House Price Watch
100 most expensive houses in Maidenhead
In the charming area of Maidenhead, part of Windsor and Maidenhead, the real estate market has seen some impressive transactions. The most expensive house sold for a staggering £6,900,000 in 2019, while the least expensive on the list came in at £1,455,000. Notably, four of the houses are located on the same street, Chauntry Road. Since 1995, there have been 27,601 sales in this vibrant community, with the latest sale recorded in 2025.
Sold in September 2019
manor house manor lane, windsor and maidenhead
£6,900,000
Sold in April 1999
2 - 3 the switchback, windsor and maidenhead
£5,425,000
Sold in April 2016
56 sheephouse road, windsor and maidenhead
£4,700,000
4.
Sold in July 2021
willowgarth chauntry road, windsor and maidenhead
£3,500,000
5.
Sold in November 2022
ditton place furze platt road, windsor and maidenhead
£3,350,000
6.
Sold in November 2001
market house providence place, windsor and maidenhead
£3,025,000
7.
Sold in July 2022
herons court winter hill road, windsor and maidenhead
£3,000,000
8.
Sold in October 1999
arcadia house , windsor and maidenhead
£2,812,500
9.
Sold in 2013
ditton place furze platt road, windsor and maidenhead
£2,800,000
10.
Sold in February 2022
7a lime walk, windsor and maidenhead
£2,750,000
Most expensive houses in areas around Maidenhead
£2,700,000
-60.87%
£5,850,000
-15.22%
£6,400,000
-7.25%
£3,740,000
-45.80%
£21,000,000
204.35%
£6,189,800
-10.29%
£21,000,000
204.35%
11.
Sold in April 2022
the forge golden ball lane, windsor and maidenhead
£2,700,000
12.
Sold in September 2011
moor place moorlands drive, windsor and maidenhead
£2,600,000
13.
Sold in October 2011
oldfield guards club road, windsor and maidenhead
£2,550,000
14.
Sold in October 2010
ditton meads winter hill road, windsor and maidenhead
£2,500,000
15.
Sold in October 2019
the coach house lee lane, windsor and maidenhead
£2,500,000
16.
Sold in June 2019
the old dairy malders lane, windsor and maidenhead
£2,456,984
17.
Sold in October 2018
the old granary malders lane, windsor and maidenhead
£2,450,000
18.
Sold in September 2024
5 castle hill terrace, windsor and maidenhead
£2,400,000
19.
Sold in April 2025
two gates the avenue, windsor and maidenhead
£2,400,000
20.
Sold in July 2023
thicket meadows cottage newlands drive, windsor and maidenhead
£2,350,000
21.
Sold in November 2023
nascot pinkneys drive, windsor and maidenhead
£2,350,000
22.
Sold in December 2023
maplewood newlands drive, windsor and maidenhead
£2,330,000
23.
Sold in June 2021
20 lower cookham road, windsor and maidenhead
£2,326,000
24.
Sold in October 2014
nyetimber chauntry road, windsor and maidenhead
£2,250,000
25.
Sold in June 2016
wickhams , windsor and maidenhead
£2,250,000
26.
Sold in 2021
extra cover chauntry road, windsor and maidenhead
£2,135,000
27.
Sold in December 2022
hunter house , windsor and maidenhead
£2,125,000
28.
Sold in November 2019
woodridge court road, windsor and maidenhead
£2,105,000
29.
Sold in September 2024
elentone court road, windsor and maidenhead
£2,050,000
30.
Sold in 2016
by the green court shoppenhangers road, windsor and maidenhead
£2,000,000
Sold for a lower amount since this price
31.
Sold in 1999
the college , windsor and maidenhead
£2,000,000
32.
Sold in November 2024
38 belmont park avenue, windsor and maidenhead
£1,875,000
33.
Sold in July 2023
tollgate house tollgate, windsor and maidenhead
£1,850,000
34.
Sold in October 2022
huntingdon lodge newlands drive, windsor and maidenhead
£1,850,000
35.
Sold in September 2016
pond house winter hill road, windsor and maidenhead
£1,850,000
36.
Sold in March 2022
11 maidenhead court park, windsor and maidenhead
£1,840,000
37.
Sold in April 2023
braywick lodge hibbert road, windsor and maidenhead
£1,800,000
38.
Sold in August 2022
greenfields altwood bailey, windsor and maidenhead
£1,800,000
39.
Sold in February 2022
deep hollow golden ball lane, windsor and maidenhead
£1,785,000
40.
Sold in March 2021
4 amberley court, windsor and maidenhead
£1,780,000
41.
Sold in May 2003
69 high street, windsor and maidenhead
£1,760,000
42.
Sold in April 2018
24 braywick road, windsor and maidenhead
£1,750,000
Sold for a lower amount since this price
43.
Sold in October 2014
westlands chauntry road, windsor and maidenhead
£1,750,000
44.
Sold in September 2003
fairway shoppenhangers road, windsor and maidenhead
£1,750,000
Sold for a lower amount since this price
45.
Sold in May 2022
white house , windsor and maidenhead
£1,750,000
46.
Sold in September 2024
6 frances avenue, windsor and maidenhead
£1,750,000
47.
Sold in April 2023
7 castle hill terrace, windsor and maidenhead
£1,720,000
48.
Sold in March 2023
14 ashton place, windsor and maidenhead
£1,720,000
49.
Sold in June 1999
units 1 and , windsor and maidenhead
£1,718,750
50.
Sold in November 2013
the fishery chauntry road, windsor and maidenhead
£1,700,000
51.
Sold in October 2023
manresa bath road, windsor and maidenhead
£1,675,000
52.
Sold in November 2024
richmond house newlands drive, windsor and maidenhead
£1,675,000
53.
Sold in September 2022
10 ray park avenue, windsor and maidenhead
£1,675,000
54.
Sold in October 2021
44 lower cookham road, windsor and maidenhead
£1,675,000
55.
Sold in September 2018
4 court drive, windsor and maidenhead
£1,675,000
56.
Sold in July 2020
mead house pinkneys drive, windsor and maidenhead
£1,665,000
57.
Sold in October 1999
69 high street, windsor and maidenhead
£1,660,000
58.
Sold in August 2017
green trees widbrook road, windsor and maidenhead
£1,650,000
Sold for a lower amount since this price
59.
Sold in July 2021
8 lime walk, windsor and maidenhead
£1,640,000
60.
Sold in 2024
13 camley park drive, windsor and maidenhead
£1,640,000
61.
Sold in August 2021
5 aspen place, windsor and maidenhead
£1,635,000
62.
Sold in October 2021
the willows winter hill road, windsor and maidenhead
£1,630,000
63.
Sold in February 2009
willowgarth chauntry road, windsor and maidenhead
£1,625,000
64.
Sold in August 2024
appletree house altwood bailey, windsor and maidenhead
£1,625,000
65.
Sold in June 2004
endfield house sandisplatt road, windsor and maidenhead
£1,610,000
66.
Sold in 2024
wilton house thicket grove, windsor and maidenhead
£1,600,000
67.
Sold in December 2024
12 frances avenue, windsor and maidenhead
£1,600,000
68.
Sold in July 2023
5 juniper drive, windsor and maidenhead
£1,595,000
69.
Sold in August 2021
4 woodfield drive, windsor and maidenhead
£1,585,000
70.
Sold in October 2008
the coach house lee lane, windsor and maidenhead
£1,575,000
71.
Sold in 2019
3a westmorland road, windsor and maidenhead
£1,565,000
72.
Sold in September 2018
leeward lee lane, windsor and maidenhead
£1,560,000
73.
Sold in May 2017
woodpeckers sandisplatt road, windsor and maidenhead
£1,555,000
74.
Sold in February 2000
park house , windsor and maidenhead
£1,550,000
75.
Sold in December 2019
the shutters sandisplatt road, windsor and maidenhead
£1,544,000
76.
Sold in March 2024
ashtons sandisplatt road, windsor and maidenhead
£1,540,000
77.
Sold in April 2024
18 college avenue, windsor and maidenhead
£1,525,000
78.
Sold in April 2025
14 lime walk, windsor and maidenhead
£1,525,000
79.
Sold in August 2017
claver house woodhurst road, windsor and maidenhead
£1,525,000
80.
Sold in April 2024
greendale ray park road, windsor and maidenhead
£1,525,000
81.
Sold in September 2022
8 ray park avenue, windsor and maidenhead
£1,520,000
82.
Sold in May 2018
9 college avenue, windsor and maidenhead
£1,515,000
83.
Sold in March 2018
2 rushington avenue, windsor and maidenhead
£1,500,000
84.
Sold in July 2016
rousbury shoppenhangers road, windsor and maidenhead
£1,500,000
85.
Sold in August 2025
4 ashton place, windsor and maidenhead
£1,500,000
86.
Sold in December 2019
12 lime walk, windsor and maidenhead
£1,500,000
87.
Sold in June 2024
68 harrow lane, windsor and maidenhead
£1,500,000
88.
Sold in December 2019
pinkneys court darlings lane, windsor and maidenhead
£1,495,000
89.
Sold in 2021
53 switchback road north, windsor and maidenhead
£1,490,000
90.
Sold in April 2025
6 lock mead, windsor and maidenhead
£1,490,000
91.
Sold in September 2024
highclere shoppenhangers road, windsor and maidenhead
£1,485,000
92.
Sold in 2022
rivers reach boulters lane, windsor and maidenhead
£1,485,000
93.
Sold in April 2021
redfern lock avenue, windsor and maidenhead
£1,483,000
94.
Sold in September 2022
17 the chase, windsor and maidenhead
£1,475,175
95.
Sold in September 2022
61 harrow lane, windsor and maidenhead
£1,475,000
96.
Sold in April 2025
30 harvest hill road, windsor and maidenhead
£1,465,000
97.
Sold in December 2016
3a westmorland road, windsor and maidenhead
£1,465,000
98.
Sold in September 2017
11 islet park drive, windsor and maidenhead
£1,462,500
99.
Sold in June 2002
74 high street, windsor and maidenhead
£1,458,000
Sold for a lower amount since this price
100.
Sold in December 2024
2 linden avenue, windsor and maidenhead
£1,455,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in 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 September 2025 (The latest available from HM Land Registry). Prices reflect actual recorded transactions, not current market valuations.