22

Newest Homes for Sale in Preston, MD

Section Image
  • 22285 Tanyard Rd, Preston, MD 21655
    22285 Tanyard Rd, Preston, MD 21655
    22285 Tanyard Rd, Preston, MD 21655
    /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
  • 7837 Shore Dr, Preston, MD 21655
    7837 Shore Dr, Preston, MD 21655
    7837 Shore Dr, Preston, MD 21655
    /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
  • 215 Apple Ln, Preston, MD 21655
    215 Apple Ln, Preston, MD 21655
    215 Apple Ln, Preston, MD 21655
    /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
  • 22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    22408 Hog Creek Rd, Preston, MD 21655
    /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
  • 21090 Marsh Creek Rd, Preston, MD 21655
    21090 Marsh Creek Rd, Preston, MD 21655
    21090 Marsh Creek Rd, Preston, MD 21655
    /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
  • 23116 Gilpin Point Rd, Preston, MD 21655
    23116 Gilpin Point Rd, Preston, MD 21655
    23116 Gilpin Point Rd, Preston, MD 21655
    /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
  • 5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    /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
  • 0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    /4

    $20,000

    • Land
    • 0.5 Acre
    • $40,000 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

    $227,000

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

    $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
  • 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
    /40

    $235,000

    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

    Ross Muir EXP Realty, LLC

    212 Main St, 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 kitchen cabinets. Luxury vinyl flooring will be installed in the Living Room first week of April. Updated bath vanities and many more updates. Recent updates; septic, heat pump and newer windows. Photos will be uploaded in mid April. It will

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank 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
  • 22403 Marsh Creek Rd, Preston, MD 21655
    22403 Marsh Creek Rd, Preston, MD 21655
    22403 Marsh Creek Rd, Preston, MD 21655
    /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
  • 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 $439,200.
How many homes have sold over the last 12 months in Preston, MD?
41 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, 21673, 21629 and 21632.
How much do you need to make to afford a house in Preston?
The median home price in Preston is $352,500. If you put a 20% down payment of $70,500 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,760 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $75K 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 38 days on the market compared to the national average of 55 days. The median sale price for homes in Preston, MD over the last 12 months is $344,000, up 3% from the median home sale price over the previous 12 months.

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%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group