Current Price

$1,465,244

1 Month Forecast

â–² $1,567,057

1-Year Forecast *

â–² $1,657,054

5-Year Forecast *

â–² $1,898,441

"Is it a good time to buy homes in Winchester?" "Does investing in real estate in Winchester (Massachusetts State, Middlesex 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 Massachusetts State, Middlesex 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 1,465,244 USD on 2026-03-03. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Winchester" area is 1,898,441 USD by 2031-03-03. For a 5-year investment the profit is expected to be around +29.56% meaning that investing 100000 USD today may yield a profit of 29,565 USD by 2031.

Current Median Listing Price: 1,465,244 USD Median Listing Price Per Square Foot: 814 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 (Massachusetts 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.

Winchester Price Target

Winchester median home price target in 12 months: $1,657,054* (upside of 13.1%)

14 Years Historical Data

DateOpening priceClosing priceMinimum priceMaximum price
2025 $1,548,707 $1,557,074 $1,548,707 $1,564,555
2024 $1,407,902 $1,465,244 $1,407,902 $1,465,244
2023 $1,285,190 $1,406,090 $1,283,698 $1,406,090
2022 $1,213,287 $1,286,541 $1,213,287 $1,331,291
2021 $1,101,213 $1,199,785 $1,101,213 $1,199,785
2020 $1,023,928 $1,089,098 $1,023,928 $1,089,098
2019 $1,023,922 $1,021,999 $1,018,780 $1,025,256
2018 $983,845 $1,025,197 $983,845 $1,026,219
2017 $946,041 $979,430 $944,671 $979,430
2016 $889,635 $944,019 $889,635 $944,019
2015 $837,469 $885,516 $837,469 $885,516
2014 $776,322 $831,478 $776,322 $831,478
2013 $712,654 $770,991 $712,654 $770,991
2012 $680,748 $707,963 $679,870 $707,963

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 $1,465,244 USD.

What is the average price per square foot in Winchester?

According to Walletinvestor the median price per square foot in Winchester is 814 USD.

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

Yes. The Winchester home prices may rise from 1,465,244 USD to 1,657,054 USD in one year.

Is it profitable to invest in Winchester homes?

Yes. The long-term profit potential is +13.09% 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 1,830,884 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 2,201,914 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 2750. largest city in the United States, located in Massachusetts State.

During the last 12 months the real estate prices in Middlesex, Winchester decreased, 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 decreased by 6.040% to 1,465,244 USD, between 2025-03-03 and 2026-03-03

The average annual profit of property investment was:

  • 13.461% in 2021
  • 11.961% in 2022
  • 12.391% in 2023
  • 14.861% in 2024
  • 14.191% in 2025
  • 13.191% in 2026

Based on our Winchester real estate market research and report the predicted sales prices will increase by 242.189% in the next 10 years.

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

Winchester (Massachusetts) 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
Winchester Housing Market Forecast with Real Estate Prices for 2025
August 2025 1567057 1479302 1654812
September 2025 1577105 1461976 1692233
October 2025 1587216 1449129 1725304
November 2025 1597393 1493562 1701224
December 2025 1606641 1518276 1695006
Winchester Housing Market Forecast with Real Estate Prices for 2026
January 2026 1610509 1500995 1720024
February 2026 1612731 1520805 1704656
March 2026 1616973 1511870 1722076
April 2026 1625585 1515045 1736125
May 2026 1636008 1514943 1757072
June 2026 1646497 1546061 1746934
July 2026 1657054 1506262 1807846
August 2026 1667678 1514252 1821105
September 2026 1678371 1574312 1782430
October 2026 1689132 1528664 1849600
November 2026 1699962 1531666 1868258
December 2026 1693787 1600629 1786946
Winchester Housing Market Forecast with Real Estate Prices for 2027
January 2027 1687224 1521876 1852572
February 2027 1680686 1588248 1773123
March 2027 1674173 1568700 1779646
April 2027 1673578 1536345 1810811
May 2027 1671821 1536404 1807239
June 2027 1669932 1544688 1795177
July 2027 1669880 1527940 1811819
August 2027 1680586 1566306 1794866
September 2027 1691362 1534065 1848658
October 2027 1702206 1566029 1838382
November 2027 1713120 1553800 1872440
December 2027 1724104 1631002 1817205
Winchester Housing Market Forecast with Real Estate Prices for 2028
January 2028 1735158 1615432 1854884
February 2028 1743886 1595655 1892116
March 2028 1750763 1615954 1885572
April 2028 1754971 1665467 1844474
May 2028 1757232 1593810 1920655
June 2028 1762845 1591849 1933840
July 2028 1774147 1673021 1875274
August 2028 1785522 1646252 1924793
September 2028 1796970 1635243 1958698
October 2028 1803410 1650120 1956700
November 2028 1801205 1671518 1930892
December 2028 1796468 1688680 1904257
Winchester Housing Market Forecast with Real Estate Prices for 2029
January 2029 1796511 1692313 1900709
February 2029 1799568 1664600 1934535
March 2029 1803124 1693134 1913115
April 2029 1806708 1701919 1911497
May 2029 1818292 1687375 1949209
June 2029 1824331 1722168 1926493
July 2029 1830884 1695398 1966369
August 2029 1836069 1685511 1986626
September 2029 1836898 1732195 1941601
October 2029 1832930 1715622 1950237
November 2029 1828115 1669069 1987161
December 2029 1839836 1746005 1933668
Winchester Housing Market Forecast with Real Estate Prices for 2030
January 2030 1851633 1720167 1983099
February 2030 1863505 1747967 1979042
March 2030 1875453 1762925 1987980
April 2030 1886310 1775018 1997603
May 2030 1890852 1726348 2055356
June 2030 1893460 1707901 2079019
July 2030 1898441 1765550 2031332
August 2030 1908552 1769228 2047877
September 2030 1920789 1797859 2043720
October 2030 1933105 1828717 2037492
November 2030 1945499 1840442 2050556
December 2030 1957973 1764133 2151812
Winchester Housing Market Forecast with Real Estate Prices for 2031
January 2031 1970526 1799091 2141962
February 2031 1983161 1792777 2173544
March 2031 1995876 1844189 2147562
April 2031 1988626 1851411 2125842
May 2031 1980920 1868008 2093833
June 2031 1973244 1839064 2107425
July 2031 1965598 1863387 2067809
August 2031 1964899 1821462 2108337
September 2031 1962837 1833289 2092384
October 2031 1960619 1776321 2144917
November 2031 1960557 1846845 2074269
December 2031 1973127 1848820 2097434
Winchester Housing Market Forecast with Real Estate Prices for 2032
January 2032 1985778 1830888 2140669
February 2032 1998510 1828637 2168384
March 2032 2011324 1868520 2154128
April 2032 2024220 1866331 2182109
May 2032 2037198 1833479 2240918
June 2032 2047445 1889792 2205099
July 2032 2055520 1913689 2197351

> 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.