Preston, MD Houses for Sale

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

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

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

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

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

Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style.

Nicole Giordano Coldwell Banker Waterman Realty

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

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.

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

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.

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

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

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

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

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

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

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

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.

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

Spacious 4-bedroom, 2 full and 1 half bath home located in desirable Preston, MD. This property offers the perfect blend of comfort and functionality, featuring a 3-car heated garage, central air, and a heat pump for year-round efficiency. Enjoy outdoor living with a deck complete with awning, a large yard supported by an underground irrigation system, and an additional shed for storage. Inside,

Katie Moore Coldwell Banker Chesapeake Real Estate Company

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.