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

101 Sheaffer Rd
Chestertown, MD 21620

Studio
2 Baths
1,664 sqft (on 1.12 acres)

$465,400

Trulia Estimate

as of Jun 30, 2026

Est. Refi. Payment $2,664/mo*

Refinance Your Home

$465,400

Trulia Estimate

as of Jun 30, 2026

Est. Refi. Payment $2,664/mo*

Refinance Your Home

Studio

2 Baths

1,664 sqft

(on 1.12 acres)

Local Information

Map ViewExplore the area around 101 Sheaffer Rd.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

***COUNTRY SETTING***AFFORDABLE, PERC-APPROVED 1.12A BUILDING LOT IN THE 'GROVE' SUBDIVISION.***LOT#16***THREE(3) OTHER LOTS AVAILABLE ! CALL L.A. FOR DETAILS !

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

Garage

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 101 Sheaffer Rd

Interior Features
Interior Details Basement
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
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2015
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 1.12 acres

Price History for 101 Sheaffer Rd

Date	Price	Event	Source
11/12/2014	$52,500	Sold	N/A
Recording Date 11/12/2014 Contract Date 10/31/2014 County Transfer Tax $263 Total Transfer Tax $525
01/20/2009	$129,900	ListingRemoved	Agent Provided

05/27/2008	$129,900	Listed For Sale	Agent Provided

12/02/2004	$120,000	Sold	N/A
Recording Date 12/02/2004 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chestertown

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

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Property Tax and Assessment

Year	2025
Tax	$3,447
Assessment	$359,600

Home facts updated by county records

Comparable Sales for 101 Sheaffer Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
136 Hilltop Dr, Chestertown, MD	0.27	Single-Family Home	$376,000	05/19/26	3	2	1,432
118 Grant Ct, Chestertown, MD	0.35	Single-Family Home	$460,000	06/29/26	3	2	1,664
216 Blakefield Dr, Chestertown, MD	0.49	Single-Family Home	$552,000	04/17/26	4	3	2,400
206 Flyway Ln, Chestertown, MD	0.44	Single-Family Home	$512,500	04/08/26	4	3.5	3,000
247 Blakefield Dr, Chestertown, MD	0.63	Single-Family Home	$435,000	12/16/25	3	3	2,500
114 Ryan Ct, Chestertown, MD	1.92	Single-Family Home	$355,000	08/12/25	2	2	1,496
107 Dutchess Rd, Chestertown, MD	1.70	Single-Family Home	$290,000	08/13/25	3	2	1,380
119 Darden Rd, Chestertown, MD	1.73	Single-Family Home	$270,000	03/18/26	3	2	1,424
105 Parma Rd, Chestertown, MD	1.78	Single-Family Home	$322,000	11/14/25	3	2	1,232
113 Pear Tree Point Rd, Chestertown, MD	1.87	Single-Family Home	$175,000	06/05/26	3	1	1,296

Nearby homes

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

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OFF MARKET
Est. $529,400
4 bd
2.5 ba
2,864 sqft
112 Sheaffer Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OFF MARKET
4 bd
3.5 ba
2,512 sqft
317 Union Church Rd,
Chestertown, MD 21620
Clark & Co Realty, LLC
SOLD
MAY 19, 2026
$376,000
3 bd
2 ba
1,432 sqft
136 Hilltop Dr,
Chestertown, MD 21620
Northrop Realty
OFF MARKET
4 bd
2 ba
1,766 sqft
130 Sheaffer Rd,
Chestertown, MD 21620
Coldwell Banker Realty
OFF MARKET
Est. $510,000
3 bd
2.5 ba
2,733 sqft
126 Hilltop Dr,
Chestertown, MD 21620
Taylor Properties
SOLD
JUN 29, 2026
$460,000
3 bd
2 ba
1,664 sqft
118 Grant Ct,
Chestertown, MD 21620
RE/MAX Executive
OFF MARKET
Est. $451,000
3 bd
2 ba
1,846 sqft
209 Myers Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
OFF MARKET
Est. $409,500
3 bd
2 ba
1,344 sqft
109 Grant Ct,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
APR 8, 2026
$512,500
4 bd
3.5 ba
3,000 sqft
206 Flyway Ln,
Chestertown, MD 21620
Integrity Real Estate
OFF MARKET
Est. $460,100
3 bd
2 ba
1,664 sqft
148 Grant Ct,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
APR 17, 2026
$552,000
4 bd
3 ba
2,400 sqft
216 Blakefield Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
OFF MARKET
3 bd
2.5 ba
1,900 sqft
220 Blakefield Dr,
Chestertown, MD 21620
Taylor Properties

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Additional Cost

Assigned Schools

These are the assigned schools for 101 Sheaffer 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.
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
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Air Conditioning

9 rentals with air conditioning in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$2,000/mo
3 bd
2.5 ba
1,848 sqft
21324 Delaware Ave,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620
PET FRIENDLY
$1,100/mo
1 bd
1 ba
409 High St #5,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
NEW - 7 HRS AGO
$2,000/mo
3 bd
1 ba
1,122 sqft
351 Calvert St,
Chestertown, MD 21620
$1,400/mo
2 bd
1.5 ba
1,040 sqft
103 S Lynchburg St,
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

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Chestertown, MD

APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$2,000/mo
3 bd
2.5 ba
1,848 sqft
21324 Delaware Ave,
Chestertown, MD 21620
$1,900/mo
3 bd
1 ba
109 Fairview Dr,
Chestertown, MD 21620
PET FRIENDLY
$1,100/mo
1 bd
1 ba
409 High St #5,
Chestertown, MD 21620
$2,400/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$1,400/mo
2 bd
1.5 ba
1,040 sqft
103 S Lynchburg St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620

Homes for sale near 101 Sheaffer Rd

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0.67 ACRES
$320,000
3 bd
1.5 ba
1,096 sqft
222 Dutchess Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
0.55 ACRES
$299,000
3 bd
1 ba
1,120 sqft
208 Central Dr,
Chestertown, MD 21620
Redfin Corp
0.34 ACRES
$324,900
3 bd
1 ba
1,248 sqft
517 Round Top Rd,
Chestertown, MD 21620
Keller Williams Flagship
0.87 ACRES
$565,000
3 bd
2.5 ba
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.61 ACRES
$1,200,000
4 bd
3 ba
2,292 sqft
202 Royston Shores Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
1.1 ACRES
$524,900
3 bd
2.5 ba
2,268 sqft
101 Coleman Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
1 ACRE
$699,500
5 bd
3.5 ba
3,256 sqft
216 Brix Dr,
Church Hill, MD 21623
CR Realty
0.51 ACRES
$334,900
3 bd
2 ba
1,820 sqft
640 Main St,
Church Hill, MD 21623
RE/MAX Executive
COMING SOON 7/17
0.46 ACRES
$735,000
4 bd
2.5 ba
2,730 sqft
210 N Queen St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 101 Sheaffer Rd

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SOLD
JUN 29, 2026
$460,000
3 bd
2 ba
1,664 sqft
118 Grant Ct,
Chestertown, MD 21620
RE/MAX Executive
SOLD
JUN 26, 2026
$410,000
3 bd
2.5 ba
1,216 sqft
109 S College Ave,
Chestertown, MD 21620
Taylor Properties
SOLD
JUN 17, 2026
$325,000
3 bd
1 ba
1,427 sqft
202 Valley Rd,
Chestertown, MD 21620
TTR Sotheby's International Realty
SOLD
JUN 12, 2026
$249,000
3 bd
1 ba
1,356 sqft
112 Elm St,
Chestertown, MD 21620
Coldwell Banker Waterman Realty
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
$660,000
3 bd
2 ba
1,600 sqft
118 Little Harbor Way #202,
Chestertown, MD 21620
Benson & Mangold, LLC
SOLD
JUN 4, 2026
$290,000
2 bd
2.5 ba
1,864 sqft
115 Acorn Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
JUN 3, 2026
$355,000
3 ba
3,664 sqft
349 High St,
Chestertown, MD 21620
SOLD
JUN 3, 2026
$264,900
111 Metcalf Rd,
Chestertown, MD 21620
See more homes for sale in
Chestertown
Take a look

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101 Sheaffer Rd, Chestertown, MD 21620 is a studio, 2 bathroom, 1,664 sqft single-family home built in 2015. This property is not currently available for sale. 101 Sheaffer Rd was last sold on Nov 12, 2014 for $52,500. The current Trulia Estimate for 101 Sheaffer Rd is $465,400.

101 Sheaffer Rd
Chestertown, MD 21620

$465,400

$465,400

Local Information