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Today: September 22, 2025

Current Price

$1,465,244

1 Month Forecast

$1,566,827

1-Year Forecast *

$1,671,007

5-Year Forecast *

$1,917,781

"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 2025-09-22. Based on our forecasts, a long-term increase is expected, the predicted price of an average home in the "Winchester" area is 1,917,781 USD by 2030-09-22. For a 5-year investment the profit is expected to be around +30.88% meaning that investing 100000 USD today may yield a profit of 30,885 USD by 2030.

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: 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: $1,671,007* (upside of 14.0%)

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 $685,324 $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 1,671,007 USD in one year.

Is it profitable to invest in Winchester homes?

Yes. The long-term profit potential is +14.04% 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 1,917,781 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 2,362,049 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 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 0.568% to 1,465,244 USD, between 2024-09-22 and 2025-09-22

The average annual profit of property investment was:

  • 13.123% in 2020
  • 15.493% in 2021
  • 13.113% in 2022
  • 14.943% in 2023
  • 13.663% in 2024
  • 12.413% in 2025

Based on our Winchester real estate market research and report the predicted sales prices will increase by 272.118% 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 (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
Winchester Housing Market Forecast with Real Estate Prices for 2025
August 2025 1566827 1425812 1707841
September 2025 1576641 1447356 1705925
October 2025 1586516 1448489 1724543
November 2025 1596453 1511841 1681065
December 2025 1606453 1468298 1744608
Winchester Housing Market Forecast with Real Estate Prices for 2026
January 2026 1616515 1456480 1776550
February 2026 1626640 1504642 1748638
March 2026 1636829 1510793 1762864
April 2026 1647081 1484020 1810142
May 2026 1657398 1571213 1743582
June 2026 1666993 1541968 1792017
July 2026 1671007 1555707 1786306
August 2026 1673311 1572913 1773710
September 2026 1677713 1526719 1828707
October 2026 1686649 1595570 1777728
November 2026 1697213 1571619 1822807
December 2026 1707844 1566093 1849595
Winchester Housing Market Forecast with Real Estate Prices for 2027
January 2027 1718541 1622303 1814779
February 2027 1729305 1597878 1860732
March 2027 1740137 1644429 1835844
April 2027 1751036 1642472 1859601
May 2027 1762004 1661570 1862438
June 2027 1755731 1664433 1847029
July 2027 1749480 1599025 1899936
August 2027 1743252 1650860 1835644
September 2027 1737046 1644982 1829109
October 2027 1736428 1621824 1851033
November 2027 1734606 1569818 1899393
December 2027 1732646 1621757 1843535
Winchester Housing Market Forecast with Real Estate Prices for 2028
January 2028 1732591 1633833 1831349
February 2028 1743443 1612685 1874202
March 2028 1754363 1587699 1921028
April 2028 1765352 1597644 1933060
May 2028 1776409 1612980 1939839
June 2028 1787536 1682071 1893001
July 2028 1798732 1645840 1951625
August 2028 1807780 1715583 1899977
September 2028 1814909 1715089 1914729
October 2028 1819271 1699199 1939343
November 2028 1821616 1668600 1974631
December 2028 1827433 1719615 1935252
Winchester Housing Market Forecast with Real Estate Prices for 2029
January 2029 1838880 1669703 2008057
February 2029 1850398 1674610 2026185
March 2029 1861988 1685099 2038877
April 2029 1868660 1717299 2020022
May 2029 1866376 1696535 2036216
June 2029 1861468 1738611 1984324
July 2029 1861512 1762851 1960172
August 2029 1864679 1678211 2051147
September 2029 1868364 1709553 2027175
October 2029 1872077 1686742 2057413
November 2029 1883803 1733099 2034507
December 2029 1890060 1780436 1999683
Winchester Housing Market Forecast with Real Estate Prices for 2030
January 2030 1896849 1765966 2027732
February 2030 1902221 1767163 2037278
March 2030 1903080 1714675 2091485
April 2030 1898968 1724263 2073674
May 2030 1893981 1774660 2013301
June 2030 1905844 1776246 2035441
July 2030 1917781 1783536 2052026
August 2030 1929793 1773480 2086106
September 2030 1941881 1802065 2081696
October 2030 1954044 1836801 2071286
November 2030 1966283 1771621 2160945
December 2030 1978599 1822290 2134908
Winchester Housing Market Forecast with Real Estate Prices for 2031
January 2031 1990992 1831713 2150271
February 2031 2003463 1811130 2195795
March 2031 2016012 1893035 2138988
April 2031 2027683 1861413 2193953
May 2031 2032565 1906546 2158584
June 2031 2035369 1894928 2175809
July 2031 2040723 1865221 2216225
August 2031 2051592 1905929 2197255
September 2031 2064442 1913738 2215146
October 2031 2077373 1967272 2187474
November 2031 2090385 1906431 2274339
December 2031 2103478 1983580 2223376
Winchester Housing Market Forecast with Real Estate Prices for 2032
January 2032 2116653 1964254 2269052
February 2032 2129911 1993597 2266225
March 2032 2143252 1969648 2316855
April 2032 2135622 1990399 2280844
May 2032 2128018 1953521 2302516
June 2032 2120442 1916880 2324005
July 2032 2112893 1907943 2317844
August 2032 2112142 1903040 2321244
September 2032 2109925 1972780 2247070
October 2032 2107541 1997949 2217134
November 2032 2107475 1964166 2250783
December 2032 2120675 1961624 2279726
Winchester Housing Market Forecast with Real Estate Prices for 2033
January 2033 2133958 1997385 2270531
February 2033 2147324 1943328 2351320
March 2033 2160774 2013841 2307707
April 2033 2174308 2017758 2330858
May 2033 2187927 2043524 2332330
June 2033 2198932 2025217 2372648
July 2033 2207604 1995674 2419534

> 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.