Callaway Real Estate

Callaway Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Callaway and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

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Newest Listings in Callaway

$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
$1,100,000
This is a great opportunity to live near your business! 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 a 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. AS AN ADDED BONUS: 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. 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.

20098 Piney Point Rd, Callaway

Listing courtesy of Samson Properties. Contact: 2407246550
$279,900
15 Acres with Two Approved Building Lots – Ready to Build Exceptional opportunity to own 15 acres comprised of two approved building lots, offering flexibility for building, investment, or a family compound. Lot 1: 5-acre parcel, mostly cleared, with an approved perc site, ready for your custom home. Lot 2: 10-acre parcel featuring both cleared and wooded areas, an existing septic system, recorded perc, and engineer drawings for the septic system. Additional features include: Recorded plat available Existing gravel access road Build-ready with valuable site improvements already in place Conveniently located just minutes from shopping, dining, and major commuter routes, including close proximity to PAX Whether you're looking to build your dream home now or develop both parcels over time, this unique property offers privacy, flexibility, and a great location.

45291 Take It Easy Ranch Rd, Callaway

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$249,900
2 Beds ⋅ 3 Baths
Spacious Callaway townhome with plenty of room to make your own. The main level features an eat-in kitchen and a large living room that opens directly to the deck and private backyard. Upstairs, you’ll find two generously sized bedrooms, one with a private en suite bathroom and the other with direct access to a full hall bathroom. The finished lower level offers a versatile recreation room with space for a home office, gym, or additional living area. Recent improvements include newer backyard fencing and a roof replaced in 2022 with a 50-year warranty. Centrally located in Callaway with convenient access to shopping, dining, NAS Patuxent River, Leonardtown, and destinations throughout St. Mary’s County.

20811 Harlequin Ln, Callaway

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$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
$250,000
2 Beds ⋅ 2 Baths
Opportunity awaits on this beautiful 3.05-acre parcel tucked away on a quiet paved road in the heart of Callaway. Whether you're looking for a renovation project, a homesite to build your dream home or an investment property, this property offers incredible potential with existing infrastructure already in place. The current mobile home is in need of significant renovation or removal, making way for a fresh start on a spacious and private lot surrounded by mature trees. Existing improvements include a detached 16' x 18' garage with 100-amp electric service, an existing well and septic system, and a circular driveway for easy access and ample parking. Enjoy the convenience of a prime location just minutes from shopping, restaurants, schools, and Patuxent River Naval Air Station, while still enjoying the peace and privacy of country living.

20275 Jackson Rd, Callaway

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$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
$85,000
Discover the perfect canvas for your dream home on this 1.5-acre parcel of land, nestled in a vibrant community that offers both tranquility and convenience. Imagine waking up each day surrounded by nature, with ample space to create your own private oasis while still being just moments away from local amenities. This prime piece of land is situated in an area known for its friendly atmosphere and strong sense of community. Enjoy leisurely strolls, where neighbors greet each other with a smile. Whether you're looking to walk, bike, or simply enjoy a picnic, the options are endless. Convenience is at your fingertips with nearby shopping centers, restaurants, and cafes that cater to every taste. Local farmers' markets offer fresh produce and artisanal goods, making it easy to embrace a healthy lifestyle. This land presents an incredible opportunity to build a residence tailored to your lifestyle, with enough space for gardens, outdoor entertaining, or even a workshop. The possibilities are limited only by your imagination. Don't miss your chance to secure this exceptional property in a neighborhood that truly feels like home. Embrace the lifestyle you've always dreamed of!

Piney Point Rd, Callaway

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
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