116 High St, Chestertown, MD 21620
OFF MARKET

$710,000

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 2,496 sqft

116 High St, Chestertown, MD 21620

Est. Refi. Payment $4,158/mo*
Refinance Your Home
Currently Off Market - Sold Jan 16, 2003 for $449,000

Home Value

Trulia Estimate
$710K
Since last month
Decreased$22K (-3%)
Since last year
Increased$24K (+3.4%)
Since last sale
Increased$265K (+59.1%)
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 +38% in the last 10 years
MonthEstimated value
2026
August 2026$714K
August 2026$710K
July 2026$737K
June 2026$744K
May 2026$717K
April 2026$708K
March 2026$719K
February 2026$708K
January 2026$704K
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
206 S Water St, Chestertown, MD
0.13
Single-Family Home
$545,000
04/30/26
4
2.5
2,008
104 N Water St, Chestertown, MD
0.07
Single-Family Home
$695,000
01/16/26
4
2
2,522
101 S Mill St, Chestertown, MD
0.24
Single-Family Home
$500,000
09/01/26
2
2.5
1,476
110 S Mill St, Chestertown, MD
0.27
Single-Family Home
$695,000
11/05/25
3
3.5
2,492
109 S College Ave, Chestertown, MD
0.47
Single-Family Home
$410,000
06/26/26
3
2.5
1,216
200 N Water St, Chestertown, MD
0.18
Single-Family Home
$950,000
04/30/26
4
3
3,034
210 N Queen St, Chestertown, MD
0.19
Single-Family Home
$730,000
09/01/26
4
2.5
2,730
222 Mount Vernon Ave, Chestertown, MD
0.51
Single-Family Home
$433,000
09/01/26
4
2
1,656
103 Maple Ave, Chestertown, MD
0.16
Single-Family Home
$615,000
08/27/26
4
2.5
4,536
211 Richard Dr, Chestertown, MD
0.42
Single-Family Home
$327,500
03/04/26
3
2
1,598

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
125 High St, Chestertown, MD 21620
0.02
$536,300
2
2
1,146
Off Market
123 High St, Chestertown, MD 21620
0.03
$806,100
3
3
1,855
Off Market
119 High St, Chestertown, MD 21620
0.03
$1,165,000
5
4.5
4,409
Recently Sold
107 N Queen St, Chestertown, MD 21620
0.03
$540,400
4
2
3,050
Off Market
106 S Queen St, Chestertown, MD 21620
0.06
$829,000
3
3.5
2,472
For Sale
108 N Queen St, Chestertown, MD 21620
0.05
$601,100
5
2.5
2,536
Off Market
105 High St, Chestertown, MD 21620
0.07
$1,245,500
5
4.5
3,243
For Sale
117 Court St, Chestertown, MD 21620
0.06
$365,400
1
1
744
Off Market
106 Water 1/2 St N, Chestertown, MD 21620
0.06
$708,900
4
3.5
2,866
Off Market
105 S Water St, Chestertown, MD 21620
0.09
$836,000
4
2.5
2,565
Off Market
109 S Water St, Chestertown, MD 21620
0.09
$650,000
4
2
2,064
Recently Sold
106 Church Aly, Chestertown, MD 21620
0.07
$502,200
2
1.5
1,416
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1735
2,496 sqft
$284/sqft

About this House

Built in 1735 and completely restored in 1977, the Buck-Bacchus House is rich with history and detail. Situated one block off the Chester River this house features hardwood floors, original fixtures and lots of character! The living room boasts a large wood burning fireplace with a Tuscan grill. The cellar is complete with heating & air and a workshop. One of Chestertowns most distinguished homes!
116 High St, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 2,496 sqft single-family home built in 1735. It last sold for $449,000 on Jan 16, 2003. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $710,000, with a rent estimate of $2,179/month.

Home Details for 116 High St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Breakfast Nook, Dining Room, Workshop
Heating & Cooling
Heating: Forced Air, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Stone, BrickGardenPorch
Parking & Garage
Parking: On Street

Property Information

Year Built
Year Built: 1735Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 1463 sqft

Price and Tax history

DateEventPrice
Oct 9, 2018
Source: Agent Provided
ListingRemoved
$574,900
Jul 19, 2018
Source: Agent Provided
PriceChange
$574,900
Price decreased by 1%
Jun 4, 2018
Source: Agent Provided
PriceChange
$579,000
Price decreased by 1%
Jan 28, 2018
Source: Agent Provided
Listed For Sale
$585,000
Oct 29, 2017
Source: Agent Provided
ListingRemoved
$585,000

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 High St

  • What is 116 High St estimated to be worth?
    Trulia's estimated value for 116 High St in Chestertown, MD is $710,000.
  • What is the price history for 116 High St?
    116 High St in Chestertown, MD last sold for $449,000 in January 2003.
  • 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.
  • Does 116 High St have air conditioning?
    Yes, 116 High St in Chestertown, MD has air conditioning.
  • Does 116 High St have laundry facilities?
    Yes, 116 High St in Chestertown, MD has in-unit laundry.

Explore by feature - Air Conditioning

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Off Market Homes Near 116 High St

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