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

965 Dennett Rd
Oakland, MD 21550

3 Beds
3 Baths
1,242 sqft (on 0.41 acres)

$265,800

Trulia Estimate

as of Jul 24, 2026

Est. Refi. Payment $1,589/mo*

Refinance Your Home

$265,800

Trulia Estimate

as of Jul 24, 2026

Est. Refi. Payment $1,589/mo*

Refinance Your Home

3 Beds

3 Baths

1,242 sqft

(on 0.41 acres)

Local Information

Map ViewExplore the area around 965 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

1989

Lot Size

0.41 acres

Living Area

1,242 sqft

Price/Sqft

$214

Parking

Garage

About this House

This single-family home is located at 965 Dennett Rd, Oakland, MD. 965 Dennett Rd is in Oakland, MD and in ZIP code 21550. This property has 3 bedrooms, 3 bathrooms and approximately 1,242 sqft of floor space. This property has a lot size of 0.41 acres and was built in 1989.

965 Dennett Rd, Oakland, MD 21550 is a 3 bedroom, 3 bathroom, 1,242 sqft single-family home built in 1989. It last sold for $143,000 on Mar 30, 2015. It is currently off market. The Trulia Estimate is $265,800, with a rent estimate of $1,997/month.

Home Details for 965 Dennett Rd

Interior Features
Interior Details BasementAtticTypes of Rooms: Dining Room
Heating & Cooling Heating: BaseboardCooling System: OtherHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2
Appliances & Utilities DishwasherDisposalRefrigerator
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Vinyl
Parking & Garage GarageParking Space: 1Parking: Garage Attached

Property Information
Year Built Year Built: 1989
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community
Units in Building: 1

Lot Information
Lot Area: 0.41 acres

Price History for 965 Dennett Rd

Date	Price	Event	Source
03/30/2015	$143,000	Sold	N/A
Recording Date 03/30/2015 Contract Date 03/26/2015 County Transfer Tax $930 Total Transfer Tax $1,645
10/04/2014	$159,000	PriceChange	Agent Provided
Price Change $10,000 (-6%)
08/20/2014	$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	$2,456
Assessment	$162,900

Home facts updated by county records

Comparable Sales for 965 Dennett Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
711 Heritage Dr, Oakland, MD	0.16	Single-Family Home	$249,000	03/20/26	3	2	1,400
705 Pensinger Blvd, Oakland, MD	0.23	Single-Family Home	$216,900	09/19/25	3	3	1,800
1101 Wheeling Ave, Oakland, MD	0.22	Single-Family Home	$85,000	10/03/25	3	2	1,718
1204 Alexander Ln, Oakland, MD	0.21	Single-Family Home	$385,000	06/03/26	3	2	2,266
920 Broadford Rd, Oakland, MD	0.03	Single-Family Home	$106,000	08/26/25	4	3	3,300
607K Mountain Rd, Oakland, MD	0.31	Single-Family Home	$115,000	11/03/25	4	2	1,332
1056 Sunrise Dr, Oakland, MD	0.52	Single-Family Home	$280,000	11/14/25	4	2.5	1,528
1307 Broadford Rd, Oakland, MD	0.49	Single-Family Home	$185,000	05/22/26	2	1	950
414 D St, Oakland, MD	0.54	Single-Family Home	$150,000	08/14/25	2	1	936
445 Dennett Rd, Oakland, MD	0.51	Single-Family Home	$305,000	11/07/25	3	1	1,410

Nearby homes

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

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OFF MARKET
Est. $435,300
5 bd
3.5 ba
3,016 sqft
1014 Madison St,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUL 23, 2026
$30,000
815 L St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
815L Mountain Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAR 20, 2026
$249,000
3 bd
2 ba
1,400 sqft
711 Heritage Dr,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
10.1 ACRES
$160,000
Dennett Rd,
Oakland, MD 21550
The KW Collective
SOLD
JUN 3, 2026
$425,000
4 bd
2.5 ba
2,250 sqft
609 Southern Pines Dr,
Oakland, MD 21550
SOLD
JUN 3, 2026
$385,000
3 bd
2 ba
2,266 sqft
1204 Alexander Ln,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
OCT 3, 2025
$85,000
3 bd
2 ba
1,718 sqft
1101 Wheeling Ave,
Oakland, MD 21550
Long & Foster Real Estate, Inc.
OFF MARKET
Lot 49 White Pine Cir,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 1, 2026
$785,000
5 bd
5 ba
6,550 sqft
1001 Sutter Ln,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $185,700
3 bd
1.5 ba
1,168 sqft
700 I St,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
$63,000
792 sqft
809 Mountain Rd,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 965 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 DAY AGO
$825/mo
Studio
1 ba
32 S 2nd St #B,
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
201 E Mason 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
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
$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 965 Dennett Rd

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NEW - 1 DAY AGO
0.39 ACRES
$225,000
3 bd
1 ba
1,260 sqft
210 F St,
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
$265,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
Oakland, MD 21550
Railey Realty, Inc.
NEW - 9 HRS AGO
FORECLOSURE
0.27 ACRES
$219,900
2 bd
2 ba
1,386 sqft
123 B St,
Oakland, MD 21550
Century 21 Downtown
0.28 ACRES
$249,000
4 bd
1 ba
1,432 sqft
106G Mountain Rd,
Oakland, MD 21550
Railey Realty, Inc.
NEW - 2 DAYS AGO
$139,900
2 bd
1 ba
816 sqft
509 Eastview Ct,
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.
$269,500
3 bd
2 ba
1,600 sqft
315 Coolidge Ave,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
$185,000
3 bd
1.5 ba
1,170 sqft
729 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
NEW - 1 DAY AGO
$365,000
5 bd
3 ba
2,652 sqft
615 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
See more homes for sale in
Oakland
Take a look

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Off Market Homes Near 965 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
$190,000
3 ba
1,260 sqft
302 N 4th St,
Oakland, MD 21550
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 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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965 Dennett Rd
Oakland, MD 21550

$265,800

$265,800