Current Price

$358,037

1 Month Forecast

â–² $367,836

1-Year Forecast *

â–² $387,394

5-Year Forecast *

â–² $445,689

"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 2026-03-03. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Chestertown" area is 445,689 USD by 2031-03-03. For a 5-year investment the profit is expected to be around +24.48% meaning that investing 100000 USD today may yield a profit of 24,481 USD by 2031.

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: 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: $387,394* (upside of 8.2%)

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 $194,203 $196,725 $193,920 $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 387,394 USD in one year.

Is it profitable to invest in Chestertown homes?

Yes. The long-term profit potential is +8.20% 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 423,368 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 514,650 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 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 0.475% to 358,037 USD, between 2025-03-03 and 2026-03-03

The average annual profit of property investment was:

  • 8.409% in 2021
  • 7.179% in 2022
  • 9.029% in 2023
  • 6.569% in 2024
  • 7.919% in 2025
  • 8.229% in 2026

Based on our Chestertown real estate market research and report the predicted sales prices will increase by 119.912% in the next 10 years.

Over the last 12 months, the value of homes in Chestertown fluctuated: increasing 4 times .

Chestertown (New York) 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 367836 335834 399838
September 2025 369697 342709 396684
October 2025 371566 349644 393489
November 2025 373446 342450 404442
December 2025 375334 349061 401608
Chestertown Housing Market Forecast with Real Estate Prices for 2026
January 2026 376922 345637 408206
February 2026 377745 356213 399276
March 2026 379655 350042 409268
April 2026 381575 352576 410575
May 2026 383505 352441 414569
June 2026 385445 351911 418979
July 2026 387394 363376 411413
August 2026 389354 364435 414272
September 2026 391323 361974 420672
October 2026 393302 365771 420833
November 2026 395292 358529 432054
December 2026 397276 369467 425086
Chestertown Housing Market Forecast with Real Estate Prices for 2027
January 2027 397082 377228 416936
February 2027 396193 358555 433832
March 2027 395307 362891 427722
April 2027 394422 355374 433470
May 2027 393539 364417 422661
June 2027 392658 357319 427998
July 2027 393384 359553 427215
August 2027 395374 372442 418305
September 2027 397373 363597 431150
October 2027 399383 378615 420151
November 2027 401403 378925 423882
December 2027 403433 378824 428043
Chestertown Housing Market Forecast with Real Estate Prices for 2028
January 2028 405474 379929 431019
February 2028 407525 378183 436866
March 2028 409586 389107 430065
April 2028 410401 372233 448568
May 2028 409482 371810 447155
June 2028 408571 386917 430226
July 2028 409036 373859 444213
August 2028 411105 385617 436594
September 2028 413184 387154 439215
October 2028 415274 382883 447666
November 2028 417375 383150 451599
December 2028 419486 388863 450108
Chestertown Housing Market Forecast with Real Estate Prices for 2029
January 2029 421607 392516 450698
February 2029 423740 396620 450859
March 2029 423909 392116 455703
April 2029 423129 388856 457403
May 2029 425269 404006 446533
June 2029 424318 389524 459112
July 2029 423368 393309 453427
August 2029 423386 392055 454717
September 2029 425328 396831 453825
October 2029 427479 392426 462532
November 2029 429641 406870 452412
December 2029 431814 390360 473268
Chestertown Housing Market Forecast with Real Estate Prices for 2030
January 2030 433998 408392 459604
February 2030 436193 393446 478940
March 2030 438399 410342 466457
April 2030 440617 415061 466172
May 2030 442480 402215 482746
June 2030 443446 403092 483799
July 2030 445689 409142 482235
August 2030 447943 406284 489602
September 2030 450209 412391 488026
October 2030 452486 417192 487780
November 2030 454774 423850 485699
December 2030 457074 427822 486327
Chestertown Housing Market Forecast with Real Estate Prices for 2031
January 2031 459386 430904 487868
February 2031 461710 428467 494953
March 2031 464045 434810 493280
April 2031 466375 436993 495757
May 2031 466147 442373 489920
June 2031 465103 441848 488359
July 2031 464062 430186 497939
August 2031 463024 419963 506085
September 2031 461988 432420 491555
October 2031 460954 430531 491377
November 2031 461806 420243 503368
December 2031 464141 438149 490133
Chestertown Housing Market Forecast with Real Estate Prices for 2032
January 2032 466489 421706 511272
February 2032 468848 423839 513858
March 2032 471219 428810 513629
April 2032 473603 442819 504387
May 2032 475998 446962 505034
June 2032 478406 442047 514765
July 2032 480825 442359 519291

> 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.