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Sell with EXIT Realty · Chestertown, MD

Sell your home in Chestertown, MD

See how the Chestertown market is moving and connect with an experienced EXIT Realty agent who can price, market, and negotiate your sale — a trusted name in real estate since 1996.

Connect with a local agentSee homes for sale

Your seller's market report

What your Chestertown sale looks like right now

A read on the Chestertown, MD market built from live MLS listing data — the numbers an agent would walk you through first.

EXIT Prosperity Realty, serving Chestertown

Across 74 homes for sale in Chestertown, the median asking price is $380,000 and the average sale takes 89 days.

That's the market, not your home — what yours is worth depends on the street, the condition, and the timing. An EXIT agent can run those numbers with you.

Get a real price opinion

Median list price of active MLS listings in Chestertown, MD — not an estimate of your home's value.

Local market data

Inside the Chestertown market

Real numbers to help you price and time your sale with confidence.

Market pace

  1. Fast
  2. Moderate
  3. Unhurried

Homes are taking their time to sell — pricing sharp from day one matters more than ever.

Based on the average days on market for active listings in Chestertown, MD.

$380,000
Median list price
74
Homes for sale
89
Avg. days on market
$256/sq ft
Median price / sq ft
1,964 Sq Ft
Median home size

What's on the market in Chestertown

  • 51%Residential74 active
  • 33%Land48 active
  • 8%Commercial11 active
  • 3%Commercial Lease5 active
  • 3%For Lease5 active
  • <1%Business1 active
  • <1%Farm1 active

Where the asking prices sit

  • Under $200K3% · 2
  • $200K-$400K50% · 37
  • $400K-$600K14% · 10
  • $600K-$800K12% · 9
  • $800K-$1M9% · 7
  • Over $1M12% · 9

Median Price Trend

Jul 2026: $300,000 +13.2%Sep 2026: $339,500

Market figures are computed from active MLS listing data for Chestertown, MD and refresh as listings change. They describe the market, not any individual property.

Your competition

Homes like yours on the market in Chestertown

What buyers comparing your home are looking at right now.

Is this what you’re selling?

Set your home’s type and bedrooms, and everything below becomes YOUR competition — the homes a buyer would weigh against yours.

Showing single-family homes in Chestertown.

  • Active
    60 photos

    $1,495,000

    9 bd, 6.5 ba, 4,776 Sq Ft

    8796 Maryland ParkwayChestertown, MD 21620#MDKE2006596

    Single Family Residence
  • Active
    54 photos

    $1,375,000

    4 bd, 5 ba, 4,257 Sq Ft

    22470 Fairgale Farm LaneChestertown, MD 21620#MDKE2006502

    Single Family Residence
  • Active
    10 photos

    $315,000

    3 bd, 2 ba, 1,232 Sq Ft

    8706 Elm RoadChestertown, MD 21620#MDKE2006390

    Single Family Residence
  • Active
    34 photos

    $325,000

    3 bd, 1 ba, 1,000 Sq Ft

    896 Washington AvenueChestertown, MD 21620#MDKE2006750

    Single Family Residence
  • Active
    13 photos

    $750,000

    1 ba, 2,045 Sq Ft

    201 N Lynchburg StreetChestertown, MD 21620#MDKE2006142

    Single Family Residence
  • Active
    27 photos

    $385,000

    4 bd, 3 ba, 2,630 Sq Ft

    23043 Bay Shore SpurChestertown, MD 21620#MDKE2005584

    Single Family Residence

View all homes for sale in Chestertown, MD

Recent results

Recently sold in Chestertown

Homes near you that found their buyer.

  • Sold

    $525,000

    4 bd · 2.5 ba · 4,086 Sq Ft

    325 DEVON DRIVE, CHESTERTOWN, MD

  • Sold

    $320,000

    4 bd · 1.5 ba · 2,418 Sq Ft

    108 E CAMPUS AVENUE, CHESTERTOWN, MD

  • Sold

    $75,000

    MCGINNES ROAD, CHESTERTOWN, MD

  • Sold

    $578,000

    MCGINNES ROAD, CHESTERTOWN, MD

  • Sold

    $341,000

    4 bd · 3 ba · 3,806 Sq Ft

    8656 MARYLAND PARKWAY, CHESTERTOWN, MD

  • Sold

    $375,000

    3 bd · 2.5 ba · 1,944 Sq Ft

    109 LYONS LANE, CHESTERTOWN, MD

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which EXIT Realty participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright ©2026 Bright MLS. All rights reserved.

Thinking about listing?

Skip the guesswork — find out what your home would actually command in today's Chestertown market.

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EXIT Prosperity Realty, serving Chestertown

About Chestertown

Nearby schools for Chestertown, MD (approximate).

Nearby Schools

Elementary 9

  • HH Garnet Elementary School Pta

    Chestertown, MD · 0.2 mi away

  • Church Hill Elementary School

    Church Hill, MD · 6.4 mi away

  • Eastern Shore Junior Academy

    Sudlersville, MD · 9.2 mi away

  • Rock Hall Elementary School

    Rock Hall, MD · 10.4 mi away

  • Sudlersville Elementary School

    Sudlersville, MD · 11.3 mi away

  • Centreville Elementary School

    Centreville, MD · 11.4 mi away

  • Kennard Elementary School

    Centreville, MD · 12.1 mi away

  • Millington Elementary School

    Millington, MD · 12.8 mi away

  • Galena Elementary School

    Galena, MD · 13.3 mi away

Secondary 4

  • Kent School

    Chestertown, MD · 3.4 mi away

  • Kent County High School

    Worton, MD · 5.2 mi away

  • Wye River Upper School

    Centreville, MD · 11.8 mi away

  • Queen Anne's County High School

    Centreville, MD · 12.1 mi away

Post-secondary 1

  • Washington College Campus Garden

    Chestertown, MD · 0.3 mi away

Other schools 6

  • Chester River Adventist School

    Chestertown, MD · 0.1 mi away

  • Maryland School of Sailing & Seamanship

    Rock Hall, MD · 8.9 mi away

  • The Gunston School

    Centreville, MD · 9.9 mi away

  • Kent County Public Schools

    Rock Hall, MD · 10.4 mi away

  • Judy Center

    Sudlersville, MD · 11.3 mi away

  • New Covenant Christian Academy

    Queenstown, MD · 16.0 mi away

Simple, guided, proven

How selling in Chestertown works

  1. Step 1: Connect with a local agent

    Tell us about your home and we'll match you with an EXIT Realty agent who knows the Chestertown market.

  2. Step 2: Get a personalized valuation

    Your agent prepares a comparative market analysis and recommends a pricing strategy built for today's market.

  3. Step 3: Market with impact

    Professional photography, online syndication, and targeted promotion reach the right buyers, faster.

  4. Step 4: Sell and close with confidence

    Your agent negotiates the strongest offer and guides you all the way through to closing day.

The number that matters

What is your home actually worth?

These figures describe the Chestertown market — not your home. A local EXIT Realty agent will prepare a precise valuation from comparable sales, your home's condition, and what buyers are paying right now. No obligation.

Tell us a little about your home. A local agent from EXIT Prosperity Realty will reach out with a personalized market analysis — no obligation.

Consent & Privacy

By submitting this form, you consent to being contacted by the agent regarding this specific inquiry using the contact information you provided.

In your corner, locally

Your local EXIT Realty offices

These EXIT Realty offices serve Chestertown. When you're ready, reach out and let an agent take it from here.

The EXIT advantage

Why sell with EXIT Realty?

Agents invested in your success

EXIT Realty's residual income model keeps our agents focused on results — your sale, not just the next deal.

Local expertise, global network

A local expert markets your home, backed by thousands of EXIT associates across North America.

Comprehensive marketing

Professional photography, online syndication, and targeted promotion put your home in front of ready buyers.