4742 Chestnut Rd, Shady Side, MD 20764
Property image
Property image
SOLD
JAN 2, 2026

$407,300

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,630 sqft (on 0.26 acres)

4742 Chestnut Rd, Shady Side, MD 20764

Est. Refi. Payment $2,532/mo*
Refinance Your Home
Currently Off Market - Sold Jan 2, 2026 for $404,000 (4% below list price)

Home Value

Trulia Estimate
$407K
Since last month
Decreased$5K (-1.3%)
Since last year
Decreased$28K (-6.5%)
Since last sale
Increased$3K (+0.8%)
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 +42% in the last 10 years
MonthEstimated value
2026
September 2026$407K
August 2026$408K
July 2026$412K
June 2026$409K
May 2026$408K
April 2026$404K
March 2026$405K
February 2026$405K
January 2026$403K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
4721 Girton Ave, Shady Side, MD
0.25
Single-Family Home
$405,000
04/17/26
3
2
1,456
4727 Oak Rd, Shady Side, MD
0.05
Single-Family Home
$525,000
09/30/25
3
2
1,806
4738 Idlewilde Rd, Shady Side, MD
0.12
Single-Family Home
$447,000
01/08/26
4
2
1,300
4728 Frederick Ave, Shady Side, MD
0.28
Single-Family Home
$615,000
04/23/26
3
2
1,308
4725 Frederick Ave, Shady Side, MD
0.25
Single-Family Home
$465,000
07/24/26
3
2
912
4738 Washington Ave, Shady Side, MD
0.18
Single-Family Home
$327,500
04/20/26
3
2
1,223
4715 Oak Rd, Shady Side, MD
0.07
Single-Family Home
$1,000,000
10/10/25
4
2.5
3,244
1700 Bayview Rd, Shady Side, MD
0.14
Single-Family Home
$325,000
10/27/25
2
1.5
852
1617 Winters Ave, Shady Side, MD
0.27
Single-Family Home
$354,500
07/24/26
2
2
1,000

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
4748 Chestnut Rd, Shady Side, MD 20764
0.04
-
-
-
-
Off Market
4726 Poplar Rd, Shady Side, MD 20764
0.01
$522,200
5
3.5
2,179
Off Market
4734 Oak Rd, Shady Side, MD 20764
0.04
$625,000
4
2.5
2,511
For Sale
4722 Oak Rd, Shady Side, MD 20764
0.03
$471,000
3
2
1,838
Off Market
4727 Oak Rd, Shady Side, MD 20764
0.05
$770,100
3
2
1,806
Off Market
4721 Oak Rd, Shady Side, MD 20764
0.05
$998,000
4
3
1,868
For Sale
Address Not Disclosed, Shady Side, MD 20764
0.09
$1,384,300
3
3
3,142
Off Market
4749 Oak Rd, Shady Side, MD 20764
0.09
$790,500
3
2
1,344
Off Market
4715 Oak Rd, Shady Side, MD 20764
0.07
$1,010,100
4
2.5
3,244
Off Market
4738 Idlewilde Rd, Shady Side, MD 20764
0.12
$447,000
4
2
1,300
Recently Sold
1700 Bayview Rd, Shady Side, MD 20764
0.14
$328,100
2
1.5
852
Off Market

Local Information

  • Map ViewExplore the area around 4742 Chestnut Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
0.26 acre lot
1,630 sqft
$248/sqft
Open Parking

About this House

Experience refined living in this beautifully maintained 3-bedroom, 2.5-bath Colonial, perfectly nestled on a quiet, tree-lined street. This distinguished residence offers timeless curb appeal with a welcoming front porch, a thoughtfully designed interior, and a nicely appointed kitchen ideal for both daily living and entertaining. The home features a spacious primary suite, generously sized secondary bedrooms, and a nice-sized fenced-in yard that provides privacy and room to relax or play. A private driveway ensures effortless parking. Situated just moments from the water—without the upkeep of waterfront ownership— access to a Felicity Cove boat launch, kayak launch, fishing/swimming pier, and located in a well-regarded school district, this property delivers an exceptional blend of comfort, style, and convenience. A rare opportunity to enjoy serene suburban living in a truly desirable setting.
4742 Chestnut Rd, Shady Side, MD 20764 is a 3 bedroom, 3 bathroom, 1,630 sqft single-family home built in 1999. It last sold for $404,000 on Jan 2, 2026 (4% below the $420,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $407,300, with a rent estimate of $3,042/month.
Last check for updates: about 10 hours ago
Listed by Diego Reyes, (301) 832-2694
Long & Foster Real Estate, Inc.
Listing Team: Sergey Team, Co-Listing Team: Sergey Team,Co-Listing Agent: Sergey A Taksis, (347) 849-4040
Long & Foster Real Estate, Inc.
Bought with: Mallory Bare, (443) 404-3425, CENTURY 21 New Millennium
Source: Bright MLS, MLS#MDAA2132492

Home Details for 4742 Chestnut Rd

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bathroom 1, Bathroom 2, Half Bath
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1630 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: None
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above GradeFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway
Pool
Pool: None
Frontage
Waterfront: BayNot on Waterfront
Water & Sewer
Sewer: Public Septic, Public Sewer
Finished Area
Finished Area (above surface): 1630 Square Feet

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Parcel Number: 020726700150000

Price & Status

Price
List Price: $420,000Price Per Sqft: $248/sqft
Status Change & Dates
Off Market Date: Mon Jan 05 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: SHADY SIDECommunity: Felicity Cove
School Information
Elementary School District: Anne Arundel County Public SchoolsJr High / Middle School District: Anne Arundel County Public SchoolsHigh School District: Anne Arundel County Public Schools

Building

Building Area
Building Area: 1630 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.26 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDAA2132492Above Grade Unfinished Area: 1630

Additional Information

Source Internet Entire Listing Display: Y

Price and Tax history

DateEventPrice
Jan 2, 2026
Source: Bright MLS #MDAA2132492
Sold
$404,000
Dec 19, 2025
Source: Bright MLS #MDAA2132492
Contingent
$420,000
Dec 5, 2025
Source: Bright MLS #MDAA2132492
Listed For Sale
$420,000
Feb 8, 2023
Source: Bright MLS #MDAA2044006
Sold
$382,000
Feb 4, 2023
Source: Bright MLS #MDAA2044006
Pending
$399,000

Market trends in Shady Side

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
2MoM

Around this home

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
    "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.
    "We have nice parks and water access, and boat slips. Neighbors are friendly and watch out for each other "
    0
    Flag
  • Renee B.
    " 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.
    "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

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 4742 Chestnut Rd

  • What is 4742 Chestnut Rd estimated to be worth?
    Trulia's estimated value for 4742 Chestnut Rd in Shady Side, MD is $407,300.
  • What is the price history for 4742 Chestnut Rd?
    4742 Chestnut Rd in Shady Side, MD last sold for $404,000 in January 2026.
  • 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.
  • Does 4742 Chestnut Rd have air conditioning?
    Yes, 4742 Chestnut Rd in Shady Side, MD has air conditioning.
  • How big is the lot at 4742 Chestnut Rd?
    The lot at 4742 Chestnut Rd in Shady Side, MD is about 0.26 acres (11,326 sq ft).

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 4742 Chestnut Rd

Skip to last item
Skip to first item

Homes for sale near 4742 Chestnut Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item