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Today: September 23, 2025

Current Price

$351,418

1 Month Forecast

$366,934

1-Year Forecast *

$389,903

5-Year Forecast *

$456,172

"Is it a good time to buy homes in Windsor?" "Does investing in real estate in Windsor (Massachusetts State, Berkshire County) worth it?" According to our live Forecast System, buying a house in Windsor is a good short-term (1-year) investment*. The Windsor average house/property forecasts are updated every month with the latest median property prices by smart technical real estate market analysis. Q&A about "Windsor" 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 Windsor in Massachusetts State, Berkshire County. If you are looking for homes for sale with good flipping profit, Windsor can be a profitable property investment option. The median price of an average house in Windsor was 351,418 USD on 2025-09-23. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Windsor" area is 456,172 USD by 2030-09-23. For a 5-year investment the profit is expected to be around +29.81% meaning that investing 100000 USD today may yield a profit of 29,809 USD by 2030.

Current Median Listing Price: 351,418 USD Median Listing Price Per Square Foot: 195 USD

Windsor 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.

Windsor (Massachusetts 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.

Windsor Price Target

Windsor median home price target in 12 months: $389,903* (upside of 11.0%)

14 Years Historical Data

DateOpening priceClosing priceMinimum priceMaximum price
2025 $357,226 $364,601 $357,226 $364,601
2024 $347,612 $351,418 $340,906 $351,418
2023 $320,340 $350,666 $320,340 $350,720
2022 $285,843 $319,480 $285,843 $324,299
2021 $251,860 $282,043 $251,860 $284,886
2020 $223,048 $247,253 $223,048 $247,253
2019 $209,743 $222,192 $207,557 $222,192
2018 $203,486 $210,912 $203,486 $211,981
2017 $191,387 $202,712 $190,312 $202,712
2016 $186,682 $192,368 $186,682 $192,838
2015 $178,669 $185,828 $178,669 $185,828
2014 $175,987 $179,290 $175,166 $180,873
2013 $175,969 $176,504 $175,074 $176,981
2012 $168,232 $176,049 $168,232 $176,049

Questions & Answers about the Windsor Housing Market Forecast

How much does an average home cost in Windsor today?

The value of an average home (the listing price) in Windsor is $351,418 USD.

What is the average price per square foot in Windsor?

According to Walletinvestor the median price per square foot in Windsor is 195 USD.

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

Yes. The Windsor home prices may rise from 351,418 USD to 389,903 USD in one year.

Is it profitable to invest in Windsor homes?

Yes. The long-term profit potential is +10.95% in one year.

Will Windsor house prices fall / drop?

No. See above.

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

The predicted home sales price of a Windsor home in 2030 in Windsor is 456,172 USD.

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

The predicted home sales price of a Windsor home in 2035 in Windsor is 570,742 USD.

Will real estate prices decrease in Windsor?

According to our analysis, it is unlikely to happen.

Short-Term Outlook Based On The Last 12 Months

Windsor is the 19636. largest city in the United States, located in Massachusetts State.

During the last 12 months the real estate prices in Berkshire, Windsor increased, looking at the past 12 months.

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

Median home values increased by 0.797% to 351,418 USD, between 2024-09-23 and 2025-09-23

The average annual profit of property investment was:

  • 11.581% in 2020
  • 9.031% in 2021
  • 11.491% in 2022
  • 9.591% in 2023
  • 10.201% in 2024
  • 11.031% in 2025

Based on our Windsor real estate market research and report the predicted sales prices will increase by 182.700% in the next 10 years.

Over the last 12 months, the value of homes in Windsor fluctuated: increasing 9 times and decreasing 1 times.

Windsor (Massachusetts) 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
Windsor Housing Market Forecast with Real Estate Prices for 2025
August 2025 366934 339414 394454
September 2025 369281 334569 403994
October 2025 371644 340797 402490
November 2025 374021 354572 393470
December 2025 376414 346677 406150
Windsor Housing Market Forecast with Real Estate Prices for 2026
January 2026 378822 354577 403066
February 2026 381245 351508 410982
March 2026 383684 346850 420518
April 2026 386139 356020 416258
May 2026 388609 357909 419309
June 2026 391095 370758 411432
July 2026 389903 359490 420315
August 2026 388633 359486 417781
September 2026 387669 356268 419070
October 2026 387905 359588 416222
November 2026 390386 364231 416542
December 2026 392884 359489 426279
Windsor Housing Market Forecast with Real Estate Prices for 2027
January 2027 395397 361788 429006
February 2027 397927 371664 424190
March 2027 400472 366032 434913
April 2027 403034 371598 434471
May 2027 405613 373164 438062
June 2027 407635 376655 438615
July 2027 406308 368928 443688
August 2027 404985 381901 428069
September 2027 403667 368144 439189
October 2027 403798 371494 436102
November 2027 404884 370064 439704
December 2027 407394 382951 431838
Windsor Housing Market Forecast with Real Estate Prices for 2028
January 2028 410001 380481 439521
February 2028 412624 373012 452235
March 2028 415263 391593 438933
April 2028 417920 378635 457204
May 2028 420593 378955 462232
June 2028 423284 381802 464766
July 2028 425992 398728 453255
August 2028 428717 402994 454440
September 2028 431460 403846 459073
October 2028 431393 399470 463316
November 2028 429989 404189 455788
December 2028 428589 397302 459876
Windsor Housing Market Forecast with Real Estate Prices for 2029
January 2029 427194 392164 462223
February 2029 427953 399280 456626
March 2029 429812 408322 451303
April 2029 432316 403351 461281
May 2029 433869 393953 473785
June 2029 435768 410929 460606
July 2029 436882 406737 467027
August 2029 437875 404158 471591
September 2029 437836 415069 460604
October 2029 440365 409099 471631
November 2029 443183 406842 479524
December 2029 446018 411228 480807
Windsor Housing Market Forecast with Real Estate Prices for 2030
January 2030 448010 419786 476235
February 2030 448220 417741 478698
March 2030 448524 407709 489340
April 2030 449211 422708 475715
May 2030 450391 416162 484621
June 2030 453273 410665 495880
July 2030 456172 428346 483999
August 2030 459091 428791 489391
September 2030 462028 423679 500376
October 2030 464983 433364 496602
November 2030 467958 431457 504459
December 2030 470952 438456 503447
Windsor Housing Market Forecast with Real Estate Prices for 2031
January 2031 473964 441261 506668
February 2031 476996 433113 520880
March 2031 480048 451245 508851
April 2031 483119 443503 522735
May 2031 481646 433963 529329
June 2031 480078 439271 520885
July 2031 478887 443928 513846
August 2031 479178 452823 505533
September 2031 482244 434502 529986
October 2031 485329 451841 518816
November 2031 488434 454243 522624
December 2031 491558 442894 540222
Windsor Housing Market Forecast with Real Estate Prices for 2032
January 2032 494703 466999 522406
February 2032 497868 451068 544667
March 2032 501053 465979 536126
April 2032 503551 476863 530239
May 2032 501911 456739 547083
June 2032 500277 464758 535797
July 2032 498649 452275 545023
August 2032 498811 466388 531234
September 2032 500153 454139 546167
October 2032 503254 453935 552573
November 2032 506473 468994 543952
December 2032 509713 481169 538257
Windsor Housing Market Forecast with Real Estate Prices for 2033
January 2033 512974 471423 554525
February 2033 516256 480118 552394
March 2033 519558 493580 545536
April 2033 522882 472163 573602
May 2033 526227 499916 552538
June 2033 529594 495700 563488
July 2033 532982 500470 565493

> 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.