2,392

Preston, MD Homes

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  • /41

    $329,000

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

    4215 Preston Rd, Preston, MD 21655

    Price Reduction! Well built and lovingly maintained by the original owner. This 3 bedroom, 2 bath rancher featuring oak floors, central air, a brick fireplace and is situated on 1 acre. This home is conveniently located and move in ready. A new roof was installed in 2024. Nice open yard with established shade trees around the house. Three season porch for casual entertaining or enjoying a crab

    Andrew Beaven Wright Real Estate

    4215 Preston 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

    Last Listing Agent Amy Betts Coldwell Banker Realty

    6238 Bethlehem Rd, Preston, MD 21655
    • /5

      Est $98,945 Not Listed For Sale

      21373 Dover Bridge Rd, Preston, MD 21655

      • Built 1890
      21373 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • $70/SF
      • 16 Days On Market

      Last Sold Price $99,000

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /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
  • /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 $357,182

    Last Listing Agent Dawn O'Day Samson Properties

    3590 Choptank Rd, Preston, MD 21655
    • /39

      Est $438,029 Not Listed For Sale

      21303 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 3 Baths
      • 2,607 Sq Ft
      • Built 1998
      21303 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 25% Above List Price
      • $134/SF
      • 16 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /45

    $485,000

    • 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
  • /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 $490,863

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    5569 Harmony Woods Dr, Preston, MD 21655
    • /23

      Est $298,708 Not Listed For Sale

      106 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1995
      106 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • $243/SF
      • 3 Days On Market

      Last Sold Price $299,900

      Last Listing Agent Sid Campen Charles C. Powell, Inc. Realtors

  • /57

    $495,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    7837 Shore Dr, Preston, MD 21655

    Two Johns – Charming Home in a Sought-After Waterfront Community Nestled between Preston and Denton in the desirable Two Johns subdivision, this beautifully maintained 4-bedroom, 2.5-bath home offers a rare blend of comfort, style, and location. Just a few houses away from the public boat landing, residents enjoy easy water access for boating, kayaking, or fishing. Take in serene water views from

    Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, 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

    Current Estimated Value $929,441

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • /53

      Est $393,417 Not Listed For Sale

      230 Main St, Preston, MD 21655

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft
      • Built 1890
      230 Main St, Preston, MD 21655

      Last Sold Summary

      • 3% Below List Price
      • $126/SF
      • 7 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Shane Slacum LPT Realty, LLC

  • /35

    $350,000

    • 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
  • /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

    Current Estimated Value $315,342

    Last Listing Agent Brooke Tephabock LPT Realty, LLC

    3622 Choptank Rd, Preston, MD 21655
    • /17

      Est $284,032 Not Listed For Sale

      104 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft
      • Built 1995
      104 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 11% Above List Price
      • $206/SF
      • 76 Days On Market

      Last Sold Price $255,000

      Last Listing Agent Amy Endzel Keller Williams Select Realtors of Annapolis

  • /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
  • /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
    • /60

      Est $368,768 Not Listed For Sale

      240 Main St, Preston, MD 21655

      • 4 Beds
      • 3 Baths
      • 2,088 Sq Ft
      • Built 1910
      240 Main St, Preston, MD 21655

      Last Sold Summary

      • 5% Above List Price
      • $168/SF
      • 24 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Dave Luptak Long & Foster

  • /29

    $434,000

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

    23116 Gilpin Point Rd, Preston, MD 21655

    A perfectly situated, water-oriented, turnkey, rancher with a piece of country 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. A second greenhouse area is framed and ready for a canopy.

    Edward Cartwright Benson & Mangold, LLC

    23116 Gilpin Point 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 $1,071,417

    Last Listing Agent Nick Campanaro The Land Group

    5890 Harmony Rd, Preston, MD 21655
    • /14

      Est $356,360 Not Listed For Sale

      111 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft
      • Built 1974
      111 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 6% Above List Price
      • $162/SF
      • 323 Days On Market

      Last Sold Price $335,000

      Last Listing Agent Barbara Nichols Results Realty Inc.

  • /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
  • /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 $431,529

    Last Listing Agent Brenda Fornos Taylor Properties

    4808 Frazier Neck Rd, Preston, MD 21655
    • /38

      Est $242,221 Not Listed For Sale

      113 Noble Ave, Preston, MD 21655

      • 2 Beds
      • 1 Bath
      • 1,314 Sq Ft
      • Built 1910
      113 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 1% Above List Price
      • $183/SF
      • 18 Days On Market

      Last Sold Price $239,900

      Last Listing Agent Benjamin Daniels The KW Collective

  • /33

    $369,000

    • 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
  • /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 $349,772

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • /14

      Est $382,667 Not Listed For Sale

      107 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2023
      107 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 8% Above List Price
      • $181/SF
      • 154 Days On Market

      Last Sold Price $352,800

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /33

    $365,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,503 Sq Ft

    22285 Tanyard Rd, Preston, MD 21655

    Tucked away just outside of town, this charming 3-bedroom, 2-bathroom home offers the perfect blend of privacy and space on a beautiful 4-acre property. The land features a mix of open, cleared yard and mature woods, providing both room to roam and a peaceful natural setting. Inside, the home offers a comfortable and functional layout, ideal for everyday living. One of the bedrooms includes a

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    22285 Tanyard Rd, 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 $473,205

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    4631 Everlea Ct, Preston, MD 21655
    • /74

      Not Listed For Sale

      4439 Bethlehem Rd, Preston, MD 21655

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft
      • Built 1900
      4439 Bethlehem Rd, Preston, MD 21655

      Last Sold Summary

      • 33% Below List Price
      • $326/SF
      • 106 Days On Market

      Last Sold Price $835,000

      Last Listing Agent Mickey Hayward Sunset Properties

  • /39

    $525,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,184 Sq Ft

    24111 Friendship Rd, Preston, MD 21655

    Welcome to 24111 Friendship Rd in Preston, MD, a beautifully maintained 3-bedroom, 2-bath rancher set on a peaceful 2-acre wooded lot. This classic home offers timeless brick accents, a large paved driveway, and a two-car attached garage, along with both a storage shed and a spacious storage building for added flexibility. Inside, you’ll find a formal living room and a formal dining room enhanced

    Billy Mister Keller Williams Realty

    24111 Friendship 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
    • /6

      Est $267,537 Not Listed For Sale

      105 Chamber St, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 2024
      105 Chamber St, Preston, MD 21655

      Last Sold Summary

      • 1% Below List Price
      • $237/SF

      Last Sold Price $269,900

      Last Listing Agent Sean Steward Century 21 Home Team Realty

  • /11

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21090 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture. There is even a storage shed on the property.

    Eddie Matthews Benson & Mangold, LLC

    21090 Marsh Creek 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 $375,875

    Last Listing Agent Benjamin Alder The Land Group

    4516 Frazier Neck Rd, Preston, MD 21655
    • /31

      Not Listed For Sale

      22510 Ash Blvd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1999
      22510 Ash Blvd, Preston, MD 21655

      Last Sold Summary

      • $129/SF
      • 4 Days On Market

      Last Sold Price $208,250

      Last Listing Agent Brooke Tephabock LPT Realty, LLC

  • /19

    $339,000

    • 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
  • /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
    • /58

      Est $485,239 Not Listed For Sale

      4925 Edmondson Creek Rd, Preston, MD 21655

      • 4 Beds
      • 3 Baths
      • 1,988 Sq Ft
      • Built 1981
      4925 Edmondson Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 12% Below List Price
      • $277/SF
      • 27 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Thomas Lucks Keller Williams Realty

  • /12

    $99,900

    • 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

Showing Results 1 - 40, Page 1 of 18

Home Trends in Preston, MD

Housing Trends

Median Sale Price
$344,000
Median Single Family Sale Price
$341,500
Average Price Per Sq Ft
$204
Number of Homes for Sale
19
Last 12 months Home Sales
41
Months of Supply
5.60
Median List Price
$352,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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