House Price Watch
100 most expensive houses in Pickering
In the charming area of Pickering, part of Ryedale, the real estate market has seen a remarkable range of home prices. The most expensive house sold for an impressive £910,000 in 2022, while the least expensive was valued at £450,000. Notably, 9 of the houses on the list are located on the same street: Derwent Road, Rye Close, Whitby Road. With a total of 4909 sales since 1995, the area continues to attract buyers, with the latest sale recorded in 2025.
Sold in June 2022
the stables porters headland, north yorkshire
£910,000
Sold in December 2020
oak tree farm yatts road, north yorkshire
£845,000
Sold in October 2025
haugh rigg farm west dike road, north yorkshire
£800,000
4.
Sold in November 2024
keswick house westgate, north yorkshire
£760,000
5.
Sold in February 2023
mount farm , ryedale
£750,000
6.
Sold in March 2022
149 middleton road, north yorkshire
£742,500
7.
Sold in September 2021
25 hall garth, north yorkshire
£730,000
8.
Sold in November 2006
shepherds hill whitby road, north yorkshire
£723,129
9.
Sold in July 2021
the craggs , north yorkshire
£660,000
10.
Sold in November 2025
2 herisson close, north yorkshire
£645,000
Most expensive houses in areas around Pickering
£2,000,000
119.78%
£2,908,234
219.59%
£1,480,000
62.64%
£2,650,000
191.21%
£1,200,000
31.87%
£890,000
-2.20%
£4,125,000
353.30%
11.
Sold in October 2021
castlegate house castlegate, north yorkshire
£630,000
12.
Sold in October 2020
beckside lendales lane, north yorkshire
£630,000
13.
Sold in November 2022
linden glade , ryedale
£627,500
14.
Sold in November 2013
19 hall garth, north yorkshire
£620,000
15.
Sold in July 2023
6 beacon park, north yorkshire
£620,000
16.
Sold in October 2002
the old rectory , ryedale
£610,000
17.
Sold in September 2024
44 rosamund avenue, north yorkshire
£590,000
18.
Sold in October 2025
8 undercliffe, north yorkshire
£580,000
19.
Sold in June 2024
heron reach , north yorkshire
£570,000
20.
Sold in February 2021
74 ruffa lane, north yorkshire
£562,500
21.
Sold in September 2012
118 eastgate, north yorkshire
£560,000
22.
Sold in March 2022
three gables hawthorn lane, north yorkshire
£560,000
Sold for a lower amount since this price
23.
Sold in 2018
keld head house keld head, north yorkshire
£560,000
24.
Sold in June 2023
22 derwent road, north yorkshire
£555,000
25.
Sold in April 2021
20 eastgate, north yorkshire
£550,000
26.
Sold in October 2025
three gables hawthorn lane, north yorkshire
£550,000
27.
Sold in July 2021
mulberry house , ryedale
£550,000
28.
Sold in April 2023
84 derwent road, north yorkshire
£545,000
29.
Sold in October 2008
37 potter hill, north yorkshire
£545,000
30.
Sold in July 2024
44 westlands, north yorkshire
£542,500
31.
Sold in December 2014
beckside lendales lane, north yorkshire
£535,000
32.
Sold in September 2019
7 castle road, north yorkshire
£531,000
33.
Sold in September 2014
100 eastgate, north yorkshire
£525,000
34.
Sold in March 2025
bramble garth , north yorkshire
£525,000
35.
Sold in August 2024
60 middleton road, north yorkshire
£525,000
36.
Sold in December 2024
milestone cottage porters headland, north yorkshire
£522,500
37.
Sold in April 2025
7 derwent road, north yorkshire
£510,000
38.
Sold in December 2022
saintoft lodge , north yorkshire
£505,000
39.
Sold in April 2008
11 smiddy hill, north yorkshire
£504,000
40.
Sold in November 2023
32 thornton road, north yorkshire
£503,000
41.
Sold in September 2006
castlegate house castlegate, north yorkshire
£500,000
42.
Sold in October 2022
49 eastgate, north yorkshire
£500,000
43.
Sold in February 2023
2 green howards road, north yorkshire
£500,000
44.
Sold in April 2021
wayside goslipgate, north yorkshire
£500,000
45.
Sold in March 2023
grafton house , north yorkshire
£499,000
46.
Sold in July 2024
70 eastgate, north yorkshire
£497,500
47.
Sold in October 2022
spring cottage keld head, north yorkshire
£496,000
48.
Sold in June 2024
4 the courtyard, north yorkshire
£495,000
49.
Sold in 2020
52 ruffa lane, north yorkshire
£495,000
50.
Sold in 2008
newbridge road, north yorkshire
£495,000
51.
Sold in October 2007
one oak , ryedale
£490,000
52.
Sold in February 2009
42 eastgate, north yorkshire
£490,000
53.
Sold in 2004
chesterfield , ryedale
£490,000
54.
Sold in April 2006
68 ruffa lane, north yorkshire
£487,000
55.
Sold in December 2021
86 derwent road, north yorkshire
£485,000
56.
Sold in October 2024
18 derwent road, north yorkshire
£485,000
57.
Sold in October 2022
25 dove road, north yorkshire
£485,000
58.
Sold in August 2022
9 derwent road, north yorkshire
£482,500
59.
Sold in December 2021
61 eastgate, north yorkshire
£480,000
60.
Sold in August 2024
9 eastfield road, north yorkshire
£480,000
61.
Sold in 2021
90 derwent road, north yorkshire
£480,000
62.
Sold in March 2020
44 westlands, north yorkshire
£475,000
63.
Sold in February 2022
44 ruffa lane, north yorkshire
£475,000
64.
Sold in 2022
87 derwent road, north yorkshire
£475,000
65.
Sold in July 2022
7 pipers acre, north yorkshire
£475,000
66.
Sold in 2017
mulberry house , ryedale
£472,000
67.
Sold in July 2025
6 willowgate, north yorkshire
£470,000
68.
Sold in April 2020
2 thornton road, north yorkshire
£470,000
69.
Sold in July 2025
castle view porters headland, north yorkshire
£470,000
70.
Sold in 2011
2 herisson close, north yorkshire
£469,000
71.
Sold in February 2015
2 thornton road, north yorkshire
£465,000
72.
Sold in February 2021
19 dove road, north yorkshire
£462,000
Sold for a lower amount since this price
73.
Sold in June 2017
23 burgate, north yorkshire
£460,000
74.
Sold in October 2023
nursery cottage whitby road, north yorkshire
£460,000
75.
Sold in October 2021
the hawthorns outgang lane, north yorkshire
£460,000
76.
Sold in 2024
11 derwent road, north yorkshire
£460,000
77.
Sold in July 2021
25 dove road, north yorkshire
£460,000
78.
Sold in 2023
3 dove road, north yorkshire
£460,000
79.
Sold in October 2023
1 middleton road, north yorkshire
£460,000
80.
Sold in December 2020
18 derwent road, north yorkshire
£459,995
81.
Sold in March 2022
lynwood beansheaf malton road, north yorkshire
£457,500
82.
Sold in July 2024
6 willowgate, north yorkshire
£456,000
83.
Sold in August 2023
26 derwent road, north yorkshire
£455,500
84.
Sold in September 2011
74 ruffa lane, north yorkshire
£455,000
85.
Sold in October 2016
72 ruffa lane, north yorkshire
£455,000
86.
Sold in June 2017
30 eastfield road, north yorkshire
£455,000
87.
Sold in November 2022
23 thornton road, north yorkshire
£455,000
88.
Sold in December 2020
20 derwent road, north yorkshire
£454,995
89.
Sold in August 2022
30 corbie way, north yorkshire
£453,000
Sold for a lower amount since this price
90.
Sold in June 2024
23 rosamund avenue, north yorkshire
£452,500
91.
Sold in November 2025
19 dove road, north yorkshire
£452,500
92.
Sold in April 2023
24 derwent road, north yorkshire
£452,000
93.
Sold in March 2025
east croft eastgate, north yorkshire
£450,000
94.
Sold in October 2023
42 rosamund avenue, north yorkshire
£450,000
95.
Sold in 2022
uplands whitby road, north yorkshire
£450,000
96.
Sold in August 2007
76 ruffa lane, north yorkshire
£450,000
97.
Sold in August 2007
the beeches hatcase lane, north yorkshire
£450,000
98.
Sold in August 2022
thornycroft malton road, north yorkshire
£450,000
99.
Sold in June 2006
buckthorn farm haygate lane, north yorkshire
£450,000
100.
Sold in November 2018
36 potter hill, north yorkshire
£450,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Pickering 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 18:02 with the latest HM Land Registry data (February 2026). The Pickering dataset covers 321 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.