House Price Watch
100 most expensive houses in Old Windsor
In the charming area of Old Windsor, which is part of Windsor and Maidenhead, the real estate market has seen some remarkable transactions. The most expensive house sold for an impressive £4,850,000 in 2016, while the least expensive was priced at £850,000. Notably, 15 of the houses on the list are located on the same street, Pelling Hill. Since 1995, there have been a total of 2392 sales in this vibrant community, with the latest sale recorded in 2025.
Sold in May 2016
dower house crimp hill road, windsor and maidenhead
£4,850,000
Sold in March 2006
dower house crimp hill road, windsor and maidenhead
£3,600,000
Sold in October 2017
kingsmead hatchet lane, windsor and maidenhead
£3,000,000
4.
Sold in September 2000
dower house crimp hill road, windsor and maidenhead
£2,550,000
5.
Sold in 2022
56 burfield road, windsor and maidenhead
£2,350,000
6.
Sold in July 2014
16 pelling hill, windsor and maidenhead
£2,330,000
7.
Sold in May 2023
27 ham island, windsor and maidenhead
£1,900,000
8.
Sold in 2020
cedar close the friary, windsor and maidenhead
£1,860,000
9.
Sold in April 2021
13 pelling hill, windsor and maidenhead
£1,832,500
10.
Sold in July 2017
56 burfield road, windsor and maidenhead
£1,800,000
Most expensive houses in areas around Old Windsor
£2,700,000
-44.33%
£5,850,000
20.62%
£6,400,000
31.96%
£3,740,000
-22.89%
£21,000,000
332.99%
£6,189,800
27.62%
£21,000,000
332.99%
11.
Sold in August 2024
10 pelling hill, windsor and maidenhead
£1,750,000
12.
Sold in June 2013
13 pelling hill, windsor and maidenhead
£1,725,000
13.
Sold in September 2019
burfield lodge burfield road, windsor and maidenhead
£1,720,000
14.
Sold in June 2014
12a pelling hill, windsor and maidenhead
£1,715,000
15.
Sold in November 2013
14 pelling hill, windsor and maidenhead
£1,650,000
16.
Sold in December 2013
15 pelling hill, windsor and maidenhead
£1,650,000
17.
Sold in July 2014
12 pelling hill, windsor and maidenhead
£1,650,000
18.
Sold in 2006
56 burfield road, windsor and maidenhead
£1,635,000
19.
Sold in March 2022
10a pelling hill, windsor and maidenhead
£1,625,000
20.
Sold in December 2021
dower house cottage crimp hill road, windsor and maidenhead
£1,600,000
21.
Sold in 2014
weir lodge ham island, windsor and maidenhead
£1,550,000
22.
Sold in December 2009
cedar close the friary, windsor and maidenhead
£1,485,000
23.
Sold in June 2013
8 pelling hill, windsor and maidenhead
£1,450,000
24.
Sold in July 2021
willow dene the friary, windsor and maidenhead
£1,420,000
25.
Sold in August 2022
selleney cottage burfield road, windsor and maidenhead
£1,400,050
26.
Sold in July 2011
maybury , windsor and maidenhead
£1,400,000
27.
Sold in 2018
3 dunboyne place, windsor and maidenhead
£1,340,000
28.
Sold in August 2016
50 burfield road, windsor and maidenhead
£1,290,000
29.
Sold in October 2024
janda the friary, windsor and maidenhead
£1,275,000
30.
Sold in August 2012
2 bears rails park, windsor and maidenhead
£1,268,000
31.
Sold in April 2021
102 straight road, windsor and maidenhead
£1,250,000
32.
Sold in February 2015
4 dunboyne place, windsor and maidenhead
£1,250,000
33.
Sold in April 2021
6 ouseley road, windsor and maidenhead
£1,225,000
34.
Sold in August 2005
3 dunboyne place, windsor and maidenhead
£1,200,000
35.
Sold in August 2006
5 dunboyne place, windsor and maidenhead
£1,200,000
Sold for a lower amount since this price
36.
Sold in June 2021
24 bears rails park, windsor and maidenhead
£1,190,000
37.
Sold in October 2023
11 datchet road, windsor and maidenhead
£1,175,000
38.
Sold in August 2010
3 dunboyne place, windsor and maidenhead
£1,175,000
39.
Sold in June 2019
7 pelling hill, windsor and maidenhead
£1,155,000
40.
Sold in May 2024
28 bears rails park, windsor and maidenhead
£1,150,000
41.
Sold in May 2025
1 the avenue, windsor and maidenhead
£1,150,000
42.
Sold in 2005
4 dunboyne place, windsor and maidenhead
£1,150,000
43.
Sold in October 2022
two acres church road, windsor and maidenhead
£1,125,000
44.
Sold in June 2019
18 bears rails park, windsor and maidenhead
£1,100,000
45.
Sold in October 1999
waterside manor windsor road, surrey
£1,100,000
46.
Sold in March 2025
14 harwood gardens, windsor and maidenhead
£1,100,000
47.
Sold in 2010
1 bears rails park, windsor and maidenhead
£1,085,000
48.
Sold in February 2000
the boatyard , windsor and maidenhead
£1,075,000
49.
Sold in March 2024
chapel stile the friary, windsor and maidenhead
£1,070,000
50.
Sold in September 2021
friary mede the friary, windsor and maidenhead
£1,060,000
51.
Sold in July 2010
5 dunboyne place, windsor and maidenhead
£1,060,000
52.
Sold in March 2022
7 bears rails park, windsor and maidenhead
£1,055,000
53.
Sold in July 2016
106 straight road, windsor and maidenhead
£1,040,000
54.
Sold in 2020
4 moram mews, windsor and maidenhead
£1,000,000
55.
Sold in June 2024
1 tudor lane, windsor and maidenhead
£1,000,000
56.
Sold in August 2014
burfield lodge east burfield road, windsor and maidenhead
£1,000,000
57.
Sold in August 2017
19 orchard road, windsor and maidenhead
£1,000,000
58.
Sold in March 2024
10 harwood gardens, windsor and maidenhead
£995,000
59.
Sold in August 2007
2 bears rails park, windsor and maidenhead
£992,500
60.
Sold in April 2023
156 straight road, windsor and maidenhead
£992,000
61.
Sold in July 2016
9 bears rails park, windsor and maidenhead
£985,000
62.
Sold in October 2023
4 hartley copse, windsor and maidenhead
£975,000
63.
Sold in June 2022
16 bears rails park, windsor and maidenhead
£970,000
64.
Sold in September 2020
13 parker gardens, windsor and maidenhead
£960,000
65.
Sold in April 2017
30 bears rails park, windsor and maidenhead
£950,000
66.
Sold in April 2017
81 burfield road, windsor and maidenhead
£950,000
67.
Sold in April 2024
20 ricardo road, windsor and maidenhead
£950,000
68.
Sold in July 2023
164 straight road, windsor and maidenhead
£950,000
69.
Sold in August 2014
18 bears rails park, windsor and maidenhead
£945,000
70.
Sold in March 2024
24 ham island, windsor and maidenhead
£940,000
71.
Sold in November 2008
4 bears rails park, windsor and maidenhead
£930,000
72.
Sold in April 2020
greensleeves , windsor and maidenhead
£930,000
73.
Sold in July 2021
the lodge burfield road, windsor and maidenhead
£925,000
74.
Sold in November 2015
kingfisher ham island, windsor and maidenhead
£925,000
75.
Sold in July 2018
29 ham island, windsor and maidenhead
£925,000
76.
Sold in February 2016
abbotsmede the friary, windsor and maidenhead
£920,000
77.
Sold in November 2019
25 ham island, windsor and maidenhead
£915,000
78.
Sold in February 2023
1 hartley copse, windsor and maidenhead
£905,000
79.
Sold in February 2023
10 bears rails park, windsor and maidenhead
£901,500
80.
Sold in October 2018
priory gate church road, windsor and maidenhead
£900,000
81.
Sold in March 2021
16 ham island, windsor and maidenhead
£900,000
Sold for a lower amount since this price
82.
Sold in February 2021
156 straight road, windsor and maidenhead
£900,000
83.
Sold in November 2020
71 burfield road, windsor and maidenhead
£896,995
84.
Sold in March 2006
10 pelling hill, windsor and maidenhead
£880,000
85.
Sold in 2021
9 ricardo road, windsor and maidenhead
£880,000
86.
Sold in August 2015
13 parker gardens, windsor and maidenhead
£880,000
87.
Sold in December 2024
8 parker gardens, windsor and maidenhead
£875,000
88.
Sold in March 2022
8 parker gardens, windsor and maidenhead
£870,000
89.
Sold in August 2016
18 ham island, windsor and maidenhead
£866,000
90.
Sold in May 2020
19 bears rails park, windsor and maidenhead
£865,000
91.
Sold in November 2010
36 bears rails park, windsor and maidenhead
£860,000
92.
Sold in February 2006
10a pelling hill, windsor and maidenhead
£860,000
93.
Sold in November 2022
61 burfield road, windsor and maidenhead
£860,000
94.
Sold in June 2021
1 parker gardens, windsor and maidenhead
£860,000
95.
Sold in November 2020
11 tudor lane, windsor and maidenhead
£855,000
96.
Sold in 2020
fairview ham lane, windsor and maidenhead
£850,000
97.
Sold in February 2025
16 ham island, windsor and maidenhead
£850,000
98.
Sold in February 2025
16 ham island, windsor and maidenhead
£850,000
99.
Sold in March 2005
8 pelling hill, windsor and maidenhead
£850,000
100.
Sold in 2013
fremington the friary, windsor and maidenhead
£850,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Old Windsor 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.