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 property prices. The most expensive house sold for an impressive £910,000 in 2022, while the least expensive on the list was £445,099. Notably, 10 houses are located on the same street, including Derwent Road, Rye Close, and Whitby Road. Since 1995, there have been a total of 4,841 sales in this vibrant community, 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 October 2021
castlegate house castlegate, north yorkshire
£630,000
Most expensive houses in areas around Pickering
£2,000,000
119.78%
£2,908,234
219.59%
£1,400,000
53.85%
£2,650,000
191.21%
£1,480,000
62.64%
£1,800,000
97.80%
£4,125,000
353.30%
11.
Sold in October 2020
beckside lendales lane, north yorkshire
£630,000
12.
Sold in November 2022
linden glade , ryedale
£627,500
13.
Sold in November 2013
19 hall garth, north yorkshire
£620,000
14.
Sold in July 2023
6 beacon park, north yorkshire
£620,000
15.
Sold in October 2002
the old rectory , ryedale
£610,000
16.
Sold in September 2024
44 rosamund avenue, north yorkshire
£590,000
17.
Sold in June 2024
heron reach , north yorkshire
£570,000
18.
Sold in February 2021
74 ruffa lane, north yorkshire
£562,500
19.
Sold in September 2012
118 eastgate, north yorkshire
£560,000
20.
Sold in March 2022
three gables hawthorn lane, north yorkshire
£560,000
Sold for a lower amount since this price
21.
Sold in 2018
keld head house keld head, north yorkshire
£560,000
22.
Sold in June 2023
22 derwent road, north yorkshire
£555,000
23.
Sold in April 2021
20 eastgate, north yorkshire
£550,000
24.
Sold in October 2025
three gables hawthorn lane, north yorkshire
£550,000
25.
Sold in July 2021
mulberry house , ryedale
£550,000
26.
Sold in April 2023
84 derwent road, north yorkshire
£545,000
27.
Sold in October 2008
37 potter hill, north yorkshire
£545,000
28.
Sold in July 2024
44 westlands, north yorkshire
£542,500
29.
Sold in December 2014
beckside lendales lane, north yorkshire
£535,000
30.
Sold in September 2019
7 castle road, north yorkshire
£531,000
31.
Sold in September 2014
100 eastgate, north yorkshire
£525,000
32.
Sold in March 2025
bramble garth , north yorkshire
£525,000
33.
Sold in August 2024
60 middleton road, north yorkshire
£525,000
34.
Sold in December 2024
milestone cottage porters headland, north yorkshire
£522,500
35.
Sold in April 2025
7 derwent road, north yorkshire
£510,000
36.
Sold in December 2022
saintoft lodge , north yorkshire
£505,000
37.
Sold in April 2008
11 smiddy hill, north yorkshire
£504,000
38.
Sold in November 2023
32 thornton road, north yorkshire
£503,000
39.
Sold in September 2006
castlegate house castlegate, north yorkshire
£500,000
40.
Sold in October 2022
49 eastgate, north yorkshire
£500,000
41.
Sold in February 2023
2 green howards road, north yorkshire
£500,000
42.
Sold in April 2021
wayside goslipgate, north yorkshire
£500,000
43.
Sold in March 2023
grafton house , north yorkshire
£499,000
44.
Sold in July 2024
70 eastgate, north yorkshire
£497,500
45.
Sold in October 2022
spring cottage keld head, north yorkshire
£496,000
46.
Sold in June 2024
4 the courtyard, north yorkshire
£495,000
47.
Sold in 2020
52 ruffa lane, north yorkshire
£495,000
48.
Sold in 2008
newbridge road, north yorkshire
£495,000
49.
Sold in October 2007
one oak , ryedale
£490,000
50.
Sold in February 2009
42 eastgate, north yorkshire
£490,000
51.
Sold in 2004
chesterfield , ryedale
£490,000
52.
Sold in April 2006
68 ruffa lane, north yorkshire
£487,000
53.
Sold in December 2021
86 derwent road, north yorkshire
£485,000
54.
Sold in October 2024
18 derwent road, north yorkshire
£485,000
55.
Sold in October 2022
25 dove road, north yorkshire
£485,000
56.
Sold in August 2022
9 derwent road, north yorkshire
£482,500
57.
Sold in December 2021
61 eastgate, north yorkshire
£480,000
58.
Sold in August 2024
9 eastfield road, north yorkshire
£480,000
59.
Sold in 2021
90 derwent road, north yorkshire
£480,000
60.
Sold in March 2020
44 westlands, north yorkshire
£475,000
61.
Sold in February 2022
44 ruffa lane, north yorkshire
£475,000
62.
Sold in 2022
87 derwent road, north yorkshire
£475,000
63.
Sold in July 2022
7 pipers acre, north yorkshire
£475,000
64.
Sold in 2017
mulberry house , ryedale
£472,000
65.
Sold in July 2025
6 willowgate, north yorkshire
£470,000
66.
Sold in April 2020
2 thornton road, north yorkshire
£470,000
67.
Sold in July 2025
castle view porters headland, north yorkshire
£470,000
68.
Sold in 2011
2 herisson close, north yorkshire
£469,000
69.
Sold in February 2015
2 thornton road, north yorkshire
£465,000
70.
Sold in February 2021
19 dove road, north yorkshire
£462,000
71.
Sold in June 2017
23 burgate, north yorkshire
£460,000
72.
Sold in October 2023
nursery cottage whitby road, north yorkshire
£460,000
73.
Sold in October 2021
the hawthorns outgang lane, north yorkshire
£460,000
74.
Sold in 2024
11 derwent road, north yorkshire
£460,000
75.
Sold in July 2021
25 dove road, north yorkshire
£460,000
76.
Sold in 2023
3 dove road, north yorkshire
£460,000
77.
Sold in October 2023
1 middleton road, north yorkshire
£460,000
78.
Sold in December 2020
18 derwent road, north yorkshire
£459,995
79.
Sold in March 2022
lynwood beansheaf malton road, north yorkshire
£457,500
80.
Sold in July 2024
6 willowgate, north yorkshire
£456,000
81.
Sold in August 2023
26 derwent road, north yorkshire
£455,500
82.
Sold in September 2011
74 ruffa lane, north yorkshire
£455,000
83.
Sold in October 2016
72 ruffa lane, north yorkshire
£455,000
84.
Sold in June 2017
30 eastfield road, north yorkshire
£455,000
85.
Sold in November 2022
23 thornton road, north yorkshire
£455,000
86.
Sold in December 2020
20 derwent road, north yorkshire
£454,995
87.
Sold in August 2022
30 corbie way, north yorkshire
£453,000
Sold for a lower amount since this price
88.
Sold in June 2024
23 rosamund avenue, north yorkshire
£452,500
89.
Sold in April 2023
24 derwent road, north yorkshire
£452,000
90.
Sold in October 2023
42 rosamund avenue, north yorkshire
£450,000
91.
Sold in 2022
uplands whitby road, north yorkshire
£450,000
92.
Sold in August 2007
76 ruffa lane, north yorkshire
£450,000
93.
Sold in August 2007
the beeches hatcase lane, north yorkshire
£450,000
94.
Sold in August 2022
thornycroft malton road, north yorkshire
£450,000
95.
Sold in June 2006
buckthorn farm haygate lane, north yorkshire
£450,000
96.
Sold in November 2018
36 potter hill, north yorkshire
£450,000
97.
Sold in April 2020
7 derwent road, north yorkshire
£448,995
98.
Sold in June 2023
28 derwent road, north yorkshire
£448,705
Sold for a lower amount since this price
99.
Sold in 2020
21 dove road, north yorkshire
£445,466
100.
Sold in October 2018
east garth eastgate, north yorkshire
£445,099
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 in September 2025 (The latest available from HM Land Registry). Prices reflect actual recorded transactions, not current market valuations.