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

SOLD

OCT 28, 2025

26 Bear Dr E
Oakland, MD 21550

$3,000

Last Sold: Oct 28, 2025

Est. Refi. Payment $92/mo*

Refinance Your Home

$3,000

Last Sold: Oct 28, 2025

Est. Refi. Payment $92/mo*

Refinance Your Home

(on 0.51 acres)

Local Information

Map ViewExplore the area around 26 Bear Dr E.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

26 Bear Dr E is in Oakland, MD and in ZIP code 21550. This property has a lot size of 0.51 acres.

26 Bear Dr E, Oakland, MD 21550 is a unknown. It last sold for $3,000 on Oct 28, 2025. It is currently off market. The Trulia Estimate rent is $1,313/month.

Home Highlights

Parking

No Info

Outdoor

No Info

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 26 Bear Dr E

Property Information
Property Type / Style Property Type: Unknown

Interior Features
Fireplace & Spa Fireplace

Lot Information
Lot Area: 0.51 acres

Price History for 26 Bear Dr E

Date	Price	Event	Source
10/28/2025	$3,000	Sold	N/A
Recording Date 10/28/2025 Contract Date 10/24/2025 County Transfer Tax $0 Total Transfer Tax $0
02/22/2012	$1,000	Sold	N/A
Recording Date 02/22/2012 Contract Date 02/17/2012 County Transfer Tax N/A Total Transfer Tax N/A
02/10/2011	$3,500	Sold	N/A
Recording Date 02/10/2011 Contract Date 02/10/2011 County Transfer Tax N/A Total Transfer Tax N/A
10/21/2005	$1,500	Sold	N/A
Recording Date 10/21/2005 County Transfer Tax N/A Total Transfer Tax N/A

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	$7
Assessment	$600

Home facts updated by county records

Comparable Sales for 26 Bear Dr E

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
22 Cub Dr, Oakland, MD	0.11	Single-Family Home	$340,000	11/13/25		3	1,824
119 Elm Dr, Oakland, MD	0.62	Single-Family Home	$165,000	11/12/25	3	1	1,300
17 Driftwood Ln, Oakland, MD	0.64	Single-Family Home	$305,000	11/06/25	3	2	2,092
1136 Black Oak Dr, Oakland, MD	0.61	Single-Family Home	$218,000	12/01/25	3	1	1,056
929 Dogwood Dr, Oakland, MD	1.01	Single-Family Home	$200,000	10/09/25	3	1	1,152
1359 Cedar Ln, Oakland, MD	0.88	Single-Family Home	$280,000	02/23/26	2	1.5	1,440
123 Deer Crossing Rd, Mc Henry, MD	1.71	Single-Family Home	$300,000	10/29/25	3	2	1,098
969 Hoyes Run Rd, Oakland, MD	1.81	Single-Family Home	$697,000	12/19/25	5	3	3,614
6485 Oakland Sang Run Rd, Oakland, MD	2.26	Single-Family Home	$255,000	04/13/26	3	2	1,170
1026 N Camp Rd, Mchenry, MD	2.44	Single-Family Home	$1,061,735	01/28/26	5	5.5	4,068

Nearby homes

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

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SOLD
OCT 24, 2025
$3,000
27 Stool Rock Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
FOR SALE
0.49 ACRES
$16,000
21 Bear Dr E,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
FOR SALE
0.48 ACRES
$3,500
2 Beaver Run Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
OFF MARKET
1 Stool Rock Rd,
Oakland, MD 21550
1 Real Estate Source LLC
FOR SALE
3.23 ACRES
$545,000
4 bd
2.5 ba
1,860 sqft
328 Stool Rock Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
7 Bear Dr E,
Piney Mountain, MD 21550
Railey Realty, Inc.
SOLD
FEB 13, 2026
$3,500
25 W Big Piney Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
20 Stool Rock Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
APR 3, 2026
$5,000
Lots 34 & 35 Fox Tail Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 24, 2026
$3,500
36 Fox Tail Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
OFF MARKET
149 Gobler Run Rd,
Oakland, MD 21550
Berkshire Hathaway HomeServices Homesale Realty
OFF MARKET
Gobler Run Rd,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 26 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

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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Homes for sale near 26 Bear Dr E

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0.58 ACRES
$349,000
3 bd
1.5 ba
1,152 sqft
552 Black Oak Dr,
Oakland, MD 21550
Long & Foster Real Estate, Inc.
0.67 ACRES
$269,000
2 bd
2 ba
560 sqft
400 Bear Dr E,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
0.46 ACRES
$329,999
3 bd
1 ba
990 sqft
931 Black Oak Dr,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
3.23 ACRES
$545,000
4 bd
2.5 ba
1,860 sqft
328 Stool Rock Rd,
Oakland, MD 21550
Railey Realty, Inc.
0.65 ACRES
$349,900
4 bd
2 ba
3,352 sqft
2448 Birchwood Dr,
Oakland, MD 21550
Railey Realty, 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
1.68 ACRES
$399,000
3 bd
2.5 ba
2,128 sqft
5024 Cranesville Rd,
Oakland, MD 21550
Railey Realty, Inc.
0.51 ACRES
$950,000
5 bd
5.5 ba
3,804 sqft
957 N Camp Rd,
Mchenry, MD 21541
The KW Collective
0.45 ACRES
$1,299,900
5 bd
5.5 ba
3,179 sqft
985 N Camp Rd,
Mchenry, MD 21541
Railey Realty, Inc.
NEW CONSTRUCTION
0.71 ACRES
$999,500
5 bd
5.5 ba
3,600 sqft
44 Ridgeline Trl,
Mc Henry, MD 21541
Railey Realty, Inc.
See more homes for sale in
Oakland
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Off Market Homes Near 26 Bear Dr E

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SOLD
JUN 24, 2026
$3,500
36 Fox Tail Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
FEB 19, 2026
$3,000
W Big piney Dr,
Oakland, MD 21550
SOLD
FEB 13, 2026
$3,500
25 W Big Piney Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
OCT 24, 2025
$3,000
27 Stool Rock Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
OCT 3, 2025
$2,500
9 Bobolink Dr,
Terra Alta, WV 26764
See more homes for sale in
Oakland
Take a look

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26 Bear Dr E
Oakland, MD 21550

$3,000

$3,000

Local Information