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

116 Longfellow Dr
Chestertown, MD 21620

Studio
1 Bath
1,000 sqft (on 0.34 acres)

$263,200

Trulia Estimate

as of May 27, 2026

Est. Refi. Payment $1,580/mo*

Refinance Your Home

$263,200

Trulia Estimate

as of May 27, 2026

Est. Refi. Payment $1,580/mo*

Refinance Your Home

Studio

1 Bath

1,000 sqft

(on 0.34 acres)

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 116 Longfellow Dr, Chestertown, MD. 116 Longfellow Dr is in Chestertown, MD and in ZIP code 21620. This property has 1 bathroom and approximately 1,000 sqft of floor space. This property has a lot size of 0.34 acres and was built in 1977.

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 116 Longfellow Dr

Interior Features
Heating & Cooling Heating: Other, ElectricAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other

Property Information
Year Built Year Built: 1977
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.34 acres

Price History for 116 Longfellow Dr

Date	Price	Event	Source
03/13/1998	$69,900	Sold	N/A
Recording Date 03/13/1998 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$1,830
Assessment	$187,900

Home facts updated by county records

Comparable Sales for 116 Longfellow Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
118 Tuxedo Rd, Chestertown, MD	0.17	Single-Family Home	$235,000	08/07/25	3	1	1,056
211 Longfellow Dr, Chestertown, MD	0.26	Single-Family Home	$180,000	08/28/25	2	1	864
513 Round Top Rd, Chestertown, MD	0.12	Single-Family Home	$220,000	04/14/26	4	1	1,248
212 Central Dr, Chestertown, MD	0.28	Single-Family Home	$309,500	07/31/25	3	1	1,104
213 Central Dr, Chestertown, MD	0.24	Single-Family Home	$317,000	03/09/26	3	2	1,232
106 Wilton Rd, Chestertown, MD	0.65	Single-Family Home	$315,000	08/29/25	3	1	1,056
114 Darden Rd, Chestertown, MD	0.69	Single-Family Home	$270,000	08/25/25	3	1	1,056
107 Longfellow Dr, Chestertown, MD	0.09	Single-Family Home	$278,500	05/14/26	3	1	-
109 Edmore Rd, Chestertown, MD	0.40	Single-Family Home	$344,900	06/25/25	3	2	1,344
104 Iris Rd, Chestertown, MD	0.32	Single-Family Home	$379,000	01/30/26	3	2	1,700

Nearby homes

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

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FOR SALE
0.55 ACRES
$299,000
3 bd
1 ba
1,120 sqft
208 Central Dr,
Chestertown, MD 21620
Redfin Corp
SOLD
APR 13, 2026
$749,500
3 bd
2.5 ba
3,136 sqft
6 Byford Ct,
Chestertown, MD 21620
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
FOR SALE
0.34 ACRES
$340,000
3 bd
1.5 ba
2,055 sqft
202 Waldo Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
APR 17, 2026
$495,000
4 bd
2.5 ba
2,220 sqft
515 N Kent St,
Chestertown, MD 21620
Cross Street Realtors LLC
FOR SALE
5.81 ACRES
$200,000
Round Top Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
APR 14, 2026
$220,000
4 bd
1 ba
1,248 sqft
513 Round Top Rd,
Chestertown, MD 21620
Cummings & Co. Realtors
FOR SALE
0.76 ACRES
$344,900
3 bd
2 ba
1,392 sqft
109 Wilton Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
APR 17, 2026
$480,000
3 bd
2 ba
1,734 sqft
104 Garland Ave,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
APR 8, 2026
$512,500
4 bd
3.5 ba
3,000 sqft
206 Flyway Ln,
Chestertown, MD 21620
Integrity Real Estate
FOR SALE
0.79 ACRES
$1,150,000
5 bd
3 ba
2,956 sqft
231 Richard Dr,
Chestertown, MD 21620
TTR Sotheby's International Realty
FOR SALE
$685,000
3 bd
3 ba
3,000 sqft
117 N Water St #1A,
Chestertown, MD 21620
TTR Sotheby's International Realty

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Additional Cost

Assigned Schools

These are the assigned schools for 116 Longfellow Dr.

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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Contact for price
1-2 bd
1-2 ba
200 Clipper Way #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
103 Hawkins Dr #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
150 Flatland Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
160 Flatland Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
501 E Campus Ave #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
101 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
200 Morgnec Rd #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
415 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
$1,700/mo
2 bd
1 ba
27318 Morgnec Rd #B,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
104 Maple Ave #6,
Chestertown, MD 21620
PET FRIENDLY
$1,520/mo
2 bd
1 ba
104 Maple Ave #3,
Chestertown, MD 21620
See more homes for rent in
Chestertown
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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
$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
7 rentals with air conditioning in Chestertown, MD

Homes for sale near 116 Longfellow Dr

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0.55 ACRES
$299,000
3 bd
1 ba
1,120 sqft
208 Central Dr,
Chestertown, MD 21620
Redfin Corp
0.76 ACRES
$344,900
3 bd
2 ba
1,392 sqft
109 Wilton Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.34 ACRES
$340,000
3 bd
1.5 ba
2,055 sqft
202 Waldo Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.79 ACRES
$1,150,000
5 bd
3 ba
2,956 sqft
231 Richard Dr,
Chestertown, MD 21620
TTR Sotheby's International Realty
$115,000
3 bd
1 ba
910 sqft
108 Pine St,
Chestertown, MD 21620
Real Broker, LLC
0.41 ACRES
$322,500
4 bd
2 ba
1,325 sqft
304 Hadaway Dr,
Chestertown, MD 21620
Redfin Corporation
$525,000
3 bd
1.5 ba
1,785 sqft
110 S Queen St,
Chestertown, MD 21620
Cross Street Realtors LLC
$225,000
3 bd
1 ba
1,200 sqft
139 Prospect St,
Chestertown, MD 21620
Redfin Corp
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 116 Longfellow Dr

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SOLD
MAY 26, 2026
$355,000
6 bd
3,664 sqft
349 & 351 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
MAY 26, 2026
$264,900
3 bd
1.5 ba
1,280 sqft
109 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
SOLD
MAY 22, 2026
$296,500
2 bd
2.5 ba
1,867 sqft
108 Oak Leaf Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
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
$259,900
3 bd
1.5 ba
1,200 sqft
107 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
SOLD
MAY 15, 2026
$150,000
3 bd
1 ba
1,140 sqft
107 Conley Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
MAY 14, 2026
$278,500
3 bd
1 ba
107 Longfellow Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
MAY 13, 2026
$155,000
2 bd
1 ba
910 sqft
132 Prospect St,
Chestertown, MD 21620
ANR Realty, LLC
SOLD
MAY 7, 2026
$264,900
119 Metcalf Rd,
Chestertown, MD 21620
SOLD
MAY 5, 2026
$347,000
5 bd
1 ba
1,645 sqft
111 Pine St,
Chestertown, MD 21620
See more homes for sale in
Chestertown
Take a look

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Homes for rent near 116 Longfellow Dr

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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
$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
See more homes for rent in
Chestertown
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116 Longfellow Dr, Chestertown, MD 21620 is a studio, 1 bathroom, 1,000 sqft single-family home built in 1977. This property is not currently available for sale. 116 Longfellow Dr was last sold on Mar 13, 1998 for $69,900. The current Trulia Estimate for 116 Longfellow Dr is $263,200.

116 Longfellow Dr
Chestertown, MD 21620

$263,200

$263,200

Local Information