2,394

Preston, MD Homes

Section Image
  • 21245 Tanyard Rd, Preston, MD 21655
    21245 Tanyard Rd, Preston, MD 21655
    21245 Tanyard Rd, Preston, MD 21655
    /10

    $275,000

    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    21245 Tanyard Rd, Preston, MD 21655

    Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • 5213A Bethlehem Rd, Preston, MD 21655
    5213A Bethlehem Rd, Preston, MD 21655
    5213A Bethlehem Rd, Preston, MD 21655
    /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 $939,450

    Last Listing Agent Amanda Morgan Brenton Realty Group

    5213A Bethlehem Rd, Preston, MD 21655
    • 4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      /58

      Est $507,891 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
  • 20915 Dover Bridge Rd, Preston, MD 21655
    20915 Dover Bridge Rd, Preston, MD 21655
    20915 Dover Bridge Rd, Preston, MD 21655
    /56

    $497,000

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    20915 Dover Bridge Rd, Preston, MD 21655

    Set on 8.6 private, fully fenced acres just across the Dover Bridge, this Eastern Shore property offers endless possibilities with scenic surroundings, expansive land, and close proximity to the Choptank River and minutes to Easton. The single-level home features 3 bedrooms and 2 full bathrooms, a country kitchen, and an open-concept layouthighlighted by a massive brick fireplace with insert and

    Alex Martinez The Agency DC

    20915 Dover Bridge Rd, Preston, MD 21655
  • 21596 Dover Bridge Rd, Preston, MD 21655
    21596 Dover Bridge Rd, Preston, MD 21655
    /2

    $99,900 Sold Feb 14, 2025

    21596 Dover Bridge Rd, Preston, MD 21655

    • Land
    • 2.13 Acres
    • $46,901 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $212,995

    Last Listing Agent Liz Kirkland Iron Valley Real Estate of Central PA

    21596 Dover Bridge Rd, Preston, MD 21655
    • 116 Main St, Preston, MD 21655
      116 Main St, Preston, MD 21655
      116 Main St, Preston, MD 21655
      /20

      Est $264,336 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,185 Sq Ft

      116 Main St, Preston, MD 21655

      116 Main St, Preston, MD 21655
  • 106 Lednum Ave, Preston, MD 21655
    106 Lednum Ave, Preston, MD 21655
    106 Lednum Ave, Preston, MD 21655
    /17

    $380,000 New Construction

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

    106 Lednum Ave, Preston, MD 21655

    New construction in Preston, MD offering 3 bedrooms and 2 full baths across 1,400 square feet. This home features an open layout with vaulted ceilings, LVP flooring in the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances and granite countertops. The primary suite includes a stand-up shower, while the guest bath offers a tub/shower combo. An

    Eric Haro The Parker Group

    106 Lednum Ave, Preston, MD 21655
  • 148 Main St, Preston, MD 21655
    148 Main St, Preston, MD 21655
    148 Main St, Preston, MD 21655
    /44

    $220,000 Sold Oct 30, 2025

    148 Main St, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft
    • Built 1880

    Last Sold Summary

    • $76/SF
    • 69 Days On Market

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    148 Main St, Preston, MD 21655
    • 23116 Gilpin Point Rd, Preston, MD 21655
      23116 Gilpin Point Rd, Preston, MD 21655
      23116 Gilpin Point Rd, Preston, MD 21655
      /24

      Est $449,671 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,880 Sq Ft

      23116 Gilpin Point Rd, Preston, MD 21655

      23116 Gilpin Point Rd, Preston, MD 21655
  • 21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    /43

    $389,999

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

    21405 Tanyard Rd, Preston, MD 21655

    Peaceful Country Living on 3.2 Acres – Recently Renovated Home with Expansive Pole Barn! Welcome to 21405 Tanyard Rd in Preston, MD – where modern updates meet serene country living. This beautifully renovated 3-bedroom, 3-bath home sits on 3.2 acres—perfect for gardening, raising animals, or simply enjoying wide-open space and quiet surroundings. Step inside to find a bright, freshly updated

    Justin Pokrywka Taylor Properties

    21405 Tanyard Rd, Preston, MD 21655
  • 22716 Havercamp Rd, Preston, MD 21655
    22716 Havercamp Rd, Preston, MD 21655
    22716 Havercamp Rd, Preston, MD 21655
    /33

    $435,000 Sold Aug 29, 2025

    22716 Havercamp Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,192 Sq Ft
    • Built 2007

    Last Sold Summary

    • $198/SF
    • 72 Days On Market

    Current Estimated Value $458,233

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    22716 Havercamp Rd, Preston, MD 21655
    • 6293 Statum Rd, Preston, MD 21655
      6293 Statum Rd, Preston, MD 21655
      6293 Statum Rd, Preston, MD 21655
      /52

      Est $637,386 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,429 Sq Ft

      6293 Statum Rd, Preston, MD 21655

      6293 Statum Rd, Preston, MD 21655
  • 4305 Langrell Rd, Preston, MD 21655
    4305 Langrell Rd, Preston, MD 21655
    4305 Langrell Rd, Preston, MD 21655
    /35

    $374,900 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,076 Sq Ft

    4305 Langrell Rd, Preston, MD 21655

    Welcome to this beautifully updated rancher that checks every box — and then some. Sitting on over half an acre, this home blends modern upgrades, spacious living, and incredible functionality, all wrapped into the perfect Eastern Shore retreat. Step inside to find new LVP floors, fresh siding, and a brand-new roof, giving the home a crisp, clean, move-in-ready feel. The heart of the home is the

    Crystal Smith RE/MAX Executive

    4305 Langrell Rd, Preston, MD 21655
  • 5480 Bethlehem Rd, Preston, MD 21655
    5480 Bethlehem Rd, Preston, MD 21655
    5480 Bethlehem Rd, Preston, MD 21655
    /34

    $324,000 Sold Mar 03, 2025

    5480 Bethlehem Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1996

    Last Sold Summary

    • $263/SF
    • 9 Days On Market

    Current Estimated Value $353,318

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    5480 Bethlehem Rd, Preston, MD 21655
    • 4191 Harmony Rd, Preston, MD 21655
      4191 Harmony Rd, Preston, MD 21655
      4191 Harmony Rd, Preston, MD 21655
      /18

      Est $535,097 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,196 Sq Ft

      4191 Harmony Rd, Preston, MD 21655

      4191 Harmony Rd, Preston, MD 21655
  • 21682 Dover Bridge Rd, Preston, MD 21655
    21682 Dover Bridge Rd, Preston, MD 21655
    21682 Dover Bridge Rd, Preston, MD 21655
    /23

    $749,000 Pending

    21682 Dover Bridge Rd, Preston, MD 21655

    Jim Corson Benson & Mangold, LLC

    21682 Dover Bridge Rd, Preston, MD 21655
  • 6074 Newton Rd, Preston, MD 21655
    6074 Newton Rd, Preston, MD 21655
    6074 Newton Rd, Preston, MD 21655
    /64

    $565,000 Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Current Estimated Value $584,781

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • 5576 Harmony Woods Dr, Preston, MD 21655
      5576 Harmony Woods Dr, Preston, MD 21655
      5576 Harmony Woods Dr, Preston, MD 21655
      /27

      Est $427,325 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      5576 Harmony Woods Dr, Preston, MD 21655

      5576 Harmony Woods Dr, Preston, MD 21655
  • 5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    /54

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 3,442 Sq Ft

    5585 Harmony Woods Dr, Preston, MD 21655

    Set on a private, wooded 1.37± acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open

    Georgi Chauvin Benson & Mangold, LLC

    5585 Harmony Woods Dr, Preston, MD 21655
  • 22329 Tanyard Rd, Preston, MD 21655
    22329 Tanyard Rd, Preston, MD 21655
    22329 Tanyard Rd, Preston, MD 21655
    /34

    $332,000 Sold Sep 05, 2025

    22329 Tanyard Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,058 Sq Ft
    • Built 1972

    Last Sold Summary

    • $314/SF
    • 29 Days On Market

    Current Estimated Value $344,333

    Last Listing Agent Laura Anderson Coldwell Banker Realty

    22329 Tanyard Rd, Preston, MD 21655
    • 282 Tidewater Cir, Preston, MD 21655
      282 Tidewater Cir, Preston, MD 21655
      282 Tidewater Cir, Preston, MD 21655
      /26

      Est $456,809 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,907 Sq Ft

      282 Tidewater Cir, Preston, MD 21655

      282 Tidewater Cir, Preston, MD 21655
  • 24383 Robins Creek Rd, Preston, MD 21655
    24383 Robins Creek Rd, Preston, MD 21655
    24383 Robins Creek Rd, Preston, MD 21655
    /30

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft

    24383 Robins Creek Rd, Preston, MD 21655

    VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXIMATELY 1/4 MILE AWAY. LARGE LIVING ROOM, KITCHEN-DINING ROOM COMBO, PANELED WALLS ARE ALL PAINTED, MOSTLY WOOD FLOORS. LARGE DECK AT REAR OF HOUSE. PATIO AREA WITH A NICE FIRE PIT FOR EVENING ENJOYMENT. MORE PICTURES TO COME SOON. ONLY 40 MILES TO WESTERN SHORE, LESS THAN 60 MILES TO THE BEACH

    Ed Quidas Long & Foster Real Estate, Inc.

    24383 Robins Creek Rd, Preston, MD 21655
  • 0 Harmony Rd Unit MDCM2003730, Preston, MD 21655
    0 Harmony Rd Unit MDCM2003730, Preston, MD 21655
    /2

    $43,000 Sold May 23, 2025

    0 Harmony Rd Unit MDCM2003730, Preston, MD 21655

    • Land
    • 1.21 Acres
    • $35,537 per Acre

    Last Sold Summary

    • 497 Days On Market

    Last Listing Agent Gary Lucks Keller Williams Realty

    0 Harmony Rd Unit MDCM2003730, Preston, MD 21655
    • 24300 Robins Creek Rd, Preston, MD 21655
      24300 Robins Creek Rd, Preston, MD 21655
      24300 Robins Creek Rd, Preston, MD 21655
      /80

      Est $410,828 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,624 Sq Ft

      24300 Robins Creek Rd, Preston, MD 21655

      24300 Robins Creek Rd, Preston, MD 21655
  • 212 Main St, Preston, MD 21655
    212 Main St, Preston, MD 21655
    212 Main St, Preston, MD 21655
    /56

    $280,000

    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    ***Unique Opportunity***Welcome to this spacious and well-cared-for property located in the peaceful town of Preston. The main home offers 5 generously sized bedrooms and 3 full bathrooms, providing ample space for comfortable family living or multi-generational needs. A large eat-in kitchen serves as the heart of the home, perfect for everyday meals or entertaining guests. This property

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • 21182 Marsh Creek Rd, Preston, MD 21655
    21182 Marsh Creek Rd, Preston, MD 21655
    21182 Marsh Creek Rd, Preston, MD 21655
    /17

    $67,000 Sold Sep 19, 2025

    21182 Marsh Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft
    • Built 2020

    Last Sold Summary

    • $60/SF
    • 25 Days On Market

    Last Listing Agent Toni McDowell Keller Williams Select Realtors of Annapolis

    21182 Marsh Creek Rd, Preston, MD 21655
    • 24461 Friendship Rd, Preston, MD 21655
      24461 Friendship Rd, Preston, MD 21655
      24461 Friendship Rd, Preston, MD 21655
      /60

      Est $805,155 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 4,546 Sq Ft

      24461 Friendship Rd, Preston, MD 21655

      24461 Friendship Rd, Preston, MD 21655
  • 5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    /2

    $359,000 Coming Soon

    • 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
  • 6315 Harmony Rd, Preston, MD 21655
    6315 Harmony Rd, Preston, MD 21655
    6315 Harmony Rd, Preston, MD 21655
    /36

    $325,000 Sold Sep 26, 2025

    6315 Harmony Rd, Preston, MD 21655

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • $161/SF
    • 28 Days On Market

    Current Estimated Value $340,870

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • 288 Tidewater Cir, Preston, MD 21655
      288 Tidewater Cir, Preston, MD 21655
      288 Tidewater Cir, Preston, MD 21655
      /32

      Est $453,055 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,842 Sq Ft

      288 Tidewater Cir, Preston, MD 21655

      288 Tidewater Cir, Preston, MD 21655
  • 4935 Edmondson Creek Rd, Preston, MD 21655
    4935 Edmondson Creek Rd, Preston, MD 21655
    4935 Edmondson Creek Rd, Preston, MD 21655
    /10

    $318,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,438 Sq Ft

    4935 Edmondson Creek Rd, Preston, MD 21655

    Approximately 2 acres (parcels 289, 196) on a point on Little Creek off the Choptank River. Two bedroom, one bath log cabin with loft. An additional accessary log cabin. Easy access to Easton or Preston. Great waterfowl location.

    Randy Staats Benson & Mangold, LLC

    4935 Edmondson Creek Rd, Preston, MD 21655
  • 6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    /5

    $201,000 Sold Dec 19, 2025

    6561 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1915

    Last Sold Summary

    • $149/SF
    • 14 Days On Market

    Last Listing Agent Barbara Dayton Long & Foster Real Estate, Inc.

    6561 Bell Creek Rd, Preston, MD 21655
    • 312 Hughlett St, Preston, MD 21655
      312 Hughlett St, Preston, MD 21655
      312 Hughlett St, Preston, MD 21655
      /18

      Est $395,410 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,130 Sq Ft

      312 Hughlett St, Preston, MD 21655

      312 Hughlett St, Preston, MD 21655
  • 5734 Bell Creek Rd, Preston, MD 21655
    5734 Bell Creek Rd, Preston, MD 21655
    5734 Bell Creek Rd, Preston, MD 21655
    /20

    $344,000 Sold Apr 30, 2025

    5734 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2001

    Last Sold Summary

    • $279/SF
    • 4 Days On Market

    Current Estimated Value $377,358

    Last Listing Agent Katie Moore Coldwell Banker Chesapeake Real Estate Company

    5734 Bell Creek Rd, Preston, MD 21655
    • 23278 Holly Park Dr, Preston, MD 21655
      23278 Holly Park Dr, Preston, MD 21655
      23278 Holly Park Dr, Preston, MD 21655
      /43

      Est $734,721 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,711 Sq Ft

      23278 Holly Park Dr, Preston, MD 21655

      23278 Holly Park Dr, Preston, MD 21655
  • 23209 Gilpin Point Rd, Preston, MD 21655
    23209 Gilpin Point Rd, Preston, MD 21655
    23209 Gilpin Point Rd, Preston, MD 21655
    /8

    $470,000 Sold Jan 30, 2025

    23209 Gilpin Point Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,560 Sq Ft
    • Built 1965

    Last Sold Summary

    • $301/SF
    • 127 Days On Market

    Current Estimated Value $499,877

    Last Listing Agent rachael harrison Coldwell Banker Realty

    23209 Gilpin Point Rd, Preston, MD 21655
    • 5577 Harmony Woods Dr, Preston, MD 21655
      5577 Harmony Woods Dr, Preston, MD 21655
      5577 Harmony Woods Dr, Preston, MD 21655
      /47

      Est $512,933 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
  • 116 Maple Ave, Preston, MD 21655
    116 Maple Ave, Preston, MD 21655
    116 Maple Ave, Preston, MD 21655
    /5

    $238,000 Sold Sep 24, 2025

    116 Maple Ave, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft
    • Built 1915

    Last Sold Summary

    • $163/SF
    • 69 Days On Market

    Current Estimated Value $244,101

    Last Listing Agent Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
    • 109 Sunset Blvd, Preston, MD 21655
      109 Sunset Blvd, Preston, MD 21655
      109 Sunset Blvd, Preston, MD 21655
      /46

      Est $359,829 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft

      109 Sunset Blvd, Preston, MD 21655

      109 Sunset Blvd, Preston, MD 21655
  • 3181 Gallagher Rd, Preston, MD 21655
    3181 Gallagher Rd, Preston, MD 21655
    3181 Gallagher Rd, Preston, MD 21655
    /15

    $265,000 Sold Aug 20, 2025

    3181 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1990

    Last Sold Summary

    • $237/SF
    • 23 Days On Market

    Current Estimated Value $277,979

    Last Listing Agent Andrew Beaven Wright Real Estate

    3181 Gallagher Rd, Preston, MD 21655

Showing Results 41 - 80, Page 2 of 18

Maryland Caroline County Preston

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group