House Price Watch
100 most expensive houses in Helmsley
In the charming area of Helmsley, part of Ryedale, the real estate market has seen a fascinating range of house prices. The most expensive house sold for an impressive £2,800,000 in 2017, while the least expensive on the list was £450,000. Notably, 15 of these homes are located on the same street, Carlton Road, Orchard Way. Since 1995, there have been a total of 1111 sales in the area, with the latest sale recorded in 2025.
Sold in July 2017
beckdale house stokesley road, north yorkshire
£2,800,000
Sold in August 2021
knipes hall high street, north yorkshire
£1,400,000
Sold in June 2024
24 castlegate, north yorkshire
£1,350,000
4.
Sold in December 2021
41 bridge street, north yorkshire
£1,250,000
5.
Sold in July 2025
5a villiers court, north yorkshire
£850,000
6.
Sold in April 2018
70 bondgate, north yorkshire
£825,000
7.
Sold in February 2020
26 carlton road, north yorkshire
£825,000
8.
Sold in May 2024
16 orchard way, north yorkshire
£800,000
9.
Sold in November 2021
13 high street, north yorkshire
£795,000
10.
Sold in September 2024
6 linkfoot close, north yorkshire
£773,925
Most expensive houses in areas around Helmsley
£2,000,000
-28.57%
£2,908,234
3.87%
£1,480,000
-47.14%
£2,650,000
-5.36%
£1,200,000
-57.14%
£890,000
-68.21%
£4,125,000
47.32%
11.
Sold in November 2024
the cottage , north yorkshire
£760,000
12.
Sold in July 2024
8 castlegate, north yorkshire
£750,000
13.
Sold in June 2024
1 pottergate, north yorkshire
£750,000
14.
Sold in July 2023
36 orchard way, north yorkshire
£750,000
15.
Sold in September 2018
buckingham house , ryedale
£740,000
16.
Sold in November 2020
18 carlton road, north yorkshire
£725,000
17.
Sold in May 2022
19 linkfoot close, north yorkshire
£715,000
18.
Sold in November 2022
8 castlegate, north yorkshire
£712,005
19.
Sold in July 2010
18 market place, north yorkshire
£700,000
20.
Sold in June 2025
3 carlton road, north yorkshire
£700,000
21.
Sold in November 2025
1 ashwood close, north yorkshire
£685,000
22.
Sold in November 2010
70 bondgate, north yorkshire
£670,000
23.
Sold in October 2025
foxglove cottage , north yorkshire
£650,000
24.
Sold in November 2018
15 station road, north yorkshire
£650,000
25.
Sold in June 2025
1 southlands, north yorkshire
£650,000
26.
Sold in 2023
7 pottergate, north yorkshire
£635,000
27.
Sold in July 2025
33 pottergate, north yorkshire
£631,000
28.
Sold in July 2025
9 linkfoot close, north yorkshire
£631,000
29.
Sold in March 2018
16 orchard way, north yorkshire
£625,000
30.
Sold in May 2019
22 carlton road, north yorkshire
£610,000
31.
Sold in February 2011
canons garth canons garth, north yorkshire
£600,000
32.
Sold in April 2025
36 bondgate, north yorkshire
£600,000
33.
Sold in September 2019
36 orchard way, north yorkshire
£599,950
34.
Sold in October 2019
25 orchard way, north yorkshire
£595,000
35.
Sold in December 2019
27 orchard way, north yorkshire
£595,000
36.
Sold in December 2020
8 acres close, north yorkshire
£590,000
37.
Sold in April 2025
2 carlton road, north yorkshire
£590,000
38.
Sold in October 2023
13 bondgate, north yorkshire
£585,000
39.
Sold in September 2019
8 acres close, north yorkshire
£580,000
40.
Sold in April 2018
14 orchard way, north yorkshire
£575,000
41.
Sold in October 2006
4 carlton road, north yorkshire
£575,000
42.
Sold in December 2022
2 ashdale road, north yorkshire
£560,000
43.
Sold in June 2023
1 crosland close, north yorkshire
£550,000
44.
Sold in October 2023
3 bondgate, north yorkshire
£550,000
45.
Sold in April 2018
12 orchard way, north yorkshire
£550,000
46.
Sold in March 2017
the cart house pottergate, north yorkshire
£545,000
47.
Sold in July 2016
6 linkfoot close, north yorkshire
£540,000
48.
Sold in March 2016
2 linkfoot close, north yorkshire
£525,000
49.
Sold in May 2016
19 linkfoot close, north yorkshire
£525,000
50.
Sold in August 2018
3 orchard way, north yorkshire
£525,000
51.
Sold in May 2024
5 high street, north yorkshire
£515,000
52.
Sold in 2024
5 orchard way, north yorkshire
£501,000
53.
Sold in July 2022
8 pottergate, north yorkshire
£500,000
54.
Sold in November 2003
westminster house buckingham square, north yorkshire
£500,000
55.
Sold in June 2013
13 carlton road, north yorkshire
£500,000
56.
Sold in August 2018
19 carlton road, north yorkshire
£500,000
57.
Sold in September 2025
7 black swan yard, north yorkshire
£495,000
58.
Sold in June 2018
22 orchard way, north yorkshire
£495,000
59.
Sold in August 2019
29 orchard way, north yorkshire
£495,000
60.
Sold in March 2013
the orchard beckdale road, north yorkshire
£490,000
61.
Sold in July 2021
3 vicarage farm, north yorkshire
£489,950
62.
Sold in April 2025
2 chapel close, north yorkshire
£485,000
63.
Sold in October 2020
4 orchard way, north yorkshire
£485,000
64.
Sold in December 2024
6 orchard way, north yorkshire
£485,000
65.
Sold in May 2019
24 carlton road, north yorkshire
£485,000
66.
Sold in July 2019
16 carlton road, north yorkshire
£480,000
67.
Sold in September 2020
31 orchard way, north yorkshire
£479,950
68.
Sold in December 2017
foxglove cottage , ryedale
£475,000
69.
Sold in August 2015
40 - 42 high street, north yorkshire
£475,000
70.
Sold in September 2023
7 black swan yard, north yorkshire
£475,000
71.
Sold in November 2014
2 vicarage farm, north yorkshire
£475,000
72.
Sold in November 2015
9 linkfoot close, north yorkshire
£475,000
73.
Sold in 2019
1 swanland road, north yorkshire
£475,000
74.
Sold in November 2020
15 carlton road, north yorkshire
£475,000
75.
Sold in December 2024
45a ashdale road, north yorkshire
£472,000
76.
Sold in September 2022
1 ryegate, north yorkshire
£470,000
77.
Sold in April 2009
13 high street, north yorkshire
£470,000
78.
Sold in December 2025
1 elmslac road, north yorkshire
£470,000
79.
Sold in September 2022
42 the limes, north yorkshire
£470,000
80.
Sold in 2016
19 black swan yard, north yorkshire
£470,000
81.
Sold in October 2021
8 linkfoot close, north yorkshire
£470,000
82.
Sold in July 2020
3 swanland road, north yorkshire
£470,000
83.
Sold in September 2022
2 swanland road, north yorkshire
£470,000
84.
Sold in March 2017
swan cottage canons garth lane, north yorkshire
£468,000
85.
Sold in December 2015
4 linkfoot close, north yorkshire
£465,000
86.
Sold in December 2014
25 high street, north yorkshire
£462,000
87.
Sold in April 2014
1 canons garth lane, north yorkshire
£460,000
88.
Sold in May 2018
8 feversham road, north yorkshire
£460,000
89.
Sold in December 2022
2 ryedale close, north yorkshire
£460,000
90.
Sold in May 2024
3 ryedale close, north yorkshire
£460,000
91.
Sold in December 2014
cragstone house elmslac close, north yorkshire
£459,000
92.
Sold in May 2018
20 ashdale road, north yorkshire
£457,000
93.
Sold in August 2023
mouse cottage , north yorkshire
£456,000
94.
Sold in August 2023
mouse cottage , north yorkshire
£456,000
95.
Sold in July 2019
8 chapel close, north yorkshire
£455,000
96.
Sold in August 2005
1 vicarage farm, north yorkshire
£455,000
97.
Sold in December 2024
29 ashwood close, north yorkshire
£452,000
98.
Sold in April 2010
10 acres close, north yorkshire
£451,000
99.
Sold in November 2016
1 linkfoot close, north yorkshire
£450,000
100.
Sold in May 2019
20 carlton road, north yorkshire
£450,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Helmsley 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 Helmsley dataset covers 198 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.