1509 Calloway Dr, Shady Side, MD 20764
Property image
Property image
SOLD
MAY 22, 2026

$377,300

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,111 sqft (on 0.36 acres)

1509 Calloway Dr, Shady Side, MD 20764

Est. Refi. Payment $2,256/mo*
Refinance Your Home
Currently Off Market - Sold May 22, 2026 for $375,000

Home Value

Trulia Estimate
$377K
Since last month
Decreased$900 (-0.2%)
Since last year
Increased$7K (+1.9%)
Since last sale
Increased$2K (+0.4%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$377K
July 2026$378K
June 2026$376K
May 2026$379K
April 2026$373K
March 2026$371K
February 2026$369K
January 2026$368K
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
1509 Callaway Dr, Shady Side, MD
0.01
Single-Family Home
$375,000
05/18/26
2
1
1,111
1731 Columbia Beach Rd, Shady Side, MD
0.05
Single-Family Home
$325,000
12/19/25
2
1
900
1503 Callaway Dr, Shady Side, MD
0.02
Single-Family Home
$276,000
12/22/25
3
2
1,356
1510 Callaway Dr, Shady Side, MD
0.04
Single-Family Home
$500,000
05/28/26
4
2
2,074
1502 Garst Rd, Shady Side, MD
0.13
Single-Family Home
$143,850
07/31/26
2
1
736
5211 Al Jones Dr, Shady Side, MD
0.39
Single-Family Home
$535,000
08/12/26
2
1.5
1,244
1605 Depriest Dr, Shady Side, MD
0.42
Single-Family Home
$565,000
09/04/25
3
1.5
1,152
1512 Lincoln Rd, Shady Side, MD
0.42
Single-Family Home
$309,000
02/16/26
3
2.5
1,512
1166 Cedar Ave, Shady Side, MD
0.90
Single-Family Home
$350,000
10/29/25
3
2
968

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
1509 Callaway Dr, Shady Side, MD 20764
0.01
$375,000
2
1
1,111
Recently Sold
1510 Callaway Dr, Shady Side, MD 20764
0.04
$500,000
4
2
2,074
Recently Sold
1500 Calloway Dr, Shady Side, MD 20764
0.04
$353,800
2
2
1,240
Off Market
1503 Callaway Dr, Shady Side, MD 20764
0.02
$276,000
3
2
1,356
Recently Sold
1503 Ellington Dr, Shady Side, MD 20764
0.06
$368,500
2
1.5
637
Off Market
1727 Columbia Beach Rd, Shady Side, MD 20764
0.05
$428,400
3
1.5
1,388
Off Market
1731 Columbia Beach Rd, Shady Side, MD 20764
0.05
$325,000
2
1
900
Recently Sold
5326 Al Jones Dr, Shady Side, MD 20764
0.07
$308,300
2
1
576
Off Market
1501 Garst Rd, Shady Side, MD 20764
0.09
$325,000
2
1
680
Off Market
1721 Columbia Beach Rd, Shady Side, MD 20764
0.08
$736,300
3
3.5
2,850
Off Market
5314 Al Jones Dr, Shady Side, MD 20764
0.11
$649,990
4
2.5
2,710
For Sale
5341 Al Jones Dr, Shady Side, MD 20764
0.06
$725,000
3
2
1,962
For Sale

Local Information

  • Map ViewExplore the area around 1509 Calloway Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1952
Lot Size
0.36 acres
Living Area
1,111 sqft
Price/Sqft
$338/sqft
Parking
Garage

About this House

Cute & Cozy Cottage Charm! This 2 Bedroom home offers one level living! Hardwood floors throughout with two living spaces. Updated kitchen with marble counter tops. Living room pellet stove, and heated 4 seasons room, perfect to use on these upcoming fall/winter nights. Two ample sized bedrooms, and full bath.
Fenced flat back yard contains 2 Sheds / workshop. Attached 1 Car Garage. Located in the Historic, Gated Columbia Beach community with its classic charm of years gone by!

Recently updated recessed lighting, HVAC system, newer windows throughout, fence and rear deck were built 2 years ago, roof is under 5 years old. You don't want to miss this perfect home a few blocks from the bay! Bayside Community has New Playground, Boat Ramp, Basketball Court as well as Community Pier and Manicured Common Areas along the water for residents enjoyment. Don't miss this great value under 300k!
1509 Calloway Dr, Shady Side, MD 20764 is a 2 bedroom, 1 bathroom, 1,111 sqft single-family home built in 1952. It last sold for $375,000 on May 22, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $377,300, with a rent estimate of $2,527/month.

Home Details for 1509 Calloway Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Price & Status

Price
Price Per Sqft: $338/sqft

Community

Units in Building: 1

Lot Information

Lot Area: 0.36 acres

Price and Tax history

DateEventPrice
May 22, 2026
Source: N/A
Sold
$375,000
Jan 13, 2022
Source: N/A
Sold
$305,000
Jul 8, 2019
Source: N/A
Sold
$245,000
May 25, 2019
Source: Agent Provided
Pending
$247,000
May 17, 2019
Source: Agent Provided
PriceChange
$247,000
Price decreased by 1%

Market trends in Shady Side

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
35
7MoM

Around this home

What Locals Say about Shady Side

At least 26 Trulia users voted on each feature.

  • 97 % Say yards are well-kept

  • 96 % Say car is needed

  • 91 % Say it's dog friendly

  • 89 % Say kids play outside

  • 81 % Say people would walk alone at night

  • 76 % Say it's quiet

  • 76 % Say parking is easy

  • 73 % Say neighbors are friendly

  • 73 % Say there's wildlife

  • 71 % Say there's holiday spirit

  • 50 % Say they plan to stay for at least 5 years

  • 43 % Say there are community events

  • 32 % Say it's walkable to restaurants

  • 29 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Krmotto@gmail.com
    "the bay is so close, and the neighborhood is perfect for our small family. bike rides are fun, and good schools we think! "
    1
    Flag
  • Julie F.
    "We have nice parks and water access, and boat slips. Neighbors are friendly and watch out for each other "
    0
    Flag
  • Renee B.
    " If you want to live in a country or water setting this is a great area for just that. It is a relatively easy commute into DC, Annapolis or Baltimore. If you want box stores forget it! it's all about keeping it local down here. Enjoy the diverse community of friendly people who like to kayak, fish, sail, bike ride, power boat, motorcycle, hunt, eat local crabs & oysters, the arts, history at Captain Avery Museum, ride horses and so much more!! I gave the traffic an Excellent rating compared to the congested surrounding areas, every now and then you might get behind a farmers tractor who usually pulls over to let you pass! Public Transportation, there is a Park & Ride 15min away that has an excellent commuter bus into DC. School buses yes. Senior Citizen busses available. Community Involvement - Small 4th of July Parade, Oyster Festival, and just some good old fashioned neighborhood get togethers. "
    1
    Flag
  • Elena H.
    "For a quaint existence on the water where waking up to the tranquility of birds singing and going to sleep following an uninhibited view of the night sky are your drivers, this bucolic neighborhood is perfect! Ideal neighborhood for the boating crowd and a weekend home. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 1509 Calloway Dr

  • What is 1509 Calloway Dr estimated to be worth?
    Trulia's estimated value for 1509 Calloway Dr in Shady Side, MD is $377,300.
  • What is the price history for 1509 Calloway Dr?
    1509 Calloway Dr in Shady Side, MD last sold for $375,000 in May 2026.
  • Is Shady Side a buyer's or seller's market?
    Shady Side is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Shady Side?
    Residents describe Shady Side, MD as well-kept, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Shady Side, MD.
  • How big is the lot at 1509 Calloway Dr?
    The lot at 1509 Calloway Dr in Shady Side, MD is about 0.36 acres (15,681 sq ft).
  • Does 1509 Calloway Dr have a garage?
    Yes, 1509 Calloway Dr in Shady Side, MD has a garage.

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