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

108 Matthew Rd
Oakland, MD 21550

3 Beds
2 Baths
1,368 sqft (on 1.40 acres)

$251,700

Trulia Estimate

as of Jul 7, 2026

Est. Refi. Payment $1,498/mo*

Refinance Your Home

$251,700

Trulia Estimate

as of Jul 7, 2026

Est. Refi. Payment $1,498/mo*

Refinance Your Home

3 Beds

2 Baths

1,368 sqft

(on 1.40 acres)

Local Information

Map ViewExplore the area around 108 Matthew Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

OWNER MUST SELL!!! ALL OFFERS WILL BE LOOKED AT!! Well maintained 3 Br. home! This property is nestled among the trees on 1.40 acres. Outdoor swimming pool for your enjoyment on those hot summer days. Yard has been beautifully landscaped, detached 2 car garage, home has been remodeled in 2008. Feel like you are away but yet so close to Oakland's schools and shopping. Call today!

108 Matthew Rd, Oakland, MD 21550 is a 3 bedroom, 2 bathroom, 1,368 sqft multi-family built in 1990. It last sold for $170,000 on Oct 20, 2008. It is currently off market. The Trulia Estimate is $251,700, with a rent estimate of $1,626/month.

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 108 Matthew Rd

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

Exterior Features
Exterior Home Features Roof: Shake ShingleDeckExterior: Other
Parking & Garage GarageParking: Carport, Garage Attached

Property Information
Year Built Year Built: 1990
Property Type / Style Property Type: Multi FamilyArchitecture: conventional

Community
Units in Building: 1

Lot Information
Lot Area: 1.40 acres

Price History for 108 Matthew Rd

Date	Price	Event	Source
10/20/2008	$170,000	Sold	N/A
Recording Date 10/20/2008 County Transfer Tax N/A Total Transfer Tax N/A
09/03/2008	$189,900	PriceChange	Agent Provided
Price Change $20,100 (-10%)
06/18/2008	$210,000	PriceChange	Agent Provided
Price Change $19,900 (-9%)
05/27/2008	$229,900	Listed For Sale	Agent Provided

08/16/2004	$90,000	Sold	N/A
Recording Date 08/16/2004 County Transfer Tax N/A Total Transfer Tax N/A
09/29/1995	$56,700	Sold	N/A
Recording Date 09/29/1995 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	$1,966
Assessment	$204,267

Home facts updated by county records

Comparable Sales for 108 Matthew Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
287 Winding Trail Ln #10B, Oakland, MD	5.20	Multi-Family Home	$560,000	03/30/26	5	4.5	3,300

Home facts updated by county records

Nearby homes

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

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OFF MARKET
Est. $251,500
2 bd
1 ba
1,976 sqft
3694 Broadford Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
NOV 21, 2025
$44,000
142 Matthew Rd,
Deer Park, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $341,000
4 bd
2.5 ba
2,240 sqft
139 Hunters Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
FEB 20, 2026
$75,000
3 bd
1 ba
1,462 sqft
3416 Broadford Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
MAY 6, 2026
$300,000
4000 Area Broadford Rd,
Oakland, MD 21550
1 Real Estate Source LLC
OFF MARKET
Est. $120,200
3 bd
2 ba
1,092 sqft
31 Mount Airy Ct,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $416,000
4 bd
3 ba
2,536 sqft
29 Crescent Ln,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $171,700
3 bd
1.5 ba
1,056 sqft
32 Rockville Ct,
Oakland, MD 21550
Corner House Realty
OFF MARKET
Est. $236,700
4 bd
2 ba
1,840 sqft
97 Shady Ln,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 11, 2026
$250,000
4 bd
2 ba
1,956 sqft
18 Ollie North Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 1, 2026
$290,000
2 bd
2 ba
2,015 sqft
3749 State St,
Oakland, MD 21550
Keller Williams Realty
OFF MARKET
Est. $237,800
3 bd
1 ba
1,420 sqft
4300 State St,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 108 Matthew Rd.

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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Oakland
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Homes for sale near 108 Matthew Rd

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Off Market Homes Near 108 Matthew Rd

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SOLD
JUL 1, 2026
$150,000
4 bd
2 ba
3395 Fingerboard Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
JUN 16, 2026
$220,000
3 bd
2 ba
1,104 sqft
53 Bird Ave,
Deer Park, MD 21550
Railey Realty, Inc.
SOLD
JUN 15, 2026
$165,000
3 bd
1 ba
1,632 sqft
505 Shenandoah Ave,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 11, 2026
$250,000
4 bd
2 ba
1,956 sqft
18 Ollie North Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 5, 2026
$190,000
1 ba
1,056 sqft
513 M St,
Oakland, MD 21550
SOLD
JUN 3, 2026
$150,000
Dennett Rd,
Oakland, MD 21550
SOLD
JUN 1, 2026
$290,000
2 bd
2 ba
2,015 sqft
3749 State St,
Oakland, MD 21550
Keller Williams Realty
SOLD
JUN 1, 2026
$150,000
8th & Dennett Road St,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
MAY 22, 2026
$185,000
2 bd
1 ba
950 sqft
1307 Broadford Rd,
Oakland, MD 21550
Keller Williams Realty Centre
SOLD
MAY 20, 2026
$295,000
3 bd
2.5 ba
1,416 sqft
163 Crestview Dr,
Oakland, MD 21550
Railey Realty, Inc.
See more homes for sale in
Oakland
Take a look

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108 Matthew Rd
Oakland, MD 21550

$251,700

$251,700

Local Information