Are yards well-kept in Shady Side, MD?

As of early 2026, 97% of users say yards are well-kept

Is a car needed in Shady Side, MD?

As of early 2026, 96% of users say car is needed

Is Shady Side, MD dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Do kids play outside in Shady Side, MD?

As of early 2026, 89% of users say kids play outside

Would people walk alone at night in Shady Side, MD?

As of early 2026, 81% of users say people would walk alone at night

Is Shady Side, MD quiet?

As of early 2026, 76% of users say it's quiet

Is parking easy in Shady Side, MD?

As of early 2026, 76% of users say parking is easy

Are neighbors friendly in Shady Side, MD?

As of early 2026, 73% of users say neighbors are friendly

Is there wildlife in Shady Side, MD?

As of early 2026, 73% of users say there's wildlife

Does Shady Side, MD show holiday spirit?

As of early 2026, 71% of users say there's holiday spirit

Do residents of Shady Side, MD plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Are there community events in Shady Side, MD?

As of early 2026, 43% of users say there are community events

Is Shady Side, MD walkable to restaurants?

As of early 2026, 32% of users say it's walkable to restaurants

Are the streets well-lit in Shady Side, MD?

As of early 2026, 29% of users say streets are well-lit

Is Shady Side, MD walkable to grocery stores?

As of early 2026, 13% of users say it's walkable to grocery stores

What is 4950 Chestnut St estimated to be worth?

Trulia's estimated value for 4950 Chestnut St in Shady Side, MD is $373,600 .

Is Shady Side a buyer's or seller's market?

Shady Side is currently a balanced market, based on recent for-sale activity.

What do residents say about Shady Side?

Residents describe Shady Side, MD as well-kept, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Shady Side, MD .

What are the closest schools to 4950 Chestnut St?

The closest schools to 4950 Chestnut St in Shady Side, MD are Shady Side Elementary School (Pre-K, rated 7/10), Southern High School (rated 6/10), Southern Middle School (rated 8/10).

Does 4950 Chestnut St have air conditioning?

Yes, 4950 Chestnut St in Shady Side, MD has air conditioning.

Does 4950 Chestnut St have laundry facilities?

Yes, 4950 Chestnut St in Shady Side, MD has in-unit laundry.

OFF MARKET

$373,600

Trulia Estimate

4 Beds
1.5 Baths
1,502 sqft

4950 Chestnut St, Shady Side, MD 20764

Refinance Your Home

Home Value

Trulia Estimate

$374K

Since last month

$12K (-3%)

Since last year

$400 (+0.1%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +49% in the last 10 years

Month	Estimated value
2026
August 2026	$375K
August 2026	$374K
July 2026	$387K
June 2026	$386K
May 2026	$386K
April 2026	$376K
March 2026	$373K
February 2026	$365K
January 2026	$364K
2025
December 2025	$367K
November 2025	$367K
October 2025	$367K
September 2025	$371K
August 2025	$375K
July 2025	$373K
June 2025	$371K
May 2025	$371K
April 2025	$372K
March 2025	$364K
February 2025	$357K
January 2025	$353K
2024
December 2024	$359K
November 2024	$349K
October 2024	$358K
September 2024	$359K
August 2024	$360K
July 2024	$366K
June 2024	$367K
May 2024	$366K
April 2024	$363K
March 2024	$357K
February 2024	$353K
January 2024	$345K
2023
December 2023	$345K
November 2023	$351K
October 2023	$347K
September 2023	$353K
August 2023	$352K
July 2023	$355K
June 2023	$358K
May 2023	$358K
April 2023	$350K
March 2023	$345K
February 2023	$337K
January 2023	$334K
2022
December 2022	$335K
November 2022	$338K
October 2022	$343K
September 2022	$344K
August 2022	$346K
July 2022	$353K
June 2022	$353K
May 2022	$351K
April 2022	$345K
March 2022	$336K
February 2022	$324K
January 2022	$320K
2021
December 2021	$324K
November 2021	$324K
October 2021	$325K
September 2021	$329K
August 2021	$330K
July 2021	$335K
June 2021	$338K
May 2021	$341K
April 2021	$344K
March 2021	$325K
February 2021	$318K
January 2021	$316K
2020
December 2020	$307K
November 2020	$304K
October 2020	$302K
September 2020	$290K
August 2020	$293K
July 2020	$294K
June 2020	$297K
May 2020	$295K
April 2020	$295K
March 2020	$290K
February 2020	$288K
January 2020	$291K
2019
December 2019	$289K
November 2019	$289K
October 2019	$292K
September 2019	$295K
August 2019	$294K
July 2019	$296K
June 2019	$298K
May 2019	$288K
April 2019	$298K
March 2019	$294K
February 2019	$290K
January 2019	$292K
2018
December 2018	$292K
November 2018	$286K
October 2018	$288K
September 2018	$281K
August 2018	$279K
July 2018	$277K
June 2018	$277K
May 2018	$279K
April 2018	$279K
March 2018	$281K
February 2018	$279K
January 2018	$274K
2017
December 2017	$276K
November 2017	$277K
October 2017	$274K
September 2017	$275K
August 2017	$272K
July 2017	$275K
June 2017	$275K
May 2017	$274K
April 2017	$267K
March 2017	$269K
February 2017	$263K
January 2017	$255K
2016
December 2016	$257K
November 2016	$258K
October 2016	$256K
September 2016	$251K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
4929 Aspen St, Shady Side, MD	0.07	Single-Family Home	$395,000	02/10/26	3	2	1,232
4951 Dogwood St, Shady Side, MD	0.06	Single-Family Home	$599,999	04/30/26	4	2.5	2,586
4913 Chestnut St, Shady Side, MD	0.17	Single-Family Home	$347,000	12/08/25	3	2	1,152
1205 Avalon Blvd, Shady Side, MD	0.17	Single-Family Home	$440,000	04/30/26	3	2.5	1,500
4939 Bonniewood Dr, Shady Side, MD	0.29	Single-Family Home	$274,000	06/26/26	4	2	2,464
4944 Beech St, Shady Side, MD	0.04	Single-Family Home	$405,000	07/01/26	3	2.5	1,344
4936 Lerch Dr, Shady Side, MD	0.18	Single-Family Home	$995,000	06/25/26	4	3	2,200
1226 Hawthorne St, Shady Side, MD	0.26	Single-Family Home	$415,000	04/01/26	3	2	1,438
1218 Juniper St, Shady Side, MD	0.29	Single-Family Home	$550,000	03/27/26	4	2.5	1,992
1306 Spruce St, Shady Side, MD	0.31	Single-Family Home	$592,860	03/27/26	4	2.5	2,424

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
4944 Beech St, Shady Side, MD 20764	0.04	$405,000	3	2.5	1,344	Recently Sold
4933 Aspen St, Shady Side, MD 20764	0.06	$638,300	4	3.5	3,613	Off Market
4937 Aspen St, Shady Side, MD 20764	0.06	$385,999	2	2	886	Recently Sold
4929 Aspen St, Shady Side, MD 20764	0.07	$395,000	3	2	1,232	Recently Sold
4935 Chestnut St, Shady Side, MD 20764	0.06	$337,300	2	1	912	Off Market
4925 Aspen St, Shady Side, MD 20764	0.09	$338,800	2	1	1,060	Off Market
4954 Dogwood St, Shady Side, MD 20764	0.05	$331,900	2	1	812	Off Market
4977 Lerch Dr, Shady Side, MD 20764	0.08	$393,800	3	1	1,407	Off Market
4951 Dogwood St, Shady Side, MD 20764	0.06	$599,999	4	2.5	2,586	Recently Sold
4929 Chestnut St, Shady Side, MD 20764	0.10	$394,000	3	2.5	1,248	Off Market
4992 Lerch Dr, Shady Side, MD 20764	0.08	$1,107,100	4	4.5	3,432	Recently Sold
4964 Lerch Dr, Shady Side, MD 20764	0.11	$928,500	3	2.5	2,280	Off Market

Local Information

Map ViewExplore the area around 4950 Chestnut St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1955

1,502 sqft

$249/sqft

About this House

This single-family home is located at 4950 Chestnut St, Shady Side, MD. 4950 Chestnut St is in Shady Side, MD and in ZIP code 20764. This property has 4 bedrooms, 2 bathrooms and approximately 1,502 sqft of floor space. This property has a lot size of 10000 sqft and was built in 1955.

4950 Chestnut St, Shady Side, MD 20764 is a 4 bedroom, 2 bathroom, 1,502 sqft single-family home built in 1955. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $373,600, with a rent estimate of $2,865/month.

Home Details for 4950 Chestnut St

Interior Features
Heating & Cooling Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1Floors: Hardwood
Interior Details AtticTypes of Rooms: Breakfast Nook, Family RoomCeiling Fan
Appliances & Utilities Cable ReadyDryerMicrowaveRefrigeratorWasher

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

Property Information
Year Built Year Built: 1955
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 10000 sqft

Price and Tax history

Year	Property tax	Tax assessment
2025	$2,828	$289,000

Home facts updated by county records

Additional Cost

Market trends in Shady Side

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Shady Side Elementary School
PK-5
Public
382 Students
Anne Arundel County Public Schools
7/10
GreatSchools Rating
Parent Rating Average
Wonderful school! Everyone is so welcoming and warm.
Parent Review
7y ago
4 Reviews

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 Shady Side

At least 26 Trulia users voted on each feature.

97 % Say yards are well-kept
96 % Say car is needed
91 % Say it's dog friendly
89 % Say kids play outside
81 % Say people would walk alone at night
76 % Say it's quiet
76 % Say parking is easy
73 % Say neighbors are friendly
73 % Say there's wildlife
71 % Say there's holiday spirit
50 % Say they plan to stay for at least 5 years
43 % Say there are community events
32 % Say it's walkable to restaurants
29 % Say streets are well-lit
13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Krmotto@gmail.com
Resident
6y ago
"the bay is so close, and the neighborhood is perfect for our small family. bike rides are fun, and good schools we think! "
1
Flag
Julie F.
Resident
8y ago
"We have nice parks and water access, and boat slips. Neighbors are friendly and watch out for each other "
0
Flag
Renee B.
11y ago
" If you want to live in a country or water setting this is a great area for just that. It is a relatively easy commute into DC, Annapolis or Baltimore. If you want box stores forget it! it's all about keeping it local down here. Enjoy the diverse community of friendly people who like to kayak, fish, sail, bike ride, power boat, motorcycle, hunt, eat local crabs & oysters, the arts, history at Captain Avery Museum, ride horses and so much more!! I gave the traffic an Excellent rating compared to the congested surrounding areas, every now and then you might get behind a farmers tractor who usually pulls over to let you pass! Public Transportation, there is a Park & Ride 15min away that has an excellent commuter bus into DC. School buses yes. Senior Citizen busses available. Community Involvement - Small 4th of July Parade, Oyster Festival, and just some good old fashioned neighborhood get togethers. "
1
Flag
Elena H.
12y ago
"For a quaint existence on the water where waking up to the tranquility of birds singing and going to sleep following an uninhibited view of the night sky are your drivers, this bucolic neighborhood is perfect! Ideal neighborhood for the boating crowd and a weekend home. "
1
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4950 Chestnut St

What is 4950 Chestnut St estimated to be worth?
Trulia's estimated value for 4950 Chestnut St in Shady Side, MD is $373,600.
Is Shady Side a buyer's or seller's market?
Shady Side is currently a balanced market, based on recent for-sale activity.
What do residents say about Shady Side?
Residents describe Shady Side, MD as well-kept, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Shady Side, MD.
What are the closest schools to 4950 Chestnut St?
The closest schools to 4950 Chestnut St in Shady Side, MD are Shady Side Elementary School (Pre-K, rated 7/10), Southern High School (rated 6/10), Southern Middle School (rated 8/10).
Does 4950 Chestnut St have air conditioning?
Yes, 4950 Chestnut St in Shady Side, MD has air conditioning.
Does 4950 Chestnut St have laundry facilities?
Yes, 4950 Chestnut St in Shady Side, MD has in-unit laundry.

Apartments for Rent

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Off Market Homes Near 4950 Chestnut St

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SOLD
SEP 4, 2026
$375,000
3 bd
1.5 ba
1,248 sqft
1311 Avalon Blvd,
Shady Side, MD 20764
Home Sweet Home Real Estate LLC
SOLD
AUG 31, 2026
$325,000
4 bd
3 ba
2,807 sqft
6201 Shady Side Rd,
Shady Side, MD 20764
Schwartz Realty, Inc.
SOLD
AUG 31, 2026
$470,000
3 bd
2.5 ba
1,344 sqft
1221 Fairfax Ave,
Churchton, MD 20733
RE/MAX One
SOLD
AUG 31, 2026
$370,000
3 bd
1.5 ba
1,386 sqft
4912 Mariners Dr,
Shady Side, MD 20764
RE/MAX United Real Estate
SOLD
AUG 28, 2026
$349,500
3 bd
2 ba
1,098 sqft
1314 Pine St,
Shady Side, MD 20764
Peninsula Properties, LLC.
SOLD
AUG 27, 2026
$355,000
2 bd
1 ba
840 sqft
302 Linden Ave,
Edgewater, MD 21037
Anne Arundel Properties, Inc.
SOLD
AUG 26, 2026
$349,870
5235 Al Jones Dr,
Shady Side, MD 20764
Long & Foster Real Estate, Inc.
SOLD
AUG 21, 2026
$415,000
3 bd
1.5 ba
1,104 sqft
5533 Franklin Blvd,
Churchton, MD 20733
Douglas Realty, LLC
SOLD
AUG 21, 2026
$489,990
3 bd
2.5 ba
1,679 sqft
5503 Manistique Ct,
Churchton, MD 20733
Long & Foster Real Estate, Inc.
SOLD
AUG 14, 2026
$485,000
3 bd
2.5 ba
1,840 sqft
1133 Delaware Ave,
Churchton, MD 20733
Samson Properties
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Homes for sale near 4950 Chestnut St

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$349,900
3 bd
1 ba
1,008 sqft
4921 Olive St,
Shady Side, MD 20764
Redfin Corp
0.33 ACRES
$470,000
3 bd
2.5 ba
1,456 sqft
4951 Bonniewood Dr,
Shady Side, MD 20764
Schwartz Realty, Inc.
0.27 ACRES
$699,000
3 bd
2.5 ba
2,176 sqft
1241 Johnson Dr,
Shady Side, MD 20764
RE/MAX One
0.39 ACRES
$775,000
3 bd
2 ba
2,304 sqft
4950 Bonniewood Dr,
Shady Side, MD 20764
RE/MAX Leading Edge
OPEN SAT, 11-1PM
$1,100,000
3 bd
4.5 ba
1,888 sqft
5060 Lerch Dr,
Shady Side, MD 20764
Redfin Corp
NEW CONSTRUCTION
$549,990
4 bd
2.5 ba
2,091 sqft
1225 Juniper St,
Shady Side, MD 20764
RE/MAX United Real Estate
$480,000
3 bd
2.5 ba
1,848 sqft
4909 Olive St,
Shady Side, MD 20764
TTR Sotheby's International Realty
$429,900
3 bd
2.5 ba
2,235 sqft
1161 Steamboat Rd,
Shady Side, MD 20764
Schwartz Realty, Inc.
0.57 ACRES
$699,000
4 bd
1.5 ba
2,144 sqft
1462 Snug Harbor Rd,
Shady Side, MD 20764
Schwartz Realty, Inc.
OPEN SAT, 10-12PM
$525,000
4 bd
3 ba
1,905 sqft
1411 Haile Pkwy,
Shady Side, MD 20764
TTR Sotheby's International Realty
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