8

Callaway Homes for Sale

Section Image
  • 20098 Piney Point Rd, Callaway, MD 20620
    20098 Piney Point Rd, Callaway, MD 20620
    20098 Piney Point Rd, Callaway, MD 20620
    /67

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 5,939 Sq Ft

    20098 Piney Point Rd, Callaway, MD 20620

    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

    Shanita Kelley Samson Properties

    20098 Piney Point Rd, Callaway, MD 20620
  • 20811 Harlequin Ln, Callaway, MD 20620
    20811 Harlequin Ln, Callaway, MD 20620
    20811 Harlequin Ln, Callaway, MD 20620
    /40

    $249,900

    • 2 Beds
    • 2.5 Baths
    • 1,588 Sq Ft

    20811 Harlequin Ln, Callaway, MD 20620

    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

    Katy Galloway Century 21 Redwood Realty

    20811 Harlequin Ln, Callaway, MD 20620
  • 45168 Irvings Place, Callaway, MD 20620
    45168 Irvings Place, Callaway, MD 20620
    /2

    $177,000

    • Land
    • 4.01 Acres
    • $44,140 per Acre

    45168 Irvings Place, Callaway, MD 20620

    Build your dream home on this beautiful 4.01-acre homesite in Callaway! Primarily cleared and ready for your vision, the property offers plenty of open space while mature trees line the perimeter, providing a wonderful sense of privacy and a natural backdrop.A huge bonus—much of the groundwork is already in place! The property features an existing septic system, shared well, and

    Heather Heath Deep Roots Real Estate

    45168 Irvings Place, Callaway, MD 20620
  • 44911 Buck Redman Rd, Callaway, MD 20620
    44911 Buck Redman Rd, Callaway, MD 20620
    /2

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    44911 Buck Redman Rd, Callaway, MD 20620

    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.

    Sheila Milburn Coldwell Banker Premier

    44911 Buck Redman Rd, Callaway, MD 20620
  • 44450 Schumann Way, Leonardtown, MD 20650
    44450 Schumann Way, Leonardtown, MD 20650
    44450 Schumann Way, Leonardtown, MD 20650
    /77

    $695,000

    • 5 Beds
    • 2.5 Baths
    • 2,953 Sq Ft

    44450 Schumann Way, Leonardtown, MD 20650

    Welcome to this beautiful custom-built home situated on over 4 acres, offering an incredible combination of space, privacy, and versatility. A welcoming covered front porch and mature landscaping create beautiful curb appeal and the perfect place to sit back and enjoy the peaceful surroundings. Inside, you’ll find a thoughtfully designed floor plan featuring a main-level primary suite, spacious

    Jesieryl Hartzer CENTURY 21 New Millennium

    44450 Schumann Way, Leonardtown, MD 20650
  • 45291 Take It Easy Ranch Rd, Callaway, MD 20620
    45291 Take It Easy Ranch Rd, Callaway, MD 20620
    45291 Take It Easy Ranch Rd, Callaway, MD 20620
    /9

    $259,900

    $20K PRICE DROP
    • Land
    • 15 Acres
    • $17,327 per Acre

    45291 Take It Easy Ranch Rd, Callaway, MD 20620

    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,

    Carol Kalmus-Choporis Century 21 Redwood Realty

    45291 Take It Easy Ranch Rd, Callaway, MD 20620
  • 0 Piney Point Rd, Callaway, MD 20620
    0 Piney Point Rd, Callaway, MD 20620
    /2

    $85,000

    $10K PRICE DROP
    • Land
    • 1.5 Acres
    • $56,667 per Acre

    0 Piney Point Rd, Callaway, MD 20620

    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

    Jessica Raley CENTURY 21 New Millennium

    0 Piney Point Rd, Callaway, MD 20620
  • 20275 Jackson Rd, Callaway, MD 20620
    20275 Jackson Rd, Callaway, MD 20620
    20275 Jackson Rd, Callaway, MD 20620
    /7

    $250,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    20275 Jackson Rd, Callaway, MD 20620

    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

    Charlotte Long EXP Realty, LLC

    20275 Jackson Rd, Callaway, MD 20620
Maryland St Marys County Leonardtown

Real Estate & Homes for Sale in Callaway, Leonardtown

Why Live in Callaway
Callaway, 8 miles southeast of Leonardtown, blends rural beauty with modern convenience. Families enjoy highly rated St. Mary’s County Public Schools, including Leonardtown High, which offers career and technical programs. Naval Air Station Patuxent River is just 5 miles away, making commuting easy. Outdoor enthusiasts will love nearby St. Mary’s River State Park, a 2,450-acre haven for hiking, cycling, kayaking and fishing. Wildlife sightings range from bobcats to white-tailed deer, and the park’s Lake Loop trail is a favorite for nature lovers. Chancellor’s Run Regional Park adds sports options like basketball and pickleball, while Take It Easy Campground offers space for tents and RVs. Callaway’s housing market is competitive, with homes selling faster than the national average. Colonial Revivals and ranch-style homes dominate, often featuring large lots and wooded privacy. Prices typically range from the mid $200,000s to the low $600,000s. While the median sale price is higher than in Lexington Park, lot sizes are much larger, offering exceptional value. Dining options include Tacos Hacienda for authentic Mexican fare, El Coqui for Puerto Rican dishes and Gridiron Grill for casual pub favorites. Weis Markets meets grocery needs, and nearby Lexington Park offers additional restaurants and coffee shops. State Route 5 provides a direct route to Leonardtown, and a local bus line serves the area.
Learn more about living in Callaway

Callaway, Leonardtown, MD Home Prices vs. Nearby Neighborhoods

Callaway California Piney Point Wildewood
Median Home Price
$409,500
$399,900
$412,499
$399,450
Median Sale Price
$409,500
-9% YoY
$399,900
+8% YoY
$380,000
-16% YoY
$385,000
0% YoY
Median Single Family Price
$472,450
$420,000
$384,949
$489,990
Median Townhouse Price
$261,000
$304,000
$575,000
$368,000
Total Active Listings
4 listings
35 listings
5 listings
21 listings
Market Conditions
3 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
6 Months of Supply
Balanced Market
1 Month of Supply
Seller's Market

Frequently Asked Questions

Is Callaway a good place to live?
Callaway is a good place to live. Callaway is considered car-dependent and somewhat bikeable with minimal transit options. Callaway has 2 parks for recreational activities.It has a median age of 41. The average household income is $125,074 which is above the national average. College graduates make up 28.5% of residents. A majority of residents in Callaway are home owners, with 31% of residents renting and 69% of residents owning their home. A local real estate agent serving Callaway can help you decide if this neighborhood is the right one for you. Learn more on our Callaway neighborhood guide.
How much do you need to make to afford a house in Callaway?
The median home price in Callaway is $409,500. If you put a 20% down payment of $81,900 and had a 30-year fixed mortgage with an interest rate of 6.71%, your estimated principal and interest payment would be $2,120 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $91K a year to afford the median home price in Callaway. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Callaway is $125K.
What are the best public schools in Callaway?
The best public schools that serve Callaway are:
What are the best private schools in Callaway?
The best private schools that serve Callaway are:
What are the most popular zip codes in Callaway, Leonardtown, MD?
The most popular zip codes in Callaway, Leonardtown, MD include 20620, 20650, 20634, 20692 and 20653.
What are the most popular neighborhoods near Callaway, Leonardtown, MD?
The most popular neighborhoods near Callaway, Leonardtown, MD are Piney Point, Saint George Island, Port Republic, Mechanicsville and Newburg.
Are home prices dropping in Callaway?
Yes, home prices in Callaway are down 9% in the last 12 months.
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