House Price Watch
100 most expensive houses in Old Windsor
Old Windsor, nestled within Windsor and Maidenhead, boasts a fascinating real estate market. The most expensive house sold here reached an impressive £4,850,000 in 2016, while the least expensive was bought for £860,000. Notably, 16 houses on the list are located on the same street, Crimp Hill. Since 1995, the area has seen a remarkable 2,425 sales, with the latest transaction recorded in 2026.
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
£14,000,000
188.66%
£2,700,000
-44.33%
£5,850,000
20.62%
£3,805,000
-21.55%
£21,000,000
332.99%
£3,740,000
-22.89%
£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 2024
27 st lukes road, windsor and maidenhead
£1,250,000
32.
Sold in April 2021
102 straight road, windsor and maidenhead
£1,250,000
33.
Sold in February 2015
4 dunboyne place, windsor and maidenhead
£1,250,000
34.
Sold in April 2021
6 ouseley road, windsor and maidenhead
£1,225,000
35.
Sold in August 2005
3 dunboyne place, windsor and maidenhead
£1,200,000
36.
Sold in August 2006
5 dunboyne place, windsor and maidenhead
£1,200,000
Sold for a lower amount since this price
37.
Sold in June 2021
24 bears rails park, windsor and maidenhead
£1,190,000
38.
Sold in October 2023
11 datchet road, windsor and maidenhead
£1,175,000
39.
Sold in August 2010
3 dunboyne place, windsor and maidenhead
£1,175,000
40.
Sold in June 2019
7 pelling hill, windsor and maidenhead
£1,155,000
41.
Sold in May 2024
28 bears rails park, windsor and maidenhead
£1,150,000
42.
Sold in May 2025
1 the avenue, windsor and maidenhead
£1,150,000
43.
Sold in 2005
4 dunboyne place, windsor and maidenhead
£1,150,000
44.
Sold in October 2022
two acres church road, windsor and maidenhead
£1,125,000
45.
Sold in June 2019
18 bears rails park, windsor and maidenhead
£1,100,000
46.
Sold in October 1999
waterside manor windsor road, surrey
£1,100,000
47.
Sold in March 2025
14 harwood gardens, windsor and maidenhead
£1,100,000
48.
Sold in 2010
1 bears rails park, windsor and maidenhead
£1,085,000
49.
Sold in February 2000
the boatyard , windsor and maidenhead
£1,075,000
50.
Sold in March 2024
chapel stile the friary, windsor and maidenhead
£1,070,000
51.
Sold in September 2021
friary mede the friary, windsor and maidenhead
£1,060,000
52.
Sold in July 2010
5 dunboyne place, windsor and maidenhead
£1,060,000
53.
Sold in March 2022
7 bears rails park, windsor and maidenhead
£1,055,000
54.
Sold in July 2016
106 straight road, windsor and maidenhead
£1,040,000
55.
Sold in September 2025
friary cottage the friary, windsor and maidenhead
£1,010,000
56.
Sold in 2020
4 moram mews, windsor and maidenhead
£1,000,000
57.
Sold in June 2024
1 tudor lane, windsor and maidenhead
£1,000,000
58.
Sold in August 2014
burfield lodge east burfield road, windsor and maidenhead
£1,000,000
59.
Sold in August 2017
19 orchard road, windsor and maidenhead
£1,000,000
60.
Sold in March 2024
10 harwood gardens, windsor and maidenhead
£995,000
61.
Sold in August 2007
2 bears rails park, windsor and maidenhead
£992,500
62.
Sold in April 2023
156 straight road, windsor and maidenhead
£992,000
63.
Sold in July 2016
9 bears rails park, windsor and maidenhead
£985,000
64.
Sold in February 2026
32 bears rails park, windsor and maidenhead
£985,000
65.
Sold in October 2023
4 hartley copse, windsor and maidenhead
£975,000
66.
Sold in June 2022
16 bears rails park, windsor and maidenhead
£970,000
67.
Sold in September 2020
13 parker gardens, windsor and maidenhead
£960,000
68.
Sold in April 2017
30 bears rails park, windsor and maidenhead
£950,000
69.
Sold in April 2017
81 burfield road, windsor and maidenhead
£950,000
70.
Sold in April 2024
20 ricardo road, windsor and maidenhead
£950,000
71.
Sold in July 2023
164 straight road, windsor and maidenhead
£950,000
72.
Sold in August 2014
18 bears rails park, windsor and maidenhead
£945,000
73.
Sold in March 2024
24 ham island, windsor and maidenhead
£940,000
74.
Sold in May 2025
3 malt house close, windsor and maidenhead
£940,000
75.
Sold in November 2008
4 bears rails park, windsor and maidenhead
£930,000
76.
Sold in April 2020
greensleeves , windsor and maidenhead
£930,000
77.
Sold in July 2021
the lodge burfield road, windsor and maidenhead
£925,000
78.
Sold in November 2015
kingfisher ham island, windsor and maidenhead
£925,000
79.
Sold in July 2018
29 ham island, windsor and maidenhead
£925,000
80.
Sold in February 2016
abbotsmede the friary, windsor and maidenhead
£920,000
81.
Sold in November 2019
25 ham island, windsor and maidenhead
£915,000
82.
Sold in February 2023
1 hartley copse, windsor and maidenhead
£905,000
83.
Sold in February 2023
10 bears rails park, windsor and maidenhead
£901,500
84.
Sold in September 2025
woodside farm house crimp hill road, windsor and maidenhead
£900,000
85.
Sold in October 2018
priory gate church road, windsor and maidenhead
£900,000
86.
Sold in March 2021
16 ham island, windsor and maidenhead
£900,000
Sold for a lower amount since this price
87.
Sold in February 2021
156 straight road, windsor and maidenhead
£900,000
88.
Sold in November 2020
71 burfield road, windsor and maidenhead
£896,995
89.
Sold in March 2006
10 pelling hill, windsor and maidenhead
£880,000
90.
Sold in 2021
9 ricardo road, windsor and maidenhead
£880,000
91.
Sold in August 2015
13 parker gardens, windsor and maidenhead
£880,000
92.
Sold in December 2024
8 parker gardens, windsor and maidenhead
£875,000
93.
Sold in March 2022
8 parker gardens, windsor and maidenhead
£870,000
94.
Sold in August 2016
18 ham island, windsor and maidenhead
£866,000
95.
Sold in May 2020
19 bears rails park, windsor and maidenhead
£865,000
96.
Sold in November 2010
36 bears rails park, windsor and maidenhead
£860,000
97.
Sold in March 2025
12 harwood gardens, windsor and maidenhead
£860,000
98.
Sold in February 2006
10a pelling hill, windsor and maidenhead
£860,000
99.
Sold in November 2022
61 burfield road, windsor and maidenhead
£860,000
100.
Sold in June 2021
1 parker gardens, windsor and maidenhead
£860,000
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 29 March 2026 at 18:31 with the latest HM Land Registry data (February 2026). The Old Windsor dataset covers 177 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.