House Price Watch
100 most expensive houses in Winterslow
Winterslow, nestled in beautiful Wiltshire, has seen a vibrant real estate market with 1,021 sales since 1995. Among these, the most expensive house fetched an impressive £2,800,000 in 2009, while the least costly was sold for £580,000. Notably, 9 of the houses on the same street, 'The Flood,' highlight the area's charm. The latest sale, occurring in 2025, suggests that Winterslow continues to attract buyers looking for their dream home.
Sold in November 2009
buckland house the street, wiltshire
£2,800,000
Sold in July 2021
plantation house weston lane, wiltshire
£1,895,000
Sold in October 2020
middleton manor , wiltshire
£1,800,000
4.
Sold in April 2025
the shooting box livery road, wiltshire
£1,475,000
5.
Sold in August 2002
buckland house the street, wiltshire
£1,400,000
6.
Sold in November 2015
toad hall , wiltshire
£1,375,000
7.
Sold in March 2021
green barn weston lane, wiltshire
£1,325,000
8.
Sold in March 2024
kestrel house middleton, wiltshire
£1,240,000
9.
Sold in September 2006
middleton manor , wiltshire
£1,180,000
10.
Sold in October 2021
south lodge roche court , wiltshire
£1,150,000
Most expensive houses in areas around Winterslow
£2,146,500
-23.34%
£4,550,000
62.50%
£2,172,500
-22.41%
£1,800,000
-35.71%
£1,537,000
-45.11%
£1,525,000
-45.54%
£19,082,218
581.51%
11.
Sold in 2021
gutteridge farm barns , wiltshire
£1,060,000
12.
Sold in August 2001
the beeches the plantation, wiltshire
£1,010,000
13.
Sold in July 2021
mulberry house beech close, wiltshire
£1,000,000
14.
Sold in November 2016
fralex middleton road, wiltshire
£975,000
Sold for a lower amount since this price
15.
Sold in September 2015
the shooting box livery road, wiltshire
£975,000
16.
Sold in 2020
the farriers middleton, wiltshire
£960,000
17.
Sold in 2020
woodlands shripple lane, wiltshire
£950,000
18.
Sold in 2009
south lodge roche court , wiltshire
£935,000
19.
Sold in April 2024
4 beech close, wiltshire
£935,000
20.
Sold in 2021
lowenva shripple lane, wiltshire
£900,000
21.
Sold in March 2020
eaton house middleton, wiltshire
£890,000
22.
Sold in October 2020
kestrel house middleton, wiltshire
£880,000
23.
Sold in October 2013
ramshill , wiltshire
£870,000
24.
Sold in April 2023
beech house livery road, wiltshire
£850,000
25.
Sold in April 2001
holly bush weston lane, wiltshire
£850,000
26.
Sold in June 2022
meadowside livery road, wiltshire
£848,000
Sold for a lower amount since this price
27.
Sold in June 2025
meadowside livery road, wiltshire
£847,000
28.
Sold in June 2023
newlyn tytherley road, wiltshire
£840,000
29.
Sold in August 2013
fourwynds tytherley road, wiltshire
£800,000
30.
Sold in October 2012
hedgemoor house easton common hill, wiltshire
£800,000
31.
Sold in September 2006
beech house , wiltshire
£795,000
32.
Sold in August 2017
lopcombe house , wiltshire
£795,000
33.
Sold in September 2022
bemerton weston lane, wiltshire
£790,000
34.
Sold in September 2025
3 wellsted close, wiltshire
£780,000
35.
Sold in 2022
kings farm house livery road, wiltshire
£770,000
36.
Sold in July 2021
1 witt road, wiltshire
£767,500
37.
Sold in December 2007
mancett house easton common hill, wiltshire
£765,000
38.
Sold in October 2020
woodleaze gunville road, wiltshire
£760,000
39.
Sold in October 2021
uplands tytherley road, wiltshire
£750,000
40.
Sold in June 2014
oak house beech close, wiltshire
£750,000
41.
Sold in September 2024
oak tree house middleton road, wiltshire
£735,000
42.
Sold in May 2019
walnut cottage middleton, wiltshire
£735,000
43.
Sold in October 2014
crewkerne farm bungalow pitton road, wiltshire
£735,000
44.
Sold in February 2011
ayres barn tytherley road, wiltshire
£725,000
45.
Sold in December 2023
tannenhaus tytherley road, wiltshire
£725,000
46.
Sold in August 2019
north lodge west dean road, wiltshire
£720,000
47.
Sold in May 2021
1 wellsted close, wiltshire
£715,000
48.
Sold in October 2017
middleton house middleton, wiltshire
£715,000
49.
Sold in April 2021
2 wellsted close, wiltshire
£710,000
50.
Sold in March 2025
douai house easton common hill, wiltshire
£710,000
51.
Sold in November 2015
3 yew tree close, wiltshire
£710,000
52.
Sold in December 2017
hillside cottage red lane, wiltshire
£705,000
53.
Sold in November 2002
beech house , wiltshire
£702,500
54.
Sold in September 2020
the calypso middleton road, wiltshire
£702,500
55.
Sold in March 2021
3 wellsted close, wiltshire
£700,000
56.
Sold in October 2006
barn owl cottage tytherley road, wiltshire
£700,000
57.
Sold in March 2021
alveus the causeway, wiltshire
£700,000
58.
Sold in October 2018
newlyn tytherley road, wiltshire
£695,000
59.
Sold in March 2025
beaulah livery road, wiltshire
£690,000
60.
Sold in February 2019
flint field house the street, wiltshire
£687,500
61.
Sold in February 2021
12 wellsted close, wiltshire
£685,000
62.
Sold in June 2015
the old shop weston lane, wiltshire
£685,000
63.
Sold in February 2007
gutteridge farm barns , wiltshire
£675,000
64.
Sold in October 2014
mulberry house beech close, wiltshire
£675,000
65.
Sold in April 2018
old post office middleton road, wiltshire
£675,000
66.
Sold in May 2015
owls thatch livery road, wiltshire
£675,000
67.
Sold in September 2025
grovely middleton road, wiltshire
£673,500
68.
Sold in September 2024
bramble cottage , wiltshire
£660,000
69.
Sold in April 2021
11 wellsted close, wiltshire
£650,000
70.
Sold in September 2000
la-vista weston lane, wiltshire
£650,000
71.
Sold in July 2014
tregonia the street, wiltshire
£650,000
72.
Sold in June 2017
chez-nous tytherley road, wiltshire
£642,500
73.
Sold in October 2020
tannenhaus tytherley road, wiltshire
£642,500
74.
Sold in October 2004
4 beech close, wiltshire
£640,000
75.
Sold in 2009
mulberry house beech close, wiltshire
£637,500
76.
Sold in October 2018
sunnymeade the causeway, wiltshire
£635,000
77.
Sold in March 2012
high walls the street, wiltshire
£635,000
78.
Sold in September 2013
flint field house the street, wiltshire
£635,000
79.
Sold in October 2014
ashton beeches tytherley road, wiltshire
£630,000
80.
Sold in July 2013
eaton house middleton, wiltshire
£627,500
81.
Sold in November 2023
mount heights stockbridge road, wiltshire
£625,000
82.
Sold in July 2007
rowan house gunville road, wiltshire
£625,000
83.
Sold in March 2003
4 beech close, wiltshire
£625,000
84.
Sold in October 2003
oak house beech close, wiltshire
£625,000
85.
Sold in December 2006
crewkerne farm bungalow pitton road, wiltshire
£623,000
86.
Sold in 2021
meadow bank livery road, wiltshire
£620,000
87.
Sold in March 2015
beechwood livery road, wiltshire
£615,000
88.
Sold in November 2007
3 kings paddock, wiltshire
£610,000
89.
Sold in October 2013
clearbury middleton road, wiltshire
£605,000
90.
Sold in February 2021
hebron middleton, wiltshire
£605,000
91.
Sold in December 2020
white gates tytherley road, wiltshire
£600,000
92.
Sold in May 2014
park house west dean road, wiltshire
£600,000
93.
Sold in February 2003
brooking house beech close, wiltshire
£600,000
94.
Sold in August 2022
plantation cottage the plantation, wiltshire
£600,000
95.
Sold in December 2024
lilac cottage , wiltshire
£595,000
96.
Sold in November 2009
sandling house , wiltshire
£595,000
97.
Sold in May 2022
little acre tytherley road, wiltshire
£590,000
98.
Sold in September 2017
5 keel close, wiltshire
£580,000
99.
Sold in 2015
gutteridge farm barns , wiltshire
£580,000
100.
Sold in July 2022
little petherton middleton, wiltshire
£580,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Winterslow 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.