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

1026 E High St
Oakland, MD 21550

3 Beds
1 Bath
1,040 sqft (on 0.37 acres)

$235,500

Trulia Estimate

as of Jul 9, 2026

Est. Refi. Payment $1,409/mo*

Refinance Your Home

$235,500

Trulia Estimate

as of Jul 9, 2026

Est. Refi. Payment $1,409/mo*

Refinance Your Home

3 Beds

1 Bath

1,040 sqft

(on 0.37 acres)

Local Information

Map ViewExplore the area around 1026 E High St.
Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This is a really well-maintained rancher with many upgrades & improvements! 3Bdr/1Ba in convenient location near all Southern schools-hardwood floors in bedrooms-updated bath w/ceramic tile-new 35 yr. warranty metal roof-2 new insulated entry doors-high efficiency Lennox gas forced air furnace-vinyl siding for minimal exterior maintenance. New 10x12 storage shed/all within Oakland town limits! For More Information and Extra Photos, please visit the Additional Links - Virtual Tour.

1026 E High St, Oakland, MD 21550 is a 3 bedroom, 1 bathroom, 1,040 sqft single-family home built in 1962. It last sold for $190,800 on May 2, 2022. It is currently off market. The Trulia Estimate is $235,500, with a rent estimate of $1,563/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 1026 E High St

Interior Features
Interior Details Basement
Heating & Cooling Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 2

Exterior Features
Exterior Home Features Roof: MetalDeckExterior: Other
Parking & Garage GarageParking Space: 1Parking: Garage Attached

Property Information
Year Built Year Built: 1962
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.37 acres

Price History for 1026 E High St

Date	Price	Event	Source
05/02/2022	$190,800	Sold	N/A
Recording Date 05/02/2022 Contract Date 04/29/2022 County Transfer Tax $14 Total Transfer Tax $19
12/05/2014	$125,000	Sold	N/A
Recording Date 12/05/2014 Contract Date 11/25/2014 County Transfer Tax $720 Total Transfer Tax $1,025
04/22/2013	$144,700	ListingRemoved	Agent Provided

08/26/2012	$144,700	Listed For Sale	Agent Provided

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	$2,206
Assessment	$181,400

Home facts updated by county records

Comparable Sales for 1026 E High St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
445 Dennett Rd, Oakland, MD	0.19	Single-Family Home	$305,000	11/07/25	3	1	1,410
215 N 10th St, Oakland, MD	0.27	Single-Family Home	$279,000	09/25/25	3	1	1,518
723 E Oak St, Oakland, MD	0.50	Single-Family Home	$180,250	03/16/26	3	1	988
711 Heritage Dr, Oakland, MD	0.53	Single-Family Home	$249,000	03/20/26	3	2	1,400
1056 Sunrise Dr, Oakland, MD	0.09	Single-Family Home	$280,000	11/14/25	4	2.5	1,528
414 D St, Oakland, MD	0.60	Single-Family Home	$150,000	08/14/25	2	1	936
1307 Broadford Rd, Oakland, MD	0.84	Single-Family Home	$185,000	05/22/26	2	1	950
206-208 N 10th St, Oakland, MD	0.23	Single-Family Home	$320,000	07/18/25	4	2	2,772
705 Pensinger Blvd, Oakland, MD	0.48	Single-Family Home	$216,900	09/19/25	3	3	1,800
320 Coolidge Ave, Oakland, MD	0.61	Single-Family Home	$135,000	09/22/25	2	1	720

Nearby homes

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

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OFF MARKET
Est. $252,000
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.
SOLD
NOV 7, 2025
$305,000
3 bd
1 ba
1,410 sqft
445 Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
9.75 ACRES
$169,000
Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $312,200
6 bd
2 ba
4,158 sqft
208 N 10th St,
Oakland, MD 21550
OFF MARKET
Est. $315,900
4 bd
2 ba
2,772 sqft
206-208 N 10th St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $642,100
4 bd
3.5 ba
4,200 sqft
45 Oakland Dr,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
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.
SOLD
JUL 2, 2026
$38,000
Lot 2 Oak Breeze Ln,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
$275,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 1026 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
706 E Alder St #776f18ccb,
Oakland, MD 21550
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
607 P St #f320a52c6,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
1113 Mary Dr #f320a52c6,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
750 Vista Sq #776f18ccb,
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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Homes for sale near 1026 E High St

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$185,000
3 bd
1.5 ba
1,170 sqft
729 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
$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
0.28 ACRES
$249,000
4 bd
1 ba
1,432 sqft
106G Mountain Rd,
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.
$259,900
3 bd
2 ba
1,998 sqft
102 N 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
0.31 ACRES
$275,900
4 bd
2 ba
1,928 sqft
449 S 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
0.49 ACRES
$375,000
5 bd
2 ba
3,660 sqft
321 N 3rd St,
Oakland, MD 21550
CENTURY 21 New Millennium
AUCTION
0.28 ACRES
Price Unknown
4 bd
2 ba
1,932 sqft
102 Roanoke Ave,
Oakland, MD 21550
See more homes for sale in
Oakland
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Off Market Homes Near 1026 E High St

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SOLD
JUL 7, 2026
$149,900
3 bd
1 ba
1,008 sqft
115 Woodmont Ln,
Oakland, MD 21550
Railey Realty, Inc.
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
See more homes for sale in
Oakland
Take a look

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1026 E High St
Oakland, MD 21550

$235,500

$235,500

Local Information