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

279 Cheeks Ln
Oakland, MD 21550

2 Beds
2 Baths

$175,500

Trulia Estimate

as of Jul 9, 2026

Est. Refi. Payment $1,069/mo*

Refinance Your Home

$175,500

Trulia Estimate

as of Jul 9, 2026

Est. Refi. Payment $1,069/mo*

Refinance Your Home

2 Beds

2 Baths

(on 0.41 acres)

Local Information

Map ViewExplore the area around 279 Cheeks Ln.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Incredible 2 Bed/2 Bath Cottage nestled among hemlocks, ferns, rhdodendrens & within walking distance (1M) to Swallow Falls State Park!

279 Cheeks Ln, Oakland, MD 21550 is a 2 bedroom, 2 bathroom single-family home built in 1977. It last sold for $50,000 on Aug 18, 2003. It is currently off market. The Trulia Estimate is $175,500, with a rent estimate of $1,433/month.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 279 Cheeks Ln

Interior Features
Heating & Cooling Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

Property Information
Year Built Year Built: 1977
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features Exterior: Stone
Parking & Garage Parking: Carport

Lot Information
Lot Area: 0.41 acres

Price History for 279 Cheeks Ln

Date	Price	Event	Source
03/14/2017	$124,900	ListingRemoved	Agent Provided

02/27/2017	$124,900	Pending	Agent Provided

02/21/2017	$124,900	PriceChange	Agent Provided
Price Change $15,000 (-11%)
12/02/2016	$139,900	Listed For Sale	Agent Provided

08/18/2003	$50,000	Sold	N/A
Recording Date 08/18/2003 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Oakland

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

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Property Tax and Assessment

Year	2025
Tax	$119
Assessment	$10,500

Home facts updated by county records

Comparable Sales for 279 Cheeks Ln

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
279 Cheeks Ln, Oakland, MD	0.02	Single-Family Home	$120,000	06/24/26	2	2	1,007
4643 Oakland Sang Run Rd, Oakland, MD	0.83	Single-Family Home	$180,000	09/12/25	2	2	864
6067 Oakland Sang Run Rd, Oakland, MD	0.77	Single-Family Home	$268,750	07/18/25	3	1.5	1,419
2045 Swallow Falls Rd, Oakland, MD	0.45	Single-Family Home	$910,000	09/25/25	5	3.5	5,416
6485 Oakland Sang Run Rd, Oakland, MD	1.05	Single-Family Home	$255,000	04/13/26	3	2	1,170
5526 Oakland Sang Run Rd, Oakland, MD	0.50	Single-Family Home	$116,500	07/17/25		1	1,196
62 Whispering Pines Ln, Oakland, MD	0.39	Single-Family Home	$850,000	07/08/26	4	3.5	2,464
1078 Swallow Falls Rd, Oakland, MD	0.92	Single-Family Home	$290,500	06/02/26		3	1,344
343 Maple Del Ln, Oakland, MD	1.43	Single-Family Home	$405,000	08/08/25	3	2.5	1,404
305 Whistlepig Way, Oakland, MD	1.01	Single-Family Home	$100,000	02/27/26		3	2,360

Nearby homes

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

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OFF MARKET
Whispering Pnes,
Oakland, MD 21550
Long & Foster Real Estate, Inc.
SOLD
JUL 8, 2026
$850,000
4 bd
3.5 ba
2,464 sqft
62 Whispering Pines Ln,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
0.51 ACRES
$60,000
Whispering Pines Ln,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
SEP 25, 2025
$910,000
5 bd
3.5 ba
5,416 sqft
2045 Swallow Falls Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $377,800
3 bd
2.5 ba
1,638 sqft
5289 Oakland Sang Run Rd,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
NEW CONSTRUCTION
3D VIEW
0.59 ACRES
$1,074,900
4 bd
5 ba
3,032 sqft
52 Dam View Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Swallow Falls Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Swallow Falls Rd,
Oakland, MD 21550
Long & Foster Real Estate, Inc.
FOR SALE
0.59 ACRES
$38,500
Lot 13 Bray Run Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $277,200
3 bd
2 ba
1,680 sqft
93 Mel Lin Ln,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
SEP 12, 2025
$180,000
2 bd
2 ba
864 sqft
4643 Oakland Sang Run Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
LOT Oakland Sang Run Rd,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 279 Cheeks Ln.

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 279 Cheeks Ln

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NEW CONSTRUCTION
0.59 ACRES
$1,074,900
4 bd
5 ba
3,032 sqft
52 Dam View Dr,
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
1.14 ACRES
$224,900
1 bd
1 ba
206 Mayhew Inn Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
0.91 ACRES
$34,900
3 bd
1 ba
1,920 sqft
3482 Oakland Sang Run Rd,
Oakland, MD 21550
Pearson Smith Realty, LLC
OPEN SAT, 11-1PM
1.95 ACRES
$749,900
5 bd
1.5 ba
1,278 sqft
222 Skippers Point Rd,
Oakland, MD 21550
The KW Collective
NEW - 1 DAY AGO
0.46 ACRES
$2,699,000
6 bd
6.5 ba
3,442 sqft
1342 Stockslager Rd,
Oakland, MD 21550
Railey Realty, Inc.
4.88 ACRES
$195,000
3 bd
1 ba
1,382 sqft
2918 Oakland Sang Run Rd,
Oakland, MD 21550
Railey Realty, Inc.
1.17 ACRES
$398,500
4 bd
2 ba
2,234 sqft
1499 Foster Rd,
Oakland, MD 21550
Railey Realty, Inc.
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
NEW CONSTRUCTION
$679,900
5 bd
4.5 ba
3,000 sqft
4A Mystic Creek Trl,
Oakland, MD 21550
Railey Realty, Inc.
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