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Preston, MD Homes for Sale

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  • 282 Tidewater Cir, Preston, MD 21655
    282 Tidewater Cir, Preston, MD 21655
    282 Tidewater Cir, Preston, MD 21655
    /33

    $449,000

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft

    282 Tidewater Cir, Preston, MD 21655

    Step into this absolutely beautiful 2-story home with a basement, where pride of ownership shines from the moment you walk through the front door. Offering approximately 3,900 finished square feet, this home features stylish LVP flooring and cozy carpet throughout, with spacious bedrooms and a layout that’s both functional and inviting. The heart of the home is the large kitchen, complete with

    Heather Brummell Keller Williams Realty

    282 Tidewater Cir, 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
  • 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
  • 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
  • 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 and minutes to Easton. The single-level home features 3 bedrooms and 2 full bathrooms, a country kitchen, and an open-concept layouthighlighted by a massive brick fireplace with insert and

    Alex Martinez The Agency DC

    20915 Dover Bridge Rd, Preston, MD 21655
  • 21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    21405 Tanyard Rd, Preston, MD 21655
    /43

    $375,000

    • 3 Beds
    • 2.5 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 3-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
  • 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
  • 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
  • 5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    /2

    $359,000 Coming Soon

    • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
Maryland Caroline County Preston

Real Estate & Homes for Sale in Preston, MD

Why Live in Preston

Buyers can find modest single-family homes and farmettes among Preston’s small-town streets and outlying cornfields. “Farming is big still; we have a lot of old farms still operating to this day,” says Mary Mabry, an Eastern Shore native and ...

Learn more about living in Preston

Frequently Asked Questions

What is the average home price in Preston, MD?
Homes for sale in Preston, MD have an average home price of $429,333.
How many homes have sold over the last 12 months in Preston, MD?
44 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, 21629 and 21632.
How much do you need to make to afford a house in Preston?
The median home price in Preston is $328,500. If you put a 20% down payment of $65,700 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $1,630 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $70K 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 45 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
$325,000
Average Price Per Sq Ft
$199
Number of Homes for Sale
16
Last 12 months Home Sales
44
Months of Supply
4.40
Median List Price
$328,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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