House Price Watch
100 most expensive houses in Winterslow
In the charming village of Winterslow, nestled in Wiltshire, the real estate market has seen a fascinating range of transactions. The most expensive house sold for an impressive £2,800,000 in 2009, while the least expensive found a new owner for £580,000. Notably, 9 of the houses on the same street, 'The Flood', highlight the area's appeal. Since 1995, there have been a remarkable 1014 sales, with the latest transaction recorded in 2025. Winterslow truly showcases a diverse housing landscape!
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
27.
Sold in June 2023
newlyn tytherley road, wiltshire
£840,000
28.
Sold in August 2013
fourwynds tytherley road, wiltshire
£800,000
29.
Sold in October 2012
hedgemoor house easton common hill, wiltshire
£800,000
30.
Sold in September 2006
beech house , wiltshire
£795,000
31.
Sold in August 2017
lopcombe house , wiltshire
£795,000
32.
Sold in September 2022
bemerton weston lane, wiltshire
£790,000
33.
Sold in September 2025
3 wellsted close, wiltshire
£780,000
34.
Sold in 2022
kings farm house livery road, wiltshire
£770,000
35.
Sold in July 2021
1 witt road, wiltshire
£767,500
36.
Sold in December 2007
mancett house easton common hill, wiltshire
£765,000
37.
Sold in October 2020
woodleaze gunville road, wiltshire
£760,000
38.
Sold in October 2021
uplands tytherley road, wiltshire
£750,000
39.
Sold in June 2014
oak house beech close, wiltshire
£750,000
40.
Sold in September 2024
oak tree house middleton road, wiltshire
£735,000
41.
Sold in May 2019
walnut cottage middleton, wiltshire
£735,000
42.
Sold in October 2014
crewkerne farm bungalow pitton road, wiltshire
£735,000
43.
Sold in February 2011
ayres barn tytherley road, wiltshire
£725,000
44.
Sold in December 2023
tannenhaus tytherley road, wiltshire
£725,000
45.
Sold in August 2019
north lodge west dean road, wiltshire
£720,000
46.
Sold in May 2021
1 wellsted close, wiltshire
£715,000
47.
Sold in October 2017
middleton house middleton, wiltshire
£715,000
48.
Sold in April 2021
2 wellsted close, wiltshire
£710,000
49.
Sold in March 2025
douai house easton common hill, wiltshire
£710,000
50.
Sold in November 2015
3 yew tree close, wiltshire
£710,000
51.
Sold in December 2017
hillside cottage red lane, wiltshire
£705,000
52.
Sold in November 2002
beech house , wiltshire
£702,500
53.
Sold in September 2020
the calypso middleton road, wiltshire
£702,500
54.
Sold in March 2021
3 wellsted close, wiltshire
£700,000
55.
Sold in October 2006
barn owl cottage tytherley road, wiltshire
£700,000
56.
Sold in March 2021
alveus the causeway, wiltshire
£700,000
57.
Sold in October 2018
newlyn tytherley road, wiltshire
£695,000
58.
Sold in March 2025
beaulah livery road, wiltshire
£690,000
59.
Sold in February 2019
flint field house the street, wiltshire
£687,500
60.
Sold in February 2021
12 wellsted close, wiltshire
£685,000
61.
Sold in June 2015
the old shop weston lane, wiltshire
£685,000
62.
Sold in February 2007
gutteridge farm barns , wiltshire
£675,000
63.
Sold in October 2014
mulberry house beech close, wiltshire
£675,000
64.
Sold in April 2018
old post office middleton road, wiltshire
£675,000
65.
Sold in May 2015
owls thatch livery road, wiltshire
£675,000
66.
Sold in September 2025
grovely middleton road, wiltshire
£673,500
67.
Sold in September 2024
bramble cottage , wiltshire
£660,000
68.
Sold in April 2021
11 wellsted close, wiltshire
£650,000
69.
Sold in September 2000
la-vista weston lane, wiltshire
£650,000
70.
Sold in July 2014
tregonia the street, wiltshire
£650,000
71.
Sold in June 2017
chez-nous tytherley road, wiltshire
£642,500
72.
Sold in October 2020
tannenhaus tytherley road, wiltshire
£642,500
73.
Sold in October 2004
4 beech close, wiltshire
£640,000
74.
Sold in 2009
mulberry house beech close, wiltshire
£637,500
75.
Sold in October 2018
sunnymeade the causeway, wiltshire
£635,000
76.
Sold in March 2012
high walls the street, wiltshire
£635,000
77.
Sold in September 2013
flint field house the street, wiltshire
£635,000
78.
Sold in October 2014
ashton beeches tytherley road, wiltshire
£630,000
79.
Sold in July 2013
eaton house middleton, wiltshire
£627,500
80.
Sold in November 2023
mount heights stockbridge road, wiltshire
£625,000
81.
Sold in July 2007
rowan house gunville road, wiltshire
£625,000
82.
Sold in March 2003
4 beech close, wiltshire
£625,000
83.
Sold in October 2003
oak house beech close, wiltshire
£625,000
84.
Sold in December 2006
crewkerne farm bungalow pitton road, wiltshire
£623,000
85.
Sold in 2021
meadow bank livery road, wiltshire
£620,000
86.
Sold in March 2015
beechwood livery road, wiltshire
£615,000
87.
Sold in November 2007
3 kings paddock, wiltshire
£610,000
88.
Sold in October 2013
clearbury middleton road, wiltshire
£605,000
89.
Sold in February 2021
hebron middleton, wiltshire
£605,000
90.
Sold in December 2020
white gates tytherley road, wiltshire
£600,000
91.
Sold in May 2014
park house west dean road, wiltshire
£600,000
92.
Sold in February 2003
brooking house beech close, wiltshire
£600,000
93.
Sold in August 2022
plantation cottage the plantation, wiltshire
£600,000
94.
Sold in December 2024
lilac cottage , wiltshire
£595,000
95.
Sold in November 2009
sandling house , wiltshire
£595,000
96.
Sold in May 2022
little acre tytherley road, wiltshire
£590,000
97.
Sold in September 2017
5 keel close, wiltshire
£580,000
98.
Sold in 2015
gutteridge farm barns , wiltshire
£580,000
99.
Sold in July 2022
little petherton middleton, wiltshire
£580,000
100.
Sold in August 2019
middleton house youngs paddock, 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 August 2025 (The latest available from HM Land Registry). Prices reflect actual recorded transactions, not current market valuations.