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

54 Bear Dr E
Oakland, MD 21550

3 Beds
2 Baths
1,564 sqft (on 1.41 acres)

$282,300

Trulia Estimate

as of May 16, 2026

Est. Refi. Payment $1,588/mo*

Refinance Your Home

$282,300

Trulia Estimate

as of May 16, 2026

Est. Refi. Payment $1,588/mo*

Refinance Your Home

3 Beds

2 Baths

1,564 sqft

(on 1.41 acres)

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 54 Bear Dr E, Oakland, MD. 54 Bear Dr E is in Oakland, MD and in ZIP code 21550. This property has 3 bedrooms, 2 bathrooms and approximately 1,564 sqft of floor space. This property has a lot size of 1.41 acres and was built in 2000.

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 only

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 54 Bear Dr E

Interior Features
Heating & Cooling Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 1Floors: Carpet
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace
Interior Details Ceiling Fan

Exterior Features
Exterior Home Features Roof: CompositionDeckExterior: Wood
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 2000
Property Type / Style Property Type: Single Family HomeArchitecture: conventional

Building
Levels, Entrance, & Accessibility Disabled Access

Community
Units in Building: 1

Lot Information
Lot Area: 1.41 acres

Price History for 54 Bear Dr E

Date	Price	Event	Source
07/31/2019	$212,780	Sold	N/A
Recording Date 07/31/2019 County Transfer Tax N/A Total Transfer Tax N/A
07/02/2019	$229,000	Pending	Agent Provided

04/10/2019	$229,000	Listed For Sale	Agent Provided

11/18/2002	$175,000	Sold	N/A
Recording Date 11/18/2002 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$274
Assessment	$21,533

Home facts updated by county records

Comparable Sales for 54 Bear Dr E

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
506 Cedar Ln, Oakland, MD	0.45	Single-Family Home	$285,000	07/03/25	3	2	1,344
22 Black Oak Dr, Oakland, MD	0.68	Single-Family Home	$220,000	05/30/25	3	2	1,296
17 Driftwood Ln, Oakland, MD	0.65	Single-Family Home	$305,000	11/06/25	3	2	2,092
22 Cub Dr, Oakland, MD	0.09	Single-Family Home	$340,000	11/13/25		3	1,824
1136 Black Oak Dr, Oakland, MD	0.64	Single-Family Home	$218,000	12/01/25	3	1	1,056
1359 Cedar Ln, Oakland, MD	0.92	Single-Family Home	$280,000	02/23/26	2	1.5	1,440
119 Elm Dr, Oakland, MD	0.66	Single-Family Home	$165,000	11/12/25	3	1	1,300
929 Dogwood Dr, Oakland, MD	1.05	Single-Family Home	$200,000	10/09/25	3	1	1,152
123 Deer Crossing Rd, Mc Henry, MD	1.74	Single-Family Home	$300,000	10/29/25	3	2	1,098
6067 Oakland Sang Run Rd, Oakland, MD	2.29	Single-Family Home	$268,750	07/18/25	3	1.5	1,419

Assigned Schools

These are the assigned schools for 54 Bear Dr E.

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

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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Homes for sale near 54 Bear Dr E

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3.23 ACRES
$545,000
4 bd
2.5 ba
1,860 sqft
328 Stool Rock Rd,
Oakland, MD 21550
Railey Realty, Inc.
0.58 ACRES
$359,000
3 bd
1.5 ba
1,152 sqft
552 Black Oak Dr,
Oakland, MD 21550
Long & Foster Real Estate, Inc.
1.72 ACRES
$339,000
4 bd
2.5 ba
1,920 sqft
961 Cedar Ln,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
0.67 ACRES
$289,000
2 bd
2 ba
560 sqft
400 Bear Dr E,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
0.46 ACRES
$349,999
3 bd
1 ba
990 sqft
931 Black Oak Dr,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
1.68 ACRES
$399,000
3 bd
2.5 ba
2,128 sqft
5024 Cranesville Rd,
Oakland, MD 21550
Railey Realty, Inc.
AUCTION
0.71 ACRES
Price Unknown
3 bd
2 ba
1,736 sqft
1078 Swallow Falls Rd,
Oakland, MD 21550
NEW - 1 DAY AGO
2.62 ACRES
$910,000
5 bd
4.5 ba
3,472 sqft
879 Fork Run Trl,
Mchenry, MD 21541
Railey Realty, Inc.
3.34 ACRES
$1,250,000
5 bd
4.5 ba
3,248 sqft
971 Fork Run Trl,
Mchenry, MD 21541
Taylor-Made Deep Creek Real Estate, LLC
7.04 ACRES
$899,000
4 bd
3.5 ba
2,464 sqft
62 Whispering Pines Ln,
Oakland, MD 21550
Railey Realty, Inc.
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Additional Cost

Homes for rent near 54 Bear Dr E

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Off Market Homes Near 54 Bear Dr E

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SOLD
APR 16, 2026
$399,900
3 bd
3 ba
1,536 sqft
33 Lakeview Ct #2B,
Mchenry, MD 21541
Railey Realty, Inc.
SOLD
APR 15, 2026
$379,000
3 bd
2,236 sqft
17 Slopeside Ter #10D,
Mc Henry, MD 21541
Railey Realty, Inc.
SOLD
APR 13, 2026
$255,000
3 bd
2 ba
1,170 sqft
6485 Oakland Sang Run Rd,
Oakland, MD 21550
Taylor Made Deep Creek Real Estate
SOLD
APR 7, 2026
$183,000
63 Camp Cir,
Mc Henry, MD 21541
Railey Realty, Inc.
SOLD
FEB 23, 2026
$280,000
2 bd
1.5 ba
1,440 sqft
1359 Cedar Ln,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
FEB 9, 2026
$160,000
Lowr camp Rd,
Mchenry, MD 21541
SOLD
JAN 12, 2026
$405,000
3 ba
1,920 sqft
2 Bright Psge #1E,
Mchenry, MD 21541
SOLD
DEC 22, 2025
$320,000
3 bd
1.5 ba
1,584 sqft
7216 Sang Run Rd,
Mc Henry, MD 21541
The KW Collective
SOLD
DEC 19, 2025
$250,000
Shingle Camp Rd,
Mc Henry, MD 21541
Railey Realty, Inc.
SOLD
DEC 11, 2025
$412,500
3 bd
3 ba
2,100 sqft
76 Bright Passage Rd #8C,
Mc Henry, MD 21541
See more homes for sale in
Oakland
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54 Bear Dr E, Oakland, MD 21550 is a 3 bedroom, 2 bathroom, 1,564 sqft single-family home built in 2000. This property is not currently available for sale. 54 Bear Dr E was last sold on Jul 31, 2019 for $212,780. The current Trulia Estimate for 54 Bear Dr E is $282,300.

54 Bear Dr E
Oakland, MD 21550

$282,300

$282,300

Local Information