Would people walk alone at night in Callaway, MD?

As of early 2026, 100% of users say people would walk alone at night

Is a car needed in Callaway, MD?

As of early 2026, 100% of users say car is needed

Is parking easy in Callaway, MD?

As of early 2026, 100% of users say parking is easy

Is Callaway, MD walkable to grocery stores?

As of early 2026, 83% of users say it's walkable to grocery stores

Is Callaway, MD quiet?

As of early 2026, 83% of users say it's quiet

Do kids play outside in Callaway, MD?

As of early 2026, 80% of users say kids play outside

Is Callaway, MD dog-friendly?

As of early 2026, 67% of users say it's dog friendly

Is Callaway, MD walkable to restaurants?

As of early 2026, 60% of users say it's walkable to restaurants

Is there wildlife in Callaway, MD?

As of early 2026, 50% of users say there's wildlife

Do residents of Callaway, MD plan to stay at least 5 years?

As of early 2026, 40% of users say they plan to stay for at least 5 years

Are yards well-kept in Callaway, MD?

As of early 2026, 40% of users say yards are well-kept

Does Callaway, MD have sidewalks?

As of early 2026, 40% of users say there are sidewalks

Does Callaway, MD show holiday spirit?

As of early 2026, 33% of users say there's holiday spirit

Are the streets well-lit in Callaway, MD?

As of early 2026, 33% of users say streets are well-lit

Are neighbors friendly in Callaway, MD?

As of early 2026, 29% of users say neighbors are friendly

Are there community events in Callaway, MD?

As of early 2026, 17% of users say there are community events

OFF MARKET

19955 Piney Point Rd
Callaway, MD 20620

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

$680,500

Trulia Estimate

as of May 24, 2026

Est. Refi. Payment $3,970/mo*

Refinance Your Home

$680,500

Trulia Estimate

as of May 24, 2026

Est. Refi. Payment $3,970/mo*

Refinance Your Home

9 Beds

5 Baths

6,048 sqft

(on 0.69 acres)

Local Information

-- mins to

Commute Destination

Description

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!

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 19955 Piney Point Rd

Interior Features
Interior Details Basement
Heating & Cooling Heating: Forced Air, OtherAir 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 History for 19955 Piney Point Rd

Date	Price	Event	Source
12/17/2018	$415,000	Sold	N/A
Recording Date 12/17/2018 Contract Date 11/30/2018 County Transfer Tax $3,850 Total Transfer Tax $4,888
08/15/2018	$425,000	ListingRemoved	Agent Provided

07/17/2018	$425,000	Pending	Agent Provided

07/07/2018	$425,000	Listed For Sale	Agent Provided

06/20/2018	$2,600	ListingRemoved	Agent Provided

05/11/2018	$2,600	PriceChange	Agent Provided
Price Change $200 (-7%)
04/26/2018	$2,800	Listed For Rent	Agent Provided

02/19/2015	$340,000	Sold	N/A
Recording Date 02/19/2015 Contract Date 01/22/2015 County Transfer Tax $3,400 Total Transfer Tax $4,250
12/23/2014	$349,000	PriceChange	Agent Provided
Price Change $15,900 (-4%)
11/05/2014	$364,900	Listed For Sale	Agent Provided

01/28/2014	$370,851	Sold	N/A
Recording Date 01/28/2014 Contract Date 01/22/2014 County Transfer Tax $3,709 Total Transfer Tax $5,563
04/01/2002	$53,000	Sold	N/A
Recording Date 04/01/2002 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$7,258
Assessment	$672,100

Home facts updated by county records

Comparable Sales for 19955 Piney Point Rd

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
44964 Hewitt Rd, Callaway, MD	0.33	Single-Family Home	$329,000	08/08/25	3	1	1,242
20314 Brent Ln, Callaway, MD	0.78	Single-Family Home	$345,000	02/03/26	3	2	1,580
44964 Hewitt Rd, Callaway, MD	0.33	Single-Family Home	$329,000	08/22/25		2	1,242
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

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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FOR SALE
OPEN SAT, 11-2PM
1.49 ACRES
$1,100,000
3 bd
2.5 ba
5,939 sqft
20098 Piney Point Rd,
Callaway, MD 20620
Samson Properties
SOLD
APR 27, 2026
$700,000
4 bd
2.5 ba
2,400 sqft
20255 Hawks Way,
Callaway, MD 20650
CENTURY 21 New Millennium
SOLD
JAN 1, 2026
$145,000
Na Millers Mill Road & Salem Cemetary Rd,
Callaway, MD 20620
McDill Real Estate
SOLD
MAR 31, 2026
$375,000
3 bd
2 ba
1,400 sqft
19830 Fall Ct,
Great Mills, MD 20634
CENTURY 21 New Millennium
SOLD
APR 14, 2026
$724,000
4 bd
3.5 ba
3,243 sqft
44545 Brewer Ln,
Leonardtown, MD 20650
CENTURY 21 New Millennium
FOR SALE
1.44 ACRES
$149,900
20265 Hawks Way,
Leonardtown, MD 20650
CENTURY 21 New Millennium
FOR SALE
1.5 ACRES
$85,000
Piney Point Rd,
Callaway, MD 20620
CENTURY 21 New Millennium
OFF MARKET
Piney Point Rd,
Callaway, MD 20620
O'Brien Realty ERA Powered
SOLD
FEB 3, 2026
$345,000
3 bd
2 ba
1,580 sqft
20314 Brent Ln,
Callaway, MD 20620
Berkshire Hathaway HomeServices PenFed Realty
SOLD
FEB 27, 2026
$519,900
3 bd
2 ba
1,557 sqft
20250 Hawks Way,
Leonardtown, MD 20650
CENTURY 21 New Millennium
SOLD
JAN 9, 2026
$575,000
3 bd
2 ba
792 sqft
44968 Hewitt Rd,
Callaway, MD 20620
CENTURY 21 New Millennium
SOLD
NOV 21, 2025
$465,000
3 bd
2 ba
2,304 sqft
44504 Watson Ln,
Leonardtown, MD 20650
O'Brien Realty ERA Powered

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Additional Cost

Assigned Schools

These are the assigned schools for 19955 Piney Point Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
Resident
5y ago
"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
Resident
6y ago
"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
Resident
6y ago
"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

Apartments for Rent

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PET FRIENDLY
$1,750 - $1,970/mo
1-2 bd
1-2 ba
Park Villas | 21295 Mayfaire Ln #74-203,
Lexington Park, MD 20653
PET FRIENDLY
$1,450/mo
1 bd
1 ba
19831 Point Lookout Rd #3,
Lexington Park, MD 20653
PET FRIENDLY
$1,300 - $1,500/mo
2-3 bd
2 ba
Admiral's Landing | 45970 Fox Chase Dr #4578688,
Great Mills, MD 20634
Contact for price
1-2 bd
1-2 ba
21280 Lexwood Ct #776f18ccb,
Lexington Park, MD 20653
Contact for price
1-2 bd
1-2 ba
45910 Indian Way #f320a52c6,
Lexington Park, MD 20653
Contact for price
1-2 bd
1-2 ba
21260 Joe Baker Ct #776f18ccb,
Lexington Park, MD 20653
$1,800/mo
3 bd
2 ba
20765 Old Great Mills Rd #20761-5,
Great Mills, MD 20634
$1,650/mo
2 bd
2 ba
20765 Old Great Mills Rd #20761-7,
Great Mills, MD 20634
APPLY INSTANTLY
$1,850/mo
2 bd
2 ba
45146 Andover Estates Rd #4,
Valley Lee, MD 20692
APPLY INSTANTLY
$1,990/mo
2 bd
1 ba
44845 Dot Banagan Ln #2,
Leonardtown, MD 20650
See more homes for rent in
Callaway
Take a look

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Homes for sale near 19955 Piney Point Rd

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OPEN SAT, 11-2PM
1.49 ACRES
$1,100,000
3 bd
2.5 ba
5,939 sqft
20098 Piney Point Rd,
Callaway, MD 20620
Samson Properties
COMING SOON 7/8
1.37 ACRES
$725,000
4 bd
3.5 ba
4,588 sqft
19305 Greens Crossing Ct,
Great Mills, MD 20634
RE/MAX One
1.12 ACRES
$629,000
5 bd
3.5 ba
3,380 sqft
46195 Kayak Ct,
Great Mills, MD 20634
CENTURY 21 New Millennium
2.79 ACRES
$594,900
5 bd
2.5 ba
2,430 sqft
45954 Burns Dr,
Valley Lee, MD 20692
EXP Realty, LLC
0.71 ACRES
$450,000
3 bd
2 ba
1,128 sqft
18866 Russell Rd,
Leonardtown, MD 20650
KW Metro Center
$475,000
4 bd
3 ba
2,020 sqft
21096 Lizson Ct,
California, MD 20619
American Homes Realty Group
See more homes for sale in
Callaway
Take a look

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Off Market Homes Near 19955 Piney Point Rd

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SOLD
MAY 15, 2026
$505,000
4 bd
2.5 ba
2,368 sqft
21027 Hunting Quarter Dr,
Callaway, MD 20620
CENTURY 21 New Millennium
SOLD
MAY 15, 2026
$439,000
3 bd
3 ba
2,379 sqft
21984 Barkentine Ct,
Great Mills, MD 20634
CENTURY 21 New Millennium
SOLD
MAY 14, 2026
$727,360
4 bd
2.5 ba
2,972 sqft
43500 Deer Run Ct,
Leonardtown, MD 20650
EXP Realty, LLC
SOLD
MAY 14, 2026
$420,000
4 bd
2.5 ba
2,424 sqft
46689 Sandalwood St,
Lexington Park, MD 20653
Samson Properties
SOLD
MAY 14, 2026
$460,000
5 bd
3.5 ba
2,870 sqft
20987 Freedom Run Dr,
Lexington Park, MD 20653
EXP Realty, LLC
SOLD
MAY 11, 2026
$640,000
4 bd
2.5 ba
3,572 sqft
18747 Vernon Ct,
Drayden, MD 20630
RE/MAX Realty Group
SOLD
MAY 11, 2026
$579,900
4 bd
2.5 ba
3,428 sqft
43552 Bayberry Ct,
Leonardtown, MD 20650
CENTURY 21 New Millennium
SOLD
MAY 1, 2026
$410,000
4 bd
3 ba
1,792 sqft
21622 Harrison St,
Great Mills, MD 20634
CENTURY 21 New Millennium
SOLD
APR 30, 2026
$365,000
3 bd
2 ba
1,644 sqft
44731 Blake Creek Rd,
Leonardtown, MD 20650
EXP Realty, LLC
SOLD
APR 27, 2026
$700,000
4 bd
2.5 ba
2,400 sqft
20255 Hawks Way,
Callaway, MD 20650
CENTURY 21 New Millennium
See more homes for sale in
Callaway
Take a look

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Homes for rent near 19955 Piney Point Rd

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APPLY INSTANTLY
$2,700/mo
3 bd
4 ba
2,170 sqft
21298 Bethmill Way,
California, MD 20619
PET FRIENDLY
$1,595/mo
1 bd
1 ba
1,200 sqft
44970 Serenity Farm Ln,
Callaway, MD 20620
See more homes for rent in
Callaway
Take a look

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19955 Piney Point Rd, Callaway, MD 20620 is a 9 bedroom, 5 bathroom, 6,048 sqft single-family home built in 2006. This property is not currently available for sale. 19955 Piney Point Rd was last sold on Dec 17, 2018 for $415,000. The current Trulia Estimate for 19955 Piney Point Rd is $680,500.

19955 Piney Point Rd
Callaway, MD 20620

$680,500

$680,500

Local Information