15,709

Caroline County, MD Homes

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  • /38

    $245,000 Sold Nov 14, 2025

    312 Fountain Ave, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft
    • Built 1982

    Last Sold Summary

    • $224/SF
    • 72 Days On Market

    Current Estimated Value $248,416

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    312 Fountain Ave, Denton, MD 21629
    • /43

      Est $337,392 Not Listed For Sale

      505 Teal Cir, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 1,952 Sq Ft
      • Built 2004
      505 Teal Cir, Greensboro, MD 21639

      Last Sold Summary

      • 20% Above List Price
      • $143/SF
      • 20 Days On Market
      • Last Sold Price $280,000
      • Jan 03, 2024

      Last Listing Agent Jillian Luna Rosendale Realty

  • /2

    $79,000

    • Land
    • 2.11 Acres
    • $37,441 per Acre

    lot 6 Harmony Woods Dr, Preston, MD 21655

    Barbara Nichols Results Realty Inc.

    lot 6 Harmony Woods Dr, Preston, MD 21655
  • 125 Park Ave, Greensboro, MD 21639

    $292,990 Sold Oct 28, 2025

    125 Park Ave, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $201/SF
    • 18 Days On Market

    Current Estimated Value $246,843

    D.R. Horton Kinnamon Meadows

    125 Park Ave, Greensboro, MD 21639
    • /28

      Est $194,511 Not Listed For Sale

      316 N Main St, Greensboro, MD 21639

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft
      • Built 1910
      316 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 13% Above List Price
      • $135/SF
      • 143 Days On Market
      • Last Sold Price $172,000
      • May 31, 2024

      Last Listing Agent Marcia Rostien Long & Foster

  • /2

    $75,000

    • Land
    • 4.66 Acres
    • $16,094 per Acre

    412 Railroad Ave, Federalsburg, MD 21632

    LIST PRICE IS OPENING BID. Online Auction Only! Bidding begins Friday, June 5th, and ends Wednesday, June 10, 2026 at 2:00PM. Potential Commercial/Industrial Development Opportunity4.66± Acres of Undeveloped Land in Federalsburg, MD This is a prime opportunity to acquire approximately 4.66 acres of undeveloped land located within the incorporated Town of Federalsburg in Caroline County,

    Larry Cooper Alex Cooper Auctioneers, Inc.

    412 Railroad Ave, Federalsburg, MD 21632
  • /77

    $590,000 Sold Jan 09, 2026

    8197 Detour Rd, Denton, MD 21629

    • 3 Beds
    • 3 Baths
    • 2,565 Sq Ft
    • Built 1989

    Last Sold Summary

    • $230/SF
    • 250 Days On Market

    Current Estimated Value $605,425

    Last Listing Agent Penny Windsor Benson & Mangold, LLC

    8197 Detour Rd, Denton, MD 21629
    • /51

      Est $310,768 Not Listed For Sale

      25720 Burrsville Rd, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft
      • Built 1999
      25720 Burrsville Rd, Denton, MD 21629

      Last Sold Summary

      • 3% Below List Price
      • $342/SF
      • 27 Days On Market
      • Last Sold Price $319,999
      • Aug 16, 2024

      Last Listing Agent Jarnell Foster Benson & Mangold, LLC

  • /4

    $92,000

    • Land
    • 14,374 Sq Ft
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • /29

    $299,000 Sold Mar 05, 2026

    121 Edenton Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1978

    Last Sold Summary

    • $243/SF
    • 98 Days On Market

    Current Estimated Value $297,361

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    121 Edenton Ln, Denton, MD 21629
    • /35

      Est $417,711 Not Listed For Sale

      1524 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 2007
      1524 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 9% Above List Price
      • $153/SF
      • 18 Days On Market
      • Last Sold Price $382,500
      • Dec 12, 2023

      Last Listing Agent Niya Davis Century 21 Harris Hawkins & Co.

  • /33

    $185,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,078 Sq Ft

    221 Denton Rd, Federalsburg, MD 21632

    Priced to Sell! Welcome to this Fully Updated Colonial on a .37 Acre Lot, Offering Modern Finishes and Move-In Ready Comfort. The Home Features a Stunning Open Kitchen (2025 Remodel) with New Cabinets, Quartz Counters, Tile Backsplash, and Stainless Steel Appliances, Perfect For Cooking and Entertaining. Enjoy Remodeled Bathrooms, New Flooring, New Lighting, and Custom Interior Paint Throughout

    Matthew Altizer ANR Realty, LLC

    221 Denton Rd, Federalsburg, MD 21632
  • /9

    $370,000 Sold Dec 23, 2025

    3345 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • Built 2025

    Last Sold Summary

    • $282/SF
    • 22 Days On Market

    Current Estimated Value $373,070

    Last Listing Agent Janiece Hines Crown Homes Real Estate

    3345 Gallagher Rd, Preston, MD 21655
    • /32

      Est $476,731 Not Listed For Sale

      10767 Collinswood Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,182 Sq Ft
      • Built 2006
      10767 Collinswood Dr, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $138/SF
      • 17 Days On Market
      • Last Sold Price $440,000
      • Oct 24, 2024

      Last Listing Agent Amanda Morgan Brenton Realty Group

  • /18

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,694 Sq Ft

    156 Main St, Preston, MD 21655

    Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP)

    Chuck Mangold Benson & Mangold, LLC

    156 Main St, Preston, MD 21655
  • /16

    $223,000 Sold May 08, 2026

    204 Maple Ave, Greensboro, MD 21639

    • 3 Beds
    • 1.5 Baths
    • 1,920 Sq Ft
    • Built 1905

    Last Sold Summary

    • 3% Below List Price
    • $116/SF
    • 13 Days On Market

    Current Estimated Value $230,997

    Last Listing Agent Ursula Encarnacion Long & Foster Real Estate, Inc.

    204 Maple Ave, Greensboro, MD 21639
    • /22

      Est $376,089 Not Listed For Sale

      110 S 8th St, Denton, MD 21629

      • 3 Beds
      • 3.5 Baths
      • 1,654 Sq Ft
      • Built 1972
      110 S 8th St, Denton, MD 21629

      Last Sold Summary

      • 19% Above List Price
      • $190/SF
      • 4 Days On Market
      • Last Sold Price $315,000
      • Jun 15, 2023

      Last Listing Agent Andy Karas Compass

  • /73

    $175,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,763 Sq Ft

    24872 Meeting House Rd, Denton, MD 21629

    Own your own vacation home only a short distnce to Ocean City Md. and Rehoboth Beach. The renovation process has been started and you are just in time to choose your own finishes. Have you ever wanted to have your very own AirBNB or vacation home for your family and friends? From here you can walk to the Choptank River where you can fish, enjoy a nice picnic area or you can bring your boat down

    Saad Jamil Samson Properties

    24872 Meeting House Rd, Denton, MD 21629
  • /24

    $125,000 Sold Mar 03, 2026

    0 Asbury Dr, Denton, MD 21629

    • Land
    • 3 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 255 Days On Market

    Last Listing Agent Coard Benson Benson & Mangold, LLC

    0 Asbury Dr, Denton, MD 21629
    • /39

      Est $310,902 Not Listed For Sale

      505 Maryland Ave, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1989
      505 Maryland Ave, Ridgely, MD 21660

      Last Sold Summary

      • 3% Below List Price
      • $286/SF
      • 0 Days On Market
      • Last Sold Price $320,000
      • Sep 29, 2023

      Last Listing Agent Lisa Lynch Keller Williams Realty

  • /23

    $227,000

    • 3 Beds
    • 1.5 Baths
    • 1,828 Sq Ft

    126 Maple Ave, Preston, MD 21655

    Step back in time with this early 1900s home. This home is full of character, from the detail in the trim work to the upper level 'porch.' This home offers great potential to be returned to the early 1900s with a little TLC and vision. Located in the heart of Preston, it is 15 minutes from historic Easton with all its amenities. Come take a look and see the vision.

    Marsha Tull Marshy Hope Realty LLC

    126 Maple Ave, Preston, MD 21655
  • /15

    $195,000 Sold Mar 17, 2026

    26732 Idlewild Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1966

    Last Sold Summary

    • $188/SF
    • 91 Days On Market

    Current Estimated Value $207,177

    Last Listing Agent Michael Shipley Benson & Mangold, LLC.

    26732 Idlewild Rd, Federalsburg, MD 21632
    • /20

      Est $254,347 Not Listed For Sale

      116 Main St, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,185 Sq Ft
      • Built 1920
      116 Main St, Preston, MD 21655

      Last Sold Summary

      • 2% Below List Price
      • $219/SF
      • 58 Days On Market
      • Last Sold Price $259,000
      • Nov 25, 2024

      Last Listing Agent Henry Gibbons-Neff Meredith Fine Properties

  • /45

    $629,900

    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Excellent investment opportunity. Also perfect for a homeowner, live in one unit and let the other units pay your mortgage. 4-unit residential apartments fully rented with long-term tenants. Additional office space available. 5 units total. Current income from 4 units is $5,100/month, potentially $6,100/month including the office. Plenty of parking for tenants, guests, and customers. Updated

    Raphael Szendro R&R Executive Realty

    310 Main St, Marydel, MD 21649
  • /67

    $385,000 Sold Dec 31, 2025

    1612 Cattail Commons Way, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft
    • Built 2007

    Last Sold Summary

    • $154/SF
    • 77 Days On Market

    Current Estimated Value $407,495

    Last Listing Agent Daniel Register Northrop Realty

    1612 Cattail Commons Way, Denton, MD 21629
    • /18

      Est $407,808 Not Listed For Sale

      1308 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,505 Sq Ft
      • Built 2007
      1308 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 13% Above List Price
      • $144/SF
      • 264 Days On Market
      • Last Sold Price $361,000
      • Sep 22, 2023

      Last Listing Agent Venita Jacobson Century 21 New Millennium

  • /32

    $450,000

    • 1 Bed
    • 1.5 Baths
    • 1,596 Sq Ft

    23629 Willow Pond Rd, Denton, MD 21629

    A Distinctive Live/Work Opportunity on Marylands Eastern Shore. This prime location tucked away between Easton & Denton, is this remarkable and beautifully maintained, 6.18 acre property that combines the tranquility of a pastoral countryside with the practicality of a live/work lifestyle. Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4

    Stephany Barrett Long & Foster Real Estate, Inc.

    23629 Willow Pond Rd, Denton, MD 21629
  • /39

    $400,000 Sold Dec 12, 2025

    1208 Painted Fern Rd, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,994 Sq Ft
    • Built 2006

    Last Sold Summary

    • $134/SF
    • 8 Days On Market

    Current Estimated Value $413,464

    Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    1208 Painted Fern Rd, Denton, MD 21629
    • /27

      Est $421,388 Not Listed For Sale

      6 W Liberty St, Ridgely, MD 21660

      • 3 Beds
      • 3.5 Baths
      • 2,184 Sq Ft
      • Built 2005
      6 W Liberty St, Ridgely, MD 21660

      Last Sold Summary

      • 15% Above List Price
      • $167/SF
      • 2 Days On Market
      • Last Sold Price $365,000
      • Jul 11, 2023

      Last Listing Agent Katie Moore Coldwell Banker Chesapeake Real Estate Company

  • /6

    $159,900

    • Land
    • 5.28 Acres
    • $30,284 per Acre

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

    Peaceful 5.281-Acre Wooded Homesite with Wildlife Pond Views. Discover the perfect blend of natural beauty and rural tranquility on this 5.281-acre perc-approved building lot, ready for your dream home. Nestled in a quiet country setting, this property offers a stunning overlook of a preserved wildlife pond, where geese, ducks, deer, and turkeys are frequent visitors—creating your own private

    Brett Schrader Taylor Properties

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
  • /2

    $258,000 Sold Aug 18, 2025

    318 S 5th Ave, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,326 Sq Ft
    • Built 1953

    Last Sold Summary

    • $195/SF
    • 1 Day On Market

    Current Estimated Value $261,549

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    318 S 5th Ave, Denton, MD 21629
    • /4

      Est $444,146 Not Listed For Sale

      10961 Greensboro Rd, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2007
      10961 Greensboro Rd, Denton, MD 21629

      Last Sold Summary

      • 23% Above List Price
      • $174/SF
      • 6 Days On Market
      • Last Sold Price $360,000
      • May 15, 2023

      Last Listing Agent Diane Wenk Wright Real Estate

  • /3

    $25,000

    • 728 Sq Ft

    23547 Jonestown Ln, Preston, MD 21655

    Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County

    Dalton Adshead Keller Williams Select Realtors of Cambridge

    23547 Jonestown Ln, Preston, MD 21655
  • /71

    $429,000 Sold Jul 07, 2025

    25612 Auction Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,648 Sq Ft
    • Built 1984

    Last Sold Summary

    • $260/SF
    • 29 Days On Market

    Current Estimated Value $440,680

    Last Listing Agent Megan Rosendale Rosendale Realty

    25612 Auction Rd, Federalsburg, MD 21632
    • /27

      Est $152,013 Not Listed For Sale

      308 Park Ave, Federalsburg, MD 21632

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft
      • Built 1904
      308 Park Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 10% Below List Price
      • $176/SF
      • 36 Days On Market
      • Last Sold Price $168,000
      • Aug 09, 2024

      Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

  • /22

    $269,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    Perry Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern cabinetry, stainless steel appliances, a spacious peninsula

    D.R. Horton Builder
    103 Park Ave Unit 36203273, Greensboro, MD 21639
  • /50

    $875,000 Sold Jul 11, 2025

    5213A Bethlehem Rd, Preston, MD 21655

    • 4 Beds
    • 3.5 Baths
    • 2,993 Sq Ft
    • Built 2014

    Last Sold Summary

    • $292/SF
    • 3 Days On Market

    Current Estimated Value $920,210

    Last Listing Agent Amanda Morgan Brenton Realty Group

    5213A Bethlehem Rd, Preston, MD 21655
    • /3

      Est $450,825 Not Listed For Sale

      12141 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1950
      12141 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 9% Below List Price
      • $382/SF
      • 0 Days On Market
      • Last Sold Price $495,000
      • Feb 22, 2024

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /18

    $120,000

    • Land
    • 1.89 Acres
    • $63,492 per Acre

    27202 Sandtown Rd, Goldsboro, MD 21636

    Discover the perfect blend of tranquility and convenience with this perc-approved 1.88-acre homesite, ready for your dream build. Overlooking a scenic tributary of the Upper Choptank River, this property offers breathtaking natural views and a serene setting that wildlife enthusiasts will truly appreciate. Ducks and geese are common visitors on the water with fishing right in your back yard.

    Brett Schrader Taylor Properties

    27202 Sandtown Rd, Goldsboro, MD 21636
  • /2

    $11,000 Sold Jul 02, 2025

    534 N N 6th St, Denton, MD 21629

    • Land
    • 22,215 Sq Ft
    • $21,569 per Acre

    Last Sold Summary

    • 370 Days On Market

    Current Estimated Value $161,000

    Last Listing Agent Heather Brummell Keller Williams Realty

    534 N N 6th St, Denton, MD 21629

Showing Results 241 - 280, Page 7 of 18

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