116 Longfellow Dr, Chestertown, MD 21620
OFF MARKET

116 Longfellow Dr
Chestertown, MD 21620

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

$245,900

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $1,496/mo*
Refinance Your Home

$245,900

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $1,496/mo*
Refinance Your Home
Studio
1 Bath
1,000 sqft
(on 0.34 acres)

Home Value

Trulia Estimate
$246K
Since last month
Increased$9K (+3.6%)
Since last year
Decreased$10K (-3.9%)
Since last sale
Increased$176K (+251.8%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$246K
July 2026$237K
June 2026$248K
May 2026$264K
April 2026$262K
March 2026$262K
February 2026$255K
January 2026$251K
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
517 Round Top Rd, Chestertown, MD
0.14
Single-Family Home
$289,000
08/21/26
3
1
1,248
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
154 Longfellow Dr, Chestertown, MD
0.18
Single-Family Home
$300,000
05/27/26
3
1
1,408
110 Tuxedo Rd, Chestertown, MD
0.15
Single-Family Home
$210,000
05/07/26
3
1,664
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
107 Longfellow Dr, Chestertown, MD
0.09
Single-Family Home
$278,500
05/14/26
3
1
-
104 Iris Rd, Chestertown, MD
0.32
Single-Family Home
$379,000
01/30/26
3
2
1,700
105 Parma Rd, Chestertown, MD
0.46
Single-Family Home
$322,000
11/14/25
3
2
1,232

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
107 Longfellow Dr, Chestertown, MD 21620
0.09
$278,500
3
1
-
Recently Sold
102 Concord Rd, Chestertown, MD 21620
0.07
$361,400
3
2
1,232
Off Market
513 Round Top Rd, Chestertown, MD 21620
0.12
$220,000
4
1
1,248
Recently Sold
517 Round Top Rd, Chestertown, MD 21620
0.14
$289,000
3
1
1,248
Recently Sold
228 Concord Rd, Chestertown, MD 21620
0.14
$351,200
4
2
1,500
Off Market
150 Longfellow Dr, Chestertown, MD 21620
0.16
$296,400
3
1
1,056
Off Market
149 Longfellow Dr, Chestertown, MD 21620
0.17
$405,600
3
2
1,811
Off Market
118 Tuxedo Rd, Chestertown, MD 21620
0.17
$245,700
3
1
1,056
Off Market
154 Longfellow Dr, Chestertown, MD 21620
0.18
$300,000
3
1
1,408
Recently Sold
218 Concord Rd, Chestertown, MD 21620
0.20
$359,000
3
2
1,200
Off Market
533 Round Top Rd, Chestertown, MD 21620
0.21
$225,000
4
1.5
1,800
For Sale
213 Central Dr, Chestertown, MD 21620
0.24
$317,000
3
2
1,232
Recently Sold

Local Information

  • Map ViewExplore the area around 116 Longfellow Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1977
Lot Size
0.34 acres
Living Area
1,000 sqft
Price/Sqft
$246

About this House

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.
116 Longfellow Dr, Chestertown, MD 21620 is a studio, 1 bathroom, 1,000 sqft single-family home built in 1977. It last sold for $69,900 on Mar 13, 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $245,900, with a rent estimate of $1,800/month.

Home Details for 116 Longfellow Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningHeating Fuel: Electric
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 and Tax history

DateEventPrice
Mar 13, 1998
Source: N/A
Sold
$69,900

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
5MoM

Around this home

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
    "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
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "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.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "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
    "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
    "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.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "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
    "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

Frequently asked questions about 116 Longfellow Dr

  • What is 116 Longfellow Dr estimated to be worth?
    Trulia's estimated value for 116 Longfellow Dr in Chestertown, MD is $245,900.
  • What is the price history for 116 Longfellow Dr?
    116 Longfellow Dr in Chestertown, MD last sold for $69,900 in March 1998.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • How big is the lot at 116 Longfellow Dr?
    The lot at 116 Longfellow Dr in Chestertown, MD is about 0.34 acres (15,000 sq ft).

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