House Price Watch
100 most expensive houses in Old Headington
Old Headington, a charming part of Headington, has seen a fascinating real estate landscape. The most expensive house sold here reached a staggering £2,260,000 in 2022, while the least expensive was priced at £540,000. Notably, 14 of the homes are located on the same street, Osler Road. Since 1995, there have been 392 sales in the area, with the latest transaction recorded in 2025. This neighborhood continues to attract attention for its diverse property values and vibrant community.
Sold in April 2022
40 osler road, oxfordshire
£2,260,000
Sold in September 2025
st andrews house st andrews road, oxfordshire
£2,020,000
Sold in December 2015
the barn barton lane, oxfordshire
£1,800,000
4.
Sold in February 2019
4a osler road, oxfordshire
£1,550,000
5.
Sold in March 2019
rookery cottage stoke place, oxfordshire
£1,489,000
6.
Sold in September 2022
meadow larkin larkins lane, oxfordshire
£1,450,000
7.
Sold in March 2020
39 st andrews road, oxfordshire
£1,325,000
8.
Sold in March 2020
39 st andrews road, oxfordshire
£1,325,000
9.
Sold in May 2017
10 stoke place, oxfordshire
£1,262,500
10.
Sold in February 2024
8 st andrews lane, oxfordshire
£1,243,000
Most expensive houses in areas around Old Headington
£1,215,000
-46.24%
£2,070,000
-8.41%
£840,000
-62.83%
£750,000
-66.81%
£5,200,000
130.09%
11.
Sold in April 2022
55 osler road, oxfordshire
£1,200,000
12.
Sold in December 2014
1 dunstan road, oxfordshire
£1,200,000
13.
Sold in November 2024
ethelred court dunstan road, oxfordshire
£1,200,000
14.
Sold in December 2019
meadow larkin larkins lane, oxfordshire
£1,200,000
15.
Sold in November 2024
58 barton lane, oxfordshire
£1,200,000
16.
Sold in March 2024
stoke cottage , oxford
£1,150,000
17.
Sold in June 2019
18 dunstan road, oxfordshire
£1,150,000
18.
Sold in November 2015
ethelred court dunstan road, oxfordshire
£1,112,452
19.
Sold in October 2011
3 william orchard close, oxfordshire
£1,075,000
20.
Sold in December 2019
ethelred court dunstan road, oxfordshire
£1,060,000
21.
Sold in July 2018
8 st andrews lane, oxfordshire
£1,050,000
22.
Sold in November 2023
white lodge osler road, oxfordshire
£1,000,000
23.
Sold in August 2024
6 stoke place, oxfordshire
£975,000
24.
Sold in December 2015
37 st andrews road, oxfordshire
£950,000
25.
Sold in 2022
2 william orchard close, oxfordshire
£940,000
26.
Sold in October 2023
7 ethelred court, oxfordshire
£925,000
27.
Sold in April 2009
72 old high street, oxfordshire
£900,000
28.
Sold in February 2002
st andrews house st andrews road, oxfordshire
£895,000
29.
Sold in September 2004
10 st andrews road, oxfordshire
£895,000
30.
Sold in June 2010
stoke cottage , oxford
£894,000
31.
Sold in February 2019
6 st andrews lane, oxfordshire
£880,000
32.
Sold in December 2004
72 old high street, oxfordshire
£880,000
33.
Sold in December 2020
7 dunstan road, oxfordshire
£865,000
34.
Sold in March 2008
14 st andrews lane, oxfordshire
£865,000
35.
Sold in 2022
1 the croft, oxfordshire
£855,000
36.
Sold in 2022
2 the croft, oxfordshire
£855,000
37.
Sold in December 2007
8 larkins lane, oxfordshire
£850,003
38.
Sold in October 2022
43 stephen road, oxfordshire
£850,000
39.
Sold in September 2009
old pound house the croft, oxfordshire
£850,000
40.
Sold in August 2014
45 stephen road, oxfordshire
£847,500
41.
Sold in May 2015
26 osler road, oxfordshire
£820,000
42.
Sold in February 2014
the old stables st andrews lane, oxfordshire
£811,000
43.
Sold in April 2018
4 old high street, oxfordshire
£810,000
44.
Sold in October 2014
22 osler road, oxfordshire
£805,000
45.
Sold in December 2020
25 stephen road, oxfordshire
£800,000
46.
Sold in September 2018
16 dunstan road, oxfordshire
£800,000
47.
Sold in 2020
7 st andrews road, oxfordshire
£780,000
48.
Sold in June 2023
6 old high street, oxfordshire
£775,000
49.
Sold in March 2014
41 old high street, oxfordshire
£772,000
50.
Sold in February 2011
30 stephen road, oxfordshire
£770,000
51.
Sold in November 2024
22 old high street, oxfordshire
£770,000
52.
Sold in August 2023
7 stephen road, oxfordshire
£752,000
53.
Sold in February 2014
4 william orchard close, oxfordshire
£750,000
54.
Sold in May 2019
28 old high street, oxfordshire
£750,000
55.
Sold in April 2018
20 osler road, oxfordshire
£738,000
56.
Sold in August 2025
31 st andrews road, oxfordshire
£700,000
57.
Sold in June 2004
56 - 58 old high street, oxfordshire
£700,000
58.
Sold in May 2025
39 old high street, oxfordshire
£699,000
59.
Sold in April 2015
7 st andrews road, oxfordshire
£695,000
60.
Sold in April 2010
17 the croft, oxfordshire
£689,000
61.
Sold in July 2023
43 osler road, oxfordshire
£685,000
62.
Sold in July 2021
1 larkins lane, oxfordshire
£680,000
63.
Sold in February 2006
83 old high street, oxfordshire
£675,000
64.
Sold in May 2019
59 old high street, oxfordshire
£675,000
65.
Sold in May 2023
17 laurel farm close, oxfordshire
£670,000
66.
Sold in August 2013
37 osler road, oxfordshire
£662,400
67.
Sold in August 2013
3b larkins lane, oxfordshire
£641,200
68.
Sold in June 2014
10 old high street, oxfordshire
£640,000
69.
Sold in November 2005
uplands dunstan road, oxfordshire
£625,000
70.
Sold in August 2020
2 larkins lane, oxfordshire
£625,000
71.
Sold in September 2008
10 osler road, oxfordshire
£620,000
72.
Sold in April 2021
40 old high street, oxfordshire
£620,000
73.
Sold in November 2022
27 stephen road, oxfordshire
£617,500
74.
Sold in September 2017
9 osler road, oxfordshire
£615,000
75.
Sold in November 2014
79 old high street, oxfordshire
£610,000
76.
Sold in June 2003
8 larkins lane, oxfordshire
£605,000
77.
Sold in February 2017
5 stephen road, oxfordshire
£600,000
78.
Sold in September 2012
39 osler road, oxfordshire
£600,000
79.
Sold in November 2005
8 the croft, oxfordshire
£600,000
80.
Sold in November 2002
ebor dunstan road, oxfordshire
£600,000
81.
Sold in December 2020
5 stoke place, oxfordshire
£597,000
82.
Sold in October 2013
7 st andrews road, oxfordshire
£595,000
83.
Sold in June 2021
49 old high street, oxfordshire
£591,000
84.
Sold in November 1999
10 st andrews road, oxfordshire
£590,000
85.
Sold in 2018
8 st andrews road, oxfordshire
£590,000
86.
Sold in October 2014
2 larkins lane, oxfordshire
£590,000
87.
Sold in April 2025
51 old high street, oxfordshire
£590,000
88.
Sold in November 2008
38 osler road, oxfordshire
£581,000
89.
Sold in 2000
14 st andrews lane, oxfordshire
£580,000
90.
Sold in October 2010
20 old high street, oxfordshire
£580,000
91.
Sold in August 2013
6 old high street, oxfordshire
£575,000
92.
Sold in September 2015
39 old high street, oxfordshire
£575,000
93.
Sold in September 2019
19 laurel farm close, oxfordshire
£565,000
94.
Sold in October 2014
41 stephen road, oxfordshire
£550,000
95.
Sold in June 2015
9 osler road, oxfordshire
£550,000
96.
Sold in August 2003
7 the croft, oxfordshire
£550,000
97.
Sold in October 2017
17 st andrews lane, oxfordshire
£545,000
98.
Sold in July 2013
1 larkins lane, oxfordshire
£545,000
99.
Sold in 2019
14 laurel farm close, oxfordshire
£540,000
100.
Sold in November 2004
3 north place, oxfordshire
£540,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Old Headington 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 November 2025 (The latest available from HM Land Registry). Prices reflect actual recorded transactions, not current market valuations.