1027 E High St, Oakland, MD 21550
OFF MARKET

$188,200

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

1027 E High St, Oakland, MD 21550

Est. Refi. Payment $1,160/mo*
Refinance Your Home
Currently Off Market - Sold Jan 1, 2015 for $102,000

Home Value

Trulia Estimate
$188K
Since last month
Increased$1K (+0.5%)
Since last year
Increased$2K (+1.2%)
Since last sale
Increased$85K (+83%)
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 +60% in the last 10 years
MonthEstimated value
2026
August 2026$187K
July 2026$186K
June 2026$194K
May 2026$191K
April 2026$188K
March 2026$185K
February 2026$180K
January 2026$178K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
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
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
210 F St, Oakland, MD
0.81
Single-Family Home
$219,000
08/28/26
3
1
1,260
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
505 Southern Pines Dr, Oakland, MD
0.53
Single-Family Home
$280,000
07/29/26
3
2
1,248

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
1070 Sunrise Dr, Oakland, MD 21550
0.09
$246,700
4
3
2,144
Off Market
1056 Sunrise Dr, Oakland, MD 21550
0.11
$280,000
4
2.5
1,528
Recently Sold
Dennett Rd, Oakland, MD 21550
0.21
-
-
-
-
Off Market
Dennett Rd, Oakland, MD 21550
0.23
$169,000
-
-
-
For Sale
445 Dennett Rd, Oakland, MD 21550
0.22
$305,000
3
1
1,410
Recently Sold
208 N 10th St, Oakland, MD 21550
0.24
$293,000
6
2
4,158
Off Market
206-208 N 10th St, Oakland, MD 21550
0.26
$314,900
4
2
2,772
Off Market
215 N 10th St, Oakland, MD 21550
0.30
$274,700
3
1
1,518
Off Market
220 N 11th St, Oakland, MD 21550
0.34
$364,600
4
2.5
3,159
Off Market
635 Dennett Rd, Oakland, MD 21550
0.33
$260,000
3
2
1,512
Recently Sold
Lot 2 Oak Breeze Ln, Oakland, MD 21550
0.37
$38,000
-
-
-
Recently Sold
8th & Dennett Road St, Oakland, MD 21550
0.42
$150,000
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 1027 E High St.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Lot Size
0.31 acres
Living Area
1,064 sqft
Price/Sqft
$177
Parking
Garage

About this House

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
1027 E High St, Oakland, MD 21550 is a 3 bedroom, 1 bathroom, 1,064 sqft single-family home built in 1956. It last sold for $102,000 on Jan 1, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $188,200, with a rent estimate of $1,514/month.

Home Details for 1027 E High St

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 1
Heating & Cooling
Air Conditioning
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 and Tax history

DateEventPrice
Jan 1, 2015
Source: Long & Foster Broker Feed #1005036936_100
Sold
$102,000
Aug 8, 2012
Source: N/A
Sold
$102,000
May 2, 2012
Source: Agent Provided
PriceChange
$110,000
Price decreased by 2%
Mar 12, 2012
Source: Agent Provided
PriceChange
$112,000
Price decreased by 7%
Feb 6, 2012
Source: Agent Provided
PriceChange
$121,000
Price decreased by 1%

Market trends in Oakland

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
82
10MoM

Around this home

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.
    "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. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 1027 E High St

  • What is 1027 E High St estimated to be worth?
    Trulia's estimated value for 1027 E High St in Oakland, MD is $188,200.
  • What is the price history for 1027 E High St?
    1027 E High St in Oakland, MD last sold for $102,000 in January 2015.
  • Is Oakland a buyer's or seller's market?
    Oakland is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Oakland?
    Residents describe Oakland, MD as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Oakland, MD.
  • How big is the lot at 1027 E High St?
    The lot at 1027 E High St in Oakland, MD is about 0.31 acres (13,503 sq ft).
  • Does 1027 E High St have a garage?
    Yes, 1027 E High St in Oakland, MD has a garage.

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Off Market Homes Near 1027 E High St

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