19955 Piney Point Rd, Callaway, MD 20620
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Property image
OFF MARKET

19955 Piney Point Rd
Callaway, MD 20620

  • 9 Beds
  • 5 Baths
  • 6,048 sqft (on 0.69 acres)

$673,500

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,958/mo*
Refinance Your Home

$673,500

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $3,958/mo*
Refinance Your Home
9 Beds
5 Baths
6,048 sqft
(on 0.69 acres)

Home Value

Trulia Estimate
$674K
Since last month
Decreased$5K (-0.7%)
Since last year
Increased$9K (+1.3%)
Since last sale
Increased$259K (+62.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +38% in the last 10 years
MonthEstimated value
2026
August 2026$674K
July 2026$679K
June 2026$685K
May 2026$684K
April 2026$676K
March 2026$673K
February 2026$661K
January 2026$653K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20035 Piney Point Rd, Callaway, MD
0.15
Single-Family Home
$340,000
11/21/25
3
2
1,488
44968 Hewitt Rd, Callaway, MD
0.31
Single-Family Home
$575,000
01/09/26
3
2
792
45151 Knotts Dr, Callaway, MD
0.66
Single-Family Home
$545,000
11/20/25
5
4
2,736
45151 Knotts Dr, Callaway, MD
0.66
Single-Family Home
$545,000
09/23/25
5
4
2,736
20314 Brent Ln, Callaway, MD
0.78
Single-Family Home
$345,000
02/03/26
3
2
1,580
44545 Brewer Ln, Leonardtown, MD
1.16
Single-Family Home
$724,000
04/14/26
4
3.5
3,243
45474 Medleys Neck Rd, Leonardtown, MD
1.14
Single-Family Home
$635,000
12/15/25
3
3
2,653
19830 Fall Ct, Great Mills, MD
1.15
Single-Family Home
$375,000
03/31/26
3
2
1,400
44906 Golden Eye Ct, Callaway, MD
1.98
Single-Family Home
$610,000
11/28/25
6
4
6,006
20260 Hawks Way, Leonardtown, MD
1.53
Single-Family Home
$565,000
05/29/26
4
2.5
2,500

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
20035 Piney Point Rd, Callaway, MD 20620
0.15
$340,000
3
2
1,488
Recently Sold
45168 Irvings Pl, Callaway, MD 20620
0.26
$177,000
-
-
-
For Sale
45052 Hewitt Rd, Callaway, MD 20620
0.23
$363,000
3
1.5
1,164
Off Market
20098 Piney Point Rd, Callaway, MD 20620
0.29
$1,100,000
3
2.5
5,939
For Sale
20140 Piney Point Rd, Callaway, MD 20620
0.35
$373,400
3
2
1,247
Off Market
44968 Hewitt Rd, Callaway, MD 20620
0.31
$575,000
3
2
792
Recently Sold
20145 Quiet Acre Ln, Callaway, MD 20620
0.37
-
-
-
-
Off Market
44964 Hewitt Rd, Callaway, MD 20620
0.33
$338,800
3
1
1,242
Off Market
45252 Happyland Rd, Valley Lee, MD 20692
0.53
$150,000
-
-
-
For Sale
45151 Knotts Dr, Callaway, MD 20620
0.66
$559,800
5
4
2,736
Off Market
44911 Buck Redman Rd, Callaway, MD 20620
0.66
$325,000
3
1
1,040
For Sale
45291 Take It Easy Ranch Rd, Callaway, MD 20620
0.73
$259,900
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 19955 Piney Point Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2006
Lot Size
0.69 acres
Living Area
6,048 sqft
Price/Sqft
$111
Parking
Garage

About this House

Do you need more space? You read that correctly, there are nine bedrooms here! You will be impressed with the fully finished basement with full size bar, theater room and more! Would you like an instant investment property with your home? Look no further! Totally separate two bedroom apartment attached with full kitchen and bath. Tons of parking space! MUST SEE!
19955 Piney Point Rd, Callaway, MD 20620 is a 9 bedroom, 5 bathroom, 6,048 sqft single-family home built in 2006. It last sold for $415,000 on Dec 17, 2018. More recently, it was listed as a rental in April 2018 with an asking price of $2,800 per month. That rental listing was removed on June 20, 2018. It is currently off market. The Trulia Estimate is $673,500, with a rent estimate of $3,665/month.

Home Details for 19955 Piney Point Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Price and Tax history

DateEventPrice
Dec 17, 2018
Source: N/A
Sold
$415,000
Aug 15, 2018
Source: Agent Provided
ListingRemoved
$425,000
Jul 17, 2018
Source: Agent Provided
Pending
$425,000
Jul 7, 2018
Source: Agent Provided
Listed For Sale
$425,000
Jun 20, 2018
Source: Agent Provided
ListingRemoved
$2,600

Market trends in Callaway

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
5

Around this home

What Locals Say about Callaway

At least 3 Trulia users voted on each feature.

  • 100 % Say people would walk alone at night

  • 100 % Say car is needed

  • 100 % Say parking is easy

  • 83 % Say it's walkable to grocery stores

  • 83 % Say it's quiet

  • 80 % Say kids play outside

  • 67 % Say it's dog friendly

  • 60 % Say it's walkable to restaurants

  • 50 % Say there's wildlife

  • 40 % Say they plan to stay for at least 5 years

  • 40 % Say yards are well-kept

  • 40 % Say there are sidewalks

  • 33 % Say there's holiday spirit

  • 33 % Say streets are well-lit

  • 29 % Say neighbors are friendly

  • 17 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Tyrone B.
    "there are a lot of dogs and places for them to run and walk. I don't have a dog and do not plan to get one in this neighborhood. "
    0
    Flag
  • Bobntess
    "A good place to walk your dogs! The neighborhood is less than a one mile walk to the Saint Mary’s Lake State Park."
    0
    Flag
  • Aaronmroy
    "It’s quite and you can be hidden. Some neighbors wave but not all of them. They walk up to your house uninvited to tell you to cut your grass. Or almost shoot you cause he was aiming in your direction. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 19955 Piney Point Rd

  • What is 19955 Piney Point Rd estimated to be worth?
    Trulia's estimated value for 19955 Piney Point Rd in Callaway, MD is $673,500.
  • What is the price history for 19955 Piney Point Rd?
    19955 Piney Point Rd in Callaway, MD last sold for $415,000 in December 2018.
  • Is Callaway a buyer's or seller's market?
    Callaway is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 19955 Piney Point Rd?
    The closest schools to 19955 Piney Point Rd in Callaway, MD are Leonardtown High School (rated 8/10), Piney Point Elementary School (Pre-K, rated 7/10), Spring Ridge Middle School (rated 5/10).
  • Does 19955 Piney Point Rd have air conditioning?
    Yes, 19955 Piney Point Rd in Callaway, MD has air conditioning.
  • Does 19955 Piney Point Rd have laundry facilities?
    Yes, 19955 Piney Point Rd in Callaway, MD has in-unit laundry.

Apartments for Rent

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