

    Andrew Beaven Wright Real Estate

    0 Houston Branch Rd Unit MDCM2006924, Federalsburg, MD 21632
  • /3

    $80,000 Sold Sep 02, 2025

    26042 Line Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1970

    Last Sold Summary

    • $111/SF
    • 9 Days On Market

    Last Listing Agent Bonnie Duley Long & Foster Real Estate, Inc.

    26042 Line Rd, Denton, MD 21629
    • /18

      Est $241,548 Not Listed For Sale

      4 N Maple Ave, Ridgely, MD 21660

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1977
      4 N Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 5% Above List Price
      • $266/SF
      • 3 Days On Market

      Last Sold Price $230,000

      Last Listing Agent Jimmy Robinson Benson & Mangold, LLC

  • /39

    $525,000 Pending

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

    24111 Friendship Rd, Preston, MD 21655

    Welcome to 24111 Friendship Rd in Preston, MD, a beautifully maintained 3-bedroom, 2-bath rancher set on a peaceful 2-acre wooded lot. This classic home offers timeless brick accents, a large paved driveway, and a two-car attached garage, along with both a storage shed and a spacious storage building for added flexibility. Inside, you’ll find a formal living room and a formal dining room enhanced

    Billy Mister Keller Williams Realty

    24111 Friendship Rd, Preston, MD 21655
  • /104

    $478,000 Sold Aug 19, 2025

    13800 Cedar Ln, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 1,372 Sq Ft
    • Built 1920

    Last Sold Summary

    • $348/SF
    • 10 Days On Market

    Current Estimated Value $476,425

    Last Listing Agent Lona Todd Taylor Properties

    13800 Cedar Ln, Greensboro, MD 21639
    • /43

      Est $735,975 Not Listed For Sale

      23278 Holly Park Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 1,711 Sq Ft
      • Built 1972
      23278 Holly Park Dr, Preston, MD 21655

      Last Sold Summary

      • 3% Below List Price
      • $442/SF
      • 35 Days On Market

      Last Sold Price $756,000

      Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

  • /10

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21090 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture. There is even a storage shed on the property.

    Eddie Matthews Benson & Mangold, LLC

    21090 Marsh Creek Rd, Preston, MD 21655
  • /24

    $165,000 Sold Nov 10, 2025

    17990 Henderson Rd, Marydel, MD 21649

    • 1 Bed
    • 1 Bath
    • 1,527 Sq Ft
    • Built 1973

    Last Sold Summary

    • $108/SF
    • 10 Days On Market

    Current Estimated Value $195,395

    Last Listing Agent Timothy Morgan Keller Williams Realty Delmarva

    17990 Henderson Rd, Marydel, MD 21649
    • /12

      Est $198,639 Not Listed For Sale

      206 Bernard Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 2004
      206 Bernard Ave, Federalsburg, MD 21632

      Last Sold Summary

      • $206/SF
      • 21 Days On Market

      Last Sold Price $198,000

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /19

    $349,000

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

    5026 Bethlehem Rd, Preston, MD 21655

    Totally renovated colonial offering nearly 2,000 sq ft of living space on a spacious 1/3-acre corner lot. Featuring 3, possibly 4 generous bedrooms and 2 full baths, this property showcases luxury vinyl plank flooring throughout. Enjoy privacy rear fencing and a large backyard—perfect for outdoor living. Ideal for a growing family and conveniently located close to Easton and Preston. This home is

    Linda Moore Long & Foster Real Estate, Inc.

    5026 Bethlehem Rd, Preston, MD 21655
  • /61

    $429,900 Sold Jan 05, 2026

    26091 Hokum Dr, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 2004

    Last Sold Summary

    • $191/SF
    • 24 Days On Market

    Current Estimated Value $445,341

    Last Listing Agent Lori Marino Long & Foster Real Estate, Inc.

    26091 Hokum Dr, Greensboro, MD 21639
    • /45

      Est $395,809 Not Listed For Sale

      202 N Central Ave, Ridgely, MD 21660

      • 3 Beds
      • 4 Baths
      • 2,668 Sq Ft
      • Built 1885
      202 N Central Ave, Ridgely, MD 21660

      Last Sold Summary

      • 1% Above List Price
      • $146/SF
      • 12 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Chris Rosendale CR Realty

  • /35

    $259,900

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft

    3540 Houston Branch Rd, Federalsburg, MD 21632

    Welcome to 3540 Houston Branch Rd. It was purchased in 2021 and has undergone extensive renovations. The interior was taken down to the studs. There is new drywall, flooring and sub flooring, a complete bath room, windows, kitchen cabinets, appliances and quartz counter tops. Even the electric was updated along with plumbing. Did I mention a new roof, well and septic system!! This is a perfect

    Eddie Matthews Benson & Mangold, LLC

    3540 Houston Branch Rd, Federalsburg, MD 21632
  • /3

    $27,500 Sold Dec 04, 2025

    222 Denton Rd, Federalsburg, MD 21632

    • Land
    • 0.23 Acre
    • $119,565 per Acre

    Last Sold Summary

    • 589 Days On Market

    Current Estimated Value $64,641

    Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

    222 Denton Rd, Federalsburg, MD 21632
    • /44

      Est $428,911 Not Listed For Sale

      18 Lister Ln, Ridgely, MD 21660

      • 4 Beds
      • 2.5 Baths
      • 3,252 Sq Ft
      • Built 2005
      18 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 3% Above List Price
      • $129/SF
      • 38 Days On Market

      Last Sold Price $417,900

      Last Listing Agent Barbara Blosser Long & Foster

  • /2

    $280,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    618 Academy Ave, Federalsburg, MD 21632

    Welcome home! This beautifully cared-for property offers small-town charm with big advantages — no town taxes and only a five-minute walk to the local elementary school. Sitting on a spacious 0.78-acre lot, you'll love the huge backyard, perfect for kids, pets, or backyard cookouts. The large circular driveway provides plenty of parking, and there’s even a storage shed for all your outdoor gear.

    Kaitlyn Collins Benson & Mangold, LLC

    618 Academy Ave, Federalsburg, MD 21632
  • /58

    $700,000 Sold Dec 17, 2025

    25211 Adams Landing Rd, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 2,273 Sq Ft
    • Built 1960

    Last Sold Summary

    • $308/SF
    • 12 Days On Market

    Current Estimated Value $698,680

    Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

    25211 Adams Landing Rd, Denton, MD 21629
    • /15

      Est $345,358 Not Listed For Sale

      23592 Henry Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 1920
      23592 Henry Rd, Ridgely, MD 21660

      Last Sold Summary

      • 11% Above List Price
      • $213/SF
      • 44 Days On Market

      Last Sold Price $310,000

      Last Listing Agent Pamela Geib Long & Foster

  • /48

    $355,000

    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • /49

    $390,000 Sold Feb 13, 2026

    1111 Ruddy Duck Ct, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,670 Sq Ft
    • Built 2006

    Last Sold Summary

    • $146/SF
    • 13 Days On Market

    Current Estimated Value $379,267

    Last Listing Agent Lee Wolff FSBO Broker

    1111 Ruddy Duck Ct, Denton, MD 21629
    • /69

      Est $418,914 Not Listed For Sale

      1130 Osprey Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,644 Sq Ft
      • Built 2005
      1130 Osprey Ln, Denton, MD 21629

      Last Sold Summary

      • 9% Above List Price
      • $146/SF
      • 4 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Butch Groom Keller Williams Flagship

  • /26

    $232,000

    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1404 Blue Heron Dr, Denton, MD 21629

    Rehab in 2025/2026. 3 story Townhome with Xtra Large Primary Bedroom with Walk in Closet and Private Bathroom. 2 other Large Bedrooms with Spacius closets. Kitchen with all new Cabinets and Granite Countertops. New flooring thru-out entire Townhome. Whole House painted. All three Bathrooms updatd with new Tile, Vanities, Bathtubs and fixtures! You will not be disappointed.!!!Located within

    Kathleen Brenton Brenton Realty Group

    1404 Blue Heron Dr, Denton, MD 21629

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