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, 33% 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

What is Upperman Rd estimated to be worth?

Trulia's estimated value for Upperman Rd in Oakland, MD is $247,700 .

What is the price history for Upperman Rd?

Upperman Rd in Oakland, MD last sold for $190,000 in March 2022.

What are the closest schools to Upperman Rd?

The closest schools to Upperman Rd in Oakland, MD are Southern Garrett High School (Middle, rated 6/10), Swan Meadow School (Elementary/Middle, rated 4/10), Yough Glades Elementary School (Pre-K, rated 5/10).

How big is the lot at Upperman Rd?

The lot at Upperman Rd in Oakland, MD is about 37 acres .

OFF MARKET

Upperman Rd
Oakland, MD 21550

Studio

$247,700

Trulia Estimate

as of Aug 20, 2026

Est. Refi. Payment $1,504/mo*

Refinance Your Home

$247,700

Trulia Estimate

as of Aug 20, 2026

Est. Refi. Payment $1,504/mo*

Refinance Your Home

Studio

(on 36.97 acres)

Home Value

Trulia Estimate

$248K

Since last month

$700 (+0.3%)

Since last year

$30K (-10.9%)

Since last sale

$58K (+30.5%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +17% in the last 10 years

Month	Estimated value
2026
August 2026	$248K
July 2026	$247K
June 2026	$249K
May 2026	$249K
April 2026	$249K
March 2026	$249K
February 2026	$250K
January 2026	$316K
2025
December 2025	$260K
October 2025	$268K
September 2025	$263K
August 2025	$278K
July 2025	$268K
June 2025	$275K
May 2025	$276K
April 2025	$352K
March 2025	$272K
February 2025	$282K
January 2025	$266K
2024
December 2024	$275K
November 2024	$280K
October 2024	$223K
September 2024	$265K
August 2024	$277K
July 2024	$272K
June 2024	$268K
May 2024	$274K
April 2024	$287K
March 2024	$253K
February 2024	$265K
January 2024	$270K
2023
December 2023	$230K
November 2023	$256K
October 2023	$232K
September 2023	$214K
August 2023	$211K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1517 Upperman Rd, Oakland, MD	1.48	Single-Family Home	$250,000	02/11/26	1	1	530
1425 Schell Rd, Oakland, MD	1.96	Single-Family Home	$265,000	07/29/26		2	1,456
794 Schell Rd, Oakland, MD	1.72	Single-Family Home	$106,250	09/26/25		1	1,232
56 Cliffside Ct, Oakland, MD	2.06	Single-Family Home	$118,800	06/18/26	1	1	608
355 Lonesome Pine Rd, Oakland, MD	3.25	Single-Family Home	$610,000	05/19/26	2	2	4,720
1570 Garrett Rd, Deer Park, MD	4.06	Single-Family Home	$225,000	02/19/26	3	1	1,408
128 Swantamont Rd, Swanton, MD	3.93	Single-Family Home	$75,500	08/25/25		1	1,040
141 Truesdale Rd, Oakland, MD	4.16	Single-Family Home	$185,000	01/23/26	3	2.5	1,834
105 Main St, Deer Park, MD	4.14	Single-Family Home	$134,000	12/12/25	3	1.5	1,466
53 Bird Ave, Deer Park, MD	4.47	Single-Family Home	$220,000	06/16/26	3	2	1,104

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
Hubbard Rd, Oakland, MD 21550	0.88	-	-	-	-	Off Market
93/ACRE S Upperman Rd, Oakland, MD 21550	1.37	-	-	-	-	Off Market
1517 Upperman Rd, Oakland, MD 21550	1.48	$250,000	1	1	530	Recently Sold
Upperman Rd, Oakland, MD 21550	1.52	$250,000	-	-	-	Recently Sold

Local Information

Map ViewExplore the area around Upperman Rd.
Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

36.97 acres

About this House

This single-family home is located at Upperman Rd, Oakland, MD. Upperman Rd is in Oakland, MD and in ZIP code 21550. This property has a lot size of 36.97 acres.

Upperman Rd, Oakland, MD 21550 is a studio single-family home. It last sold for $190,000 on Mar 25, 2022. It is currently off market. The Trulia Estimate is $247,700, with a rent estimate of $1,876/month.

Home Details for Upperman Rd

Property Information
Property Type / Style Property Type: Single Family Home

Interior Features
Fireplace & Spa Fireplace

Lot Information
Lot Area: 36.97 acres

Price and Tax history

Date	Event	Price
Mar 25, 2022 Source: N/A	Sold	$190,000
Aug 5, 1997 Source: N/A	Sold	$41,000

Year	Property tax	Tax assessment
2025	$78	$6,900

Additional Cost

Market trends in Oakland

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

10MoM

Around this home

Yough Glades Elementary School
PK-5
Public
295 Students
Garrett County Public Schools
5/10
GreatSchools Rating
Parent Rating Average
This is a WONDERFUL school! My daughter started attending this school midway through the year. She was attending Broadford, but i was unsatisfied with the teaching methods. After starting this school she has already learned to write, spell, and read!! I am so proud of her accomplishments at her new school!!
Parent Review
14y ago
1 Reviews

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
33 % 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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Frequently asked questions about Upperman Rd

What is Upperman Rd estimated to be worth?
Trulia's estimated value for Upperman Rd in Oakland, MD is $247,700.
What is the price history for Upperman Rd?
Upperman Rd in Oakland, MD last sold for $190,000 in March 2022.
What are the closest schools to Upperman Rd?
The closest schools to Upperman Rd in Oakland, MD are Southern Garrett High School (Middle, rated 6/10), Swan Meadow School (Elementary/Middle, rated 4/10), Yough Glades Elementary School (Pre-K, rated 5/10).
How big is the lot at Upperman Rd?
The lot at Upperman Rd in Oakland, MD is about 37 acres.

Apartments for Rent

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Off Market Homes Near Upperman Rd

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SOLD
JUL 29, 2026
$265,000
2 ba
1,456 sqft
1425 Schell Rd,
Oakland, MD 21550
SOLD
JUL 27, 2026
$150,000
584 Old Wilson Rd,
Swanton, MD 21561
Homes & Land Real Estate
SOLD
FEB 27, 2026
$200,000
Laurel Run,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
FEB 19, 2026
$225,000
3 bd
1 ba
1,408 sqft
1570 Garrett Rd,
Deer Park, MD 21550
1 Real Estate Source LLC
SOLD
FEB 11, 2026
$250,000
1 bd
1 ba
530 sqft
1517 Upperman Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
FEB 5, 2026
$250,000
Upperman Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JAN 23, 2026
$185,000
3 bd
2.5 ba
1,834 sqft
141 Truesdale Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
DEC 12, 2025
$134,000
3 bd
1.5 ba
1,466 sqft
105 Main St,
Deer Park, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $289,200
2 bd
1 ba
1,050 sqft
2360 Garrett Rd,
Oakland, MD 21550
Railey Realty, Inc.
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Homes for sale near Upperman Rd

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NEW CONSTRUCTION
63.42 ACRES
$3,249,000
4 bd
5 ba
6,036 sqft
415 Nazelrod Rd,
Oakland, MD 21550
Railey Realty, Inc.
327.72 ACRES
$2,499,900
4 bd
1.5 ba
2,190 sqft
83 Bethlehem Rd,
Oakland, MD 21550
Railey Realty, Inc.
8.05 ACRES
$699,000
5 bd
3 ba
2,560 sqft
170 Cherrywood Dr,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
32.2 ACRES
$350,000
5 bd
1.5 ba
1,536 sqft
511 Main St,
Deer Park, MD 21550
1 Real Estate Source LLC
27.04 ACRES
$639,900
3 bd
2 ba
3,640 sqft
1651 Swanton Rd,
Swanton, MD 21561
Railey Realty, Inc.
2.3 ACRES
$460,000
5 bd
2 ba
2,860 sqft
5154 State St,
Oakland, MD 21550
Coldwell Banker Home Town Realty
0.96 ACRES
$384,500
3 bd
2 ba
2,476 sqft
321 Deer Park Hotel Rd,
Oakland, MD 21550
Houwzer, LLC
4 ACRES
$699,000
4 bd
4.5 ba
2,970 sqft
1909 Pysell Crosscut Rd,
Deer Park, MD 21550
Railey Realty, Inc.
1.83 ACRES
$699,000
5 bd
3.5 ba
4,230 sqft
312 Moss Creek Cir,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
0.46 ACRES
$164,000
3 bd
1 ba
816 sqft
63 Wallman Rd,
Oakland, MD 21550
Railey Realty, Inc.
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Upperman Rd
Oakland, MD 21550

$247,700

$247,700