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

966 E High St
Oakland, MD 21550

2 Beds
1 Bath
660 sqft (on 0.41 acres)

$162,500

Trulia Estimate

as of Jul 12, 2026

Est. Refi. Payment $1,003/mo*

Refinance Your Home

$162,500

Trulia Estimate

as of Jul 12, 2026

Est. Refi. Payment $1,003/mo*

Refinance Your Home

2 Beds

1 Bath

660 sqft

(on 0.41 acres)

Local Information

Map ViewExplore the area around 966 E High St.
Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Cozy 2-bedroom rancher, nicely updated with fresh carpet and paint, and just waiting for your special touches! Enjoy one-level living in a town location that's so convenient to schools, shopping, dining, and more. Features a cheery living room, eat-in kitchen with lots of cabinets, and versatile full basement. Plus a covered side porch, beautiful yard with mature trees, and plenty of room for fun!

966 E High St, Oakland, MD 21550 is a 2 bedroom, 1 bathroom, 660 sqft single-family home built in 1945. It last sold for $88,500 on Nov 21, 2017. It is currently off market. The Trulia Estimate is $162,500, with a rent estimate of $1,259/month.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 966 E High St

Interior Features
Interior Details BasementCeiling Fan
Heating & Cooling Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2
Appliances & Utilities MicrowaveRefrigerator

Exterior Features
Exterior Home Features Roof: MetalExterior: Metal

Property Information
Year Built Year Built: 1945
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.41 acres

Price History for 966 E High St

Date	Price	Event	Source
11/21/2017	$88,500	Sold	N/A
Recording Date 11/21/2017 Contract Date 11/17/2017 County Transfer Tax $385 Total Transfer Tax $606
09/25/2017	$92,000	Pending	Agent Provided

07/14/2017	$92,000	Listed For Sale	Agent Provided

01/01/2015	$50,000	Sold	Long & Foster Broker Feed #MDGA101884_100
Recording Date 01/01/2015 County Transfer Tax N/A Total Transfer Tax N/A
10/19/2010	$99,900	ListingRemoved	Agent Provided

08/11/2010	$99,900	Listed For Sale	Agent Provided

10/06/2006	$50,000	Sold	N/A
Recording Date 10/06/2006 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	$1,609
Assessment	$100,300

Home facts updated by county records

Comparable Sales for 966 E High St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
320 Coolidge Ave, Oakland, MD	0.54	Single-Family Home	$135,000	09/22/25	2	1	720
215 N 10th St, Oakland, MD	0.29	Single-Family Home	$279,000	09/25/25	3	1	1,518
445 Dennett Rd, Oakland, MD	0.25	Single-Family Home	$305,000	11/07/25	3	1	1,410
414 D St, Oakland, MD	0.70	Single-Family Home	$150,000	08/14/25	2	1	936
723 E Oak St, Oakland, MD	0.41	Single-Family Home	$180,250	03/16/26	3	1	988
1307 Broadford Rd, Oakland, MD	0.91	Single-Family Home	$185,000	05/22/26	2	1	950
120 N 3rd St, Oakland, MD	0.69	Single-Family Home	$70,000	01/15/26	3	1	1,660
110 W Pennington St, Oakland, MD	1.00	Single-Family Home	$110,000	09/26/25	2	1	768
206-208 N 10th St, Oakland, MD	0.23	Single-Family Home	$320,000	07/18/25	4	2	2,772
1056 Sunrise Dr, Oakland, MD	0.19	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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OFF MARKET
Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $250,800
4 bd
3 ba
2,144 sqft
1070 Sunrise Dr,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
9.75 ACRES
$169,000
Dennett Rd,
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
Est. $303,700
6 bd
2 ba
4,158 sqft
208 N 10th St,
Oakland, MD 21550
OFF MARKET
Est. $313,700
4 bd
2 ba
2,772 sqft
206-208 N 10th St,
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
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
JUN 1, 2026
$150,000
8th & Dennett Road St,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
OFF MARKET
N 8th St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $145,000
2 bd
1 ba
1,494 sqft
116 N 8th St,
Oakland, MD 21550
Keller Williams Realty Centre

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Additional Cost

Assigned Schools

These are the assigned schools for 966 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
1113 Mary Dr #f320a52c6,
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
750 Vista Sq #776f18ccb,
Oakland, MD 21550
Contact for price
1-2 bd
1-2 ba
108 Decatur St #776f18ccb,
Oakland, MD 21550
NEW - 2 DAYS AGO
APPLY INSTANTLY
$600/mo
1 bd
1 ba
408 E Alder St #4,
Oakland, MD 21550
See more homes for rent in
Oakland
Take a look

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Homes for sale near 966 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.
$269,500
3 bd
2 ba
1,600 sqft
315 Coolidge Ave,
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.
0.46 ACRES
$289,000
3 bd
2.5 ba
2,242 sqft
163 Mitchell Dr,
Oakland, MD 21550
Railey Realty, Inc.
0.28 ACRES
$249,000
4 bd
1 ba
1,432 sqft
106G Mountain Rd,
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
NEW
COMING SOON 7/20
$350,000
5 bd
3 ba
2,165 sqft
112 E Pennington St,
Oakland, MD 21550
Lake Homes Realty, LLC
See more homes for sale in
Oakland
Take a look

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Off Market Homes Near 966 E High St

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SOLD
JUL 10, 2026
$185,000
2 bd
1.5 ba
960 sqft
512 Roanoke Ave,
Oakland, MD 21550
Coldwell Banker Premier
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 5, 2026
$190,000
1 ba
1,056 sqft
513 M St,
Oakland, MD 21550
SOLD
JUN 3, 2026
$90,000
1 ba
1,528 sqft
2664 Pleasant Valley Rd,
Oakland, MD 21550
SOLD
JUN 3, 2026
$150,000
Dennett Rd,
Oakland, MD 21550
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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966 E High St
Oakland, MD 21550

$162,500

$162,500

Local Information