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 435 Underwood Rd estimated to be worth?

Trulia's estimated value for 435 Underwood Rd in Oakland, MD is $282,300 .

What is the price history for 435 Underwood Rd?

435 Underwood Rd in Oakland, MD last sold for $157,000 in December 2014.

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 435 Underwood Rd?

The lot at 435 Underwood Rd in Oakland, MD is about 2.6 acres .

Does 435 Underwood Rd have a garage?

Yes, 435 Underwood Rd in Oakland, MD has a garage.

OFF MARKET

$282,300

Trulia Estimate

3 Beds
2 Baths
1,612 sqft (on 2.57 acres)

435 Underwood Rd, Oakland, MD 21550

Refinance Your Home

Currently Off Market - Sold Dec 5, 2014 for $157,000

Home Value

Trulia Estimate

$282K

Since last month

$5K (-1.7%)

Since last year

$6K (-1.9%)

Since last sale

$127K (+81%)

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 +72% in the last 10 years

Month	Estimated value
2026
August 2026	$284K
August 2026	$282K
July 2026	$289K
June 2026	$294K
May 2026	$290K
April 2026	$287K
March 2026	$276K
February 2026	$274K
January 2026	$272K
2025
December 2025	$273K
November 2025	$281K
October 2025	$282K
September 2025	$288K
August 2025	$290K
July 2025	$295K
June 2025	$294K
May 2025	$290K
April 2025	$288K
March 2025	$287K
February 2025	$285K
January 2025	$280K
2024
December 2024	$285K
November 2024	$286K
October 2024	$283K
September 2024	$283K
August 2024	$292K
July 2024	$289K
June 2024	$291K
May 2024	$288K
April 2024	$283K
March 2024	$276K
February 2024	$270K
January 2024	$268K
2023
December 2023	$272K
November 2023	$277K
October 2023	$276K
September 2023	$280K
August 2023	$274K
July 2023	$274K
June 2023	$270K
May 2023	$275K
April 2023	$268K
March 2023	$264K
February 2023	$257K
January 2023	$256K
2022
December 2022	$259K
November 2022	$267K
October 2022	$270K
September 2022	$269K
August 2022	$270K
July 2022	$274K
June 2022	$277K
May 2022	$273K
April 2022	$269K
March 2022	$265K
February 2022	$256K
January 2022	$257K
2021
December 2021	$256K
November 2021	$253K
October 2021	$250K
September 2021	$246K
August 2021	$245K
July 2021	$246K
June 2021	$226K
May 2021	$195K
April 2021	$190K
March 2021	$176K
February 2021	$180K
January 2021	$179K
2020
December 2020	$177K
November 2020	$176K
October 2020	$168K
September 2020	$173K
August 2020	$177K
July 2020	$176K
June 2020	$176K
May 2020	$176K
April 2020	$178K
March 2020	$177K
February 2020	$177K
January 2020	$177K
2019
December 2019	$178K
November 2019	$180K
October 2019	$184K
September 2019	$185K
August 2019	$184K
July 2019	$184K
June 2019	$182K
May 2019	$180K
April 2019	$180K
March 2019	$180K
February 2019	$179K
January 2019	$180K
2018
December 2018	$176K
November 2018	$177K
October 2018	$178K
September 2018	$177K
August 2018	$171K
July 2018	$174K
June 2018	$178K
May 2018	$176K
April 2018	$176K
March 2018	$175K
February 2018	$174K
January 2018	$175K
2017
December 2017	$173K
November 2017	$173K
October 2017	$172K
September 2017	$172K
August 2017	$171K
July 2017	$170K
June 2017	$170K
May 2017	$169K
April 2017	$169K
March 2017	$168K
February 2017	$167K
January 2017	$167K
2016
December 2016	$166K
November 2016	$166K
October 2016	$165K
September 2016	$165K

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
290 Crellin Underwood Rd, Oakland, MD	0.54	Single-Family Home	$280,500	09/12/25	3	2	2,208
22 Shady Hill Dr, Oakland, MD	0.97	Single-Family Home	$210,000	08/28/26	2	1	1,056
1764 Underwood Rd, Oakland, MD	1.20	Single-Family Home	$285,000	10/31/25	4	1.5	2,304
204 Sunnyside Rd, Oakland, MD	1.33	Single-Family Home	$10,000	06/30/26	3	2	1,400
1358 Crellin Underwood Rd, Oakland, MD	1.54	Single-Family Home	$84,000	07/17/26	2	1	864
1597 Hutton Rd, Oakland, MD	2.72	Single-Family Home	$150,000	11/19/25	3	2	1,984
679 G Swauger Rd, Oakland, MD	1.97	Single-Family Home	$312,656	03/03/26		3	1,888
115 Woodmont Ln, Oakland, MD	2.64	Single-Family Home	$149,900	07/07/26	3	1	1,008
1990 Silver Knob Rd, Oakland, MD	1.74	Single-Family Home	$120,000	11/04/25		1	1,020
29 Woodmont Ln, Oakland, MD	2.62	Single-Family Home	$305,000	07/17/26	4	3	2,016

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
479 Underwood Rd, Oakland, MD 21550	0.06	$280,600	3	1	1,944	Off Market
422 Underwood Rd, Oakland, MD 21550	0.06	$191,400	3	1	960	Off Market
365 Crellin Underwood Rd, Oakland, MD 21550	0.42	$719,300	3	2	2,528	Off Market
198 Crellin Underwood Rd, Oakland, MD 21550	0.47	$220,200	2	1	1,000	Off Market
290 Crellin Underwood Rd, Oakland, MD 21550	0.54	$276,000	3	2	2,208	Off Market
644 Silver Knob Rd, Oakland, MD 21550	0.93	$307,700	3	1	1,728	Off Market
22 Shady Hill Dr, Oakland, MD 21550	0.97	$210,000	2	1	1,056	Recently Sold
1764 Underwood Rd, Oakland, MD 21550	1.20	$315,900	4	1.5	2,304	Off Market
405 Sunnyside Rd, Oakland, MD 21550	1.44	$216,600	3	2	2,184	Off Market
223 Old Crellin Rd, Deer Park, MD 21550	1.48	$103,800	1	1	980	Off Market
1358 Crellin Underwood Rd, Oakland, MD 21550	1.54	$84,000	2	1	864	Recently Sold

Local Information

Map ViewExplore the area around 435 Underwood Rd.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1959

2.57 acre lot

1,612 sqft

$175/sqft

Garage

About this House

This single-family home is located at 435 Underwood Rd, Oakland, MD. 435 Underwood Rd is in Oakland, MD and in ZIP code 21550. This property has 3 bedrooms, 2 bathrooms and approximately 1,612 sqft of floor space. This property has a lot size of 2.57 acres and was built in 1959.

435 Underwood Rd, Oakland, MD 21550 is a 3 bedroom, 2 bathroom, 1,612 sqft single-family home built in 1959. It last sold for $157,000 on Dec 5, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $282,300, with a rent estimate of $1,833/month.

Home Details for 435 Underwood Rd

Interior Features
Heating & Cooling Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 3
Interior Details AtticTypes of Rooms: Dining Room
Appliances & Utilities DishwasherRefrigerator
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Stone, WoodPatioPorch
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 1959
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community
Units in Building: 1

Lot Information
Lot Area: 2.57 acres

Price and Tax history

Date	Event	Price
Dec 5, 2014 Source: N/A	Sold	$157,000
Sep 19, 2014 Source: Agent Provided	PriceChange	$159,900 Price decreased by 11%
Jul 5, 2014 Source: Agent Provided	PriceChange	$179,900 Price decreased by 10%
Feb 27, 2014 Source: Agent Provided	Listed For Sale	$199,000

Year	Property tax	Tax assessment
2025	$1,894	$182,400

Additional Cost

Market trends in Oakland

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Crellin Elementary School
K-5
Public
158 Students
Garrett County Public Schools
7/10
GreatSchools Rating
Parent Rating Average
As a former military spouse with two school-aged children, I can say with confidence Crellin Elementary is among THE best of the best. The staff know each child personally- from lunch personnel to the principal and love them as their own. The community is strongly engaged in the success of the school and its students. The children are excited to go to school and feel it is more a chance to "hang out" with friends rather than a grueling workday. The children not only bond over periods of recess but enjoy instructional learning within the Spruce Forest and other parts of the grounds. The children assist with caring for sheep, chickens, and an abundant garden- of which the community is welcome to enjoy as needed. I love seeing their little muck boots all lined up at the elementary door. I love everything about this school.
Parent Review
3y ago
3 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 435 Underwood Rd

What is 435 Underwood Rd estimated to be worth?
Trulia's estimated value for 435 Underwood Rd in Oakland, MD is $282,300.
What is the price history for 435 Underwood Rd?
435 Underwood Rd in Oakland, MD last sold for $157,000 in December 2014.
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 435 Underwood Rd?
The lot at 435 Underwood Rd in Oakland, MD is about 2.6 acres.
Does 435 Underwood Rd have a garage?
Yes, 435 Underwood Rd in Oakland, MD has a garage.

Apartments for Rent

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Off Market Homes Near 435 Underwood Rd

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SOLD
AUG 28, 2026
$210,000
2 bd
1 ba
1,056 sqft
22 Shady Hill Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
AUG 7, 2026
$318,500
4 bd
2 ba
2,052 sqft
105 Jasper Riley Rd,
Oakland, MD 21550
The KW Collective
SOLD
JUL 17, 2026
$305,000
4 bd
3 ba
2,016 sqft
29 Woodmont Ln,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUL 7, 2026
$335,000
3 bd
3 ba
2,288 sqft
1740 Old Crellin Rd,
Oakland, MD 21550
The KW Collective
SOLD
JUL 7, 2026
$149,900
3 bd
1 ba
1,008 sqft
115 Woodmont Ln,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAY 21, 2026
$179,900
2 bd
1 ba
1,024 sqft
1730 Shoemaker Cole Rd,
Aurora, WV 26705
SOLD
MAR 3, 2026
$312,656
3 ba
1,888 sqft
679 G Swauger Rd,
Oakland, MD 21550
SOLD
FEB 25, 2026
$199,000
2 bd
1 ba
960 sqft
1108 Hutton Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
FEB 11, 2026
$239,000
3 bd
1 ba
1,199 sqft
5202 Hutton Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
DEC 30, 2025
$265,000
3 bd
2 ba
1,792 sqft
968 Hutton Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
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Homes for sale near 435 Underwood Rd

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0.96 ACRES
$169,000
3 bd
1 ba
1,516 sqft
40 Sunshine Ln,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
64 ACRES
$1,095,000
2 bd
2.5 ba
2,914 sqft
826 G Swauger Rd,
Oakland, MD 21550
Railey Realty, Inc.
2.28 ACRES
$329,000
3 bd
2 ba
1,954 sqft
100 W Youghiogheny Dr,
Aurora, WV 26705
1.13 ACRES
$225,000
4 bd
3 ba
2,290 sqft
27645 George Washington Hwy,
Aurora, WV 26705
11.68 ACRES
$349,000
2 bd
2.5 ba
1,920 sqft
1167 Tall Oaks Dr,
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.
$259,900
3 bd
2 ba
1,998 sqft
102 N 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
$174,900
2 bd
1 ba
2,008 sqft
206 W Liberty St,
Oakland, MD 21550
Railey Realty, Inc.
$365,000
5 bd
3 ba
2,652 sqft
615 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
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