Chestnut Way
Princes Risborough · HP27 9SB, HP27 9SD
Average sold price
£406,762
49 sales since 1996
Median
£380,000
middle of every sale
Last sold
£630k
17 Feb 2026
Properties
26
detached most common
Average sold price by year
Properties on Chestnut Way
| Address | Type | Last sold | Price | Sales |
|---|---|---|---|---|
| CHILTERN, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 17 Feb 2026 | £630,000 | 1 |
| CUB COTTAGE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 14 Oct 2025 | £415,000 | 2 |
| SEAGRAMS, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 25 Jul 2024 | £715,000 | 2 |
| THE ACORNS, 1, CHESTNUT WAY, LONGWICK HP27 9SD | Semi-Detached | 8 Apr 2024 | £550,000 | 3 |
| AMBERLEY, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 6 Nov 2023 | £711,000 | 3 |
| IVY COTTAGE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 27 Oct 2023 | £655,000 | 1 |
| DUNSTER, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 27 Jan 2023 | £590,000 | 1 |
| SERENDIPITY HOUSE, CHESTNUT WAY, LONGWICK HP27 9SD | Semi-Detached | 3 Dec 2021 | £428,750 | 4 |
| THE TIMBERS, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 5 Nov 2021 | £650,000 | 3 |
| LODORE, CHESTNUT WAY, LONGWICK HP27 9SD | Semi-Detached | 19 Feb 2021 | £415,000 | 1 |
| HIGH DENE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 4 Feb 2021 | £525,000 | 1 |
| THE PANTILES, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 12 Jun 2020 | £780,000 | 2 |
| BELL FARM, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 14 Dec 2018 | £600,000 | 2 |
| BUTLEY COTTAGE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 29 Jun 2018 | £472,000 | 1 |
| CHURCH FARM COTTAGE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 21 Jul 2016 | £782,500 | 3 |
| RYCOTE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 17 Jul 2015 | £450,000 | 3 |
| KINGSWOOD, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 16 May 2014 | £317,500 | 2 |
| ROSE COTTAGES, 2, CHESTNUT WAY, LONGWICK HP27 9SD | Semi-Detached | 24 Feb 2012 | £343,000 | 1 |
| WOODBINE COTTAGE, CHESTNUT WAY, LONGWICK HP27 9SB | Detached | 30 Sep 2011 | £345,000 | 3 |
| THE ACORNS, 2, CHESTNUT WAY, LONGWICK HP27 9SD | Semi-Detached | 18 Feb 2008 | £366,000 | 2 |
| PELNEE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 15 Jun 2007 | £315,000 | 2 |
| VIDON, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 19 Mar 2004 | £345,000 | 1 |
| CHESTNUT FARM, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 30 May 2003 | £705,000 | 1 |
| REGENCY COTTAGE, CHESTNUT WAY, LONGWICK HP27 9SD | Terraced | 28 Feb 2003 | £199,000 | 1 |
| CHILTERN HOUSE, CHESTNUT WAY, LONGWICK HP27 9SD | Detached | 25 Sep 2002 | £299,950 | 1 |
| ROSE COTTAGES, 1, CHESTNUT WAY, LONGWICK HP27 9SD | Semi-Detached | 3 Sep 1999 | £137,950 | 2 |
Recent sales
| Date | Address | Type | Tenure | Price |
|---|---|---|---|---|
| 17 Feb 2026 | CHILTERN, CHESTNUT WAY, LONGWICK | Detached | Freehold | £630,000 |
| 14 Oct 2025 | CUB COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £415,000 |
| 25 Jul 2024 | SEAGRAMS, CHESTNUT WAY, LONGWICK | Detached | Freehold | £715,000 |
| 8 Apr 2024 | THE ACORNS, 1, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £550,000 |
| 6 Nov 2023 | AMBERLEY, CHESTNUT WAY, LONGWICK | Detached | Freehold | £711,000 |
| 27 Oct 2023 | IVY COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £655,000 |
| 27 Jan 2023 | DUNSTER, CHESTNUT WAY, LONGWICK | Detached | Freehold | £590,000 |
| 3 Dec 2021 | SERENDIPITY HOUSE, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £428,750 |
| 5 Nov 2021 | THE TIMBERS, CHESTNUT WAY, LONGWICK | Detached | Freehold | £650,000 |
| 19 Feb 2021 | LODORE, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £415,000 |
| 4 Feb 2021 | HIGH DENE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £525,000 |
| 12 Jun 2020 | THE PANTILES, CHESTNUT WAY, LONGWICK | Detached | Freehold | £780,000 |
| 4 Oct 2019 | THE ACORNS, 1, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £480,000 |
| 14 Dec 2018 | BELL FARM, CHESTNUT WAY, LONGWICK | Detached | Freehold | £600,000 |
| 13 Aug 2018 | THE PANTILES, CHESTNUT WAY, LONGWICK | Detached | Freehold | £380,000 |
| 29 Jun 2018 | BUTLEY COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £472,000 |
| 14 Sep 2017 | AMBERLEY, CHESTNUT WAY, LONGWICK | Detached | Freehold | £510,000 |
| 25 May 2017 | SERENDIPITY HOUSE, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £430,000 |
| 21 Jul 2016 | CHURCH FARM COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £782,500 |
| 20 Nov 2015 | THE TIMBERS, CHESTNUT WAY, LONGWICK | Detached | Freehold | £536,000 |
| 17 Jul 2015 | RYCOTE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £450,000 |
| 16 May 2014 | KINGSWOOD, CHESTNUT WAY, LONGWICK | Detached | Freehold | £317,500 |
| 2 Dec 2013 | KINGSWOOD, CHESTNUT WAY, LONGWICK | Detached | Freehold | £308,750 |
| 24 Feb 2012 | ROSE COTTAGES, 2, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £343,000 |
| 30 Sep 2011 | WOODBINE COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £345,000 |
| 11 Dec 2009 | THE TIMBERS, CHESTNUT WAY, LONGWICK | Detached | Freehold | £286,000 |
| 20 Nov 2009 | CHURCH FARM COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £593,000 |
| 18 Feb 2008 | THE ACORNS, 2, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £366,000 |
| 29 Jun 2007 | THE ACORNS, 1, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £385,000 |
| 15 Jun 2007 | PELNEE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £315,000 |
| 28 Apr 2006 | WOODBINE COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £289,950 |
| 31 Mar 2006 | BELL FARM, CHESTNUT WAY, LONGWICK | Detached | Freehold | £500,000 |
| 28 Nov 2005 | THE ACORNS, 2, CHESTNUT WAY, LONGWICK | Detached | Freehold | £295,000 |
| 19 Mar 2004 | VIDON, CHESTNUT WAY, LONGWICK | Detached | Freehold | £345,000 |
| 30 May 2003 | CHESTNUT FARM, CHESTNUT WAY, LONGWICK | Detached | Freehold | £705,000 |
| 28 Feb 2003 | REGENCY COTTAGE, CHESTNUT WAY, LONGWICK | Terraced | Freehold | £199,000 |
| 23 Oct 2002 | RYCOTE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £335,000 |
| 25 Sep 2002 | CHILTERN HOUSE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £299,950 |
| 23 Oct 2001 | CUB COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £247,500 |
| 18 Apr 2001 | AMBERLEY, CHESTNUT WAY, LONGWICK | Detached | Freehold | £290,000 |
| 6 Oct 2000 | SEAGRAMS, CHESTNUT WAY, LONGWICK | Detached | Freehold | £300,000 |
| 15 Sep 2000 | WOODBINE COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £165,000 |
| 3 Sep 1999 | ROSE COTTAGES, 1, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £137,950 |
| 15 Jul 1999 | PELNEE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £140,000 |
| 6 Nov 1998 | SERENDIPITY HOUSE, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £142,500 |
| 29 Jun 1998 | CHURCH FARM COTTAGE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £242,500 |
| 23 Jul 1997 | SERENDIPITY HOUSE, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £129,000 |
| 9 Feb 1996 | RYCOTE, CHESTNUT WAY, LONGWICK | Detached | Freehold | £132,500 |
| 19 Jan 1996 | ROSE COTTAGES, 1, CHESTNUT WAY, LONGWICK | Semi-Detached | Freehold | £71,000 |
Other streets in Princes Risborough
Frequently asked questions
What is the average house price on Chestnut Way, Princes Risborough?
The average sold price on Chestnut Way is £406,762, across 49 sales since 1996. The median is £380,000 — the middle price, which a few unusually expensive sales cannot pull upward.
When did a property on Chestnut Way last sell?
The most recent recorded sale on Chestnut Way was CHILTERN, CHESTNUT WAY, LONGWICK, which sold for £630,000 on 17 Feb 2026.
How many properties are there on Chestnut Way?
26 separate addresses have sold on Chestnut Way since 1996, across 2 postcodes (HP27 9SB, HP27 9SD). That is not the same as the number of homes on the street — a property that has never changed hands since 1995 does not appear in Land Registry records.
About this data
Every figure on this page is calculated from the 49 sales HM Land Registry has recorded on Chestnut Way since 1996 — what buyers actually paid, not asking prices or estimates. A home that has not changed hands since records began in 1995 will not appear. Sales are matched to this street by postcode and by the street component of the registered address, so a neighbouring street with a similar name is not counted. The Price Paid dataset covers England and Wales only; see Scotland and Northern Ireland.