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

809 Winter Pl
Oakland, MD 21550

Studio
2 Baths
1,392 sqft (on 0.60 acres)

$292,400

Trulia Estimate

as of Jul 7, 2026

Est. Refi. Payment $1,728/mo*

Refinance Your Home

$292,400

Trulia Estimate

as of Jul 7, 2026

Est. Refi. Payment $1,728/mo*

Refinance Your Home

Studio

2 Baths

1,392 sqft

(on 0.60 acres)

Local Information

Map ViewExplore the area around 809 Winter Pl.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 809 Winter Pl, Oakland, MD. 809 Winter Pl is in Oakland, MD and in ZIP code 21550. This property has 2 bathrooms and approximately 1,392 sqft of floor space. This property has a lot size of 0.60 acres and was built in 1992.

809 Winter Pl, Oakland, MD 21550 is a studio, 2 bathroom, 1,392 sqft single-family home built in 1992. It last sold for $120,000 on Jun 18, 2001. It is currently off market. The Trulia Estimate is $292,400, with a rent estimate of $1,846/month.

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 809 Winter Pl

Interior Features
Heating & Cooling Heating: Other, ElectricHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

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

Property Information
Year Built Year Built: 1992
Property Type / Style Property Type: Single Family HomeArchitecture: conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.60 acres

Price History for 809 Winter Pl

Date	Price	Event	Source
06/18/2001	$120,000	Sold	N/A
Recording Date 06/18/2001 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Oakland

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

—

Available listings

5MoM

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Property Tax and Assessment

Year	2025
Tax	$2,914
Assessment	$216,000

Home facts updated by county records

Comparable Sales for 809 Winter Pl

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
702 Sunshine Dr, Oakland, MD	0.18	Single-Family Home	$250,000	03/27/26	3	2	1,848
707 Sunshine Dr, Oakland, MD	0.19	Single-Family Home	$310,000	07/31/25	3	2	2,052
612 Harvey Winters Dr, Oakland, MD	0.09	Single-Family Home	$465,000	08/12/25	4	3	2,473
11 Sunset Dr, Oakland, MD	0.73	Single-Family Home	$270,000	11/21/25	3	2	1,400
220 N 12th St, Oakland, MD	0.73	Single-Family Home	$190,000	09/15/25		2	1,252
1307 Broadford Rd, Oakland, MD	0.41	Single-Family Home	$185,000	05/22/26	2	1	950
163 Crestview Dr, Oakland, MD	0.76	Single-Family Home	$295,000	05/20/26	3	2.5	1,416
143 Manor Dr, Oakland, MD	0.81	Single-Family Home	$285,000	02/19/26	3	1.5	1,786
1220 Broadford Rd, Oakland, MD	0.47	Single-Family Home	$365,000	08/12/25	4	2.5	2,092
445 Dennett Rd, Oakland, MD	0.87	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. $458,900
4 bd
3 ba
2,473 sqft
612 Harvey Winters Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $270,800
3 bd
2 ba
1,328 sqft
1638 Memorial Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
812 Winter Pl,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $674,400
5 bd
3.5 ba
3,982 sqft
604 Harvey Winters Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAR 27, 2026
$250,000
3 bd
2 ba
1,848 sqft
702 Sunshine Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $305,800
3 bd
2 ba
2,052 sqft
707 Sunshine Dr,
Oakland, MD 21550
Burch Real Estate Group, LLC
OFF MARKET
Est. $484,900
5 bd
3 ba
2,048 sqft
1506 Broadford Rd,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
33.93 ACRES
$699,000
Memorial Dr,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAY 22, 2026
$185,000
2 bd
1 ba
950 sqft
1307 Broadford Rd,
Oakland, MD 21550
Keller Williams Realty Centre
OFF MARKET
Est. $353,200
4 bd
2.5 ba
2,345 sqft
1262 Memorial Dr,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Smith Dr,
Oakland, MD 21550
OFF MARKET
Not On File,
Oakland, MD 21550

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Additional Cost

Assigned Schools

These are the assigned schools for 809 Winter Pl.

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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1-2 bd
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Oakland, MD 21550
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1-2 bd
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1-2 bd
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706 E Alder St #776f18ccb,
Oakland, MD 21550
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1-2 bd
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201 E Mason St #776f18ccb,
Oakland, MD 21550
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1-2 bd
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750 Vista Sq #776f18ccb,
Oakland, MD 21550
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1-2 bd
1-2 ba
108 Decatur St #776f18ccb,
Oakland, MD 21550
$1,550/mo
3 bd
1 ba
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Oakland, MD 21550
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Oakland
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Homes for sale near 809 Winter Pl

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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
0.49 ACRES
$375,000
5 bd
2 ba
3,660 sqft
321 N 3rd St,
Oakland, MD 21550
CENTURY 21 New Millennium
$275,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
Oakland, MD 21550
Railey Realty, Inc.
NEW CONSTRUCTION
0.71 ACRES
$399,999
3 bd
2 ba
1,464 sqft
654 N Bradley Ln,
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.
$259,900
3 bd
2 ba
1,998 sqft
102 N 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
0.28 ACRES
$249,000
4 bd
1 ba
1,432 sqft
106G Mountain Rd,
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.
AUCTION
0.28 ACRES
Price Unknown
4 bd
2 ba
1,932 sqft
102 Roanoke Ave,
Oakland, MD 21550
See more homes for sale in
Oakland
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Off Market Homes Near 809 Winter Pl

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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 24, 2026
$425,000
4 bd
2.5 ba
2,190 sqft
609 Southern Pines Dr,
Mt Lake Park, 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.
SOLD
JUN 5, 2026
$190,000
1 ba
1,056 sqft
513 M St,
Oakland, MD 21550
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
JUN 3, 2026
$150,000
Dennett Rd,
Oakland, MD 21550
SOLD
JUN 1, 2026
$290,000
2 bd
2 ba
2,015 sqft
3749 State St,
Oakland, MD 21550
Keller Williams Realty
See more homes for sale in
Oakland
Take a look

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809 Winter Pl
Oakland, MD 21550

$292,400

$292,400

Local Information