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Today: September 22, 2025

Current Price

$358,037

1 Month Forecast

$367,932

1-Year Forecast *

$389,623

5-Year Forecast *

$452,384

"Is it a good time to buy homes in Chestertown?" "Does investing in real estate in Chestertown (New York State, Warren County) worth it?" According to our live Forecast System, buying a house in Chestertown is a acceptable 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 New York State, Warren 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 358,037 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 452,384 USD by 2030-09-22. For a 5-year investment the profit is expected to be around +26.35% meaning that investing 100000 USD today may yield a profit of 26,351 USD by 2030.

Current Median Listing Price: 358,037 USD Median Listing Price Per Square Foot: 199 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 (New York 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: $389,623* (upside of 8.8%)

14 Years Historical Data

DateOpening priceClosing priceMinimum priceMaximum price
2025 $362,270 $365,985 $359,746 $365,985
2024 $340,542 $358,037 $339,785 $358,698
2023 $307,604 $341,326 $306,700 $341,326
2022 $281,969 $309,566 $281,969 $313,435
2021 $248,937 $278,092 $248,937 $278,092
2020 $225,377 $245,363 $225,377 $245,363
2019 $222,463 $224,528 $219,462 $224,528
2018 $219,175 $222,597 $218,978 $223,788
2017 $209,833 $219,027 $209,833 $219,027
2016 $209,252 $208,614 $208,162 $209,581
2015 $204,704 $209,083 $204,704 $209,364
2014 $202,019 $203,524 $201,544 $203,524
2013 $198,079 $201,754 $198,079 $201,879
2012 $193,462 $196,725 $193,462 $196,725

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 $358,037 USD.

What is the average price per square foot in Chestertown?

According to Walletinvestor the median price per square foot in Chestertown is 199 USD.

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

Yes. The Chestertown home prices may rise from 358,037 USD to 389,623 USD in one year.

Is it profitable to invest in Chestertown homes?

Yes. The long-term profit potential is +8.82% 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 452,384 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 559,179 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 12437. largest city in the United States, located in New York State.

During the last 12 months the real estate prices in Warren, 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 0.489% to 358,037 USD, between 2024-09-22 and 2025-09-22

The average annual profit of property investment was:

  • 6.972% in 2020
  • 10.142% in 2021
  • 10.512% in 2022
  • 8.012% in 2023
  • 9.472% in 2024
  • 10.352% in 2025

Based on our Chestertown real estate market research and report the predicted sales prices will increase by 132.896% 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 (New York) 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 367932 337394 398470
September 2025 369890 336600 403180
October 2025 371857 352893 390822
November 2025 373836 350284 397387
December 2025 375825 352899 398750
Chestertown Housing Market Forecast with Real Estate Prices for 2026
January 2026 377824 352510 403138
February 2026 379834 348308 411360
March 2026 381855 360471 403239
April 2026 383887 348185 419588
May 2026 385929 365861 405997
June 2026 387982 362763 413201
July 2026 389623 360791 418455
August 2026 390473 360797 420149
September 2026 392551 362324 422777
October 2026 394639 363068 426210
November 2026 396739 363809 429668
December 2026 398849 371329 426370
Chestertown Housing Market Forecast with Real Estate Prices for 2027
January 2027 400971 378918 423025
February 2027 403105 376500 429710
March 2027 405249 378098 432401
April 2027 407405 371554 443257
May 2027 409573 374759 444386
June 2027 411629 376229 447029
July 2027 411428 385508 437348
August 2027 410543 374005 447081
September 2027 409660 377297 442024
October 2027 408780 372398 445161
November 2027 407901 384650 431151
December 2027 407024 385858 428189
Chestertown Housing Market Forecast with Real Estate Prices for 2028
January 2028 407776 371892 443660
February 2028 409945 371820 448070
March 2028 412126 372562 451690
April 2028 414319 377859 450779
May 2028 416523 389449 443597
June 2028 418739 397802 439676
July 2028 420967 394025 447909
August 2028 423206 387234 459179
September 2028 425458 402058 448858
October 2028 426304 396037 456572
November 2028 425388 389230 461546
December 2028 424473 389242 459704
Chestertown Housing Market Forecast with Real Estate Prices for 2029
January 2029 424956 390110 459802
February 2029 427217 388767 465666
March 2029 429490 404150 454830
April 2029 431775 395937 467612
May 2029 434072 407159 460984
June 2029 436381 401471 471292
July 2029 438703 408432 468973
August 2029 441037 405754 476320
September 2029 441213 412535 469892
October 2029 440401 415299 465504
November 2029 442744 409539 475950
December 2029 441792 398055 485530
Chestertown Housing Market Forecast with Real Estate Prices for 2030
January 2030 440843 398522 483163
February 2030 440861 415292 466431
March 2030 442883 406124 479643
April 2030 445239 420751 469728
May 2030 447608 411352 483865
June 2030 449990 427490 472489
July 2030 452384 425241 479527
August 2030 454790 425229 484352
September 2030 457210 416061 498359
October 2030 459642 434362 484923
November 2030 462088 431590 492586
December 2030 464546 437603 491490
Chestertown Housing Market Forecast with Real Estate Prices for 2031
January 2031 467018 425920 508115
February 2031 469502 429125 509879
March 2031 472000 446512 497488
April 2031 474511 449362 499660
May 2031 476518 439826 513210
June 2031 477558 432668 522449
July 2031 480099 436410 523788
August 2031 482653 443558 521748
September 2031 485221 456108 514334
October 2031 487802 450242 525363
November 2031 490397 442339 538456
December 2031 493006 459482 526531
Chestertown Housing Market Forecast with Real Estate Prices for 2032
January 2032 495629 460935 530323
February 2032 498266 455914 540619
March 2032 500917 467857 533978
April 2032 503432 464165 542700
May 2032 503186 463434 542938
June 2032 502104 473986 530222
July 2032 501024 473468 528581
August 2032 499947 454452 545442
September 2032 498872 457965 539780
October 2032 497800 451504 544095
November 2032 498719 449346 548093
December 2032 501373 457252 545493
Chestertown Housing Market Forecast with Real Estate Prices for 2033
January 2033 504040 468253 539827
February 2033 506722 479865 533578
March 2033 509417 461023 557812
April 2033 512128 482936 541319
May 2033 514852 469030 560674
June 2033 517591 476702 558481
July 2033 520345 468311 572380

> 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.