Sort by Most recent sale Address Highest price Highest £ per sqm Largest area Smallest area	Last sold	Price paid	Floor area (m²) Floor area (sq ft)	£ per m² £ per sq ft	Type	Sold	m² sq ft	£/m² £/sq ft
Flat 3 Chancery House, 11, Upper High Street, Winchester, SO23 8UT -	12 Sep 2025	£200,000	45 m² 484 sqft	£4,444 £412	Flat (1 bed)
Sherwood House 2, 8a, Upper High Street, Winchester, SO23 8UT	02 Dec 2024	£1,500,000 B			Other
8, Upper High Street, Winchester, SO23 8UT	19 Nov 2024	£465,000 B			Terrace
Monument House, 5, Upper High Street, Winchester, SO23 8UT	30 Aug 2024	£800,000 B			Terrace
10, Upper High Street, Winchester, SO23 8UT -	23 May 2024	£365,000	98 m² 1054 sqft	£3,724 £345	Flat (3 bed)
29, Upper High Street, Winchester, SO23 8UX -	17 May 2024	£490,100	76 m² 818 sqft	£6,448 £599	Terrace (2 bed)
Flat 2 Chancery House, 11, Upper High Street, Winchester, SO23 8UT -	07 Aug 2023	£141,000	31 m² 333 sqft	£4,548 £422	Flat (1 bed)
18, Upper High Street, Winchester, SO23 8UT -	30 Jan 2023	£565,000	145 m² 1560 sqft	£3,896 £361	Terrace (3 bed)
Flat 4 Wessex Court, 4a, Upper High Street, Winchester, SO23 8UT -	21 Dec 2022	£357,500	72 m² 775 sqft	£4,965 £461	Flat (2 bed)
3 - 4, Upper High Street, Winchester, SO23 8UT	29 Sep 2022	£772,949 B			Other
30, Upper High Street, Winchester, SO23 8UX -	28 Oct 2021	£375,500	69 m² 742 sqft	£5,442 £505	Terrace (2 bed)
14, Upper High Street, Winchester, SO23 8UT	30 Sep 2021	£307,500 B	72 m² 775 sqft	£4,270 £396	Flat
18b, Upper High Street, Winchester, SO23 8UT -	10 Sep 2021	£425,000	140 m² 1506 sqft	£3,035 £281	Terrace (2 bed)
19, Upper High Street, Winchester, SO23 8UX -	22 Jan 2021	£665,000	98 m² 1054 sqft	£6,785 £630	Terrace (3 bed)
Flat 2 Wessex Court, 4a, Upper High Street, Winchester, SO23 8UT -	12 Jan 2021	£272,500	53 m² 570 sqft	£5,141 £477	Flat (1 bed)
26, Upper High Street, Winchester, SO23 8UX -	03 Aug 2020	£390,000	80 m² 861 sqft	£4,875 £452	Terrace (2 bed)
Flat 5 Chancery House, 11, Upper High Street, Winchester, SO23 8UT	02 Jul 2018	£340,000	33 m² 355 sqft	£10,303 £957	Flat (2 bed)
31, Upper High Street, Winchester, SO23 8UX	25 Sep 2017	£300,000	62 m² 667 sqft	£4,838 £449	Terrace (1 bed)
10a, Upper High Street, Winchester, SO23 8UT -	05 Sep 2016	£347,250	106 m² 1140 sqft	£3,275 £304	Flat (2 bed)
32, Upper High Street, Winchester, SO23 8UX -	18 Mar 2016	£399,000	59 m² 635 sqft	£6,762 £628	Terrace (2 bed)
3 - 4, Upper High Street, Winchester, SO23 8UT	19 Feb 2016	£661,000 B			Other
Flat 3 Wessex Court, 4a, Upper High Street, Winchester, SO23 8UT -	20 Sep 2013	£384,000	170 m² 1829 sqft	£2,258 £209	Flat (2 bed)
7, Upper High Street, Winchester, SO23 8UT	05 Aug 2013	£500,000			Terrace
Flat 5 Wessex Court, 4a, Upper High Street, Winchester, SO23 8UT -	20 Jul 2012	£265,000	77 m² 828 sqft	£3,441 £319	Flat (2 bed)
18c, Upper High Street, Winchester, SO23 8UT -	28 Oct 2011	£225,000	57 m² 613 sqft	£3,947 £366	Terrace (2 bed)
Flat 7 Wessex Court, 4a, Upper High Street, Winchester, SO23 8UT -	30 Sep 2011	£292,000	99 m² 1065 sqft	£2,949 £273	Flat (1 bed)
21, Upper High Street, Winchester, SO23 8UX	25 Oct 2010	£410,000			Terrace
20, Upper High Street, Winchester, SO23 8UX -	01 Jul 2010	£344,000	90 m² 968 sqft	£3,822 £355	Terrace (2 bed)
17, Upper High Street, Winchester, SO23 8UT -	19 Jun 2009	£375,000	114 m² 1227 sqft	£3,289 £305	Terrace (3 bed)
Flat 6 Wessex Court, 4a, Upper High Street, Winchester, SO23 8UT -	16 Jan 2009	£230,000			Flat (2 bed)
Flat 3 Chancery House, 11, Upper High St -	£200,000 Sep-2025	45 484	4,444 412
Sherwood House 2, 8a, Upper High St	£1,500,000 B Dec-2024
8, Upper High St	£465,000 B Nov-2024
Monument House, 5, Upper High St	£800,000 B Aug-2024
10, Upper High St -	£365,000 May-2024	98 1054	3,724 345
29, Upper High St -	£490,100 May-2024	76 818	6,448 599
Flat 2 Chancery House, 11, Upper High St -	£141,000 Aug-2023	31 333	4,548 422
18, Upper High St -	£565,000 Jan-2023	145 1560	3,896 361
Flat 4 Wessex Court, 4a, Upper High St -	£357,500 Dec-2022	72 775	4,965 461
3 - 4, Upper High St	£772,949 B Sep-2022
30, Upper High St -	£375,500 Oct-2021	69 742	5,442 505
14, Upper High St	£307,500 B Sep-2021	72 775	4,270 396
18b, Upper High St -	£425,000 Sep-2021	140 1506	3,035 281
19, Upper High St -	£665,000 Jan-2021	98 1054	6,785 630
Flat 2 Wessex Court, 4a, Upper High St -	£272,500 Jan-2021	53 570	5,141 477
26, Upper High St -	£390,000 Aug-2020	80 861	4,875 452
Flat 5 Chancery House, 11, Upper High St	£340,000 Jul-2018	33 355	10,303 957
31, Upper High St	£300,000 Sep-2017	62 667	4,838 449
10a, Upper High St -	£347,250 Sep-2016	106 1140	3,275 304
32, Upper High St -	£399,000 Mar-2016	59 635	6,762 628
3 - 4, Upper High St	£661,000 B Feb-2016
Flat 3 Wessex Court, 4a, Upper High St -	£384,000 Sep-2013	170 1829	2,258 209
7, Upper High St	£500,000 Aug-2013
Flat 5 Wessex Court, 4a, Upper High St -	£265,000 Jul-2012	77 828	3,441 319
18c, Upper High St -	£225,000 Oct-2011	57 613	3,947 366
Flat 7 Wessex Court, 4a, Upper High St -	£292,000 Sep-2011	99 1065	2,949 273
21, Upper High St	£410,000 Oct-2010
20, Upper High St -	£344,000 Jul-2010	90 968	3,822 355
17, Upper High St -	£375,000 Jun-2009	114 1227	3,289 305
Flat 6 Wessex Court, 4a, Upper High St -	£230,000 Jan-2009

The data above for Upper High Street can be visualised as a scatter graph, this will show price trends over time.

The average price per square metre (per square foot) in Upper High Street, Winchester is £4,670 sqm (£433 per sq ft), this is from the price paid of the 6 most recent sales.
The majority of homes in Winchester are now selling for between £4,300 and £6,060 per square metre (£399 and £562 per square foot) , find out more in this local analysis of SO23 8 (Winchester) house prices.
There are roughly 30 homes on Upper High Street, we would have expected approximately 4 sales each year given that in the UK people sell their homes on average once every 7 years.
In the last 4 years there have been 6 property sales in Upper High Street, averaging approximately 1 home sales per year .
The average size of all the properties on Upper High Street is 83 m2 (893 sqft).