Is a car needed in Chestertown, MD?

As of early 2026, 85% of users say car is needed

Does Chestertown, MD show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Is Chestertown, MD dog-friendly?

As of early 2026, 83% of users say it's dog friendly

Would people walk alone at night in Chestertown, MD?

As of early 2026, 77% of users say people would walk alone at night

Is parking easy in Chestertown, MD?

As of early 2026, 77% of users say parking is easy

Are yards well-kept in Chestertown, MD?

As of early 2026, 76% of users say yards are well-kept

Is Chestertown, MD quiet?

As of early 2026, 74% of users say it's quiet

Are neighbors friendly in Chestertown, MD?

As of early 2026, 61% of users say neighbors are friendly

Is there wildlife in Chestertown, MD?

As of early 2026, 57% of users say there's wildlife

Is Chestertown, MD walkable to restaurants?

As of early 2026, 56% of users say it's walkable to restaurants

Does Chestertown, MD have sidewalks?

As of early 2026, 54% of users say there are sidewalks

Do kids play outside in Chestertown, MD?

As of early 2026, 49% of users say kids play outside

Is Chestertown, MD walkable to grocery stores?

As of early 2026, 46% of users say it's walkable to grocery stores

Are the streets well-lit in Chestertown, MD?

As of early 2026, 44% of users say streets are well-lit

Are there community events in Chestertown, MD?

As of early 2026, 41% of users say there are community events

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

As of early 2026, 38% of users say they plan to stay for at least 5 years

OFF MARKET

106 E Step Rd
Chestertown, MD 21620

4 Beds
2 Baths
1,400 sqft (on 0.34 acres)

$347,600

Trulia Estimate

as of May 26, 2026

Est. Refi. Payment $2,063/mo*

Refinance Your Home

$347,600

Trulia Estimate

as of May 26, 2026

Est. Refi. Payment $2,063/mo*

Refinance Your Home

4 Beds

2 Baths

1,400 sqft

(on 0.34 acres)

Local Information

-- mins to

Commute Destination

Description

Beautiful 4 bedroom 2 bath in lovely Chestertown. Under Construction, but will be done within the month. An open kitchen to allow for all of the family to gather. Separate laundry room off of the kitchen. Master Bedroom has 2 large closets. This home has everything you need! Large family room, with lots of natural lighting. Settlement on date of completion.$1000.00 credit towards buyer if used preferred lender.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 106 E Step Rd

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1Floors: Carpet, Linoleum Vinyl
Appliances & Utilities DishwasherMicrowaveRefrigerator
Interior Details Ceiling Fan

Exterior Features
Exterior Home Features Roof: OtherExterior: OtherSprinkler System

Property Information
Year Built Year Built: 2021
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 0.34 acres

Price History for 106 E Step Rd

Date	Price	Event	Source
06/29/2021	$259,500	Sold	Bright MLS #MDQA147184
Recording Date 06/29/2021 County Transfer Tax N/A Total Transfer Tax N/A
05/21/2021	$250,000	Pending	Bright MLS #MDQA147184

05/03/2021	$250,000	PriceChange	Bright MLS #MDQA147184
Price Change $2,500 (1%)
04/18/2021	$247,500	PriceChange	Bright MLS #MDQA147184
Price Change $2,500 (1%)
03/30/2021	$245,000	Listed For Sale	Bright MLS #MDQA147184

01/25/2021	$17,500	Sold	N/A
Recording Date 01/25/2021 Contract Date 01/20/2021 County Transfer Tax $1 Total Transfer Tax $2

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Property Tax and Assessment

Year	2025
Tax	$2,439
Assessment	$252,500

Home facts updated by county records

Comparable Sales for 106 E Step Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
111 Cee Jay Rd, Chestertown, MD	0.04	Single-Family Home	$349,000	10/16/25	4	2	1,400
148 E Step Rd, Chestertown, MD	0.14	Single-Family Home	$365,000	04/17/26	4	2	1,400
124 Char Nor Manor Blvd, Chestertown, MD	0.06	Single-Family Home	$250,000	11/11/25	2	2	1,024
134 Char Nor Manor Blvd, Chestertown, MD	0.09	Single-Family Home	$260,000	02/18/26	3	1	1,128
165 Char Nor Manor Blvd, Chestertown, MD	0.23	Single-Family Home	$424,000	01/30/26	4	2.5	2,258
111 Cee Jay Rd, Chestertown, MD	0.03	Single-Family Home	$349,000	10/23/25		2	1,400
127 Char Nor Manor Blvd, Chestertown, MD	0.10	Single-Family Home	$355,000	10/02/25	2	1	832
129 Char Nor Manor Blvd, Chestertown, MD	0.10	Single-Family Home	$412,000	02/20/26	2	1	810
143 Char Nor Manor Blvd, Chestertown, MD	0.13	Single-Family Home	$868,000	10/15/25	3	2.5	2,073
300 Merganser Dr, Chestertown, MD	0.44	Single-Family Home	$80,000	11/07/25	3	1	1,260

Nearby homes

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

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FOR SALE
0.53 ACRES
$138,000
3 bd
2 ba
1,666 sqft
127 Wood Duck Ln,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
FOR SALE
OPEN SUN, 12-2PM
3D VIEW
0.51 ACRES
$425,000
3 bd
2 ba
1,120 sqft
240 Merganser Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
FOR SALE
0.51 ACRES
$99,000
228 Merganser Dr,
Chestertown, MD 21620
Benson & Mangold, LLC
SOLD
APR 29, 2026
$50,000
144 Char Nor Manor Blvd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
APR 17, 2026
$365,000
4 bd
2 ba
1,400 sqft
148 E Step Rd,
Chestertown, MD 21620
Anne Arundel Properties, Inc.
FOR SALE
0.87 ACRES
$565,000
3 bd
2.5 ba
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JAN 23, 2026
$325,000
3 bd
2.5 ba
1,468 sqft
676 Deep Landing Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
NOV 11, 2025
$250,000
2 bd
2 ba
1,024 sqft
124 Char Nor Manor Blvd,
Chestertown, MD 21620
RE/MAX Executive
SOLD
OCT 16, 2025
$349,000
4 bd
2 ba
1,400 sqft
111 Cee Jay Rd,
Chestertown, MD 21620
Rosendale Realty
SOLD
OCT 2, 2025
$355,000
2 bd
1 ba
832 sqft
127 Char Nor Manor Blvd,
Chestertown, MD 21620
Iron Valley Real Estate of Central PA
SOLD
OCT 15, 2025
$868,000
3 bd
2.5 ba
2,073 sqft
143 Char Nor Manor Blvd,
Chestertown, MD 21620
Redfin Corp
SOLD
JAN 30, 2026
$424,000
4 bd
2.5 ba
2,258 sqft
165 Char Nor Manor Blvd,
Chestertown, MD 21620
RE/MAX Executive

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Additional Cost

Assigned Schools

These are the assigned schools for 106 E Step Rd.

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 Chestertown

At least 34 Trulia users voted on each feature.

85 % Say car is needed
84 % Say there's holiday spirit
83 % Say it's dog friendly
77 % Say people would walk alone at night
77 % Say parking is easy
76 % Say yards are well-kept
74 % Say it's quiet
61 % Say neighbors are friendly
57 % Say there's wildlife
56 % Say it's walkable to restaurants
54 % Say there are sidewalks
49 % Say kids play outside
46 % Say it's walkable to grocery stores
44 % Say streets are well-lit
41 % Say there are community events
38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Visitor
3y ago
"Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
1
Flag
Trulia User
Visitor
5y ago
"Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
1
Flag
Trulia User
Prev. Resident
5y ago
"I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
0
Flag
Kesha C.
Resident
6y ago
"Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
0
Flag
Tracy W.
Resident
6y ago
"The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
0
Flag
Rancraw
Resident
7y ago
"This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
9
Flag
Acaldwell1297
Resident
7y ago
"I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
1
Flag
Guillermo A.
11y ago
"Good Community, friendly people, good services. "
0
Flag
Nancy M.
11y ago
"People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
5
Flag
asso
12y ago
"Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
0
Flag
Dafoster
12y ago
"Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
5
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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$1,700/mo
2 bd
1 ba
27318 Morgnec Rd #B,
Chestertown, MD 21620
See more homes for rent in
Chestertown
Take a look

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Explore by feature

APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
$1,100/mo
Total price
1 ba
750 sqft
866 Washington Ave #B,
Chestertown, MD 21620
APPLY INSTANTLY
$2,150/mo
3 bd
2.5 ba
1,365 sqft
110 Island Lark Way,
Chestertown, MD 21620
APPLY INSTANTLY
$2,095/mo
3 bd
2.5 ba
1,222 sqft
210 Hilltop Ln,
Chestertown, MD 21620
$1,700/mo
2 bd
1 ba
1,100 sqft
27318 Morgnec Rd #B,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620
PET FRIENDLY
$1,520/mo
2 bd
1 ba
800 sqft
104 Maple Ave #3,
Chestertown, MD 21620
8 rentals with air conditioning in Chestertown, MD

Homes for sale near 106 E Step Rd

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OPEN SUN, 12-2PM
0.51 ACRES
$425,000
3 bd
2 ba
1,120 sqft
240 Merganser Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.87 ACRES
$565,000
3 bd
2.5 ba
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.76 ACRES
$344,900
3 bd
2 ba
1,392 sqft
109 Wilton Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.46 ACRES
$339,900
3 bd
2 ba
1,280 sqft
102 Pine St,
Crumpton, MD 21628
Clark & Co Realty, LLC
0.46 ACRES
$337,500
3 bd
2 ba
1,250 sqft
209 3rd St,
Crumpton, MD 21628
EXP Realty, LLC
OPEN SAT, 12-2PM
COMING SOON 5/30
1 ACRE
$457,500
3 bd
2 ba
1,664 sqft
118 Grant Ct,
Chestertown, MD 21620
RE/MAX Executive
0.55 ACRES
$299,000
3 bd
1 ba
1,120 sqft
208 Central Dr,
Chestertown, MD 21620
Redfin Corp
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 106 E Step Rd

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SOLD
MAY 19, 2026
$376,000
3 bd
2 ba
1,432 sqft
136 Hilltop Dr,
Chestertown, MD 21620
Northrop Realty
SOLD
MAY 18, 2026
$220,000
6 bd
3 ba
2,948 sqft
1517 Dudley Corners Rd,
Millington, MD 21651
Coldwell Banker Chesapeake Real Estate Company
SOLD
MAY 14, 2026
$278,500
3 bd
1 ba
107 Longfellow Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
MAY 4, 2026
$480,000
4 bd
2 ba
1,848 sqft
101 Pine Tree Rd,
Chestertown, MD 21620
Rosendale Realty
SOLD
APR 24, 2026
$475,900
1 ba
1,849 sqft
207 Pine Tree Rd,
Millington, MD 21651
SOLD
APR 21, 2026
$339,900
3 bd
2.5 ba
1,724 sqft
103 Flying Cloud Dr,
Chestertown, MD 21620
American Premier Realty, LLC
SOLD
APR 21, 2026
$365,000
1 sqft
E Step Rd,
Chestertown, MD 21620
SOLD
APR 17, 2026
$510,000
3 bd
1 ba
1,202 sqft
110 Dogwood Ct,
Millington, MD 21651
RE/MAX Executive
SOLD
APR 17, 2026
$475,900
3 bd
2 ba
1,677 sqft
108 Springbrook Ln,
Millington, MD 21651
Chesapeake Real Estate Associates, LLC
SOLD
APR 17, 2026
$365,000
4 bd
2 ba
1,400 sqft
148 E Step Rd,
Chestertown, MD 21620
Anne Arundel Properties, Inc.
See more homes for sale in
Chestertown
Take a look

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Homes for rent near 106 E Step Rd

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106 E Step Rd, Chestertown, MD 21620 is a 4 bedroom, 2 bathroom, 1,400 sqft single-family home built in 2021. This property is not currently available for sale. 106 E Step Rd was last sold on Jun 29, 2021 for $259,500. The current Trulia Estimate for 106 E Step Rd is $347,600.

106 E Step Rd
Chestertown, MD 21620

$347,600

$347,600

Local Information