Callaway Homes for Sale

Callaway Homes for Sale

Welcome to Callaway, Maryland—a hidden gem nestled in the serene landscapes of St. Mary’s County. This charming community offers a perfect blend of small-town charm and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle. With its picturesque surroundings, Callaway is renowned for its lush greenery, scenic waterfront views, and a close-knit community that welcomes newcomers with open arms.

The heart of Callaway is its rich history and vibrant culture, with local parks and recreational areas that provide endless opportunities for outdoor activities. Enjoy a leisurely stroll along the waterfront, or spend a sunny afternoon picnicking at one of the many parks. The area is also known for its proximity to the Chesapeake Bay, offering residents a chance to indulge in boating, fishing, and other water sports.

For those considering a move to Callaway, you’ll be delighted to find a variety of homes for sale that cater to diverse tastes and budgets. From charming single-family homes with sprawling yards to modern townhouses with contemporary finishes, there’s something for everyone. Many properties boast beautiful views, spacious interiors, and easy access to local amenities, ensuring that you can enjoy the best of what this lovely community has to offer.

Whether you’re looking to settle down or invest in a vacation home, Callaway, MD, is a place where you can create lasting memories. Explore the homes for sale today and discover the perfect place to call your own in this enchanting corner of Maryland. Your dream home awaits in Callaway!

Newest Callaway Homes for Sale

$625,000
3 Beds ⋅ 3 Baths
Welcome to 20890 Aster Drive, where privacy, efficiency, and timeless charm come together on more than 4 peaceful acres in the heart of Callaway. This inviting Cape Cod offers the freedom of country living with no HOA, while providing exceptional value through major system upgrades that make homeownership both comfortable and economical. Step inside to discover a light-filled family room with soaring cathedral ceilings, abundant windows, and a cozy wood-burning fireplace that creates the perfect gathering space. The thoughtfully designed floor plan features a desirable main-level primary suite, spacious laundry room complete with cabinetry and a utility sink, and an upgraded kitchen equipped with a new refrigerator and induction range. Outside, the established landscaping and attractive hardscaping create a beautiful setting to enjoy from the welcoming wraparound front porch. A two-car attached garage and unfinished basement provide abundant storage and future possibilities. Woodworking enthusiasts will especially appreciate the basement's built-in dust collection system, making it an ideal workshop. The true value of this home lies in its extensive recent improvements. A brand-new geothermal HVAC system (2025), new 50-year architectural shingle roof (2025), and owned solar panels combine to deliver remarkably low utility costs for years to come. While a few cosmetic updates could further personalize the home, all the major investments have already been made, and the property has been meticulously maintained throughout ownership. If you've been searching for acreage, privacy, low operating costs, and a solid home with incredible potential, 20890 Aster Drive is a rare opportunity to make your own while enjoying peace of mind from day one.

20980 Aster Dr, Callaway

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$499,000
5 Beds ⋅ 4 Baths
Welcome home to this well-maintained, beautifully landscaped property offering the perfect blend of convenience, comfort, and functionality! Ideally located just minutes from shopping, dining, and Patuxent River Naval Air Station (PAX NAS), this home makes daily commuting and errands a breeze. Inside, you'll find a spacious floor plan featuring a large primary suite with a private ensuite bathroom and two walk-in closets, providing the perfect retreat at the end of the day. The kitchen is equipped with newer appliances, combining modern convenience with everyday practicality for cooking and entertaining. Step outside to enjoy the fully fenced backyard, ideal for pets, play, gardening, or relaxing in your own private outdoor oasis. The beautifully landscaped yard enhances the home's curb appeal and creates a welcoming outdoor environment. The garage is a standout feature with durable epoxy flooring and built-in shelving, offering exceptional storage and organization. For added peace of mind, the roof was replaced in 2020, making this home as dependable as it is inviting. Home has already been fully inspected by licensed home inspection company. Inspection results available upon request. Don't miss your opportunity to make it yours!

44905 Widgeon Pl, Callaway

Listing courtesy of OE Realty. Contact: 2404848887
$325,000
3 Beds ⋅ 1 Baths
Nestled on a serene 2.17-acre lot, this charming ranch-style home offers a perfect blend of comfort and nature. Surrounded by lush trees and partly wooded areas, the property provides a tranquil retreat, ideal for those seeking peace and privacy. Imagine sipping your morning coffee while enjoying views of the garden and woods from your rear yard, where you can create your own outdoor oasis. Inside, the home features three cozy bedrooms and a full bathroom, making it a delightful space for relaxation. The detached garage and gravel driveway offer ample parking and storage options. Focus on enjoying the expansive outdoor space, perfect for gardening or simply unwinding in the fresh air. This property is a rare find, making it an inviting place to call home. Embrace the opportunity to create lasting memories in this peaceful setting, where nature and comfort come together.

44911 Buck Redman Rd, Callaway

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500
$1,100,000
3 Beds ⋅ 3 Baths
Want to live near your business?! This beautiful and classic 3 bedroom, 2 and half bathroom rancher has well-maintained curb appeal and the interior to match, beginning with the flower bed enriched porch. From the front door you are greeted with a spacious living room great for relaxing and enjoying the view from the large picturesque windows. This area also includes a separate kitchen/dining room area that blends well for entertaining. The kitchen's focal point is its large island with a solid brass footrest. From the kitchen you are led to the 1.49 acre backyard with a patio area to enjoy nature. The main area of the home also has a home office, family room and pub-style game room; all can be transformed to fit your lifestyle! The laundry room includes a 3-year-old washer and dryer, powder room and build-in ironing board. On the other end of home there is a full bathroom, along with two bedrooms and a true primary suite. This primary suite is guaranteed to provide you your very own private oasis! Enter into its personal hallway that leads to a generous bedroom with two walk-in closets. The bathroom includes a double sink countertop, a soaker tub and a separate walk-in shower. It doesn't stop there! The suite extends to its very own sunroom full of windows and has a separate heating and cooling system. AS AN ADDED BONUS: This property includes a Commercial shop with ample parking space. The shop consists of a very sizable workshop area with a bay door, lobby and office areas, storage room and two restrooms. Due to the lack of use for a few years, it will need your TLC and vision. This building was originally the home of Smith's Repair. Recognized by St Mary's County Economic Development for six decades of service this would be a great location to bring your business. On the land there is also a shed with a sink as well as a 2-car garage. Perks: All structures have a new roof (2025), all building have electricity. This property is being sold As-Is. Preferred title company is Cardinal Title. Professional photos coming soon.

20098 Piney Point Rd, Callaway

Listing courtesy of Samson Properties. Contact: 2407246550
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