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Today: September 22, 2025

Current Price

$364,916

1 Month Forecast

$390,567

1-Year Forecast *

$416,982

5-Year Forecast *

$487,772

"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 2025-09-22. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Chestertown" area is 487,772 USD by 2030-09-22. For a 5-year investment the profit is expected to be around +33.67% meaning that investing 100000 USD today may yield a profit of 33,667 USD by 2030.

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: 2025-2031

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: $416,982* (upside of 14.3%)

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 $201,755 $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 416,982 USD in one year.

Is it profitable to invest in Chestertown homes?

Yes. The long-term profit potential is +14.27% 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 487,772 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 612,849 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 increased, 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 increased by 0.893% to 364,916 USD, between 2024-09-22 and 2025-09-22

The average annual profit of property investment was:

  • 15.068% in 2020
  • 14.838% in 2021
  • 13.368% in 2022
  • 13.758% in 2023
  • 14.328% in 2024
  • 13.218% in 2025

Based on our Chestertown real estate market research and report the predicted sales prices will increase by 279.520% in the next 10 years.

Over the last 12 months, the value of homes in Chestertown fluctuated: increasing 7 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 2025, 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 390567 357759 423374
September 2025 392925 373279 412571
October 2025 395298 366046 424550
November 2025 397685 375812 419558
December 2025 400086 376081 424092
Chestertown Housing Market Forecast with Real Estate Prices for 2026
January 2026 402502 379560 425445
February 2026 404933 374563 435303
March 2026 407378 367862 446894
April 2026 409838 377051 442625
May 2026 412313 379328 445298
June 2026 414803 374567 455039
July 2026 416982 393631 440333
August 2026 417937 395786 440087
September 2026 419671 398687 440655
October 2026 422205 384629 459782
November 2026 424755 384403 465106
December 2026 427320 401253 453386
Chestertown Housing Market Forecast with Real Estate Prices for 2027
January 2027 429900 406256 453545
February 2027 432496 389679 475313
March 2027 435108 392902 477313
April 2027 437735 396588 478882
May 2027 439465 399473 479456
June 2027 438685 411486 465883
July 2027 437293 415429 459158
August 2027 435907 404521 467292
September 2027 434524 408453 460596
October 2027 433490 396210 470771
November 2027 433750 408592 458907
December 2027 434567 391980 477155
Chestertown Housing Market Forecast with Real Estate Prices for 2028
January 2028 435555 396790 474319
February 2028 437297 404499 470094
March 2028 439937 410022 469853
April 2028 442594 403646 481542
May 2028 445266 406974 483559
June 2028 447343 419160 475525
July 2028 449003 413981 484025
August 2028 450585 424901 476268
September 2028 452708 426904 478512
October 2028 454459 425373 483544
November 2028 455679 419224 492133
December 2028 457221 429788 484654
Chestertown Housing Market Forecast with Real Estate Prices for 2029
January 2029 459982 427323 492641
February 2029 462760 426664 498855
March 2029 465554 435293 495815
April 2029 468094 433923 502265
May 2029 469663 428802 510524
June 2029 470991 436609 505373
July 2029 472432 441724 503140
August 2029 473926 445490 502361
September 2029 475121 433310 516932
October 2029 476651 440426 512877
November 2029 479529 446442 512617
December 2029 481230 448988 513473
Chestertown Housing Market Forecast with Real Estate Prices for 2030
January 2030 482034 455040 509028
February 2030 482388 440420 524356
March 2030 482365 444259 520472
April 2030 482173 446010 518336
May 2030 481934 437114 526754
June 2030 484844 438299 531389
July 2030 487772 440458 535086
August 2030 490718 452442 528994
September 2030 493681 459123 528239
October 2030 496662 463386 529938
November 2030 499661 467683 531639
December 2030 502678 465480 539877
Chestertown Housing Market Forecast with Real Estate Prices for 2031
January 2031 505714 470820 540608
February 2031 508768 476715 540820
March 2031 511840 475499 548180
April 2031 514931 472191 557670
May 2031 517635 479848 555423
June 2031 518821 478872 558770
July 2031 520974 486590 555358
August 2031 524120 473805 574436
September 2031 527285 493011 561559
October 2031 530469 479014 581925
November 2031 533672 500585 566760
December 2031 536895 495554 578236
Chestertown Housing Market Forecast with Real Estate Prices for 2032
January 2032 540137 505028 575246
February 2032 543399 510251 576546
March 2032 545546 508994 582097
April 2032 544577 516259 572895
May 2032 542850 514079 571621
June 2032 541129 503250 579008
July 2032 539413 495720 583105
August 2032 538129 487545 588714
September 2032 538451 486222 590681
October 2032 539466 486599 592334
November 2032 540692 509873 571511
December 2032 542854 491826 593883
Chestertown Housing Market Forecast with Real Estate Prices for 2033
January 2033 546132 494250 598015
February 2033 549430 500531 598330
March 2033 552748 516819 588677
April 2033 555326 517008 593643
May 2033 557387 505550 609223
June 2033 559350 521314 597386
July 2033 561986 523209 600763

> 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.