Do kids play outside in Oakland, MD?

As of early 2026, 100% of users say kids play outside

Are yards well-kept in Oakland, MD?

As of early 2026, 100% of users say yards are well-kept

Is parking easy in Oakland, MD?

As of early 2026, 86% of users say parking is easy

Does Oakland, MD show holiday spirit?

As of early 2026, 78% of users say there's holiday spirit

Is Oakland, MD dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Would people walk alone at night in Oakland, MD?

As of early 2026, 75% of users say people would walk alone at night

Is there wildlife in Oakland, MD?

As of early 2026, 75% of users say there's wildlife

Is a car needed in Oakland, MD?

As of early 2026, 73% of users say car is needed

Are neighbors friendly in Oakland, MD?

As of early 2026, 63% of users say neighbors are friendly

Is Oakland, MD quiet?

As of early 2026, 50% of users say it's quiet

Does Oakland, MD have sidewalks?

As of early 2026, 46% of users say there are sidewalks

Are the streets well-lit in Oakland, MD?

As of early 2026, 36% of users say streets are well-lit

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

As of early 2026, 36% of users say they plan to stay for at least 5 years

Are there community events in Oakland, MD?

As of early 2026, 33% of users say there are community events

Is Oakland, MD walkable to grocery stores?

As of early 2026, 27% of users say it's walkable to grocery stores

Is Oakland, MD walkable to restaurants?

As of early 2026, 25% of users say it's walkable to restaurants

OFF MARKET

21 E Pennington St
Oakland, MD 21550

Studio
2 Baths
1,712 sqft

Studio

2 Baths

1,712 sqft

Local Information

Map ViewExplore the area around 21 E Pennington St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 21 E Pennington St, Oakland, MD. 21 E Pennington St is in Oakland, MD and in ZIP code 21550. This property has 2 bathrooms and approximately 1,712 sqft of floor space. This property has a lot size of 7500 sqft and was built in 1916.

21 E Pennington St, Oakland, MD 21550 is a studio, 2 bathroom, 1,712 sqft single-family home built in 1916. It is currently off market. The Trulia Estimate rent is $1,660/month.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 21 E Pennington St

Interior Features
Heating & Cooling Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 2

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

Property Information
Year Built Year Built: 1916
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 7500 sqft

Market trends in Oakland

Last updated May 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

—

Available listings

5MoM

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Property Tax and Assessment

Year	2025
Tax	$892
Assessment	$55,600

Home facts updated by county records

Comparable Sales for 21 E Pennington St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
120 N 3rd St, Oakland, MD	0.18	Single-Family Home	$70,000	01/15/26	3	1	1,660
511 E Green St, Oakland, MD	0.41	Single-Family Home	$250,000	12/31/25	4	2	1,880
502 E Oak St, Oakland, MD	0.45	Single-Family Home	$239,900	09/12/25	3	2	1,680
110 W Pennington St, Oakland, MD	0.15	Single-Family Home	$110,000	09/26/25	2	1	768
525 E Poplar St, Oakland, MD	0.53	Single-Family Home	$249,000	08/12/25		2	1,636
425 E Alder St, Oakland, MD	0.41	Single-Family Home	$150,000	05/06/26		2	2,752
226 N Hammond St, Oakland, MD	0.20	Single-Family Home	$276,000	05/08/26	2	2	1,000
313 W Liberty St, Oakland, MD	0.32	Single-Family Home	$210,000	05/06/26	2	1	1,064
351 N Bradley Ln, Oakland, MD	0.49	Single-Family Home	$148,000	08/05/25	4	2	1,902
723 E Oak St, Oakland, MD	0.62	Single-Family Home	$180,250	03/16/26	3	1	988

Nearby homes

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

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OFF MARKET
Est. $73,000
3 bd
1 ba
1,380 sqft
112 E Pennington St,
Oakland, MD 21550
Custer Realty & Auction
OFF MARKET
Est. $112,200
2 bd
2 ba
1,536 sqft
2 E Center St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
JAN 30, 2026
$99,000
125 N 2nd St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $205,800
3 bd
2.5 ba
1,472 sqft
216 E Center St,
Oakland, MD 21550
Lake Homes Realty, LLC
SOLD
DEC 19, 2025
$20,000
Hammond St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
MAR 3, 2026
$20,000
Hammond St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
FOR SALE
NEW - 2 DAYS AGO
$259,900
3 bd
2 ba
1,998 sqft
102 N 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $445,400
3 bd
2.5 ba
2,800 sqft
305 Crook Crest Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
SEP 26, 2025
$110,000
2 bd
1 ba
768 sqft
110 W Pennington St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $262,900
3 bd
1.5 ba
1,504 sqft
209 E Crook St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
3 bd
1 ba
1,528 sqft
111 W Liberty St,
Oakland, MD 21550
Ashland Auction Group LLC
SOLD
MAY 8, 2026
$276,000
2 bd
2 ba
1,000 sqft
226 N Hammond St,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 21 E Pennington St.

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 Oakland

At least 8 Trulia users voted on each feature.

100 % Say kids play outside
100 % Say yards are well-kept
86 % Say parking is easy
78 % Say there's holiday spirit
75 % Say it's dog friendly
75 % Say people would walk alone at night
75 % Say there's wildlife
73 % Say car is needed
63 % Say neighbors are friendly
50 % Say it's quiet
46 % Say there are sidewalks
36 % Say streets are well-lit
36 % Say they plan to stay for at least 5 years
33 % Say there are community events
27 % Say it's walkable to grocery stores
25 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

Bonnie S.
12y ago
"Year round outdoor adventures and sports await you in Garrett County, Md. Enjoy Deep Creek Lake and Wisp ski resort, a thriving community college for extended learning, hunting, fishing and more. Quaint home on 2.3 acres within easy commute to above amenities. "
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Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
108 Decatur St #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
607 P St #f320a52c6,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
201 E Mason St #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
1113 Mary Dr #f320a52c6,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
750 Vista Sq #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
706 E Alder St #776f18ccb,
Oakland, MD 21550
$1,550/mo
3 bd
1 ba
400 E Alder St #3,
Oakland, MD 21550
See more homes for rent in
Oakland
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Homes for sale near 21 E Pennington St

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NEW - 2 DAYS AGO
$259,900
3 bd
2 ba
1,998 sqft
102 N 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
$269,500
3 bd
2 ba
1,600 sqft
315 Coolidge Ave,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
0.31 ACRES
$275,900
4 bd
2 ba
1,928 sqft
449 S 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
$185,000
3 bd
1.5 ba
1,170 sqft
729 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
0.49 ACRES
$375,000
5 bd
2 ba
3,660 sqft
321 N 3rd St,
Oakland, MD 21550
CENTURY 21 New Millennium
0.46 ACRES
$289,000
3 bd
2.5 ba
2,242 sqft
163 Mitchell Dr,
Oakland, MD 21550
Railey Realty, Inc.
NEW CONSTRUCTION
0.71 ACRES
$399,999
3 bd
2 ba
1,464 sqft
654 N Bradley Ln,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
$275,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
Oakland, MD 21550
Railey Realty, Inc.
0.71 ACRES
$599,000
5 bd
3.5 ba
3,542 sqft
428 Sam Snead Cir,
Oakland, MD 21550
Railey Realty, Inc.
0.5 ACRES
$287,500
3 bd
2 ba
1,248 sqft
505 Southern Pines Dr,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
See more homes for sale in
Oakland
Take a look