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

95 Pine Cir
Oakland, MD 21550

Studio
4 Baths
3,380 sqft (on 1.29 acres)

$1,595,900

Trulia Estimate

as of Jul 31, 2026

$1,595,900

Trulia Estimate

as of Jul 31, 2026

Studio

4 Baths

3,380 sqft

(on 1.29 acres)

Local Information

Map ViewExplore the area around 95 Pine Cir.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

2008

Lot Size

1.29 acres

Living Area

3,380 sqft

Price/Sqft

$472

Parking

Garage

About this House

This single-family home is located at 95 Pine Cir, Oakland, MD. 95 Pine Cir is in Oakland, MD and in ZIP code 21550. This property has 4 bathrooms and approximately 3,380 sqft of floor space. This property has a lot size of 1.29 acres and was built in 2008.

95 Pine Cir, Oakland, MD 21550 is a studio, 4 bathroom, 3,380 sqft single-family home built in 2008. It last sold for $898,500 on Dec 3, 2018. It is currently off market. The Trulia Estimate is $1,595,900, with a rent estimate of $3,740/month.

Home Details for 95 Pine Cir

Interior Features
Heating & Cooling Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2008
Property Type / Style Property Type: Single Family HomeArchitecture: conventional

Community
Units in Building: 1

Lot Information
Lot Area: 1.29 acres

Price History for 95 Pine Cir

Date	Price	Event	Source
12/03/2018	$898,500	Sold	N/A
Recording Date 12/03/2018 Contract Date 11/30/2018 County Transfer Tax $90 Total Transfer Tax $135
07/28/2005	$425,000	Sold	N/A
Recording Date 07/28/2005 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	$16,359
Assessment	$1,384,000

Home facts updated by county records

Comparable Sales for 95 Pine Cir

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
186 Thornberry Rd, Oakland, MD	0.52	Single-Family Home	$915,000	09/15/25	5	3.5	2,347
254 Middleton Rd, Oakland, MD	0.63	Single-Family Home	$920,000	08/22/25	4	4	2,400
590 S Blakeslee Rd, Oakland, MD	0.74	Single-Family Home	$1,150,000	10/24/25	4	3.5	3,071
870 Holy Cross Dr, Oakland, MD	0.25	Single-Family Home	$3,375,000	11/13/25	7	6.5	5,681
62 Middleton Rd, Oakland, MD	0.70	Single-Family Home	$780,000	07/02/26	3	2.5	1,929
1010 Holy Cross Dr, Oakland, MD	0.25	Single-Family Home	$4,700,000	07/09/26	8	8.5	10,300
1461 Shoreline Dr, Swanton, MD	0.67	Single-Family Home	$960,000	05/12/26	3	2.5	1,008
1100 S Blakeslee Rd, Oakland, MD	0.56	Single-Family Home	$2,550,000	08/01/25	5	5.5	6,572
8 Hidden Cove Ct, Oakland, MD	1.22	Single-Family Home	$880,000	07/09/26	4	3	2,856
336 Paradise Hts, Oakland, MD	1.21	Single-Family Home	$1,340,000	04/08/26	5	3	2,826

Nearby homes

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

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OFF MARKET
25 Holy Cross Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $1,969,400
3 bd
3.5 ba
3,498 sqft
971 Holy Cross Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUL 9, 2026
$4,700,000
8 bd
8.5 ba
10,300 sqft
1010 Holy Cross Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
NOV 13, 2025
$3,375,000
7 bd
6.5 ba
5,681 sqft
870 Holy Cross Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Boy Scout Rd,
Oakland, MD 21550
The KW Collective
OFF MARKET
Est. $2,544,900
4 bd
4.5 ba
4,350 sqft
2433 Boy Scout Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Holy Cross Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $3,785,200
6 bd
4.5 ba
4,632 sqft
18 Holy Cross Cir,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
3D VIEW
1.64 ACRES
$6,499,900
8 bd
8.5 ba
11,417 sqft
47 Holy Cross Cir,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $1,680,000
3 bd
3 ba
3,096 sqft
2353 Boy Scout Rd,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $729,100
3 bd
2 ba
1,355 sqft
14 Wanderer Ln #C-4,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAY 22, 2026
$829,000
3 bd
2 ba
1,355 sqft
34 Hooppole Ct #B-1,
Oakland, MD 21550
Railey Realty, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 95 Pine Cir.

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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Homes for sale near 95 Pine Cir

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1.64 ACRES
$6,499,900
8 bd
8.5 ba
11,417 sqft
47 Holy Cross Cir,
Oakland, MD 21550
Railey Realty, Inc.
1.48 ACRES
$5,495,000
6 bd
5.5 ba
6,225 sqft
218 Smith Pointe Rd,
Swanton, MD 21561
Railey Realty, Inc.
1.01 ACRES
$459,900
3 bd
2 ba
1,458 sqft
718 Boy Scout Crosscut Rd,
Oakland, MD 21550
Railey Realty, Inc.
1.26 ACRES
$1,025,000
3 bd
2.5 ba
2,240 sqft
127 Paradise Hts,
Oakland, MD 21550
XRealty.NET LLC
0.76 ACRES
$1,400,000
5 bd
3.5 ba
2,832 sqft
827 Penn Point Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
1 ACRE
$1,329,000
6 bd
4.5 ba
4,113 sqft
439 Paradise Hts,
Oakland, MD 21550
Railey Realty, Inc.
1.29 ACRES
$769,900
4 bd
3.5 ba
3,780 sqft
467 Paradise Ridge Rd,
Oakland, MD 21550
Railey Realty, Inc.
1.01 ACRES
$4,000,000
4 bd
4.5 ba
3,009 sqft
180 Glen Cove Rd,
Swanton, MD 21561
Taylor-Made Deep Creek Real Estate, LLC
1 ACRE
$949,000
5 bd
5 ba
3,716 sqft
723 Pinnacle Dr,
Swanton, MD 21561
Railey Realty, Inc.
0.45 ACRES
$1,450,000
3 bd
2 ba
1,695 sqft
187 Lower Penn Point Dr,
Oakland, MD 21550
Railey Realty, Inc.
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Oakland
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Off Market Homes Near 95 Pine Cir

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SOLD
JUL 29, 2026
$950,000
4 bd
2 ba
2,730 sqft
137 Paradise Gardens Rd,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
SOLD
JUL 24, 2026
$1,880,000
6 bd
6 ba
6,697 sqft
282 Lakefront Links Dr,
Swanton, MD 21561
Railey Realty, Inc.
SOLD
JUL 14, 2026
$975,000
3 bd
2.5 ba
2,520 sqft
1250 Pergin Farm Rd,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUL 9, 2026
$880,000
4 bd
3 ba
2,856 sqft
8 Hidden Cove Ct,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUL 8, 2026
$1,190,000
4 bd
3 ba
2,624 sqft
125 Ruta Ln,
Swanton, MD 21561
Taylor-Made Deep Creek Real Estate, LLC
SOLD
JUL 1, 2026
$1,200,000
4 bd
2.5 ba
2,520 sqft
1244 Glendale Rd,
Swanton, MD 21561
Railey Realty, Inc.
SOLD
JUN 30, 2026
$1,400,000
3,032 sqft
239 Stilwater Dr,
Swanton, MD 21561
SOLD
JUN 30, 2026
$1,200,000
2 bd
2 ba
1,156 sqft
209 Black Angus Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 26, 2026
$1,130,000
3 bd
1 ba
1,568 sqft
34 Shingle Camp Ter,
Mchenry, MD 21541
Taylor-Made Deep Creek Real Estate, LLC
SOLD
JUN 26, 2026
$815,000
3 bd
4 ba
3,990 sqft
891 Mountainview Dr,
Oakland, MD 21550
Railey Realty, Inc.
See more homes for sale in
Oakland
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95 Pine Cir
Oakland, MD 21550

$1,595,900

$1,595,900