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Newest Homes for Sale in Preston, MD

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  • 4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    /6

    $2,999,000

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

    4218 Harmony Rd, Preston, MD 21655

    PROFESSIONAL PHOTOS COMING SOON. CHECK WITH LISTING AGENT FOR MORE DETAILS. A True Eastern Shore Estate! Experience unparalleled living at this magnificent 58+ acre Preston estate, an extraordinary opportunity to own a property that perfectly blends luxury, comfort, and versatility. The stately main residence features 5 bedrooms, 6 full and 3 half baths, and an impressive foyer with a grand

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • 4305 Langrell Rd, Preston, MD 21655
    4305 Langrell Rd, Preston, MD 21655
    4305 Langrell Rd, Preston, MD 21655
    /35

    $399,000

    • 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
  • 5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    /50

    $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
  • 6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    /5

    $198,500

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

    6561 Bell Creek Rd, Preston, MD 21655

    Looking for peace, privacy, and wide-open views?Escape the subdivision life — no HOA, no close neighbors, just you and open fields. This charming property, tucked back from the road and surrounded by farmland, has been lovingly held since 1972. Traditional styling and ready for a your new chapter. The home is livable, but will not qualify for USDA, Rural Home or VA. Pinterest, AI and bring

    Barbara Dayton Long & Foster Real Estate, Inc.

    6561 Bell Creek Rd, Preston, MD 21655
  • 3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    /7

    $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
  • 4215 Preston Rd, Preston, MD 21655
    4215 Preston Rd, Preston, MD 21655
    4215 Preston Rd, Preston, MD 21655
    /15

    $359,000 Coming Soon

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

    4215 Preston Rd, Preston, MD 21655

    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
  • 21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    /43

    $440,000

    • 4 Beds
    • 3 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 4-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
  • 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
  • 212 Main St, Preston, MD 21655
    212 Main St, Preston, MD 21655
    212 Main St, Preston, MD 21655
    /56

    $320,000

    • 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

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • 21090 Marsh Creek Rd, Preston, MD 21655
    21090 Marsh Creek Rd, Preston, MD 21655
    21090 Marsh Creek Rd, Preston, MD 21655
    /10

    $299,900

    • 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.

    Eddie Matthews Benson & Mangold, LLC

    21090 Marsh Creek Rd, Preston, MD 21655
  • 21084 Marsh Creek Rd, Preston, MD 21655
    21084 Marsh Creek Rd, Preston, MD 21655
    21084 Marsh Creek Rd, Preston, MD 21655
    /9

    $299,900

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

    21084 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.

    Eddie Matthews Benson & Mangold, LLC

    21084 Marsh Creek Rd, Preston, MD 21655
  • 7837 Shore Dr, Preston, MD 21655
    7837 Shore Dr, Preston, MD 21655
    7837 Shore Dr, Preston, MD 21655
    /57

    $529,000

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

    7837 Shore Dr, Preston, MD 21655

    Two Johns – Charming Home in a Sought-After Waterfront CommunityNestled 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

    Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, Preston, MD 21655
  • 7844 Shore Dr, Preston, MD 21655
    7844 Shore Dr, Preston, MD 21655
    7844 Shore Dr, Preston, MD 21655
    /39

    $750,000

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

    7844 Shore Dr, Preston, MD 21655

    Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    7844 Shore 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
    /14

    $279,000

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

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD Additional Photos coming. This home is currently getting a fresh coat of interior paint, new appliances and updates coming. It will be turn key ready for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • 158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    /34

    $245,000

    • 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
  • 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
  • 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
  • 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
  • 22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    /51

    $525,000

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Two Tranquil Country Acres with No Restrictions, backs to open farmland. Deep Back Yard includes an above ground pool with a deck for your summer enjoyment, large vinyl fenced area for pets and kids, more fenced area for farm animals (pets) and includes a shooting mound should that be of interest. This lovely home Boasts 2,667 Sq. Ft. of Family Space with new LVP flooring though out

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, 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

    $525,000

    • Land
    • 63.16 Acres
    • $8,312 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
  • 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. New Well and septic being installed. Upgrades include new windows, CAC, new roof new electric service and plumbing

    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

Newest Listings for Sale in Preston, MD

Frequently Asked Questions

What is the average home price in Preston, MD?
Homes for sale in Preston, MD have an average home price of $457,616.
How many homes have sold over the last 12 months in Preston, MD?
48 homes have sold in Preston, MD over the last 12 months.
What are the most popular zip codes in Preston, MD?
The most popular zip codes in Preston, MD include 21655, 21643, 21632, 21629 and 21601.
How much do you need to make to afford a house in Preston?
The median home price in Preston is $344,450. If you put a 20% down payment of $68,900 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $1,700 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $73K a year to afford the median home price in Preston. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Preston, MD?
Preston, MD has highly rated public and private schools. Some of the best schools in Preston based on Niche Grades are Preston Elementary School, Colonel Richardson Middle School and Colonel Richardson High School. Browse all the schools in Preston, MD to learn more.

Home Trends in Preston, MD

On average, homes in Preston, MD sell after 54 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 $338,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$338,000
Median Single Family Sale Price
$338,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
20
Last 12 months Home Sales
48
Months of Supply
5.00
Median List Price
$344,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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