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

40 Dennett Rd
Oakland, MD 21550

5 Beds
2 Baths
2,160 sqft (on 0.75 acres)

$234,300

Trulia Estimate

as of Jul 23, 2026

Est. Refi. Payment $1,263/mo*

Refinance Your Home

$234,300

Trulia Estimate

as of Jul 23, 2026

Est. Refi. Payment $1,263/mo*

Refinance Your Home

5 Beds

2 Baths

2,160 sqft

(on 0.75 acres)

Local Information

Map ViewExplore the area around 40 Dennett Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1930

Lot Size

0.75 acres

Living Area

2,160 sqft

Price/Sqft

$108

Description

This single-family home is located at 40 Dennett Rd, Oakland, MD. 40 Dennett Rd is in Oakland, MD and in ZIP code 21550. This property has 5 bedrooms, 2 bathrooms and approximately 2,160 sqft of floor space. This property has a lot size of 0.75 acres and was built in 1930.

40 Dennett Rd, Oakland, MD 21550 is a 5 bedroom, 2 bathroom, 2,160 sqft single-family home built in 1930. It is currently off market. The Trulia Estimate is $234,300, with a rent estimate of $2,548/month.

Home Details for 40 Dennett Rd

Interior Features
Interior Details BasementTypes of Rooms: Dining Room
Heating & Cooling Heating: RadiantHeating Fuel: Radiant
Levels, Entrance, & Accessibility Stories: 3

Exterior Features
Exterior Home Features Roof: MetalExterior: Shingle Not Wood, Vinyl

Property Information
Year Built Year Built: 1930
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Building
Levels, Entrance, & Accessibility Disabled Access

Community
Units in Building: 1

Lot Information
Lot Area: 0.75 acres

Price History for 40 Dennett Rd

Date	Price	Event	Source
08/19/2019	$169,000	ListingRemoved	Agent Provided

02/07/2018	$169,000	Listed For Sale	Agent Provided

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	$2,494
Assessment	$155,500

Home facts updated by county records

Comparable Sales for 40 Dennett Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1056 Sunrise Dr, Oakland, MD	0.44	Single-Family Home	$280,000	11/14/25	4	2.5	1,528
511 E Green St, Oakland, MD	0.38	Single-Family Home	$250,000	12/31/25	4	2	1,880
143 Manor Dr, Oakland, MD	0.51	Single-Family Home	$285,000	02/19/26	3	1.5	1,786
220 N 11th St, Oakland, MD	0.46	Single-Family Home	$370,000	10/10/25	4	2.5	3,159
215 N 10th St, Oakland, MD	0.35	Single-Family Home	$279,000	09/25/25	3	1	1,518
445 Dennett Rd, Oakland, MD	0.41	Single-Family Home	$305,000	11/07/25	3	1	1,410
502 E Oak St, Oakland, MD	0.48	Single-Family Home	$239,900	09/12/25	3	2	1,680
531 S 3rd St, Oakland, MD	0.84	Single-Family Home	$320,000	11/05/25	5	2.5	2,477
11 Sunset Dr, Oakland, MD	0.74	Single-Family Home	$270,000	11/21/25	3	2	1,400
320 Coolidge Ave, Oakland, MD	0.27	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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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. $255,900
3 bd
1.5 ba
1,248 sqft
132 N 8th St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $143,600
2 bd
1 ba
1,494 sqft
116 N 8th St,
Oakland, MD 21550
Keller Williams Realty Centre
OFF MARKET
Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
SEP 26, 2025
$80,000
Coolidge Ave,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
FOR SALE
$269,500
3 bd
2 ba
1,600 sqft
315 Coolidge Ave,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
FOR SALE
9.75 ACRES
$169,000
Dennett Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $131,500
2 bd
1 ba
720 sqft
320 Coolidge Ave,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $231,000
4 bd
2 ba
2,180 sqft
615 E High St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $310,600
4 bd
2 ba
2,772 sqft
206-208 N 10th St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $290,600
6 bd
2 ba
4,158 sqft
208 N 10th St,
Oakland, MD 21550

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Additional Cost

Assigned Schools

These are the assigned schools for 40 Dennett Rd.

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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NEW - 1 HR AGO
$825/mo
Studio
1 ba
32 S 2nd St #B,
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
201 E Mason 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
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
APPLY INSTANTLY
$600/mo
1 bd
1 ba
408 E Alder St #4,
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 40 Dennett Rd

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0.49 ACRES
$365,000
5 bd
2 ba
3,660 sqft
321 N 3rd St,
Oakland, MD 21550
CENTURY 21 New Millennium
$269,500
3 bd
2 ba
1,600 sqft
315 Coolidge Ave,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
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.
$350,000
5 bd
3 ba
2,165 sqft
112 E Pennington St,
Oakland, MD 21550
Lake Homes Realty, LLC
$185,000
3 bd
1.5 ba
1,170 sqft
729 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
$265,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
Oakland, MD 21550
Railey Realty, Inc.
0.46 ACRES
$325,000
3 bd
2 ba
1,539 sqft
610 Harvey Winters Dr,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
NEW CONSTRUCTION
0.71 ACRES
$379,999
3 bd
2 ba
1,464 sqft
654 N Bradley Ln,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
See more homes for sale in
Oakland
Take a look

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Off Market Homes Near 40 Dennett Rd

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SOLD
JUL 20, 2026
$217,350
3 bd
1 ba
1,092 sqft
407 Seneca Ave,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
JUL 17, 2026
$305,000
4 bd
3 ba
2,016 sqft
29 Woodmont Ln,
Oakland, MD 21550
Railey Realty, Inc.
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
$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
JUL 1, 2026
$150,000
4 bd
2 ba
3395 Fingerboard Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
JUN 25, 2026
$150,000
2 ba
1,512 sqft
398 Youghiogheny Path,
Oakland, MD 21550
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.
See more homes for sale in
Oakland
Take a look

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40 Dennett Rd
Oakland, MD 21550

$234,300

$234,300