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Newest Homes for Sale in Preston, MD

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  • 24111 Friendship Rd, Preston, MD 21655
    24111 Friendship Rd, Preston, MD 21655
    24111 Friendship Rd, Preston, MD 21655
    /39

    $525,000

    • 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
  • 21182 Marsh Creek Rd, Preston, MD 21655
    21182 Marsh Creek Rd, Preston, MD 21655
    21182 Marsh Creek Rd, Preston, MD 21655
    /20

    $60,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    21182 Marsh Creek Rd, Preston, MD 21655

    Adorable and move-in ready 3BR/2BA single-wide home located in the quiet community of Prettyman Manor. A private driveway with parking for three cars sits just steps from the front door of your new home. Step inside to an inviting open floor plan with a spacious living room featuring a cozy wood-burning stove, and a well-equipped kitchen with plenty of cabinet and counter space, plus a double

    Shane Slacum VYBE Realty

    21182 Marsh Creek Rd, Preston, MD 21655
  • 23116 Gilpin Point Rd, Preston, MD 21655
    23116 Gilpin Point Rd, Preston, MD 21655
    23116 Gilpin Point Rd, Preston, MD 21655
    /10

    $434,000 Coming Soon

    • 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 8 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
  • 0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    /4

    $19,999

    • Land
    • 0.5 Acre
    • $39,998 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

    $230,000

    • 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
  • 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,

    Donna Harrington Coldwell Banker Realty

    21269 Dover Bridge 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, just minutes from Easton.The single-level home features three bedrooms and two full bathrooms, a country kitchen, and an open-concept layout highlighted by a massive brick fireplace

    Alex Martinez The Agency DC

    20915 Dover Bridge Rd, Preston, MD 21655
  • 3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    3675 Seaman Rd, Preston, MD 21655
    /28

    $284,900

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

    $115,000

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

    $369,000

    • 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
    /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
  • 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

    $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
  • 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
    • 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
  • 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

    $499,000

    • Land
    • 63.16 Acres
    • $7,901 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. 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

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 $437,719.
How many homes have sold over the last 12 months in Preston, MD?
42 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, 21631, 21673 and 21629.
How much do you need to make to afford a house in Preston?
The median home price in Preston is $332,000. If you put a 20% down payment of $66,400 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $1,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $68K 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 46 days on the market compared to the national average of 54 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
$324,950
Average Price Per Sq Ft
$205
Number of Homes for Sale
15
Last 12 months Home Sales
42
Months of Supply
4.30
Median List Price
$332,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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