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Maryland

Realtors in Chestertown, MD

1 local real estate professional in Chestertown, plus 13 more from nearby towns

Typical home $391,257+1.9% in 1 year Pop. 5,093 9:46 AM in Chestertown

Maryland photo: Fell's Point Aerial by Matthew Binebrink, CC BY-SA 4.0 via Wikimedia Commons

One real estate professional is listed in Chestertown, Maryland. Chestertown has about 5,093 residents in Kent County and is part of the Baltimore-Columbia-Towson, MD metro area. The typical home is valued at about $391,257 (Zillow, August 2026); over twelve months that value rose 1.9%. The closest towns with listed professionals are Chester (20 mi, 2), Nottingham (23 mi, 1), and Bel Air (27 mi, 3).

Realtors based in Chestertown

Campbell LLC Realtors logo

Campbell LLC Realtors

Real Estate Brokerage

Chestertown, MD

More realtors near Chestertown

Crystal Smith profile photo

Crystal Smith

Real Estate Agent · REMAX Executive

Chester, MD 20 mi

Ginny Dauses profile photo

Ginny Dauses

Realtor · Coldwell Banker Waterman Realty

Chester, MD 20 mi

Juston Ibanez Panambo profile photo

Juston Ibanez Panambo

Realtor

Nottingham, MD 23 mi

Black Dog Realty logo

Black Dog Realty

Real Estate Brokerage

Bel Air, MD 27 mi

Nicole Gentry profile photo

Nicole Gentry

Realtor

Bel Air, MD 27 mi

Weichert Realtors logo

Weichert Realtors

Real Estate Brokerage

Bel Air, MD 27 mi

Alice Is Your Realtor profile photo

Alice Is Your Realtor

Realtor

Port Deposit, MD 28 mi

Alex Archer profile photo

Alex Archer

Realtor

Annapolis, MD 28 mi

  • Investment Property
Annapolis Fine Homes Office logo

Annapolis Fine Homes Office

Real Estate Brokerage

Annapolis, MD 28 mi

Brad Kappel profile photo

Brad Kappel

Real Estate Agent

Annapolis, MD 28 mi

  • Luxury Homes
  • Waterfront & Lake Homes
Greater Annapolis Realty logo

Greater Annapolis Realty

Real Estate Brokerage

Annapolis, MD 28 mi

  • Waterfront & Lake Homes
Kevin Cooke profile photo

Kevin Cooke

Real Estate Agent

Annapolis, MD 28 mi

Rosie Rothamer profile photo

Rosie Rothamer

Real Estate Agent

Annapolis, MD 28 mi

Chestertown housing market

Typical home$391K
1-year+1.9%
5-year+21.7%
10-year+74.1%
$200K$270K$340K$410KAug 2016 · $224,693Feb 2017 · $225,999Aug 2017 · $230,561Feb 2018 · $237,869Aug 2018 · $243,320Feb 2019 · $245,614Aug 2019 · $254,616Feb 2020 · $258,408Aug 2020 · $265,191Feb 2021 · $292,910Aug 2021 · $321,576Feb 2022 · $333,241Aug 2022 · $347,903Feb 2023 · $342,524Aug 2023 · $354,827Feb 2024 · $362,663Aug 2024 · $376,869Feb 2025 · $384,096Aug 2025 · $384,025Feb 2026 · $389,065Aug 2026 · $391,257Aug 2016Aug 2021Aug 2026

As of August 2026, Zillow’s home value index puts a typical Chestertown home at roughly $391,257. Over twelve months the typical value rose 1.9%. The five-year change stands at +21.7%. Chestertown sits 9% below the Maryland typical value of $428,308.

Monthly payment calculator

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Values: Zillow Home Value Index, August 2026.

Chestertown at a glance

StateMaryland (MD)
CountyKent County
Metro areaBaltimore-Columbia-Towson, MD
Population (approx.)5,093
Elevation23 ft
Time zoneEastern Time
Realtors listed1
Typical home value$391,257
1-year change+1.9%
License regulatorMaryland Real Estate Commission
Local timeWednesday, October 14 · 9:46 AM

Realtors in Chestertown — common questions

How many realtors are listed in Chestertown, MD?
One real estate professional is listed in Chestertown today.
What is the typical home value in Chestertown?
About $391,257 according to the Zillow Home Value Index (August 2026), a change of +1.9% over one year and +21.7% over five years.
What would the monthly payment be on a typical Chestertown home?
With 10% down and a 6.5% 30-year fixed rate, principal and interest on a $391,257 home comes to roughly $2,226 a month, before taxes, insurance and any HOA dues.
Which nearby towns have realtors listed?
Chester (20 mi, 2 listings), Nottingham (23 mi, 1 listing), Bel Air (27 mi, 3 listings), and Port Deposit (28 mi, 1 listing).