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

88 Cheeks Ln
Oakland, MD 21550

Studio
1 Bath
984 sqft (on 2.16 acres)

$144,000

Trulia Estimate

as of Jul 18, 2026

Est. Refi. Payment $899/mo*

Refinance Your Home

$144,000

Trulia Estimate

as of Jul 18, 2026

Est. Refi. Payment $899/mo*

Refinance Your Home

Studio

1 Bath

984 sqft

(on 2.16 acres)

Local Information

Map ViewExplore the area around 88 Cheeks Ln.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 88 Cheeks Ln, Oakland, MD. 88 Cheeks Ln is in Oakland, MD and in ZIP code 21550. This property has 1 bathroom and approximately 984 sqft of floor space. This property has a lot size of 2.16 acres and was built in 1957.

88 Cheeks Ln, Oakland, MD 21550 is a studio, 1 bathroom, 984 sqft single-family home built in 1957. It last sold for $35,000 on Sep 16, 2002. It is currently off market. The Trulia Estimate is $144,000, with a rent estimate of $1,408/month.

Home Highlights

Parking

No Info

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 88 Cheeks Ln

Interior Features
Heating & Cooling Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleDeckExterior: Other

Property Information
Year Built Year Built: 1957
Property Type / Style Property Type: Single Family HomeArchitecture: conventional

Community
Units in Building: 1

Lot Information
Lot Area: 2.16 acres

Price History for 88 Cheeks Ln

Date	Price	Event	Source
09/16/2002	$35,000	Sold	N/A
Recording Date 09/16/2002 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Oakland

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

12MoM

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Property Tax and Assessment

Year	2025
Tax	$1,035
Assessment	$88,800

Home facts updated by county records

Comparable Sales for 88 Cheeks Ln

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
279 Cheeks Ln, Oakland, MD	0.21	Single-Family Home	$120,000	06/24/26	2	2	1,007
4643 Oakland Sang Run Rd, Oakland, MD	1.01	Single-Family Home	$180,000	09/12/25	2	2	864
62 Whispering Pines Ln, Oakland, MD	0.32	Single-Family Home	$850,000	07/08/26	4	3.5	2,464
2045 Swallow Falls Rd, Oakland, MD	0.32	Single-Family Home	$910,000	09/25/25	5	3.5	5,416
1078 Swallow Falls Rd, Oakland, MD	0.73	Single-Family Home	$290,500	06/02/26		3	1,344
6485 Oakland Sang Run Rd, Oakland, MD	1.09	Single-Family Home	$255,000	04/13/26	3	2	1,170
305 Whistlepig Way, Oakland, MD	1.03	Single-Family Home	$100,000	02/27/26		3	2,360
398 Youghiogheny Path, Oakland, MD	1.63	Single-Family Home	$150,000	06/25/26		2	1,512
929 Dogwood Dr, Oakland, MD	1.86	Single-Family Home	$200,000	10/09/25	3	1	1,152
136 Henry Clay Dr, Oakland, MD	2.40	Single-Family Home	$80,000	02/19/26		1	1,056

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.
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
Swallow Falls Rd,
Oakland, MD 21550
Railey Realty, 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.
OFF MARKET
Swallow Falls Rd,
Oakland, MD 21550
Long & Foster Real Estate, 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.
FOR SALE
0.59 ACRES
$38,500
Lot 13 Bray Run Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $274,800
3 bd
2 ba
1,680 sqft
93 Mel Lin Ln,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
FOR SALE
1.14 ACRES
$224,900
1 bd
1 ba
206 Mayhew Inn Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
OFF MARKET
Est. $175,200
2 bd
2 ba
864 sqft
4643 Oakland Sang Run Rd,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 88 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 88 Cheeks Ln

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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
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.
0.91 ACRES
$34,900
3 bd
1 ba
1,920 sqft
3482 Oakland Sang Run Rd,
Oakland, MD 21550
Pearson Smith Realty, LLC
1.95 ACRES
$729,000
5 bd
1.5 ba
1,278 sqft
222 Skippers Point Rd,
Oakland, MD 21550
The KW Collective
4.88 ACRES
$185,000
3 bd
1 ba
1,382 sqft
2918 Oakland Sang Run Rd,
Oakland, MD 21550
Railey Realty, Inc.
NEW - 2 DAYS AGO
0.46 ACRES
$875,000
4 bd
3 ba
2,280 sqft
37 Skippers Point Rd,
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
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
1.17 ACRES
$398,500
4 bd
2 ba
2,234 sqft
1499 Foster Rd,
Oakland, MD 21550
Railey Realty, Inc.
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