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

20271 Jackson Rd
Callaway, MD 20620

3 Beds
2 Baths
2,566 sqft (on 3.01 acres)

$476,900

Trulia Estimate

as of May 22, 2026

Est. Refi. Payment $2,804/mo*

Refinance Your Home

$476,900

Trulia Estimate

as of May 22, 2026

Est. Refi. Payment $2,804/mo*

Refinance Your Home

3 Beds

2 Baths

2,566 sqft

(on 3.01 acres)

Local Information

-- mins to

Commute Destination

Description

Private location for this large ranch style home, sited on 3 acres of land. Over 2500 sqft of living space allows for a lot of potential. Detached 2 car + garage. See attachment for PAS requirements and WFHM offer submittal information in MLS document section. To report any concerns with a listing broker/agent or to report any property condition or other concern needing escalation, please call: 1-877-617-5274

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 20271 Jackson Rd

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1
Interior Details Types of Rooms: Dining Room
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Vinyl
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 2004
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 3.01 acres

Price History for 20271 Jackson Rd

Date	Price	Event	Source
03/30/2015	$109,000	Sold	N/A
Recording Date 03/30/2015 Contract Date 01/21/2015 County Transfer Tax $790 Total Transfer Tax $1,335
08/12/2014	$109,900	Listed For Sale	Agent Provided

10/03/2006	$160,500	Sold	N/A
Recording Date 10/03/2006 County Transfer Tax N/A Total Transfer Tax N/A
11/17/1998	$37,500	Sold	N/A
Recording Date 11/17/1998 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$166
Assessment	$402,800

Home facts updated by county records

Comparable Sales for 20271 Jackson Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
20314 Brent Ln, Callaway, MD	0.14	Single-Family Home	$345,000	02/03/26	3	2	1,580
44504 Watson Ln, Leonardtown, MD	0.58	Single-Family Home	$465,000	11/21/25	3	2	2,304
44871 Rickle Dr, Callaway, MD	0.57	Single-Family Home	$465,000	08/12/25	3	2	1,538
20035 Piney Point Rd, Callaway, MD	0.72	Single-Family Home	$340,000	11/21/25	3	2	1,488
45151 Knotts Dr, Callaway, MD	0.60	Single-Family Home	$545,000	09/23/25	5	4	2,736
45151 Knotts Dr, Callaway, MD	0.60	Single-Family Home	$545,000	11/20/25	5	4	2,736
44545 Brewer Ln, Leonardtown, MD	0.69	Single-Family Home	$724,000	04/14/26	4	3.5	3,243
44964 Hewitt Rd, Callaway, MD	0.85	Single-Family Home	$329,000	08/08/25	3	1	1,242
20250 Hawks Way, Leonardtown, MD	0.93	Single-Family Home	$519,900	02/27/26	3	2	1,557
20255 Hawks Way, Callaway, MD	0.93	Single-Family Home	$700,000	04/27/26	4	2.5	2,400

Nearby homes

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

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FOR SALE
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
APR 17, 2026
$261,000
3 bd
1.5 ba
1,188 sqft
44826 Wood Duck Ln,
Callaway, MD 20620
CENTURY 21 New Millennium
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
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 13, 2026
$280,000
4 bd
2.5 ba
1,693 sqft
20801 Harlequin Ln,
Callaway, MD 20620
RE/MAX Galaxy
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
JAN 15, 2026
$289,900
3 bd
1.5 ba
1,488 sqft
44895 Canvas Back Dr,
Callaway, MD 20620
RE/MAX One

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Additional Cost

Assigned Schools

These are the assigned schools for 20271 Jackson 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
21260 Joe Baker Ct #776f18ccb,
Lexington Park, MD 20653
Contact for price
1-2 bd
1-2 ba
45910 Foxchase Dr #f320a52c6,
Great Mills, MD 20634
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
21280 Lexwood 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
$1,990/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 20271 Jackson Rd

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1.49 ACRES
$1,100,000
3 bd
2.5 ba
5,939 sqft
20098 Piney Point Rd,
Callaway, MD 20620
Samson Properties
$475,000
4 bd
3 ba
2,020 sqft
21096 Lizson Ct,
California, MD 20619
American Homes Realty Group
0.92 ACRES
$389,900
3 bd
2 ba
1,144 sqft
21983 Point Lookout Rd,
Leonardtown, MD 20650
RE/MAX One
NEW - 2 DAYS AGO
2.67 ACRES
$585,000
4 bd
3 ba
2,448 sqft
20600 Old Gravel Ln,
Lexington Park, MD 20653
The Southside Group Real Estate
0.71 ACRES
$450,000
3 bd
2 ba
1,128 sqft
18866 Russell Rd,
Leonardtown, MD 20650
KW Metro Center
2.79 ACRES
$594,900
5 bd
2.5 ba
2,430 sqft
45954 Burns Dr,
Valley Lee, MD 20692
EXP Realty, LLC
See more homes for sale in
Callaway
Take a look

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Off Market Homes Near 20271 Jackson Rd

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SOLD
MAY 18, 2026
$520,000
3 bd
2,730 sqft
45526 Longfields Blvd,
Great Mills, MD 20634
Berkshire Hathaway HomeServices PenFed Realty
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
$420,000
4 bd
2.5 ba
2,424 sqft
46689 Sandalwood St,
Lexington Park, MD 20653
Samson Properties
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 7, 2026
$300,000
2 ba
1,450 sqft
44161 Little Holly Ln,
Leonardtown, MD 20650
SOLD
MAY 7, 2026
$314,900
3 bd
2.5 ba
1,800 sqft
46098 W Westbury Blvd,
Lexington Park, MD 20653
EXP Realty, LLC
SOLD
MAY 7, 2026
$415,000
4 bd
2.5 ba
1,572 sqft
45642 Taras Ct,
Great Mills, MD 20634
RE/MAX One
SOLD
MAY 6, 2026
$375,700
4 bd
2 ba
1,536 sqft
46461 Rosewood Dr,
Lexington Park, MD 20653
Open Door Brokerage, LLC
SOLD
MAY 4, 2026
$327,795
4 bd
3 ba
2,221 sqft
20893 Dry Mill St,
Great Mills, MD 20634
See more homes for sale in
Callaway
Take a look

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Homes for rent near 20271 Jackson Rd

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NEW - 2 DAYS AGO
APPLY INSTANTLY
PET FRIENDLY
$2,500/mo
3 bd
2 ba
2,159 sqft
21403 Carmen Woods Dr,
Lexington Park, MD 20653
NEW - 1 DAY AGO
APPLY INSTANTLY
$2,700/mo
3 bd
4 ba
2,170 sqft
21298 Bethmill Way,
California, MD 20619
PET FRIENDLY
$2,500/mo
3 bd
2.5 ba
1,848 sqft
20503 Chestnut Ridge Dr,
Leonardtown, MD 20650
NEW - 21 HRS AGO
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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20271 Jackson Rd, Callaway, MD 20620 is a 3 bedroom, 2 bathroom, 2,566 sqft single-family home built in 2004. This property is not currently available for sale. 20271 Jackson Rd was last sold on Mar 30, 2015 for $109,000. The current Trulia Estimate for 20271 Jackson Rd is $476,900.

20271 Jackson Rd
Callaway, MD 20620

$476,900

$476,900

Local Information