20271 Jackson Rd, Callaway, MD 20620
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Property image
OFF MARKET

20271 Jackson Rd
Callaway, MD 20620

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

$477,800

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,820/mo*
Refinance Your Home

$477,800

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,820/mo*
Refinance Your Home
3 Beds
2 Baths
2,566 sqft
(on 3.01 acres)

Home Value

Trulia Estimate
$478K
Since last month
Increased$4K (+0.8%)
Since last year
Increased$51K (+11.8%)
Since last sale
Increased$370K (+339.5%)
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 +56% in the last 10 years
MonthEstimated value
2026
August 2026$479K
July 2026$475K
June 2026$484K
May 2026$477K
April 2026$465K
March 2026$466K
February 2026$456K
January 2026$448K
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
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
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
20250 Hawks Way, Leonardtown, MD
0.93
Single-Family Home
$519,900
02/27/26
3
2
1,557
20260 Hawks Way, Leonardtown, MD
0.93
Single-Family Home
$565,000
05/29/26
4
2.5
2,500
20255 Hawks Way, Callaway, MD
0.93
Single-Family Home
$700,000
04/27/26
4
2.5
2,400
44564 Deerfield Rd, Leonardtown, MD
0.52
Single-Family Home
$225,000
04/02/26
3
1,512

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
20275 Jackson Rd, Callaway, MD 20620
0.06
$250,000
2
2
924
For Sale
44874 Buck Redman Rd, Callaway, MD 20620
0.13
$329,000
3
1
1,008
Off Market
20314 Brent Ln, Callaway, MD 20620
0.14
$345,000
3
2
1,580
Recently Sold
20361 Jackson Rd, Callaway, MD 20620
0.15
$387,500
3
2
1,948
Off Market
44911 Buck Redman Rd, Callaway, MD 20620
0.21
$325,000
3
1
1,040
For Sale
44661 Deerfield Rd, Leonardtown, MD 20650
0.31
$495,600
3
2
2,016
Off Market
20450 Piney Point Rd, Callaway, MD 20620
0.36
$595,500
4
3.5
3,504
Off Market
20426 Killdeer Ln, Callaway, MD 20620
0.43
$470,800
3
2
2,172
Off Market
20145 Quiet Acre Ln, Callaway, MD 20620
0.50
-
-
-
-
Off Market
Piney Point Rd, Callaway, MD 20620
0.53
$85,000
-
-
-
For Sale
Piney Point Rd, Callaway, MD 20620
0.53
-
-
-
-
Off Market
44646 Medleys Neck Rd, Leonardtown, MD 20650
0.56
$50,000
3
1
924
Recently Sold

Local Information

  • Map ViewExplore the area around 20271 Jackson 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
2004
Lot Size
3.01 acres
Living Area
2,566 sqft
Price/Sqft
$186
Parking
Garage

About this House

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
20271 Jackson Rd, Callaway, MD 20620 is a 3 bedroom, 2 bathroom, 2,566 sqft single-family home built in 2004. It last sold for $109,000 on Mar 30, 2015. It is currently off market. The Trulia Estimate is $477,800, with a rent estimate of $2,479/month.

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 and Tax history

DateEventPrice
Mar 30, 2015
Source: N/A
Sold
$109,000
Aug 12, 2014
Source: Agent Provided
Listed For Sale
$109,900
Oct 3, 2006
Source: N/A
Sold
$160,500
Nov 17, 1998
Source: N/A
Sold
$37,500

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 20271 Jackson Rd

  • What is 20271 Jackson Rd estimated to be worth?
    Trulia's estimated value for 20271 Jackson Rd in Callaway, MD is $477,800.
  • What is the price history for 20271 Jackson Rd?
    20271 Jackson Rd in Callaway, MD last sold for $109,000 in March 2015.
  • 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 20271 Jackson Rd?
    The closest schools to 20271 Jackson 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).
  • How big is the lot at 20271 Jackson Rd?
    The lot at 20271 Jackson Rd in Callaway, MD is about 3 acres.
  • Does 20271 Jackson Rd have a garage?
    Yes, 20271 Jackson Rd in Callaway, MD has a garage.

Apartments for Rent

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Off Market Homes Near 20271 Jackson Rd

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