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

SOLD

OCT 23, 2025

111 Cee Jay Rd
Chestertown, MD 21620

Studio
2 Baths
1,400 sqft (on 0.34 acres)

$349,000

Last Sold: Oct 23, 2025

$249/sqft

$349,000

Last Sold: Oct 23, 2025

$249/sqft

Studio

2 Baths

1,400 sqft

(on 0.34 acres)

Local Information

Map ViewExplore the area around 111 Cee Jay Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

2021

Lot Size

0.34 acres

Living Area

1,400 sqft

Price/Sqft

$249/sqft

About this House

This single-family home is located at 111 Cee Jay Rd, Chestertown, MD. 111 Cee Jay Rd is in Chestertown, MD and in ZIP code 21620. This property has 2 bathrooms and approximately 1,400 sqft of floor space. The last sold price per dimension was $249/sqft. This property has a lot size of 0.34 acres and was built in 2021.

111 Cee Jay Rd, Chestertown, MD 21620 is a studio, 2 bathroom, 1,400 sqft single-family home built in 2021. It last sold for $349,000 on Oct 23, 2025. It is currently off market. The Trulia Estimate is $361,400, with a rent estimate of $2,543/month.

Home Details for 111 Cee Jay Rd

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other

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

Price & Status
Price Price Per Sqft: $249/sqft

Community
Units in Building: 1

Lot Information
Lot Area: 0.34 acres

Price History for 111 Cee Jay Rd

Date	Price	Event	Source
10/23/2025	$349,000	Sold	N/A
Recording Date 10/23/2025 Contract Date 10/16/2025 County Transfer Tax $9 Total Transfer Tax $17
06/08/2021	$245,000	Sold	N/A
Recording Date 06/08/2021 Contract Date 06/04/2021 County Transfer Tax $6 Total Transfer Tax $12
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
03/07/2006	$16,700	Sold	N/A
Recording Date 03/07/2006 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chestertown

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

5MoM

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Property Tax and Assessment

Year	2025
Tax	$2,361
Assessment	$244,300

Home facts updated by county records

Comparable Sales for 111 Cee Jay Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
111 Cee Jay Rd, Chestertown, MD	0.00	Single-Family Home	$349,000	10/16/25	4	2	1,400
126 Char Nor Manor Blvd, Chestertown, MD	0.09	Single-Family Home	$349,500	06/05/26	3	2	1,304
148 E Step Rd, Chestertown, MD	0.12	Single-Family Home	$365,000	04/17/26	4	2	1,400
124 Char Nor Manor Blvd, Chestertown, MD	0.09	Single-Family Home	$250,000	11/11/25	2	2	1,024
165 Char Nor Manor Blvd, Chestertown, MD	0.22	Single-Family Home	$424,000	01/30/26	4	2.5	2,258
127 Char Nor Manor Blvd, Chestertown, MD	0.13	Single-Family Home	$355,000	10/02/25	2	1	832
134 Char Nor Manor Blvd, Chestertown, MD	0.10	Single-Family Home	$260,000	02/18/26	3	1	1,128
129 Char Nor Manor Blvd, Chestertown, MD	0.13	Single-Family Home	$412,000	02/20/26	2	1	810
143 Char Nor Manor Blvd, Chestertown, MD	0.15	Single-Family Home	$868,000	10/15/25	3	2.5	2,073

Nearby homes

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

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SOLD
OCT 16, 2025
$349,000
4 bd
2 ba
1,400 sqft
111 Cee Jay Rd,
Chestertown, MD 21620
Rosendale Realty
OFF MARKET
Est. $269,600
3 bd
2 ba
1,900 sqft
131 E Step Rd,
Chestertown, MD 21620
Taylor Properties
SOLD
JUN 5, 2026
$349,500
3 bd
2 ba
1,304 sqft
126 Char Nor Manor Blvd,
Chestertown, MD 21620
RE/MAX Executive
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
FEB 18, 2026
$260,000
3 bd
1 ba
1,128 sqft
134 Char Nor Manor Blvd,
Chestertown, MD 21620
Meredith Fine Properties
OFF MARKET
Est. $323,200
4 bd
2 ba
1,400 sqft
906 Double Creek Point,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $279,100
3 bd
2 ba
1,114 sqft
118 Char Nor Manor Blvd,
Chestertown, MD 21620
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.
SOLD
FEB 20, 2026
$412,000
2 bd
1 ba
810 sqft
129 Char Nor Manor Blvd,
Chestertown, MD 21620
Iron Valley Real Estate of Central PA
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
APR 29, 2026
$50,000
144 Char Nor Manor Blvd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
OCT 15, 2025
$868,000
3 bd
2.5 ba
2,073 sqft
143 Char Nor Manor Blvd,
Chestertown, MD 21620
Redfin Corp

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Additional Cost

Assigned Schools

These are the assigned schools for 111 Cee Jay 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
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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
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Kesha C.
Resident
6y ago
"Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
0
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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
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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.
12y 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
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LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 111 Cee Jay Rd

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0.51 ACRES
$365,000
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
0.67 ACRES
$320,000
3 bd
1.5 ba
1,096 sqft
222 Dutchess Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
0.52 ACRES
$349,000
3 bd
2 ba
1,792 sqft
123 Heath Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.46 ACRES
$337,500
3 bd
2 ba
1,250 sqft
209 3rd St,
Crumpton, MD 21628
EXP Realty, LLC
0.3 ACRES
$200,000
3 bd
1.5 ba
2,206 sqft
107 2nd St,
Crumpton, MD 21628
Marathon Real Estate
0.34 ACRES
$299,900
3 bd
1 ba
1,248 sqft
517 Round Top Rd,
Chestertown, MD 21620
Keller Williams Flagship
2.6 ACRES
$589,000
1 bd
2 ba
760 sqft
114 Front St,
Crumpton, MD 21628
Coldwell Banker Chesapeake Real Estate Company
0.34 ACRES
$380,000
4 bd
2 ba
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
NEW
COMING SOON 8/10
0.29 ACRES
$205,000
3 bd
1 ba
1,341 sqft
202 Pine St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
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Chestertown
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Off Market Homes Near 111 Cee Jay Rd

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SOLD
JUL 22, 2026
$365,000
3 bd
2 ba
1,934 sqft
521 N Kent St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
JUL 16, 2026
$435,000
3 bd
2.5 ba
1,784 sqft
215 Fairview Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
SOLD
JUL 15, 2026
$275,000
Crumpton Rd,
Crumpton, MD 21628
SOLD
JUL 13, 2026
$228,000
3 bd
1.5 ba
2,260 sqft
221 Dutchess Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUN 29, 2026
$460,000
3 bd
2 ba
1,664 sqft
118 Grant Ct,
Chestertown, MD 21620
RE/MAX Executive
SOLD
JUN 12, 2026
$385,000
3 bd
2.5 ba
1,484 sqft
321 Front St,
Crumpton, MD 21628
Chesapeake Real Estate Associates, LLC
SOLD
JUN 12, 2026
$360,000
3 bd
2 ba
1,271 sqft
720 Deep Landing Rd,
Chestertown, MD 21620
Coldwell Banker Waterman Realty
SOLD
JUN 5, 2026
$349,500
3 bd
2 ba
1,304 sqft
126 Char Nor Manor Blvd,
Chestertown, MD 21620
RE/MAX Executive
SOLD
JUN 5, 2026
$175,000
3 bd
1 ba
1,296 sqft
113 Pear Tree Point Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
MAY 29, 2026
$430,000
3 bd
2 ba
1,588 sqft
201 Birch Run Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Chestertown
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111 Cee Jay Rd
Chestertown, MD 21620

$349,000

$349,000