15,625

Caroline County, MD Homes

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  • /24

    $235,000

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

    122 Julie Ln, Federalsburg, MD 21632

    Welcome to this beautifully maintained newer town home that has been virtually staged was built in late 2025, in the charming Riverwalk community of Federalsburg. Offering 3 bedrooms, 2.5 bathrooms, and modern construction, this home combines today's sought-after finishes with the warmth and small-town charm that make Maryland's Eastern Shore such a desirable place to call home. Close to

    Donna Hollifield Remax Vision

    122 Julie Ln, Federalsburg, MD 21632
  • /2

    $269,990

    Sold Oct 13, 2025

    113 Parkland Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $221/SF
    • 19 Days On Market

    D.R. Horton Kinnamon Meadows

    113 Parkland Rd, Greensboro, MD 21639
    • /24

      Est $228,150

      Not Listed For Sale

      108 Liberty Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft
      • Built 1890
      108 Liberty Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 177 Days On Market

      Last Listing Agent Carolina Mosquera Weichert, REALTORS

  • /13

    $274,990

    New Construction $12K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    125 Hobbs St, Greensboro, MD 21639

    **Red Tag Sales Event through August 2, 2026! Was $279,990 Now: $274,990!** Discover 125 Hobbs Street, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms, two bathrooms, and a two-car driveway. As you enter the home through the front porch, this thoughtfully designed home has a

    Justin Wood D.R. Horton Realty of Virginia, LLC

    125 Hobbs St, Greensboro, MD 21639
  • /25

    $260,000

    Sold Oct 30, 2025

    1904 Blue Heron Dr, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft
    • Built 2007

    Last Sold Summary

    • $98/SF
    • 61 Days On Market

    Current Estimated Value $265,311

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
    • /11

      Est $313,825

      Not Listed For Sale

      505 S 2nd St, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,058 Sq Ft
      • Built 1941
      505 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Pamela Geib Long & Foster Real Estate, Inc.

  • /23

    $298,990

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    123 Hobbs St, Greensboro, MD 21639

    Welcome to 123 Hobbs Street where a soon to be built new home can be yours in Kinnamon Meadows in Greensboro, MD. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen

    Justin Wood D.R. Horton Realty of Virginia, LLC

    123 Hobbs St, Greensboro, MD 21639
  • /57

    $950,000

    Sold Jul 10, 2026

    7805 Dyer Rd, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 2022

    Last Sold Summary

    • $528/SF
    • 2 Days On Market

    Current Estimated Value $518,415

    Last Listing Agent Brody Sergent Northrop Realty

    7805 Dyer Rd, Denton, MD 21629
    • /20

      Est $223,189

      Not Listed For Sale

      217 Greenridge Rd, Federalsburg, MD 21632

      • 2 Beds
      • 1.5 Baths
      • 1,276 Sq Ft
      • Built 1950
      217 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /67

    $659,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    132 Deep Shore Rd, Denton, MD 21629

    Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons. Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5 baths. An

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /12

    $60,027

    Sold Mar 31, 2026

    21269 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1996

    Last Sold Summary

    • $45/SF
    • 64 Days On Market

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
    • /25

      Est $271,487

      Not Listed For Sale

      26280 Hobbs Rd, Denton, MD 21629

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 1983
      26280 Hobbs Rd, Denton, MD 21629

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

  • /25

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    113 Chamber St, Preston, MD 21655

    Welcome to 113 Chamber Street in the heart of Preston! This well-maintained single-story home offers comfortable living on a spacious 0.42-acre lot within town limits. Featuring 2 full bathrooms, a practical floor plan, and a large detached garage with approximately 880 square feet of space, this property provides plenty of room for parking, storage, hobbies, or a workshop. Enjoy outdoor living

    Heather Brummell Keller Williams Realty

    113 Chamber St, Preston, MD 21655
  • /13

    $230,000

    Sold Feb 27, 2026

    1202 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $131/SF
    • 46 Days On Market

    Current Estimated Value $231,291

    Last Listing Agent SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
    • /50

      Est $396,464

      Not Listed For Sale

      1104 Ruddy Duck Ct, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,577 Sq Ft
      • Built 2005
      1104 Ruddy Duck Ct, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /27

    $330,000

    • 3 Beds
    • 2.5 Baths
    • 1,212 Sq Ft

    104 Chambers St, Federalsburg, MD 21632

    Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes

    Kaitlyn Collins Benson & Mangold, LLC

    104 Chambers St, Federalsburg, MD 21632
  • /16

    $215,000

    Sold Oct 24, 2025

    522 Lincoln St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1961

    Last Sold Summary

    • $336/SF
    • 10 Days On Market

    Current Estimated Value $210,760

    Last Listing Agent Amanda Morgan Brenton Realty Group

    522 Lincoln St, Denton, MD 21629
    • /54

      Est $437,113

      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

      • 7 Days On Market

      Last Listing Agent Glenn Hedgecoth Compass

  • /56

    $525,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft

    27518 Possum Hill Rd, Federalsburg, MD 21632

    Situated on 10.2+/- acres with wide-open farm views, this 4-bedroom, 3-bath Cape Cod offers a practical layout and plenty of space to enjoy country living. The main level features a primary suite, an additional bedroom, and a kitchen with stainless steel appliances that opens to the living room. Hardwood floors run throughout the main living areas. Upstairs, you'll find a lounge area, two

    Alicia Gannon Dulin Benson & Mangold, LLC

    27518 Possum Hill Rd, Federalsburg, MD 21632
  • /4

    $110,000

    Sold Dec 15, 2025

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952

    • Land
    • 2 Acres
    • $55,000 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Amy Torbert Diamond State Cooperative LLC

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952
    • /50

      Est $371,007

      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

      • 31 Days On Market

      Last Listing Agent Jillian Luna Rosendale Realty

  • /3

    $575,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,426 Sq Ft

    22733 Squire Ln, Queen Anne, MD 21657

    Photos Coming Soon. You'll love this custom home nestled on 2.13 private acres, offering nearly 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open floor plan is highlighted by rich Brazilian hardwood floors, cathedral ceiling, and a welcoming great room anchored by a dramatic floor-to-ceiling brick fireplace. The spacious kitchen opens seamlessly to

    Jimmy White Long & Foster Real Estate, Inc.

    22733 Squire Ln, Queen Anne, MD 21657
  • /19

    $315,000

    Sold Jan 09, 2026

    25607 Garey Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 920 Sq Ft
    • Built 1998

    Last Sold Summary

    • $342/SF
    • 39 Days On Market

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    25607 Garey Rd, Denton, MD 21629
    • /44

      Est $423,389

      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

      • 16 Days On Market

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /36

    $289,000

    New Construction $10K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    210 W 2nd St, Ridgely, MD 21660

    WHAT A DEAL!!!! New construction. Welcome to 210 W. 2nd Street in Ridgely, where modern construction meets small-town charm. Built in 2026 with a Builder 10 year structural warranty. This beautifully designed 4-bedroom, 2-bath home offers approximately 1,800 square feet of thoughtfully designed living space, perfect for today's lifestyle.Step inside to discover bright, open living areas ideal

    Kat Thompson Benson & Mangold, LLC.

    210 W 2nd St, Ridgely, MD 21660
  • /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
    • /41

      Est $311,796

      Not Listed For Sale

      118 Edenton Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1975
      118 Edenton Ln, Denton, MD 21629

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Nishta Gupta Samson Properties

  • /59

    $1,350,000

    Open Sat 10AM - 1PM $150K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    Price Improvement Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, 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 $1,184,426

    Last Listing Agent Travis Gray Engel & Völkers Annapolis

    14271 Cedar Ln, Greensboro, MD 21639
    • /29

      Est $405,635

      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

      • 24 Days On Market

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • /29

    $700,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • /52

    $465,000

    Sold Jun 16, 2026

    14418 Poplar St, Goldsboro, MD 21636

    • 2 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1989

    Last Sold Summary

    • 5% Above List Price
    • $252/SF
    • 6 Days On Market

    Current Estimated Value $455,942

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    14418 Poplar St, Goldsboro, MD 21636
    • /70

      Est $408,902

      Not Listed For Sale

      1110 Osprey Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2005
      1110 Osprey Ln, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Judith Germain Benson & Mangold, LLC

  • /74

    $624,900

    • 3 Beds
    • 2 Baths
    • 1,938 Sq Ft

    23130 Sparks Rd, Ridgely, MD 21660

    Robert Walker McClain-Williamson Realty, LLC

    23130 Sparks Rd, Ridgely, MD 21660
  • /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
    • /43

      Est $496,728

      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

      • 36 Days On Market

      Last Listing Agent Blake Hoffman Fathom Realty MD, LLC

  • /31

    $287,000

    $23K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,234 Sq Ft

    106 Main St, Preston, MD 21655

    Welcome to this charming and spacious home in Preston offering 3 bedrooms, 1.5 bathrooms, and 2,050 square feet of comfortable living space. Freshly painted throughout, this home features beautiful hardwood flooring that adds warmth and timeless character. With generous living areas and a move-in-ready feel, this property blends comfort and style while providing plenty of space for everyday

    Shay Prattis Keller Williams Realty

    106 Main St, Preston, MD 21655
  • /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 $737,260

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
    • /43

      Est $747,284

      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

      • 35 Days On Market

      Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

  • /45

    $459,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,839 Sq Ft

    128 Main St, Preston, MD 21655

    Blending warmth, character, and thoughtful updates, this beautifully maintained post-and-beam home offers a truly inviting living experience both inside and out. The spacious main level features all tile flooring, a huge living room anchored by a cozy wood stove, a flexible study/sitting room, and a charming 3-season room. The kitchen and dining combination creates an ideal gathering space with

    Jessica Clark Wilson Realty & Staging LLC

    128 Main St, Preston, MD 21655

Showing Results 481 - 520, Page 13 of 18

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