2,394

Preston, MD Homes

Section Image
  • 103 Chamber St, Preston, MD 21655
    103 Chamber St, Preston, MD 21655
    103 Chamber St, Preston, MD 21655
    /12

    $125,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chamber 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 Chamber St, Preston, MD 21655
  • 22721 Marsh Creek Rd, Preston, MD 21655
    22721 Marsh Creek Rd, Preston, MD 21655
    22721 Marsh Creek Rd, Preston, MD 21655
    /28

    $2,100 per month

    • 4 Beds
    • 2 Baths
    • 2,688 Sq Ft
    • House for Rent

    22721 Marsh Creek Rd, Preston, MD 21655

    Enjoy the unique charm of country living in this spacious 4-bedroom, 2-bathroom Sears Farmhouse. Situated on one acre, this farmhouse offers picturesque views of an active farm. This home has classic farmhouse feel featuring generous rooms filled with natural light. The main level includes a large living room, a family room, kitchen, sunroom and a full bath. This house radiates vintage charm with

    Lisa Lynch Keller Williams Realty

    22721 Marsh Creek Rd, Preston, MD 21655
  • 6238 Bethlehem Rd, Preston, MD 21655
    6238 Bethlehem Rd, Preston, MD 21655
    6238 Bethlehem Rd, Preston, MD 21655
    /37

    $238,000 Sold Oct 07, 2025

    6238 Bethlehem Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,234 Sq Ft
    • Built 1875

    Last Sold Summary

    • $193/SF
    • 34 Days On Market

    Current Estimated Value $361,620

    Last Listing Agent Amy Betts Coldwell Banker Realty

    6238 Bethlehem Rd, Preston, MD 21655
    • 24207 Mallow Dr, Preston, MD 21655
      24207 Mallow Dr, Preston, MD 21655
      24207 Mallow Dr, Preston, MD 21655
      /18

      Est $368,080 Not Listed For Sale

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

      24207 Mallow Dr, Preston, MD 21655

      24207 Mallow Dr, Preston, MD 21655
  • 0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    /22

    $510,000

    • Land
    • 63.16 Acres
    • $8,075 per Acre

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    Dover Bridge Road | Preston, MarylandThis 63 ± acre parcel on Dover Bridge Road offers a rare opportunity to own a sizeable tract of woodland conveniently located just four miles from Preston, seven and a half miles from Easton, and about fifteen minutes from Route 50.The property is perc-approved for residential use and includes a forestry management plan documenting that roughly 58

    Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
  • 3590 Choptank Rd, Preston, MD 21655
    3590 Choptank Rd, Preston, MD 21655
    3590 Choptank Rd, Preston, MD 21655
    /44

    $355,000 Sold Aug 29, 2025

    3590 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1994

    Last Sold Summary

    • $241/SF
    • 32 Days On Market

    Current Estimated Value $377,560

    Last Listing Agent Dawn O'Day Samson Properties

    3590 Choptank Rd, Preston, MD 21655
    • 21373 Dover Bridge Rd, Preston, MD 21655
      21373 Dover Bridge Rd, Preston, MD 21655
      21373 Dover Bridge Rd, Preston, MD 21655
      /5

      Est $108,075 Not Listed For Sale

      21373 Dover Bridge Rd, Preston, MD 21655

      21373 Dover Bridge Rd, Preston, MD 21655
  • 3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    /46

    $875,000 Coming Soon

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

    3547 Prchal Rd, Preston, MD 21655

    Pride of ownership shines throughout this home, lovingly maintained since 1992. A major renovation in 2006 nearly doubled the living space, transforming this property into a spacious 4-bedroom, 3-bathroom home ideal for comfortable living and entertaining.The impressive 20' x 27' kitchen is the heart of the home, featuring cherry cabinetry, quartz countertops, a walk-in pantry, and a cozy

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • 5569 Harmony Woods Dr, Preston, MD 21655
    5569 Harmony Woods Dr, Preston, MD 21655
    5569 Harmony Woods Dr, Preston, MD 21655
    /52

    $470,000 Sold Jun 11, 2025

    5569 Harmony Woods Dr, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft
    • Built 2005

    Last Sold Summary

    • $162/SF
    • 185 Days On Market

    Current Estimated Value $513,963

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    5569 Harmony Woods Dr, Preston, MD 21655
    • 21303 Dover Bridge Rd, Preston, MD 21655
      21303 Dover Bridge Rd, Preston, MD 21655
      21303 Dover Bridge Rd, Preston, MD 21655
      /39

      Est $392,624 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,607 Sq Ft

      21303 Dover Bridge Rd, Preston, MD 21655

      21303 Dover Bridge Rd, Preston, MD 21655
  • 158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    /34

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    158 Wright St, Preston, MD 21655
  • 3069 Choptank Rd, Preston, MD 21655
    3069 Choptank Rd, Preston, MD 21655
    3069 Choptank Rd, Preston, MD 21655
    /88

    $930,000 Sold Sep 30, 2025

    3069 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,512 Sq Ft
    • Built 2003

    Last Sold Summary

    • $370/SF
    • 11 Days On Market

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • 106 Noble Ave, Preston, MD 21655
      106 Noble Ave, Preston, MD 21655
      106 Noble Ave, Preston, MD 21655
      /23

      Est $324,698 Not Listed For Sale

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

      106 Noble Ave, Preston, MD 21655

      106 Noble Ave, Preston, MD 21655
  • 4215 Preston Rd, Preston, MD 21655
    4215 Preston Rd, Preston, MD 21655
    4215 Preston Rd, Preston, MD 21655
    /40

    $329,000

    • 3 Beds
    • 2 Baths
    • 1,642 Sq Ft

    4215 Preston Rd, Preston, MD 21655

    Price Reduction! Well built and lovingly maintained 3 bedroom, 2 bath rancher on 1 acre. New roof installed 2024. Nice open yard with established shade trees around the house. Small barn at rear of the property.

    Andrew Beaven Wright Real Estate

    4215 Preston Rd, Preston, MD 21655
  • 3622 Choptank Rd, Preston, MD 21655
    3622 Choptank Rd, Preston, MD 21655
    3622 Choptank Rd, Preston, MD 21655
    /44

    $295,900 Sold Dec 31, 2025

    3622 Choptank Rd, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,700 Sq Ft
    • Built 1961

    Last Sold Summary

    • $174/SF
    • 2 Days On Market

    Last Listing Agent Brooke Tephabock VYBE Realty

    3622 Choptank Rd, Preston, MD 21655
    • 230 Main St, Preston, MD 21655
      230 Main St, Preston, MD 21655
      230 Main St, Preston, MD 21655
      /53

      Est $446,201 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft

      230 Main St, Preston, MD 21655

      230 Main St, 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
  • 22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    /46

    $348,000 Sold Oct 14, 2025

    22490 Ash Blvd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2001

    Last Sold Summary

    • $188/SF
    • 22 Days On Market

    Last Listing Agent Kathryn Tennant Douglas Realty, LLC

    22490 Ash Blvd, Preston, MD 21655
    • 104 Noble Ave, Preston, MD 21655
      104 Noble Ave, Preston, MD 21655
      104 Noble Ave, Preston, MD 21655
      /17

      Est $303,771 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft

      104 Noble Ave, Preston, MD 21655

      104 Noble Ave, 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
    • 0.33 Acre
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • 5890 Harmony Rd, Preston, MD 21655
    5890 Harmony Rd, Preston, MD 21655
    5890 Harmony Rd, Preston, MD 21655
    /11

    $1,050,000 Sold May 16, 2025

    5890 Harmony Rd, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1920

    Last Sold Summary

    • $464/SF
    • 6 Days On Market

    Current Estimated Value $1,122,331

    Last Listing Agent Nick Campanaro The Land Group

    5890 Harmony Rd, Preston, MD 21655
    • 240 Main St, Preston, MD 21655
      240 Main St, Preston, MD 21655
      240 Main St, Preston, MD 21655
      /60

      Est $361,852 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,088 Sq Ft

      240 Main St, Preston, MD 21655

      240 Main St, 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
  • 4808 Frazier Neck Rd, Preston, MD 21655
    4808 Frazier Neck Rd, Preston, MD 21655
    4808 Frazier Neck Rd, Preston, MD 21655
    /30

    $435,000 Sold Aug 11, 2025

    4808 Frazier Neck Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1920

    Last Sold Summary

    • $275/SF
    • 88 Days On Market

    Current Estimated Value $454,685

    Last Listing Agent Brenda Fornos Taylor Properties

    4808 Frazier Neck Rd, Preston, MD 21655
    • 111 Fooks Ave, Preston, MD 21655
      111 Fooks Ave, Preston, MD 21655
      111 Fooks Ave, Preston, MD 21655
      /14

      Est $383,987 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft

      111 Fooks Ave, Preston, MD 21655

      111 Fooks Ave, Preston, MD 21655
  • 3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    /35

    $289,900

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

    3675 Seaman Rd, Preston, MD 21655

    Charming Eastern Shore property set on a peaceful stretch of Seaman’s Road in Preston, MD. Enjoy the tranquility of country living with convenient access to nearby towns, outdoor recreation, and local amenities. A great opportunity for those seeking space, privacy, and small-town charm.

    Brian Jones Keller Williams Select Realtors of Annapolis

    3675 Seaman Rd, Preston, MD 21655
  • 24316 Auction Rd, Preston, MD 21655
    24316 Auction Rd, Preston, MD 21655
    24316 Auction Rd, Preston, MD 21655
    /33

    $350,000 Sold Sep 26, 2025

    24316 Auction Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1975

    Last Sold Summary

    • $243/SF
    • 19 Days On Market

    Current Estimated Value $372,843

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • 113 Noble Ave, Preston, MD 21655
      113 Noble Ave, Preston, MD 21655
      113 Noble Ave, Preston, MD 21655
      /38

      Est $261,865 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,314 Sq Ft

      113 Noble Ave, Preston, MD 21655

      113 Noble Ave, Preston, MD 21655
  • 21269 Dover Bridge Rd, Preston, MD 21655
    21269 Dover Bridge Rd, Preston, MD 21655
    21269 Dover Bridge Rd, Preston, MD 21655
    /12

    $60,000

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

    21269 Dover Bridge Rd, Preston, MD 21655

    Nestled in Dover Bridge Mobile Home Park—formerly Prettyman Manor—this double-wide manufactured home sits on one of the largest lots in this peaceful community. The property offers plenty of space and potential, with a few upcoming improvements to help set the stage for its next owner. While it could use a bit of attention, it’s a wonderful opportunity to make this home your own in a quiet,

    Kelly Howard Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
  • 4631 Everlea Ct, Preston, MD 21655
    4631 Everlea Ct, Preston, MD 21655
    4631 Everlea Ct, Preston, MD 21655
    /26

    $475,000 Sold Oct 15, 2025

    4631 Everlea Ct, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 2,228 Sq Ft
    • Built 1997

    Last Sold Summary

    • $213/SF
    • 4 Days On Market

    Current Estimated Value $480,447

    Last Listing Agent Elizabeth Tryon Meredith Fine Properties

    4631 Everlea Ct, Preston, MD 21655
    • 107 Fooks Ave, Preston, MD 21655
      107 Fooks Ave, Preston, MD 21655
      107 Fooks Ave, Preston, MD 21655
      /14

      Est $394,674 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft

      107 Fooks Ave, Preston, MD 21655

      107 Fooks Ave, Preston, MD 21655
  • 3485 Gallagher Rd, Preston, MD 21655
    3485 Gallagher Rd, Preston, MD 21655
    3485 Gallagher Rd, Preston, MD 21655
    /74

    $740,000 Under Contract

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

    3485 Gallagher Rd, Preston, MD 21655

    **Accepting other offers** Situated on 4.14± private acres, this 3-bedroom, 2.5-bath home couples serene country living with exceptional craftsmanship. Inside, the first floor offers a formal dining room, large eat in kitchen with stainless steel appliances, vaulted ceiling living room with two story stone fireplace, first floor primary with walk in closet and Whirlpool tub, office with built

    Alicia Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
  • 3297 Gallagher Rd, Preston, MD 21655
    3297 Gallagher Rd, Preston, MD 21655
    3297 Gallagher Rd, Preston, MD 21655
    /72

    $320,000 Sold May 02, 2025

    3297 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1994

    Last Sold Summary

    • $207/SF
    • 84 Days On Market

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

    3297 Gallagher Rd, Preston, MD 21655
    • 4439 Bethlehem Rd, Preston, MD 21655
      4439 Bethlehem Rd, Preston, MD 21655
      4439 Bethlehem Rd, Preston, MD 21655
      /74

      Est $556,000 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft

      4439 Bethlehem Rd, Preston, MD 21655

      4439 Bethlehem Rd, Preston, MD 21655
  • 4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    /127

    $2,999,000

    • 8 Beds
    • 16 Baths
    • 9,364 Sq Ft

    4218 Harmony Rd, Preston, MD 21655

    A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • 4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    /13

    $350,000 Sold Sep 05, 2025

    4516 Frazier Neck Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1969

    Last Sold Summary

    • $333/SF
    • 5 Days On Market

    Current Estimated Value $370,581

    Last Listing Agent Benjamin Alder The Land Group

    4516 Frazier Neck Rd, Preston, MD 21655
    • 105 Chamber St, Preston, MD 21655
      105 Chamber St, Preston, MD 21655
      105 Chamber St, Preston, MD 21655
      /6

      Est $289,548 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft

      105 Chamber St, Preston, MD 21655

      105 Chamber 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

    $384,900

    • 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
  • 3345 Gallagher Rd, Preston, MD 21655
    3345 Gallagher Rd, Preston, MD 21655
    3345 Gallagher Rd, Preston, MD 21655
    /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

    Last Listing Agent Janiece Hines Crown Homes Real Estate

    3345 Gallagher Rd, Preston, MD 21655
    • 22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft

      22510 Ash Blvd, Preston, MD 21655

      22510 Ash Blvd, Preston, MD 21655

Showing Results 1 - 40, Page 1 of 18

Maryland Caroline County Preston

Real Estate & Homes

Home Trends in Preston, MD

On average, homes in Preston, MD sell after 49 days on the market compared to the national average of 53 days. The median sale price for homes in Preston, MD over the last 12 months is $324,950, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$324,950
Median Single Family Sale Price
$330,500
Average Price Per Sq Ft
$206
Number of Homes for Sale
16
Last 12 months Home Sales
44
Months of Supply
4.40
Median List Price
$338,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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