House Price Watch
100 most expensive houses in Winterslow
In the charming area of Winterslow, nestled in Wiltshire, the property market has seen a fascinating range of house prices. The most expensive house sold for an impressive £2,800,000 in 2009, while the least expensive was priced at £580,000. Notably, 9 of the houses on the same street, The Flood, highlight a sense of community. Since 1995, there have been 1,024 sales in the area, with the latest transaction occurring in 2025, showcasing a vibrant and evolving real estate 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
£4,550,000
62.50%
£2,172,500
-22.41%
£1,800,000
-35.71%
£2,146,500
-23.34%
£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 February 2025
fourwynds tytherley road, wiltshire
£880,000
23.
Sold in October 2020
kestrel house middleton, wiltshire
£880,000
24.
Sold in October 2013
ramshill , wiltshire
£870,000
25.
Sold in April 2023
beech house livery road, wiltshire
£850,000
26.
Sold in April 2001
holly bush weston lane, wiltshire
£850,000
27.
Sold in June 2022
meadowside livery road, wiltshire
£848,000
Sold for a lower amount since this price
28.
Sold in June 2025
meadowside livery road, wiltshire
£847,000
29.
Sold in June 2023
newlyn tytherley road, wiltshire
£840,000
30.
Sold in August 2013
fourwynds tytherley road, wiltshire
£800,000
31.
Sold in October 2012
hedgemoor house easton common hill, wiltshire
£800,000
32.
Sold in September 2006
beech house , wiltshire
£795,000
33.
Sold in August 2017
lopcombe house , wiltshire
£795,000
34.
Sold in September 2022
bemerton weston lane, wiltshire
£790,000
35.
Sold in September 2025
3 wellsted close, wiltshire
£780,000
36.
Sold in 2022
kings farm house livery road, wiltshire
£770,000
37.
Sold in July 2021
1 witt road, wiltshire
£767,500
38.
Sold in December 2007
mancett house easton common hill, wiltshire
£765,000
39.
Sold in October 2020
woodleaze gunville road, wiltshire
£760,000
40.
Sold in October 2021
uplands tytherley road, wiltshire
£750,000
41.
Sold in June 2014
oak house beech close, wiltshire
£750,000
42.
Sold in December 2025
1 wellsted close, wiltshire
£740,000
43.
Sold in September 2024
oak tree house middleton road, wiltshire
£735,000
44.
Sold in May 2019
walnut cottage middleton, wiltshire
£735,000
45.
Sold in October 2014
crewkerne farm bungalow pitton road, wiltshire
£735,000
46.
Sold in February 2011
ayres barn tytherley road, wiltshire
£725,000
47.
Sold in December 2023
tannenhaus tytherley road, wiltshire
£725,000
48.
Sold in August 2019
north lodge west dean road, wiltshire
£720,000
49.
Sold in May 2021
1 wellsted close, wiltshire
£715,000
50.
Sold in October 2017
middleton house middleton, wiltshire
£715,000
51.
Sold in April 2021
2 wellsted close, wiltshire
£710,000
52.
Sold in March 2025
douai house easton common hill, wiltshire
£710,000
53.
Sold in November 2015
3 yew tree close, wiltshire
£710,000
54.
Sold in December 2017
hillside cottage red lane, wiltshire
£705,000
55.
Sold in November 2002
beech house , wiltshire
£702,500
56.
Sold in September 2020
the calypso middleton road, wiltshire
£702,500
57.
Sold in March 2021
3 wellsted close, wiltshire
£700,000
58.
Sold in October 2006
barn owl cottage tytherley road, wiltshire
£700,000
59.
Sold in March 2021
alveus the causeway, wiltshire
£700,000
60.
Sold in October 2018
newlyn tytherley road, wiltshire
£695,000
61.
Sold in March 2025
beaulah livery road, wiltshire
£690,000
62.
Sold in February 2019
flint field house the street, wiltshire
£687,500
63.
Sold in February 2021
12 wellsted close, wiltshire
£685,000
64.
Sold in June 2015
the old shop weston lane, wiltshire
£685,000
65.
Sold in February 2007
gutteridge farm barns , wiltshire
£675,000
66.
Sold in October 2014
mulberry house beech close, wiltshire
£675,000
67.
Sold in April 2018
old post office middleton road, wiltshire
£675,000
68.
Sold in May 2015
owls thatch livery road, wiltshire
£675,000
69.
Sold in September 2025
grovely middleton road, wiltshire
£673,500
70.
Sold in September 2024
bramble cottage , wiltshire
£660,000
71.
Sold in April 2021
11 wellsted close, wiltshire
£650,000
72.
Sold in September 2000
la-vista weston lane, wiltshire
£650,000
73.
Sold in July 2014
tregonia the street, wiltshire
£650,000
74.
Sold in June 2017
chez-nous tytherley road, wiltshire
£642,500
75.
Sold in October 2020
tannenhaus tytherley road, wiltshire
£642,500
76.
Sold in October 2004
4 beech close, wiltshire
£640,000
77.
Sold in 2009
mulberry house beech close, wiltshire
£637,500
78.
Sold in October 2018
sunnymeade the causeway, wiltshire
£635,000
79.
Sold in March 2012
high walls the street, wiltshire
£635,000
80.
Sold in September 2013
flint field house the street, wiltshire
£635,000
81.
Sold in October 2014
ashton beeches tytherley road, wiltshire
£630,000
82.
Sold in July 2013
eaton house middleton, wiltshire
£627,500
83.
Sold in November 2023
mount heights stockbridge road, wiltshire
£625,000
84.
Sold in July 2007
rowan house gunville road, wiltshire
£625,000
85.
Sold in March 2003
4 beech close, wiltshire
£625,000
86.
Sold in October 2003
oak house beech close, wiltshire
£625,000
87.
Sold in December 2006
crewkerne farm bungalow pitton road, wiltshire
£623,000
88.
Sold in 2021
meadow bank livery road, wiltshire
£620,000
89.
Sold in March 2015
beechwood livery road, wiltshire
£615,000
90.
Sold in November 2007
3 kings paddock, wiltshire
£610,000
91.
Sold in October 2013
clearbury middleton road, wiltshire
£605,000
92.
Sold in February 2021
hebron middleton, wiltshire
£605,000
93.
Sold in December 2020
white gates tytherley road, wiltshire
£600,000
94.
Sold in May 2014
park house west dean road, wiltshire
£600,000
95.
Sold in February 2003
brooking house beech close, wiltshire
£600,000
96.
Sold in August 2022
plantation cottage the plantation, wiltshire
£600,000
97.
Sold in December 2024
lilac cottage , wiltshire
£595,000
98.
Sold in November 2009
sandling house , wiltshire
£595,000
99.
Sold in May 2022
little acre tytherley road, wiltshire
£590,000
100.
Sold in September 2017
5 keel close, 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 29 March 2026 at 17:42 with the latest HM Land Registry data (November 2025). The Winterslow dataset covers 84 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.