Current Price

$364,916

1 Month Forecast

â–² $390,461

1-Year Forecast *

â–² $413,642

5-Year Forecast *

â–² $483,818

"Is it a good time to buy homes in Chestertown?" "Does investing in real estate in Chestertown (Maryland State, Kent County) worth it?" According to our live Forecast System, buying a house in Chestertown is a good short-term (1-year) investment*. The Chestertown average house/property forecasts are updated every month with the latest median property prices by smart technical real estate market analysis. Q&A about "Chestertown" projections.
At Walletinvestor.com we predict future home values/prices with real estate market analysis for a wide selection of properties, for example houses in Chestertown in Maryland State, Kent County. If you are looking for homes for sale with good flipping profit, Chestertown can be a profitable property investment option. The median price of an average house in Chestertown was 364,916 USD on 2026-02-15. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Chestertown" area is 483,818 USD by 2031-02-15. For a 5-year investment the profit is expected to be around +32.58% meaning that investing 100000 USD today may yield a profit of 32,583 USD by 2031.

Current Median Listing Price: 364,916 USD Median Listing Price Per Square Foot: 203 USD

Chestertown Real Estate Forecast Chart, Short-Term Housing Market Forecast for The Upcoming Months and Year

The short-term real estate market forecast is based on the median home listing prices from the last 5 years.

Chestertown (Maryland State) Forecast Chart, Long-Term Predictions for Next Months and Years: 2026-2032

The long-term housing forecast is based on all the available median listing price recorded up to today.

Chestertown Price Target

Chestertown median home price target in 12 months: $413,642* (upside of 13.4%)

14 Years Historical Data

DateOpening priceClosing priceMinimum priceMaximum price
2025 $386,285 $388,222 $386,285 $388,588
2024 $345,820 $364,916 $345,820 $364,916
2023 $327,106 $344,894 $327,106 $344,894
2022 $316,297 $326,911 $316,297 $333,461
2021 $275,931 $313,448 $275,931 $313,448
2020 $246,304 $271,640 $246,304 $271,640
2019 $233,550 $245,796 $233,550 $245,796
2018 $226,365 $233,176 $226,365 $233,527
2017 $216,238 $225,154 $216,167 $225,154
2016 $217,688 $216,019 $214,983 $218,439
2015 $210,911 $216,739 $210,438 $216,739
2014 $211,076 $210,990 $210,990 $213,579
2013 $206,794 $210,520 $206,714 $211,104
2012 $201,624 $206,534 $201,624 $206,534

Questions & Answers about the Chestertown Housing Market Forecast

How much does an average home cost in Chestertown today?

The value of an average home (the listing price) in Chestertown is $364,916 USD.

What is the average price per square foot in Chestertown?

According to Walletinvestor the median price per square foot in Chestertown is 203 USD.

Will the median listing price of homes in Chestertown grow / rise / go up?

Yes. The Chestertown home prices may rise from 364,916 USD to 413,642 USD in one year.

Is it profitable to invest in Chestertown homes?

Yes. The long-term profit potential is +13.35% in one year.

Will Chestertown house prices fall / drop?

No. See above.

What is the predicted price of a Chestertown home in 2030?

The predicted home sales price of a Chestertown home in 2030 in Chestertown is 464,288 USD.

What is the predicted price of a Chestertown home in 2035?

The predicted home sales price of a Chestertown home in 2035 in Chestertown is 563,325 USD.

Will real estate prices decrease in Chestertown?

According to our analysis, it is unlikely to happen.

Short-Term Outlook Based On The Last 12 Months

Chestertown is the 4772. largest city in the United States, located in Maryland State.

During the last 12 months the real estate prices in Kent, Chestertown decreased, looking at the past 12 months.

According to Walletinvestor's Chestertown real estate market research, home values will increase in the next 12 months.

Median home values decreased by 5.866% to 364,916 USD, between 2025-02-15 and 2026-02-15

The average annual profit of property investment was:

  • 12.753% in 2021
  • 11.563% in 2022
  • 12.603% in 2023
  • 14.703% in 2024
  • 11.733% in 2025
  • 12.843% in 2026

Based on our Chestertown real estate market research and report the predicted sales prices will increase by 250.196% in the next 10 years.

Over the last 12 months, the value of homes in Chestertown fluctuated: increasing 2 times and decreasing 3 times.

Chestertown (Maryland) Housing Market Price Prediction, Forecast for next months and years

Below you will find the price predictions for 2026, 2027, 2028, 2029, 2030, 2031, 2032, 2033.

Date Average price Minimum price Maximum price
Chestertown Housing Market Forecast with Real Estate Prices for 2025
August 2025 390461 351806 429117
September 2025 392713 370721 414705
October 2025 394978 366934 423021
November 2025 397256 363886 430625
December 2025 399547 372777 426316
Chestertown Housing Market Forecast with Real Estate Prices for 2026
January 2026 401851 372114 431588
February 2026 403962 363566 444358
March 2026 404887 364803 444971
April 2026 406567 370789 442345
May 2026 408912 379470 438354
June 2026 411270 380836 441704
July 2026 413642 387996 439288
August 2026 416027 385241 446813
September 2026 418427 387881 448972
October 2026 420840 381281 460399
November 2026 423267 396601 449932
December 2026 424939 383295 466583
Chestertown Housing Market Forecast with Real Estate Prices for 2027
January 2027 424185 394916 453454
February 2027 422792 401652 443931
March 2027 421403 386848 455958
April 2027 420019 395658 444381
May 2027 419020 381308 456732
June 2027 419271 381537 457005
July 2027 420061 379735 460387
August 2027 421016 381440 460591
September 2027 422699 384656 460742
October 2027 425137 399629 450645
November 2027 427589 404071 451106
December 2027 430055 387479 472630
Chestertown Housing Market Forecast with Real Estate Prices for 2028
January 2028 432060 390150 473970
February 2028 433664 407210 460117
March 2028 435191 393848 476534
April 2028 437242 404449 470035
May 2028 438933 396356 481509
June 2028 440111 409303 470919
July 2028 441601 417754 465447
August 2028 444148 414834 473461
September 2028 446709 411866 481552
October 2028 449285 409748 488822
November 2028 451737 412435 491038
December 2028 453250 423336 483165
Chestertown Housing Market Forecast with Real Estate Prices for 2029
January 2029 454532 422260 486804
February 2029 455922 429935 481910
March 2029 457364 416659 498069
April 2029 458518 416334 500701
May 2029 459994 433775 486214
June 2029 462647 425173 500122
July 2029 464288 425752 502824
August 2029 465064 439950 490177
September 2029 465405 422588 508222
October 2029 465383 424430 506337
November 2029 465198 420074 510322
December 2029 464967 425910 504025
Chestertown Housing Market Forecast with Real Estate Prices for 2030
January 2030 467649 427431 507867
February 2030 470346 444477 496215
March 2030 473058 444675 501442
April 2030 475786 441530 510043
May 2030 478530 451733 505328
June 2030 481290 434123 528456
July 2030 483818 439307 528329
August 2030 484926 444192 525660
September 2030 486939 448470 525407
October 2030 489747 456444 523050
November 2030 492571 457106 528036
December 2030 495412 470641 520182
Chestertown Housing Market Forecast with Real Estate Prices for 2031
January 2031 498269 464885 531653
February 2031 501142 471575 530710
March 2031 504032 458670 549395
April 2031 506939 480578 533300
May 2031 508942 466700 551184
June 2031 508039 476540 539537
July 2031 506370 460291 552450
August 2031 504708 462312 547103
September 2031 503050 463309 542791
October 2031 501853 468229 535477
November 2031 502154 474033 530274
December 2031 503100 459330 546870
Chestertown Housing Market Forecast with Real Estate Prices for 2032
January 2032 504243 455836 552650
February 2032 506260 468796 543723
March 2032 509179 462335 556024
April 2032 512116 480877 543355
May 2032 515069 465622 564516
June 2032 517471 466759 568183
July 2032 519391 485112 553671

> Page 2: detailed data / price table <

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* Our real estate forecasts and predictions are made by Machine Learning & AI, and shouldn't been used for financial decisions. We can't guarantee any profit.