House Price Watch
100 most expensive houses in Winston
In the charming area of Winston, part of Mid Suffolk, the real estate market has seen some fascinating trends. The most expensive house sold for an impressive £730,000 in 2015, while the least expensive was just £20,000. Over the years, 46 sales have occurred since 1996, with the latest transaction on the list happening in 2025. Notably, 22 of these homes are located on the same street, Debenham Road, showcasing a unique cluster of properties in this picturesque locale.
Sold in December 2015
parkchace , suffolk
£730,000
Sold in July 2025
rogers farm cottage , suffolk
£675,000
Sold in August 2019
smokey bakers lane, suffolk
£600,000
4.
Sold in 2023
brick kiln barn fenn street, suffolk
£545,000
5.
Sold in April 2024
1 grange road, suffolk
£480,000
6.
Sold in August 2023
the old cottage debenham road, suffolk
£460,000
7.
Sold in June 2001
winston house , suffolk
£450,000
8.
Sold in September 2022
11 debenham road, suffolk
£450,000
9.
Sold in 2025
1 debenham road, suffolk
£410,000
10.
Sold in November 2022
7 debenham road, suffolk
£400,000
Most expensive houses in areas around Winston
£1,100,000
50.68%
£1,300,000
78.08%
£1,500,000
105.48%
£740,000
1.37%
£860,000
17.81%
£1,150,000
57.53%
£3,500,000
379.45%
11.
Sold in September 2015
brockle , suffolk
£365,000
12.
Sold in May 2007
brick kiln cottage fenn street, suffolk
£365,000
13.
Sold in February 2014
boundary cottage , suffolk
£352,000
14.
Sold in December 2015
the old cottage debenham road, suffolk
£330,000
15.
Sold in September 2006
shingle cottage , suffolk
£325,000
16.
Sold in August 1999
barkers barn , suffolk
£320,000
17.
Sold in July 2021
4 fenn street, suffolk
£315,000
18.
Sold in March 2015
harkaway cottage , mid suffolk
£305,000
19.
Sold in August 2003
brick kiln barn fenn street, suffolk
£295,000
20.
Sold in 2010
boundary cottage , suffolk
£272,000
21.
Sold in November 1996
winston house , suffolk
£271,500
22.
Sold in December 2014
1 debenham road, suffolk
£270,000
23.
Sold in February 2003
7 fenn street, suffolk
£260,020
24.
Sold in June 2019
2 fenn street, suffolk
£249,000
25.
Sold in July 2018
8 fenn street, suffolk
£241,500
26.
Sold in October 2017
2 christmas eve cottage, suffolk
£234,995
27.
Sold in October 2001
hedgerow cottage debenham road, suffolk
£215,000
28.
Sold in September 2008
13 debenham road, suffolk
£215,000
29.
Sold in July 2015
4 fenn street, suffolk
£215,000
30.
Sold in June 2007
the old cottage debenham road, suffolk
£195,000
31.
Sold in December 2010
4 fenn street, suffolk
£178,000
32.
Sold in February 2006
3 christmas eve cottage, suffolk
£175,000
33.
Sold in July 2004
sunny view debenham road, suffolk
£170,000
34.
Sold in June 2003
2 fenn street, suffolk
£170,000
35.
Sold in December 2012
2 fenn street, suffolk
£167,500
36.
Sold in February 2004
8 fenn street, suffolk
£150,000
37.
Sold in December 2001
2 fenn street, suffolk
£135,000
38.
Sold in December 1997
shingle cottage , suffolk
£130,000
39.
Sold in May 1998
meadow entry debenham road, suffolk
£110,250
40.
Sold in April 1998
5 fenn street, suffolk
£96,500
41.
Sold in June 1999
4 christmas eve cottage, suffolk
£95,000
42.
Sold in March 1998
13 debenham road, suffolk
£78,000
43.
Sold in May 1996
1 fenn street, suffolk
£45,000
44.
Sold in September 1996
8 fenn street, suffolk
£43,000
45.
Sold in December 1997
5 debenham road, suffolk
£39,950
46.
Sold in May 1996
1 grange road, suffolk
£20,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Winston is compiled from all-time residential sales recorded by the HM Land Registry. Each entry includes the sale price and transaction date. The dataset was last updated 20 May 2026 at 15:11 with the latest HM Land Registry data (December 2025). The Winston dataset covers 12 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.