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 809 E Chestnut St estimated to be worth?

Trulia's estimated value for 809 E Chestnut St in Deer Park, MD is $114,800 .

What is the price history for 809 E Chestnut St?

809 E Chestnut St in Deer Park, MD last sold for $28,350 in January 2018.

Is Deer Park a buyer's or seller's market?

Deer Park is currently a balanced market, based on recent for-sale activity.

What do residents say about Deer Park?

Residents describe Deer Park, MD as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Deer Park, MD .

Does 809 E Chestnut St have air conditioning?

Yes, 809 E Chestnut St in Deer Park, MD has air conditioning.

Does 809 E Chestnut St have laundry facilities?

Yes, 809 E Chestnut St in Deer Park, MD has in-unit laundry.

OFF MARKET

809 E Chestnut St
Deer Park, MD 21550

2 Beds
1 Bath
1,020 sqft

$114,800

Trulia Estimate

as of Aug 10, 2026

Est. Refi. Payment $737/mo*

Refinance Your Home

$114,800

Trulia Estimate

as of Aug 10, 2026

Est. Refi. Payment $737/mo*

Refinance Your Home

2 Beds

1 Bath

1,020 sqft

Local Information

Map ViewExplore the area around 809 E Chestnut St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1951

Living Area

1,020 sqft

Price/Sqft

$113

About this House

Entire house has just been repainted, landscaped and new sidewalks. Right in town, but has a fairly private back yard with a beautiful little creek running along it. No smoking.

809 E Chestnut St, Deer Park, MD 21550 is a 2 bedroom, 1 bathroom, 1,020 sqft single-family home built in 1951. It last sold for $28,350 on Jan 3, 2018. More recently, it was listed as a rental in January 2019 with an asking price of $800 per month. That rental listing was removed on March 24, 2021. It is currently off market. The Trulia Estimate is $114,800, with a rent estimate of $1,385/month.

Home Details for 809 E Chestnut St

Interior Features
Interior Details Basement
Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1
Appliances & Utilities DryerWasher

Exterior Features
Exterior Home Features Roof: MetalExterior: Other
Parking & Garage Parking: Off Street

Property Information
Year Built Year Built: 1951
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 8712 sqft

Price History for 809 E Chestnut St

Date	Price	Event	Source
03/24/2021		ListingRemoved	N/A

02/18/2019	$800	ListingRemoved	N/A

01/09/2019	$800	Listed For Rent	N/A

01/03/2018	$28,350	Sold	N/A
Recording Date 01/03/2018 Contract Date 12/20/2017 County Transfer Tax $71 Total Transfer Tax $71
11/30/2017	$29,900	PriceChange	Agent Provided
Price Change $8,000 (-21%)
10/18/2017	$37,900	Listed For Sale	Agent Provided

09/29/2017	$23,625	Sold	N/A
Recording Date 09/29/2017 Contract Date 09/27/2017 County Transfer Tax N/A Total Transfer Tax N/A
05/30/2017	$49,900	PriceChange	Agent Provided
Price Change $5,000 (-9%)
04/28/2017	$54,900	PriceChange	Agent Provided
Price Change $5,000 (-8%)
03/29/2017	$59,900	Listed For Sale	Agent Provided

02/23/2017	$69,382	Sold	N/A
Recording Date 02/23/2017 Contract Date 02/16/2017 County Transfer Tax N/A Total Transfer Tax N/A
10/30/2008	$83,900	Sold	N/A
Recording Date 10/30/2008 County Transfer Tax N/A Total Transfer Tax N/A
09/17/2007	$50,000	Sold	N/A
Recording Date 09/17/2007 County Transfer Tax N/A Total Transfer Tax N/A
03/15/2000	$15,000	Sold	N/A
Recording Date 03/15/2000 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

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Price per sq ft

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Available listings

12MoM

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Property Tax and Assessment

Year	2025
Tax	$1,476
Assessment	$92,000

Home facts updated by county records

Comparable Sales for 809 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
723 E Oak St, Oakland, MD	0.11	Single-Family Home	$180,250	03/16/26	3	1	988
120 N 3rd St, Oakland, MD	0.64	Single-Family Home	$70,000	01/15/26	3	1	1,660
502 E Oak St, Oakland, MD	0.29	Single-Family Home	$239,900	09/12/25	3	2	1,680
110 W Pennington St, Oakland, MD	0.85	Single-Family Home	$110,000	09/26/25	2	1	768
627 Hamill St, Oakland, MD	0.71	Single-Family Home	$180,000	11/24/25	3	1	1,322
511 E Green St, Oakland, MD	0.32	Single-Family Home	$250,000	12/31/25	4	2	1,880
313 W Liberty St, Oakland, MD	0.98	Single-Family Home	$210,000	05/06/26	2	1	1,064
320 Coolidge Ave, Oakland, MD	0.76	Single-Family Home	$135,000	09/22/25	2	1	720
414 D St, Oakland, MD	0.87	Single-Family Home	$150,000	08/14/25	2	1	936
215 N 10th St, Oakland, MD	0.71	Single-Family Home	$279,000	09/25/25	3	1	1,518

Nearby homes

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

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OFF MARKET
E Reese St,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
MAR 16, 2026
$180,250
3 bd
1 ba
988 sqft
723 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $250,800
3 bd
2 ba
1,764 sqft
723 E Alder St,
Oakland, MD 21550
Railey Realty, Inc.
FOR SALE
$365,000
5 bd
3 ba
2,652 sqft
615 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $273,600
4 bd
2.5 ba
1,744 sqft
601 E Oak St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $634,000
4 bd
3.5 ba
4,200 sqft
45 Oakland Dr,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $195,800
3 bd
3 ba
1,668 sqft
620 E Green St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $237,400
3 bd
2 ba
1,680 sqft
502 E Oak St,
Oakland, MD 21550
Railey Realty, Inc.
OFF MARKET
Est. $261,200
4 bd
2 ba
2,152 sqft
514 E Alder St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
Est. $231,700
4 bd
2 ba
2,180 sqft
615 E High St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
SOLD
DEC 31, 2025
$250,000
4 bd
2 ba
1,880 sqft
511 E Green St,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales
OFF MARKET
3 Weber Rd,
Oakland, MD 21550
Taylor Made Deep Creek Vacations & Sales

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Additional Cost

Assigned Schools

These are the assigned schools for 809 E Chestnut St.

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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Apartments for Rent

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$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
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
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
$1,550/mo
3 bd
1 ba
400 E Alder St #3,
Oakland, MD 21550
See more homes for rent in
Deer Park
Take a look

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Homes for sale near 809 E Chestnut St

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$189,000
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.
0.31 ACRES
$275,900
4 bd
2 ba
1,928 sqft
449 S 3rd St,
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
$259,900
3 bd
2 ba
1,998 sqft
102 N 3rd St,
Oakland, MD 21550
Railey Realty, Inc.
FORECLOSURE
0.27 ACRES
$219,900
2 bd
2 ba
1,386 sqft
123 B St,
Oakland, MD 21550
Century 21 Downtown
$265,000
4 bd
2 ba
1,913 sqft
127 S Oakhall Dr,
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.
$350,000
5 bd
3 ba
2,165 sqft
112 E Pennington St,
Oakland, MD 21550
Lake Homes Realty, LLC
0.46 ACRES
$279,000
3 bd
2.5 ba
2,242 sqft
163 Mitchell Dr,
Oakland, MD 21550
Railey Realty, Inc.
See more homes for sale in
Deer Park
Take a look

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Off Market Homes Near 809 E Chestnut St

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SOLD
JUL 31, 2026
$114,000
2 bd
1 ba
1,029 sqft
5151 Hutton Rd,
Oakland, MD 21550
Julian Agency Real Estate
SOLD
JUL 20, 2026
$110,000
3 bd
1.5 ba
128 Shaffer Ln,
New Cumberland, WV 26047
Howard Hanna Mortimer Realty, MLS Now
SOLD
JUL 20, 2026
$150,000
1 ba
1,264 sqft
1525 Lynndale Rd,
Oakland, MD 21550
SOLD
JUL 17, 2026
$84,000
2 bd
1 ba
864 sqft
1358 Crellin Underwood Rd,
Oakland, MD 21550
Railey Realty, Inc.
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 15, 2026
$165,000
3 bd
1 ba
1,632 sqft
505 Shenandoah Ave,
Oakland, MD 21550
Railey Realty, Inc.
SOLD
JUN 3, 2026
$90,000
1 ba
1,528 sqft
2664 Pleasant Valley Rd,
Oakland, MD 21550
SOLD
JUN 3, 2026
$150,000
Dennett Rd,
Oakland, MD 21550
SOLD
JUN 1, 2026
$150,000
8th & Dennett Road St,
Oakland, MD 21550
Taylor-Made Deep Creek Real Estate, LLC
See more homes for sale in
Deer Park
Take a look

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Frequently asked questions about 809 E Chestnut St

What is 809 E Chestnut St estimated to be worth?
Trulia's estimated value for 809 E Chestnut St in Deer Park, MD is $114,800.
What is the price history for 809 E Chestnut St?
809 E Chestnut St in Deer Park, MD last sold for $28,350 in January 2018.
Is Deer Park a buyer's or seller's market?
Deer Park is currently a balanced market, based on recent for-sale activity.
What do residents say about Deer Park?
Residents describe Deer Park, MD as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Deer Park, MD.
Does 809 E Chestnut St have air conditioning?
Yes, 809 E Chestnut St in Deer Park, MD has air conditioning.
Does 809 E Chestnut St have laundry facilities?
Yes, 809 E Chestnut St in Deer Park, MD has in-unit laundry.

809 E Chestnut St
Deer Park, MD 21550

$114,800

$114,800