29

Homes for Sale in 21655

Section Image Section Image
  • 128 Main St, Preston, MD 21655
    128 Main St, Preston, MD 21655
    /2

    $459,900

    Coming Soon
    • 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
  • 106 Main St, Preston, MD 21655
    106 Main St, Preston, MD 21655
    106 Main St, Preston, MD 21655
    /31

    $310,000

    Open Sun 12PM - 2PM
    • 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
  • 3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    /3

    $259,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,787 Sq Ft

    3675 Seaman Rd, Preston, MD 21655

    3 bedroom, 2 bath rancher. Quiet, rural setting that's approximately 15 minutes from Easton and less than 1 hour from MD/DE beaches. More info and photos next week.

    Andrew Beaven Wright Real Estate

    3675 Seaman Rd, Preston, MD 21655
  • 3720 Payne Rd, Preston, MD 21655
    3720 Payne Rd, Preston, MD 21655
    3720 Payne Rd, Preston, MD 21655
    /42

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    3720 Payne Rd, Preston, MD 21655

    Welcome to your private countryside retreat on over 18 acres in the heart of Caroline County. This charming farmhouse-style home offers 4 bedrooms and 2.5 baths with over 2,300 sq ft of living space, combining comfort and functionality in a peaceful rural setting. The property features a mix of open land and wooded acreage, including over 6 acres in Forest Conservation, providing both privacy and

    Heather Brummell Keller Williams Realty

    3720 Payne Rd, Preston, MD 21655
  • 4310 Bethlehem Rd, Preston, MD 21655
    4310 Bethlehem Rd, Preston, MD 21655
    4310 Bethlehem Rd, Preston, MD 21655
    /16

    $129,000

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft

    4310 Bethlehem Rd, Preston, MD 21655

    Investment opportunity or enjoy a very private (1) one acre country location to develop and enjoy. Oportities to improve and / or expand this small cottage home. Included is a solid (2) two car detached garage. PR believes septic drain fields have failed and well is original to 1976. This is an estate sale.

    James Bent Benson & Mangold, LLC

    4310 Bethlehem Rd, Preston, MD 21655
  • 6101 Bethlehem Rd, Preston, MD 21655
    6101 Bethlehem Rd, Preston, MD 21655
    6101 Bethlehem Rd, Preston, MD 21655
    /36

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft

    6101 Bethlehem Rd, Preston, MD 21655

    *Please note Mother Nature has blessed this house with baby birds at the entrance, Showings are put off till the 8th of May, this should give the little feather family time to move on. Searching for quiet and private yet close to everything home - you just found it! Three bedroom rancher sits on 1.37 acres overlooking farmland makes this a very special find. Very well maintained and updated house

    Kat Thompson Benson & Mangold, LLC.

    6101 Bethlehem Rd, Preston, MD 21655
  • 147 Mill St, Preston, MD 21655
    147 Mill St, Preston, MD 21655
    147 Mill St, Preston, MD 21655
    /33

    $339,900

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

    147 Mill St, Preston, MD 21655

    Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

    Kathleen Brenton Brenton Realty Group

    147 Mill St, Preston, MD 21655
  • 3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    /76

    $875,000

    • 4 Beds
    • 3 Baths
    • 3,149 Sq Ft

    3547 Prchal Rd, Preston, MD 21655

    Pride of ownership shines throughout this beautifully appointed home set on over 4 acres, including approximately 2.5 wooded acres with peaceful walking trails —or a great spot for hunting already equipped with a deer stand.A major renovation in 2006 nearly doubled the living space, transforming the property into a spacious 4-bedroom, 3-bathroom residence designed for both comfortable living

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • 156 Main St, Preston, MD 21655
    156 Main St, Preston, MD 21655
    156 Main St, Preston, MD 21655
    /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
  • 112 Noble Ave, Preston, MD 21655
    112 Noble Ave, Preston, MD 21655
    /2

    $210,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    112 Noble Ave, Preston, MD 21655

    Investor Alert! 100% occupied duplex with a 2 bedroom, 1 bath downstairs and a 1 bedroom 1 bath upstairs. Situated in the heart of Preston and close proximity to the school.

    Chuck Mangold Benson & Mangold, LLC

    112 Noble Ave, Preston, MD 21655
  • 7844 Shore Dr, Preston, MD 21655
    7844 Shore Dr, Preston, MD 21655
    7844 Shore Dr, Preston, MD 21655
    /30

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft

    7844 Shore Dr, Preston, MD 21655

    Unplug from the hustle and bustle in this well maintained one floor home on the banks of the Choptank River. The views of the native wetlands and its wildlife are unique and beautiful in a way only mother nature can create. The spacious and quiet yard receives abundant sunlight and could provide for amazing gardening opportunities. An old dock remains in need of extensive repair but the next

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    7844 Shore Dr, Preston, MD 21655
  • Parcel 15 Newton Rd, 4, Preston, MD 21655
    Parcel 15 Newton Rd, 4, Preston, MD 21655
    Parcel 15 Newton Rd, 4, Preston, MD 21655
    /20

    $175,000

    • Land
    • 6.3 Acres
    • $27,778 per Acre

    Parcel 15 Newton Rd, 4, Preston, MD 21655

    Discover the perfect blend of privacy and waterfront living with this 6.3-acre parcel on Newton Rd in Denton, MD. This beautiful wooded lot offers a serene setting with direct water views, making it ideal for building your dream home or a peaceful weekend retreat. The property is already perc-approved, saving you time and bringing you one step closer to construction. Enjoy nature, abundant

    Brent Starling Blackwell Real Estate, LLC

    Parcel 15 Newton Rd, 4, Preston, MD 21655
  • 7392 Todds Wharf Rd, Preston, MD 21655
    7392 Todds Wharf Rd, Preston, MD 21655
    7392 Todds Wharf Rd, Preston, MD 21655
    /63

    $407,500

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This comfortable rancher with a large above-ground pool with direct access to sunroom and into the home without getting feet dirty (yeah)! Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Working wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance. Convenient mudroom off garage with washer and dryer on

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (667) 843-7490

    7392 Todds Wharf Rd, Preston, MD 21655
  • 7192 American Corner Rd, Denton, MD 21629
    7192 American Corner Rd, Denton, MD 21629
    7192 American Corner Rd, Denton, MD 21629
    /37

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft

    7192 American Corner Rd, Denton, MD 21629

    Come make this updated and move in ready rancher your new home. Considerable improvements have been made over the last two years to include the following. This home has a new deep well, new septic system, new tankless propane water heater, new washer/dryer. new range and refrigerator, new roof, new siding, new hvac, renovated bathroom, new flooring, fresh paint, new privacy and chain link fencing

    Andrew Beaven Wright Real Estate

    7192 American Corner Rd, Denton, MD 21629
  • 215 Apple Ln, Preston, MD 21655
    215 Apple Ln, Preston, MD 21655
    215 Apple Ln, Preston, MD 21655
    /33

    $354,900

    $14K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    215 Apple Ln, Preston, MD 21655

    Welcome to this beautiful 3-bedroom, 2-bathroom home filled with wonderful updates throughout. As you arrive, you’ll immediately notice the brand-new roof, offering peace of mind for years to come. Step inside to discover a stunning updated kitchen featuring quartz countertops and stainless steel appliances, perfect for both everyday living and entertaining. With spring just around the corner,

    Amy Endzel Keller Williams Select Realtors of Annapolis

    215 Apple Ln, Preston, MD 21655
  • 22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    /45

    $469,900

    $25K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Enjoy peace and space on two tranquil country acres with no deed restrictions adjacent to open farmland. The deep backyard features a large vinyl-fenced area ideal for kids and pets, an above-ground pool with deck perfect for summer fun. This lovely home offers 2,667 Square feet (estimated) of living space, new LVP flooring on the main floor, and a versitile loft upstairs. The spacious

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • 21611 Everlea Dr, Preston, MD 21655
    21611 Everlea Dr, Preston, MD 21655
    21611 Everlea Dr, Preston, MD 21655
    /13

    $339,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    21611 Everlea Dr, Preston, MD 21655

    Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style.

    Nicole Giordano Coldwell Banker Waterman Realty

    21611 Everlea Dr, Preston, MD 21655
  • 23116 Gilpin Point Rd, Preston, MD 21655
    23116 Gilpin Point Rd, Preston, MD 21655
    23116 Gilpin Point Rd, Preston, MD 21655
    /31

    $399,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    23116 Gilpin Point Rd, Preston, MD 21655

    Improved price on a perfectly situated, water-oriented, turnkey, rancher with a piece of country that is ready for your enjoyment. Produce your own vegetables, flowers or the like in the already established rear garden beds, collect your peaches, pears and other fruits from fruit bearing trees. Start your plants early in an enclosed greenhouse/produce stand. Complete your 4H projects. A second

    Edward Cartwright Benson & Mangold, LLC

    23116 Gilpin Point Rd, Preston, MD 21655
  • 5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    /23

    $310,000

    $49K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    5026 Bethlehem Rd, Preston, MD 21655

    MAJOR PRICE IMPROVEMENT!!! 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

    Linda Moore Long & Foster Real Estate, Inc.

    5026 Bethlehem Rd, Preston, MD 21655
  • 0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    /4

    $20,000

    • Land
    • 21,780 Sq Ft
    • $40,000 per Acre

    0 Nelpine Rd, Preston, MD 21655

    Discover a hidden gem on Nelpine Rd, a 0.50-acre property located in a small community just north of Preston off Harmony Road. This half-acre of vacant land is a blank canvas awaiting your vision. Whether you're a developer, an investor, or someone looking to build a personal sanctuary, this property offers limitless potential. Only 15 minutes to Choptank River, 20 minutes to Easton, under an

    ryan byrd Coldwell Banker Realty

    0 Nelpine Rd, Preston, MD 21655
  • 126 Maple Ave, Preston, MD 21655
    126 Maple Ave, Preston, MD 21655
    126 Maple Ave, Preston, MD 21655
    /23

    $224,000

    $6K PRICE DROP
    • 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
  • 103 Chambers St, Preston, MD 21655
    103 Chambers St, Preston, MD 21655
    103 Chambers St, Preston, MD 21655
    /12

    $89,900

    $45K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chambers St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chambers St, 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
  • lot 6 Harmony Woods Dr, Preston, MD 21655
    lot 6 Harmony Woods Dr, Preston, MD 21655
    /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
  • 2697 Choptank Main St, Preston, MD 21655
    2697 Choptank Main St, Preston, MD 21655
    2697 Choptank Main St, Preston, MD 21655
    /37

    $279,000

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • 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
  • 162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    /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
  • 22403 Marsh Creek Rd, Preston, MD 21655
    22403 Marsh Creek Rd, Preston, MD 21655
    22403 Marsh Creek Rd, Preston, MD 21655
    /35

    $379,900

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • 23547 Jonestown Ln, Preston, MD 21655
    23547 Jonestown Ln, Preston, MD 21655
    23547 Jonestown Ln, Preston, MD 21655
    /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
Maryland Caroline County Preston 21655

Real Estate & Homes for Sale in 21655

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

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