House Price Watch
100 most expensive houses in Helmsley
In the picturesque area of Helmsley, nestled within Ryedale, the housing market has seen a remarkable range of prices. The most expensive house sold for an impressive £2,800,000 in 2017, while the least expensive fetched £440,000. Notably, 15 of these homes are located on the same street, Carlton Road, Orchard Way. Since 1995, there have been a total of 1,084 sales, with the latest transaction occurring in 2025, showcasing the area's vibrant real estate activity.
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 November 2024
the cottage , north yorkshire
£760,000
Most expensive houses in areas around Helmsley
£2,000,000
-28.57%
£1,400,000
-50.00%
£2,650,000
-5.36%
£1,480,000
-47.14%
£1,800,000
-35.71%
£852,000
-69.57%
£4,125,000
47.32%
11.
Sold in July 2024
8 castlegate, north yorkshire
£750,000
12.
Sold in June 2024
1 pottergate, north yorkshire
£750,000
13.
Sold in July 2023
36 orchard way, north yorkshire
£750,000
14.
Sold in September 2018
buckingham house , ryedale
£740,000
15.
Sold in November 2020
18 carlton road, north yorkshire
£725,000
16.
Sold in May 2022
19 linkfoot close, north yorkshire
£715,000
17.
Sold in November 2022
8 castlegate, north yorkshire
£712,005
18.
Sold in July 2010
18 market place, north yorkshire
£700,000
19.
Sold in June 2025
3 carlton road, north yorkshire
£700,000
20.
Sold in November 2010
70 bondgate, north yorkshire
£670,000
21.
Sold in November 2018
15 station road, north yorkshire
£650,000
22.
Sold in 2023
7 pottergate, north yorkshire
£635,000
23.
Sold in July 2025
33 pottergate, north yorkshire
£631,000
24.
Sold in March 2018
16 orchard way, north yorkshire
£625,000
25.
Sold in May 2019
22 carlton road, north yorkshire
£610,000
26.
Sold in February 2011
canons garth canons garth, north yorkshire
£600,000
27.
Sold in April 2025
36 bondgate, north yorkshire
£600,000
28.
Sold in September 2019
36 orchard way, north yorkshire
£599,950
29.
Sold in October 2019
25 orchard way, north yorkshire
£595,000
30.
Sold in December 2019
27 orchard way, north yorkshire
£595,000
31.
Sold in December 2020
8 acres close, north yorkshire
£590,000
32.
Sold in April 2025
2 carlton road, north yorkshire
£590,000
33.
Sold in October 2023
13 bondgate, north yorkshire
£585,000
34.
Sold in September 2019
8 acres close, north yorkshire
£580,000
35.
Sold in April 2018
14 orchard way, north yorkshire
£575,000
36.
Sold in October 2006
4 carlton road, north yorkshire
£575,000
37.
Sold in December 2022
2 ashdale road, north yorkshire
£560,000
38.
Sold in June 2023
1 crosland close, north yorkshire
£550,000
39.
Sold in October 2023
3 bondgate, north yorkshire
£550,000
40.
Sold in April 2018
12 orchard way, north yorkshire
£550,000
41.
Sold in March 2017
the cart house pottergate, north yorkshire
£545,000
42.
Sold in July 2016
6 linkfoot close, north yorkshire
£540,000
43.
Sold in March 2016
2 linkfoot close, north yorkshire
£525,000
44.
Sold in May 2016
19 linkfoot close, north yorkshire
£525,000
45.
Sold in August 2018
3 orchard way, north yorkshire
£525,000
46.
Sold in May 2024
5 high street, north yorkshire
£515,000
47.
Sold in 2024
5 orchard way, north yorkshire
£501,000
48.
Sold in July 2022
8 pottergate, north yorkshire
£500,000
49.
Sold in November 2003
westminster house buckingham square, north yorkshire
£500,000
50.
Sold in June 2013
13 carlton road, north yorkshire
£500,000
51.
Sold in August 2018
19 carlton road, north yorkshire
£500,000
52.
Sold in June 2018
22 orchard way, north yorkshire
£495,000
53.
Sold in August 2019
29 orchard way, north yorkshire
£495,000
54.
Sold in March 2013
the orchard beckdale road, north yorkshire
£490,000
55.
Sold in July 2021
3 vicarage farm, north yorkshire
£489,950
56.
Sold in April 2025
2 chapel close, north yorkshire
£485,000
57.
Sold in October 2020
4 orchard way, north yorkshire
£485,000
58.
Sold in December 2024
6 orchard way, north yorkshire
£485,000
59.
Sold in May 2019
24 carlton road, north yorkshire
£485,000
60.
Sold in July 2019
16 carlton road, north yorkshire
£480,000
61.
Sold in September 2020
31 orchard way, north yorkshire
£479,950
62.
Sold in December 2017
foxglove cottage , ryedale
£475,000
63.
Sold in August 2015
40 - 42 high street, north yorkshire
£475,000
64.
Sold in September 2023
7 black swan yard, north yorkshire
£475,000
65.
Sold in November 2014
2 vicarage farm, north yorkshire
£475,000
66.
Sold in November 2015
9 linkfoot close, north yorkshire
£475,000
67.
Sold in 2019
1 swanland road, north yorkshire
£475,000
68.
Sold in November 2020
15 carlton road, north yorkshire
£475,000
69.
Sold in December 2024
45a ashdale road, north yorkshire
£472,000
70.
Sold in September 2022
1 ryegate, north yorkshire
£470,000
71.
Sold in April 2009
13 high street, north yorkshire
£470,000
72.
Sold in September 2022
42 the limes, north yorkshire
£470,000
73.
Sold in 2016
19 black swan yard, north yorkshire
£470,000
74.
Sold in October 2021
8 linkfoot close, north yorkshire
£470,000
75.
Sold in July 2020
3 swanland road, north yorkshire
£470,000
76.
Sold in September 2022
2 swanland road, north yorkshire
£470,000
77.
Sold in March 2017
swan cottage canons garth lane, north yorkshire
£468,000
78.
Sold in December 2015
4 linkfoot close, north yorkshire
£465,000
79.
Sold in December 2014
25 high street, north yorkshire
£462,000
80.
Sold in April 2014
1 canons garth lane, north yorkshire
£460,000
81.
Sold in May 2018
8 feversham road, north yorkshire
£460,000
82.
Sold in December 2022
2 ryedale close, north yorkshire
£460,000
83.
Sold in May 2024
3 ryedale close, north yorkshire
£460,000
84.
Sold in December 2014
cragstone house elmslac close, north yorkshire
£459,000
85.
Sold in May 2018
20 ashdale road, north yorkshire
£457,000
86.
Sold in August 2023
mouse cottage , north yorkshire
£456,000
87.
Sold in August 2023
mouse cottage , north yorkshire
£456,000
88.
Sold in July 2019
8 chapel close, north yorkshire
£455,000
89.
Sold in August 2005
1 vicarage farm, north yorkshire
£455,000
90.
Sold in December 2024
29 ashwood close, north yorkshire
£452,000
91.
Sold in April 2010
10 acres close, north yorkshire
£451,000
92.
Sold in November 2016
1 linkfoot close, north yorkshire
£450,000
93.
Sold in May 2019
20 carlton road, north yorkshire
£450,000
94.
Sold in October 2024
7 feversham road, north yorkshire
£450,000
95.
Sold in September 2018
10 chapel close, north yorkshire
£447,500
96.
Sold in April 2021
28 high street, north yorkshire
£445,000
97.
Sold in December 2024
20 ashwood close, north yorkshire
£445,000
98.
Sold in March 2023
4 black swan yard, north yorkshire
£444,100
99.
Sold in July 2021
6 stone garth, north yorkshire
£440,000
100.
Sold in December 2007
28 bondgate, north yorkshire
£440,000
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 in June 2025 (The latest available from HM Land Registry). Prices reflect actual recorded transactions, not current market valuations.