2025 Compare Cities Housing:
Chestertown, MD vs Annapolis, MD

Change Cities
Highlights
- The median age of a home in Chestertown is 26.3% younger than the median age of a home in Annapolis.
 Chestertown, MDAnnapolis, MDUnited States
 Median Home Age38  Unlock42
 Median Home Cost  Unlock$552,900$338,100
 Home Appr. Last 12 months14.5%  Unlock16.6%
 Home Appr. Last 5 yrs.  Unlock33.8%57.0%
 Home Appr. Last 10 yrs.56.7%  Unlock101.1%
 Property Tax Rate  Unlock$10.9$11.0
 Homes Owned42.3%  Unlock57.4%
 Housing Vacant  Unlock8.3%11.2%
 Homes Rented50.7%  Unlock31.4%
 space
 Avg Rent For Home Or Apartment
 Chestertown, MDAnnapolis, MDUnited States
 Average Rent  Unlock$2,660$1,840
 Studio Apartment$960  Unlock$1,080
 1 Bedroom Home or Apartment  Unlock$1,680$1,180
 2 Bedroom Home or Apartment$1,200  Unlock$1,430
 3 Bedroom Home or Apartment  Unlock$2,700$1,860
 4 Bedroom Home or Apartment$2,010  Unlock$2,160
 space1
 Vacant Housing
 Chestertown, MDAnnapolis, MDUnited States
 Vacant For Rent  Unlock2.2%1.9%
 Vacant Rented0.0%  Unlock0.4%
 Vacant For Sale  Unlock0.9%0.7%
 Vacant Sold0.0%  Unlock0.4%
 Vacant Vacation  Unlock1.0%3.6%
 Vacant Other5.0%  Unlock4.1%
 space2
 Owner-Occupied Housing Value
 Chestertown, MDAnnapolis, MDUnited States
 Less Than $20,000  Unlock1.1%2.6%
 $20,000 to $39,9990.0%  Unlock2.4%
 $40,000 to $59,999  Unlock0.1%2.8%
 $60,000 to $79,9990.0%  Unlock3.9%
 $80,000 to $99,999  Unlock0.0%4.5%
 $100,000 to $149,9996.6%  Unlock11.3%
 $150,000 to $199,999  Unlock6.5%13.0%
 $200,000 to $299,99943.3%  Unlock20.1%
 $300,000 to $399,999  Unlock18.0%13.6%
 $400,000 to $499,9995.6%  Unlock8.3%
 $500,000 to $749,999  Unlock21.2%9.7%
 $750,000 to $999,9990.6%  Unlock3.9%
 $1,000,000 to $1,499,999  Unlock5.3%2.2%
 $1,500,000 to $1,999,9990.0%  Unlock0.8%
 $2,000,000 and over  Unlock1.7%1.1%
 space3
 Housing Units By Year Built
 Chestertown, MDAnnapolis, MDUnited States
 2015 and Newer0.0%  Unlock0.2%
 2010 to 2014  Unlock10.3%13.6%
 2000 to 200914.2%  Unlock13.6%
 1990 to 1999  Unlock10.6%13.6%
 1980 to 198920.6%  Unlock13.2%
 1970 to 1979  Unlock18.5%14.8%
 1960 to 196919.7%  Unlock13.6%
 1950 to 1959  Unlock10.1%10.0%
 1940 to 19493.5%  Unlock4.7%
 1939 or Earlier  Unlock15.5%12.2%
Reviews for Chestertown    3 Reviews

I have lived in Queen Anne's county most of my life, which is on the other side of the river from Chestertown. When I was younger, I remember ice cream shoppes, music  More

   |    Reply

Over 18 years ago

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More

   |    Reply

Over 18 years ago

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More

   |    Reply

Start Your Review of Chestertown

Reviews for Annapolis    31 Reviews

Annapolis has extremely charming areas (mostly old Annapolis neighborhood's)-- Those very old area near the water have Amazing charm. You can start with downtown West  More

   |    Reply

Well, I really would give living in Annapolis 3.5 stars. I moved here by myself several years ago. One of the highs of this place is that there are a lot of terrific  More

   |    Reply

When we were trying to decide where in the USA to relocate to, Annapolis had enough interest that it made our list. Ultimately, we found a different city that offered  More

   |    Reply

Start Your Review of Annapolis


Premium Subscription
Includes Cost of Living compares for child care, utilities, transportation, health, taxes, housing for home owners vs renters, weather, insurance premiums and so much more.


The premier source for comprehensive city data for over 30 years.

© Best Places. All rights reserved.