House Price Watch
100 most expensive houses in Upper Winchendon
In the charming area of Upper Winchendon, part of Aylesbury Vale, the property market has seen some fascinating transactions. The most expensive house sold in this area reached a staggering £645,000 back in 1998, while the least expensive was just £42,000. Over the years, there have been 13 sales since 1995, with the latest transaction occurring in 2021. Interestingly, 9 of these houses are located on the same street, known as Main Road, showcasing a unique community vibe.
Sold in August 1998
the waterhouse , buckinghamshire
£645,000
Sold for a lower amount since this price
Sold in July 1995
the waterhouse , buckinghamshire
£500,000
Sold for a lower amount since this price
Sold in November 2021
highclere , buckinghamshire
£410,000
4.
Sold in July 2014
8 main road, buckinghamshire
£335,000
5.
Sold in September 2012
rivendell main road, buckinghamshire
£320,000
6.
Sold in December 2018
highclere , buckinghamshire
£310,000
7.
Sold in July 2013
1 william neary cottages, buckinghamshire
£300,000
8.
Sold in February 1998
the waterhouse , buckinghamshire
£298,255
9.
Sold in May 2003
1 william neary cottages, buckinghamshire
£295,000
10.
Sold in May 2004
eythrope park farm , buckinghamshire
£250,000
Most expensive houses in areas around Upper Winchendon
£1,430,000
121.71%
£1,150,000
78.29%
£1,600,000
148.06%
£2,700,000
318.60%
£3,250,000
403.88%
£1,500,000
132.56%
£12,550,000
1845.74%
11.
Sold in October 2000
8 main road, buckinghamshire
£175,000
12.
Sold in June 1999
8 main road, buckinghamshire
£132,000
13.
Sold in July 1999
1 william neary cottages, buckinghamshire
£42,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Upper Winchendon 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 18:29 with the latest HM Land Registry data (October 2021). The Upper Winchendon dataset covers 8 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.