House Price Watch
100 most expensive houses in Windsor and Maidenhead
In the beautiful area of Windsor and Maidenhead, part of Berkshire, the real estate market has seen some remarkable transactions. The most expensive house sold for an impressive £21,000,000 in 2017, while the least expensive on the list was £3,725,000. Interestingly, 7 of the houses on this list are located on the same street, Fishers Wood. Since 1995, there have been a staggering 79,819 sales in the area, with the latest recorded sale happening in 2025.
Sold in September 2017
lambourn hall titlarks hill, windsor and maidenhead
£21,000,000
Sold in August 1999
the gate house london road, windsor and maidenhead
£8,949,158
Sold in August 2022
kingsmoor titlarks hill, windsor and maidenhead
£7,300,000
4.
Sold in April 2021
west court fishery road, windsor and maidenhead
£7,125,000
5.
Sold in February 2022
carolina ridgemount road, windsor and maidenhead
£7,000,000
6.
Sold in November 2007
titlarks titlarks hill, windsor and maidenhead
£6,950,000
7.
Sold in September 2019
manor house manor lane, windsor and maidenhead
£6,900,000
8.
Sold in November 2018
gresham house fireball hill, windsor and maidenhead
£6,550,000
9.
Sold in May 2025
2 regents walk, windsor and maidenhead
£6,495,000
10.
Sold in March 2023
the bethel fishery road, windsor and maidenhead
£6,425,000
Most expensive houses in areas around Windsor and Maidenhead
£6,500,000
-69.05%
£9,000,000
-57.14%
£10,000,000
-52.38%
£3,500,000
-83.33%
£3,900,000
-81.43%
£21,000,000
0.00%
11.
Sold in November 2015
temple house temple lane, windsor and maidenhead
£6,400,000
12.
Sold in November 2002
kingsmoor titlarks hill, windsor and maidenhead
£6,300,000
13.
Sold in November 2008
st annes titlarks hill, windsor and maidenhead
£6,200,000
14.
Sold in February 2024
gibraltar house gibraltar lane, windsor and maidenhead
£6,189,800
15.
Sold in May 2023
edenwood house horse gate ride, windsor and maidenhead
£6,100,000
16.
Sold in April 2018
hillsend titlarks hill, windsor and maidenhead
£6,000,000
17.
Sold in June 2020
foxfields st georges lane, windsor and maidenhead
£6,000,000
18.
Sold in November 2018
the thatched house bisham road, windsor and maidenhead
£6,000,000
Sold for a lower amount since this price
19.
Sold in December 2019
larksmead titlarks hill, windsor and maidenhead
£5,900,000
20.
Sold in November 2021
winterbrook west end, windsor and maidenhead
£5,850,000
21.
Sold in November 2021
wedgewood fireball hill, windsor and maidenhead
£5,850,000
22.
Sold in December 2018
earleydene orchard earleydene, windsor and maidenhead
£5,770,000
23.
Sold in August 2023
braydene heathfield avenue, windsor and maidenhead
£5,750,000
24.
Sold in March 2008
charters charters road, windsor and maidenhead
£5,660,000
Sold for a lower amount since this price
25.
Sold in December 2015
links house fishers wood, windsor and maidenhead
£5,610,000
Sold for a lower amount since this price
26.
Sold in August 2019
hunters moon fishers wood, windsor and maidenhead
£5,500,000
27.
Sold in 2023
hurst place bradcutts lane, windsor and maidenhead
£5,500,000
28.
Sold in April 1999
2 - 3 the switchback, windsor and maidenhead
£5,425,000
29.
Sold in October 2016
2 regents walk, windsor and maidenhead
£5,400,000
30.
Sold in August 2014
edenwood house horsegate ride, windsor and maidenhead
£5,300,000
31.
Sold in June 2013
waters edge fishery road, windsor and maidenhead
£5,148,500
32.
Sold in May 2013
links house fishers wood, windsor and maidenhead
£5,000,000
Sold for a lower amount since this price
33.
Sold in July 2017
9 park street, windsor and maidenhead
£4,900,000
34.
Sold in May 2016
dower house crimp hill road, windsor and maidenhead
£4,850,000
35.
Sold in February 2013
wedgewood fireball hill, windsor and maidenhead
£4,850,000
36.
Sold in April 2021
virginia house fishers wood, windsor and maidenhead
£4,840,000
37.
Sold in October 2016
lyndale house devenish lane, windsor and maidenhead
£4,800,000
38.
Sold in October 2019
links house fishers wood, windsor and maidenhead
£4,750,000
39.
Sold in July 2020
the jordans sunning avenue, windsor and maidenhead
£4,750,000
40.
Sold in April 2016
56 sheephouse road, windsor and maidenhead
£4,700,000
41.
Sold in September 2024
candlemas heathfield avenue, windsor and maidenhead
£4,650,000
42.
Sold in July 2015
the jordans sunning avenue, windsor and maidenhead
£4,650,000
43.
Sold in August 2020
oakwood bagshot road, windsor and maidenhead
£4,600,000
44.
Sold in April 2023
sachels coronation road, windsor and maidenhead
£4,600,000
45.
Sold in September 2015
the willows , windsor and maidenhead
£4,593,000
Sold for a lower amount since this price
46.
Sold in September 2024
the willows , windsor and maidenhead
£4,550,000
47.
Sold in October 2020
7 regents walk, windsor and maidenhead
£4,536,515
48.
Sold in October 2015
april wood st marys road, windsor and maidenhead
£4,500,000
49.
Sold in July 2014
holland place bagshot road, windsor and maidenhead
£4,500,000
Sold for a lower amount since this price
50.
Sold in November 2014
oakwood bagshot road, windsor and maidenhead
£4,500,000
51.
Sold in August 2019
amberley house devenish lane, windsor and maidenhead
£4,500,000
52.
Sold in October 2021
milldale priory road, windsor and maidenhead
£4,500,000
53.
Sold in 2014
wensleydale broomhall lane, windsor and maidenhead
£4,400,000
54.
Sold in 2021
byron house fishers wood, windsor and maidenhead
£4,390,000
55.
Sold in April 2022
birchlands shrubbs hill lane, windsor and maidenhead
£4,350,000
56.
Sold in June 2020
fairwinds church lane, windsor and maidenhead
£4,350,000
57.
Sold in June 2021
sunning house , windsor and maidenhead
£4,350,000
58.
Sold in October 2017
woodberry down st marys road, windsor and maidenhead
£4,250,000
59.
Sold in November 2021
priory lodge priory road, windsor and maidenhead
£4,250,000
60.
Sold in August 2022
kiln meadow bedwins lane, windsor and maidenhead
£4,250,000
61.
Sold in November 2021
highbank stonehouse lane, windsor and maidenhead
£4,200,000
62.
Sold in August 2018
7 regents walk, windsor and maidenhead
£4,150,000
63.
Sold in July 2006
temple house temple, windsor and maidenhead
£4,150,000
64.
Sold in June 2017
virginia house fishers wood, windsor and maidenhead
£4,125,000
65.
Sold in August 2016
holland place bagshot road, windsor and maidenhead
£4,100,000
Sold for a lower amount since this price
66.
Sold in March 2024
barbary house gibraltar lane, windsor and maidenhead
£4,085,000
67.
Sold in December 2014
chartwood , windsor and maidenhead
£4,070,000
68.
Sold in February 2025
moor cottage high street, windsor and maidenhead
£4,055,000
69.
Sold in June 2000
nightingale house london road, windsor and maidenhead
£4,000,000
70.
Sold in 2022
derryville burleigh lane, windsor and maidenhead
£4,000,000
71.
Sold in September 2010
cadena house fishery road, windsor and maidenhead
£4,000,000
Sold for a lower amount since this price
72.
Sold in February 2022
holly house alleyns lane, windsor and maidenhead
£4,000,000
73.
Sold in October 2018
riversway marlow bridge lane, windsor and maidenhead
£4,000,000
74.
Sold in November 2020
the thatched house bisham road, windsor and maidenhead
£4,000,000
75.
Sold in 2024
st charles house titlarks hill, windsor and maidenhead
£3,975,000
76.
Sold in August 2014
holland place bagshot road, windsor and maidenhead
£3,950,000
Sold for a lower amount since this price
77.
Sold in April 2014
cadena house fishery road, windsor and maidenhead
£3,950,000
78.
Sold in February 2015
titlarks house titlarks hill, windsor and maidenhead
£3,900,000
79.
Sold in October 2021
south court london road, windsor and maidenhead
£3,900,000
80.
Sold in September 2022
sandhills cross road, windsor and maidenhead
£3,895,000
81.
Sold in November 2012
hatfield house st marys road, windsor and maidenhead
£3,890,000
82.
Sold in July 2018
18 horton road, windsor and maidenhead
£3,880,000
83.
Sold in February 2020
boundary house lady margaret road, windsor and maidenhead
£3,875,000
84.
Sold in December 2021
holland place bagshot road, windsor and maidenhead
£3,850,000
85.
Sold in March 2024
little acorns st leonards hill, windsor and maidenhead
£3,837,500
86.
Sold in August 2021
bigfrith end bigfrith lane, windsor and maidenhead
£3,835,000
87.
Sold in September 2017
riverside house fishery road, windsor and maidenhead
£3,810,000
88.
Sold in May 2022
cottingham woolley avenue, windsor and maidenhead
£3,805,000
89.
Sold in December 2014
11 sunning avenue, windsor and maidenhead
£3,800,000
90.
Sold in October 2020
lilley woolley avenue, windsor and maidenhead
£3,800,000
91.
Sold in September 2021
meadowbrook heather drive, windsor and maidenhead
£3,750,000
92.
Sold in June 2019
dalkeith house shrubbs hill lane, windsor and maidenhead
£3,750,000
93.
Sold in March 2014
holland place bagshot road, windsor and maidenhead
£3,750,000
94.
Sold in April 2016
13 sunning avenue, windsor and maidenhead
£3,750,000
95.
Sold in April 2016
inglewood fishery road, windsor and maidenhead
£3,750,000
96.
Sold in June 2020
winter cottage terrys lane, windsor and maidenhead
£3,750,000
97.
Sold in June 2015
glenmead quarry wood road, windsor and maidenhead
£3,750,000
98.
Sold in 2007
tythe barn high street, windsor and maidenhead
£3,740,000
99.
Sold in February 2021
portland house monks close, windsor and maidenhead
£3,725,000
100.
Sold in February 2021
chalkpit house burchetts green road, windsor and maidenhead
£3,725,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Windsor and Maidenhead 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.