House Price Watch
100 most expensive houses in Winchester
In the beautiful area of Winchester, part of Hampshire, the real estate market has seen some remarkable transactions. The most expensive house sold for an impressive £18,500,000 in 2021, while the least expensive was valued at £2,387,500. Notably, seven of these luxurious homes are located on the same street, 'Sleepers Hill'. Since 1995, there have been a staggering 65,151 sales in the area, showcasing Winchester's vibrant property market, with the latest sale recorded in 2025.
Sold in February 2021
cobham house high street, hampshire
£18,500,000
Sold in December 2020
avington park house east , hampshire
£16,000,000
Sold in September 2020
meonstoke house chapel road, hampshire
£8,204,250
4.
Sold in October 2022
mulberry house , winchester
£6,500,000
5.
Sold in February 2020
ovington house , hampshire
£6,000,000
6.
Sold in February 2018
mulberry house , winchester
£5,500,000
7.
Sold in 2020
the dower house , hampshire
£5,350,000
8.
Sold in February 2017
whitedale house east street, hampshire
£5,300,000
9.
Sold in August 2018
west end house green lane, hampshire
£4,900,000
10.
Sold in April 2019
manor house church lane, hampshire
£4,847,830
Most expensive houses in areas around Winchester
£5,500,000
-70.27%
£20,000,000
8.11%
£12,500,000
-32.43%
£1,710,000
-90.76%
£8,050,000
-56.49%
£20,000,000
8.11%
11.
Sold in February 2008
the old rectory , hampshire
£4,300,000
12.
Sold in October 2020
chalkdell house , hampshire
£4,250,000
13.
Sold in October 2021
symonds house symonds street, hampshire
£4,200,000
14.
Sold in February 2021
tytheland farm woodlands, hampshire
£3,975,000
15.
Sold in September 2024
dashwood house sleepers hill, hampshire
£3,950,000
16.
Sold in October 2023
140 st cross road, hampshire
£3,716,935
17.
Sold in September 2019
restharrow house woodlands, hampshire
£3,650,000
18.
Sold in December 2020
fir hill garrison hill, hampshire
£3,650,000
19.
Sold in October 2024
15 clifton road, hampshire
£3,550,000
20.
Sold in August 2009
northbrook lodge northbrook, hampshire
£3,500,000
21.
Sold in March 2018
ashburton place 5, winchester
£3,500,000
Sold for a lower amount since this price
22.
Sold in March 2018
ashburton place 5, winchester
£3,500,000
Sold for a lower amount since this price
23.
Sold in November 2022
57 st cross road, hampshire
£3,500,000
24.
Sold in November 2018
park house colden lane, hampshire
£3,500,000
25.
Sold in September 2020
itchen stoke manor alresford road, hampshire
£3,475,000
26.
Sold in October 2024
the vineyard east street, hampshire
£3,450,000
27.
Sold in February 2022
grange view house rectory lane, hampshire
£3,450,000
28.
Sold in 2019
taylors mead woodman lane, hampshire
£3,450,000
29.
Sold in August 2024
the old rectory , hampshire
£3,365,000
30.
Sold in September 2022
50 broad street, hampshire
£3,350,000
31.
Sold in March 2019
meadowlands stockbridge road, hampshire
£3,315,000
Sold for a lower amount since this price
32.
Sold in December 2009
upham place upham street, hampshire
£3,300,000
Sold for a lower amount since this price
33.
Sold in September 2023
the old rectory maypole green, hampshire
£3,250,000
34.
Sold in 2012
glasspools farm longwood, hampshire
£3,210,000
35.
Sold in December 2015
dashwood house sleepers hill, hampshire
£3,200,000
36.
Sold in 2017
sleepers hill house george eyston drive, hampshire
£3,148,000
37.
Sold in July 2021
heybridge clifton road, hampshire
£3,125,000
38.
Sold in March 2023
greys lea main road, hampshire
£3,100,000
39.
Sold in March 2022
little snakemoor sleepers hill, hampshire
£3,100,000
40.
Sold in June 2023
breach plain cottage , hampshire
£3,100,000
41.
Sold in December 2022
carle end school lane, hampshire
£3,040,000
42.
Sold in March 2019
gifford house st giles hill, hampshire
£3,035,000
43.
Sold in April 2019
1 kerrfield, hampshire
£3,008,000
Sold for a lower amount since this price
44.
Sold in February 2014
chilland place lower chilland lane, hampshire
£3,000,000
45.
Sold in May 2024
st. catherines place sleepers hill, hampshire
£3,000,000
46.
Sold in March 2018
seagrave house george eyston drive, hampshire
£3,000,000
47.
Sold in May 2013
the beeches , winchester
£3,000,000
48.
Sold in August 2023
the house southwick road, hampshire
£2,999,999
49.
Sold in 2021
studwell lodge south hill, hampshire
£2,995,000
50.
Sold in March 2016
edmund house sleepers hill, hampshire
£2,950,000
51.
Sold in October 2011
upham place upham street, hampshire
£2,950,000
52.
Sold in November 2024
meadows , hampshire
£2,905,000
53.
Sold in December 2022
stanmore house , hampshire
£2,900,000
54.
Sold in April 2022
hillcote house airlie lane, hampshire
£2,880,000
55.
Sold in April 2022
the old rectory old rectory lane, hampshire
£2,875,000
56.
Sold in October 2015
6 st james lane, hampshire
£2,875,000
57.
Sold in September 2019
elizabeth house hurdle way, hampshire
£2,865,000
58.
Sold in October 2023
upper chilland house lower chilland lane, hampshire
£2,850,000
59.
Sold in April 2014
highgrove house st thomas street, hampshire
£2,850,000
60.
Sold in August 2020
tall trees , hampshire
£2,842,000
61.
Sold in October 2024
hinton shepherds lane, hampshire
£2,826,000
62.
Sold in August 2024
erdely clease way, hampshire
£2,800,000
63.
Sold in October 2023
52 cheriton road, hampshire
£2,800,000
64.
Sold in August 2021
hive house , winchester
£2,800,000
65.
Sold in December 2016
the holt sleepers hill, hampshire
£2,750,000
Sold for a lower amount since this price
66.
Sold in April 2023
northington links road, hampshire
£2,750,000
67.
Sold in December 2017
fairfield house rectory lane, hampshire
£2,700,000
68.
Sold in September 2007
mildmay house church lane, hampshire
£2,700,000
69.
Sold in August 2025
tinnisbourne beacon hill lane, hampshire
£2,700,000
70.
Sold in March 2017
the holt sleepers hill, hampshire
£2,650,000
Sold for a lower amount since this price
71.
Sold in October 2023
barton house rectory lane, hampshire
£2,632,500
72.
Sold in March 2022
2 haig road, hampshire
£2,615,000
73.
Sold in 2020
sanders links road, hampshire
£2,610,000
74.
Sold in July 2017
arthurs court sleepers hill, hampshire
£2,605,381
Sold for a lower amount since this price
75.
Sold in February 2022
willowmead church lane, hampshire
£2,600,000
76.
Sold in October 2007
west stratton house , hampshire
£2,600,000
77.
Sold in August 2008
dawn house sleepers hill, hampshire
£2,600,000
78.
Sold in September 2023
durley oaks durley hall lane, hampshire
£2,600,000
79.
Sold in October 2021
mayhill cottage mayhill lane, hampshire
£2,600,000
80.
Sold in June 2023
holly lodge southdown road, hampshire
£2,585,000
81.
Sold in February 2017
olive house , winchester
£2,585,000
Sold for a lower amount since this price
82.
Sold in November 2019
26 bereweeke road, hampshire
£2,550,000
83.
Sold in February 2001
blackdown house blackdown lane, hampshire
£2,525,000
84.
Sold in 2020
knowle house mincingfield lane, hampshire
£2,525,000
85.
Sold in February 2007
knighton park lane, hampshire
£2,510,000
86.
Sold in April 2021
rosecroft east street, hampshire
£2,500,000
87.
Sold in September 2020
barn close house main road, hampshire
£2,500,000
88.
Sold in 2011
the coachmans cottage , hampshire
£2,500,000
89.
Sold in February 2024
1 lockburn place, hampshire
£2,500,000
90.
Sold in June 2022
37a dean lane, hampshire
£2,445,000
91.
Sold in February 2023
the white house , winchester
£2,425,000
92.
Sold in August 2005
east hoe manor east hoe road, hampshire
£2,415,000
93.
Sold in February 2021
strawberry hill alresford road, hampshire
£2,400,000
94.
Sold in October 2019
longdown house watley lane, hampshire
£2,400,000
95.
Sold in September 2023
windrose house sleepers hill, hampshire
£2,400,000
96.
Sold in November 2015
15 clifton road, hampshire
£2,400,000
97.
Sold in September 2011
old alresford lodge colden lane, hampshire
£2,400,000
98.
Sold in July 2021
the old rectory , hampshire
£2,400,000
99.
Sold in August 2020
hockley house church lane, hampshire
£2,392,000
100.
Sold in December 2015
knightley sleepers hill, hampshire
£2,387,500
Data Source & Update Note:
This list of the 100 most expensive homes sold in Winchester 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 in July 2025 (The latest available from HM Land Registry). Prices reflect actual recorded transactions, not current market valuations.