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Today: September 22, 2025

Current Price

$374,333

1 Month Forecast

$391,963

1-Year Forecast *

$413,238

5-Year Forecast *

$513,099

"Is it a good time to buy homes in Winchester?" "Does investing in real estate in Winchester (Connecticut State, Litchfield County) worth it?" According to our live Forecast System, buying a house in Winchester is a good short-term (1-year) investment*. The Winchester average house/property forecasts are updated every month with the latest median property prices by smart technical real estate market analysis. Q&A about "Winchester" 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 Winchester in Connecticut State, Litchfield County. If you are looking for homes for sale with good flipping profit, Winchester can be a profitable property investment option. The median price of an average house in Winchester was 374,333 USD on 2025-09-23. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Winchester" area is 513,099 USD by 2030-09-23. For a 5-year investment the profit is expected to be around +37.07% meaning that investing 100000 USD today may yield a profit of 37,070 USD by 2030.

Current Median Listing Price: 374,333 USD Median Listing Price Per Square Foot: 208 USD

Winchester 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.

Winchester (Connecticut 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.

Winchester Price Target

Winchester median home price target in 12 months: $413,238* (upside of 10.4%)

14 Years Historical Data

DateOpening priceClosing priceMinimum priceMaximum price
2025 $387,484 $389,242 $386,204 $389,242
2024 $346,561 $374,333 $346,561 $374,333
2023 $309,723 $342,854 $309,723 $342,854
2022 $276,239 $309,308 $276,239 $310,026
2021 $243,446 $272,421 $243,446 $275,233
2020 $206,792 $236,658 $0 $236,658
2019 $201,933 $206,251 $201,933 $206,251
2018 $198,852 $201,565 $198,852 $202,012
2017 $189,256 $197,925 $189,256 $197,925
2016 $184,904 $189,065 $184,535 $189,065
2015 $183,469 $184,850 $183,469 $186,696
2014 $185,994 $181,835 $181,260 $185,994
2013 $188,602 $188,491 $187,908 $190,978
2012 $198,068 $187,833 $186,980 $198,068

Questions & Answers about the Winchester Housing Market Forecast

How much does an average home cost in Winchester today?

The value of an average home (the listing price) in Winchester is $374,333 USD.

What is the average price per square foot in Winchester?

According to Walletinvestor the median price per square foot in Winchester is 208 USD.

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

Yes. The Winchester home prices may rise from 374,333 USD to 413,238 USD in one year.

Is it profitable to invest in Winchester homes?

Yes. The long-term profit potential is +10.39% in one year.

Will Winchester house prices fall / drop?

No. See above.

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

The predicted home sales price of a Winchester home in 2030 in Winchester is 513,099 USD.

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

The predicted home sales price of a Winchester home in 2035 in Winchester is 676,368 USD.

Will real estate prices decrease in Winchester?

According to our analysis, it is unlikely to happen.

Short-Term Outlook Based On The Last 12 Months

Winchester is the 8839. largest city in the United States, located in Connecticut State.

During the last 12 months the real estate prices in Litchfield, Winchester increased, looking at the past 12 months.

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

Median home values increased by 1.246% to 374,333 USD, between 2024-09-23 and 2025-09-23

The average annual profit of property investment was:

  • 11.993% in 2020
  • 11.563% in 2021
  • 11.983% in 2022
  • 11.463% in 2023
  • 10.343% in 2024
  • 8.473% in 2025

Based on our Winchester real estate market research and report the predicted sales prices will increase by 168.793% in the next 10 years.

Over the last 12 months, the value of homes in Winchester fluctuated: increasing 8 times and decreasing 2 times.

Winchester (Connecticut) 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
Winchester Housing Market Forecast with Real Estate Prices for 2025
August 2025 391963 368445 415480
September 2025 394703 356022 433383
October 2025 397462 358908 436015
November 2025 400240 377026 423454
December 2025 403038 376437 429638
Winchester Housing Market Forecast with Real Estate Prices for 2026
January 2026 405855 366893 444817
February 2026 408692 376406 440979
March 2026 411549 381506 441592
April 2026 414426 385416 443436
May 2026 415758 394554 436962
June 2026 414496 392528 436464
July 2026 413238 384311 442165
August 2026 412594 375461 449728
September 2026 414474 390020 438928
October 2026 417371 385234 449509
November 2026 420289 394231 446347
December 2026 423227 387252 459201
Winchester Housing Market Forecast with Real Estate Prices for 2027
January 2027 426185 389107 463263
February 2027 429164 397406 460922
March 2027 432164 404938 459391
April 2027 435185 406028 464343
May 2027 435222 407803 462641
June 2027 433901 400490 467311
July 2027 433153 410629 455677
August 2027 433517 402304 464730
September 2027 434674 400335 469014
October 2027 435258 400873 469644
November 2027 436689 413108 460270
December 2027 439137 396980 481294
Winchester Housing Market Forecast with Real Estate Prices for 2028
January 2028 442206 415674 468739
February 2028 445298 420806 469789
March 2028 448410 425990 470831
April 2028 451545 407745 495345
May 2028 454701 431057 478346
June 2028 457880 432239 483521
July 2028 461081 422811 499350
August 2028 463504 434304 492705
September 2028 466744 435939 497550
October 2028 470007 434287 505728
November 2028 473293 442529 504057
December 2028 476601 447052 506150
Winchester Housing Market Forecast with Real Estate Prices for 2029
January 2029 479933 442978 516888
February 2029 483288 442208 524367
March 2029 486008 438379 533637
April 2029 487185 441390 532980
May 2029 488946 446408 531485
June 2029 490631 450399 530863
July 2029 493183 445837 540528
August 2029 495581 464855 526307
September 2029 496747 458000 535493
October 2029 500219 461202 539236
November 2029 499471 467505 531437
December 2029 498566 473637 523494
Winchester Housing Market Forecast with Real Estate Prices for 2030
January 2030 498616 455236 541995
February 2030 499386 472919 525854
March 2030 500744 474204 527283
April 2030 502488 454249 550726
May 2030 506000 478676 533324
June 2030 509537 458583 560491
July 2030 513099 480774 545424
August 2030 516686 469667 563704
September 2030 520298 473471 567124
October 2030 523935 489879 557990
November 2030 527597 491193 564001
December 2030 531285 489845 572725
Winchester Housing Market Forecast with Real Estate Prices for 2031
January 2031 534999 500759 569239
February 2031 536718 487877 585560
March 2031 535089 485861 584318
April 2031 533465 505192 561739
May 2031 532634 502274 562994
June 2031 535061 498677 571445
July 2031 538801 493003 584599
August 2031 542567 493736 591399
September 2031 546360 513579 579142
October 2031 550179 517169 583190
November 2031 554025 515244 592807
December 2031 557898 522751 593046
Winchester Housing Market Forecast with Real Estate Prices for 2032
January 2032 561798 523596 600000
February 2032 561845 525887 597803
March 2032 560140 527652 592628
April 2032 559175 504376 613974
May 2032 559644 529983 589305
June 2032 561139 526348 595929
July 2032 561892 519750 604034
August 2032 563739 518076 609402
September 2032 566899 513611 620188
October 2032 570862 530331 611393
November 2032 574852 535762 613942
December 2032 578871 520984 636758
Winchester Housing Market Forecast with Real Estate Prices for 2033
January 2033 582917 533952 631882
February 2033 586992 537098 636886
March 2033 591095 547354 634836
April 2033 595227 544038 646417
May 2033 598356 552283 644430
June 2033 602539 566989 638089
July 2033 606751 572166 641336

> 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.