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Callaway Homes for Sale

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  • /67

    $1,100,000

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

    20098 Piney Point Rd, Callaway, MD 20620

    Welcome to Ms. Piney Point! 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

    Shanita Kelley Samson Properties

    20098 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

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.

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.
Is Callaway, MD a safe neighborhood?
Callaway, MD is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
How much do you need to make to afford a house in Callaway?
The median home price in Callaway is $457,500. If you put a 20% down payment of $91,500 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $2,310 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $99K 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 20634, 20619, 20692, 20650 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.

Callaway Home Prices vs. Nearby Leonardtown, MD Neighborhoods

Callaway Piney Point Shady Side Saint Leonard
Median Home Price
$457,500
$485,000
$466,000
$537,000
Median Sale Price
$450,000
+15% YoY
$419,999
+3% YoY
$449,975
+7% YoY
$515,000
+10% YoY
Median Single Family Price
$469,900
$452,499
$466,000
$525,000
Total Active Listings
1
4
29
35
Market Conditions
1 Months
Seller's Market
3 Months
Seller's Market
3 Months
Seller's Market
5 Months
Balanced Market
How to Buy a Home How to Finance a Home How to Sell a Home