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

1027 E High St
Oakland, MD 21550

3 Beds
1 Bath
1,064 sqft (on 0.31 acres)

$190,900

Trulia Estimate

as of Jun 6, 2026

Est. Refi. Payment $1,154/mo*

Refinance Your Home

$190,900

Trulia Estimate

as of Jun 6, 2026

Est. Refi. Payment $1,154/mo*

Refinance Your Home

3 Beds

1 Bath

1,064 sqft

(on 0.31 acres)

Local Information

-- mins to

Commute Destination

Description

Cozy 3 bedroom home within walking distance to Southern High School offers attached garage and paved drive. Unfinished basement provides plenty of storage space and woodstove provides economical heat source. Backyard offers pavilion, playhouse, grape arbor and huge trees for plenty of shade. Great home for first time homebuyers. If you would like more information about this property, call Vicki Taylor at 301-616-6152 or 301-387-4700 extension 284. Toll Free: 1-800-336-5253 extension 284. Email: vicki.taylor@LNF.com

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 1027 E High St

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

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1956
Property Type / Style Property Type: Single Family HomeArchitecture: conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.31 acres

Price History for 1027 E High St

Date	Price	Event	Source
01/01/2015	$102,000	Sold	Long & Foster Broker Feed #1005036936_100
Recording Date 01/01/2015 County Transfer Tax N/A Total Transfer Tax N/A
08/08/2012	$102,000	Sold	N/A
Recording Date 08/08/2012 Contract Date 08/03/2012 County Transfer Tax $520 Total Transfer Tax $1,030
05/02/2012	$110,000	PriceChange	Agent Provided
Price Change $2,000 (-2%)
03/12/2012	$112,000	PriceChange	Agent Provided
Price Change $9,000 (-7%)
02/06/2012	$121,000	PriceChange	Agent Provided
Price Change $1,000 (-1%)
01/04/2012	$122,000	PriceChange	Agent Provided
Price Change $1,000 (-1%)
12/01/2011	$123,000	PriceChange	Agent Provided
Price Change $1,000 (-1%)
10/28/2011	$124,000	PriceChange	Agent Provided
Price Change $1,000 (-1%)
10/09/2010	$125,000	Listed For Sale	Agent Provided

Market trends in Oakland

Last updated April 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

11MoM

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Property Tax and Assessment

Year	2025
Tax	$1,234
Assessment	$117,800

Home facts updated by county records

Comparable Sales for 1027 E High St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
445 Dennett Rd, Oakland, MD	0.22	Single-Family Home	$305,000	11/07/25	3	1	1,410
215 N 10th St, Oakland, MD	0.30	Single-Family Home	$279,000	09/25/25	3	1	1,518
723 E Oak St, Oakland, MD	0.48	Single-Family Home	$180,250	03/16/26	3	1	988
116 N 8th St, Oakland, MD	0.43	Single-Family Home	$148,000	07/02/25	2	1	1,494
414 D St, Oakland, MD	0.59	Single-Family Home	$150,000	08/14/25	2	1	936
120 N 3rd St, Oakland, MD	0.81	Single-Family Home	$70,000	01/15/26	3	1	1,660
320 Coolidge Ave, Oakland, MD	0.63	Single-Family Home	$135,000	09/22/25	2	1	720
711 Heritage Dr, Oakland, MD	0.54	Single-Family Home	$249,000	03/20/26	3	2	1,400
705 Pensinger Blvd, Oakland, MD	0.49	Single-Family Home	$216,900	09/19/25	3	3	1,800
1056 Sunrise Dr, Oakland, MD	0.11	Single-Family Home	$280,000	11/14/25	4	2.5	1,528

Nearby homes

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

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FOR SALE
0.36 ACRES
$234,000
3 bd
2 ba
1,520 sqft
1021 E High St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $250,100
4 bd
3 ba
2,144 sqft
1070 Sunrise Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
NOV 14, 2025
$280,000
4 bd
2.5 ba
1,528 sqft
1056 Sunrise Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $636,400
4 bd
3.5 ba
4,200 sqft
45 Oakland Dr,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
NOV 7, 2025
$305,000
3 bd
1 ba
1,410 sqft
445 Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $281,800
6 bd
2 ba
4,158 sqft
208 N 10th St,
Oakland, MD 21550
OFF MARKET
Est. $317,500
4 bd
2 ba
2,772 sqft
206-208 N 10th St,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
SEP 25, 2025
$279,000
3 bd
1 ba
1,518 sqft
215 N 10th St,
Oakland, MD 21550
SOLD
OCT 10, 2025
$370,000
4 bd
2.5 ba
3,159 sqft
220 N 11th St,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
0.53 ACRES
$44,900
Lot 2 Oak Breeze Ln,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 1, 2026
$150,000
8th & Dennett Road St,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 1027 E High St.

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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Contact for price
1-2 bd
1-2 ba
201 E Mason St #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
108 Decatur St #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
750 Vista Sq #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
607 P St #f320a52c6,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
706 E Alder St #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
1113 Mary Dr #f320a52c6,
Oakland, MD 21550
APPLY INSTANTLY
PET FRIENDLY
$850/mo
2 bd
1 ba
401 Dave Turney St #2,
Oakland, MD 21550
$1,550/mo
3 bd
1 ba
400 E Alder St #3,
Oakland, MD 21550
See more homes for rent in
Oakland
Take a look

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Explore by feature

APPLY INSTANTLY
$1,750/mo
3 bd
2.5 ba
1,867 sqft
88 Knoll Crest Heights Dr,
Oakland, MD 21550
APPLY INSTANTLY
$1,575/mo
3 bd
2 ba
1,542 sqft
13750 Garrett Hwy,
Oakland, MD 21550
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$1,400/mo
2 bd
2 ba
950 sqft
1275 Foster Rd,
Oakland, MD 21550
APPLY INSTANTLY
$1,990/mo
3 bd
1 ba
3,350 sqft
604 E Oak St,
Oakland, MD 21550
$2,000/mo
5 bd
2.5 ba
704 Old Crellin Rd,
Oakland, MD 21550
$1,550/mo
3 bd
1 ba
2,312 sqft
400 E Alder St #3,
Oakland, MD 21550
6 rentals with air conditioning in Oakland, MD

Homes for sale near 1027 E High St

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0.36 ACRES
$234,000
3 bd
2 ba
1,520 sqft
1021 E High St,
Oakland, MD 21550
Railey Realty, Inc.
$185,000
3 bd
1.5 ba
1,170 sqft
729 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
0.5 ACRES
$287,500
3 bd
2 ba
1,248 sqft
505 Southern Pines Dr,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
$275,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
Oakland, MD 21550
Railey Realty, Inc.
$269,500
3 bd
2 ba
1,600 sqft
315 Coolidge Ave,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
FORECLOSURE
0.27 ACRES
$149,900
2 bd
2 ba
1,386 sqft
123 B St,
Oakland, MD 21550
Century 21 Downtown
0.34 ACRES
$40,000
2 bd
1 ba
782 sqft
820 N 4th St,
Oakland, MD 21550
The KW Collective
0.31 ACRES
$275,900
4 bd
2 ba
1,928 sqft
449 S 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
0.46 ACRES
$289,000
3 bd
2.5 ba
2,242 sqft
163 Mitchell Dr,
Oakland, MD 21550
Railey Realty, Inc.
0.41 ACRES
$369,000
3 bd
3 ba
2,388 sqft
215 H St,
Oakland, MD 21550
Railey Realty, Inc.
See more homes for sale in
Oakland
Take a look

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Off Market Homes Near 1027 E High St

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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
$205,000
2 bd
1 ba
1,492 sqft
207 Shenandoah Ave,
Loch Lynn Heights, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
MAY 12, 2026
$276,000
Hammond St,
Oakland, MD 21550
SOLD
MAY 8, 2026
$276,000
2 bd
2 ba
1,000 sqft
226 N Hammond St,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
MAY 6, 2026
$210,000
2 bd
1 ba
1,064 sqft
313 W Liberty St,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAY 6, 2026
$150,000
2 ba
2,752 sqft
425 E Alder St,
Oakland, MD 21550
SOLD
APR 21, 2026
$185,000
3 bd
1 ba
1,563 sqft
108 W 2nd Ave,
Oakland, MD 21550
SOLD
MAR 31, 2026
$247,500
2 bd
2 ba
1,386 sqft
123 B St,
Oakland, MD 21550
SOLD
MAR 27, 2026
$250,000
3 bd
2 ba
1,848 sqft
702 Sunshine Dr,
Oakland, MD 21550
Railey Realty, Inc.
See more homes for sale in
Oakland
Take a look

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Homes for rent near 1027 E High St

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APPLY INSTANTLY
$1,750/mo
3 bd
2.5 ba
1,867 sqft
88 Knoll Crest Heights Dr,
Oakland, MD 21550
APPLY INSTANTLY
$1,575/mo
3 bd
2 ba
1,542 sqft
13750 Garrett Hwy,
Oakland, MD 21550
APPLY INSTANTLY
$1,990/mo
3 bd
1 ba
3,350 sqft
604 E Oak St,
Oakland, MD 21550
See more homes for rent in
Oakland
Take a look

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1027 E High St, Oakland, MD 21550 is a 3 bedroom, 1 bathroom, 1,064 sqft single-family home built in 1956. This property is not currently available for sale. 1027 E High St was last sold on Jan 1, 2015 for $102,000. The current Trulia Estimate for 1027 E High St is $190,900.

1027 E High St
Oakland, MD 21550

$190,900

$190,900

Local Information