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
Hollyhock House, 50, Cheltenham Road, Winchcombe, GL54 5NQ -	25 Nov 2025	£1,290,000 B	288 m² 3100 sqft	£4,479 £416	Other (4 bed)
21, Cheltenham Road, Winchcombe, GL54 5NF -	10 Oct 2025	£825,000	170 m² 1829 sqft	£4,852 £450	Detached (4 bed)
35, Cheltenham Road, Winchcombe, GL54 5NF -	15 Sep 2025	£249,000 B	67 m² 721 sqft	£3,716 £345	Terrace (3 bed)
Orchard House, Cheltenham Road, Winchcombe, GL54 5NQ	09 Sep 2025	£1,250,000	191 m² 2055 sqft	£6,544 £607	Detached
39, Cheltenham Road, Winchcombe, GL54 5NQ -	05 Sep 2025	£400,000	145 m² 1560 sqft	£2,758 £256	Terrace (3 bed)
9, Cheltenham Road, Winchcombe, GL54 5ND -	18 Aug 2025	£60,000 B	122 m² 1313 sqft	£491 £45	Other (4 bed)
22, Cheltenham Road, Winchcombe, GL54 5ND -	13 Aug 2025	£780,000	167 m² 1797 sqft	£4,670 £433	Detached (4 bed)
18, Cheltenham Road, Winchcombe, GL54 5ND -	24 May 2024	£300,000	76 m² 818 sqft	£3,947 £366	Semi-D (2 bed)
27, Cheltenham Road, Winchcombe, GL54 5NF -	24 Nov 2023	£319,000	64 m² 688 sqft	£4,984 £463	Semi-D (3 bed)
41, Cheltenham Road, Winchcombe, GL54 5NQ -	03 Feb 2023	£285,000	107 m² 1151 sqft	£2,663 £247	Terrace (3 bed)
Humblebee View, 6, Cheltenham Road, Winchcombe, GL54 5ND -	27 Jan 2023	£540,000	113 m² 1216 sqft	£4,778 £443	Semi-D (2 bed)
36, Cheltenham Road, Winchcombe, GL54 5NF -	29 Sep 2022	£435,000	95 m² 1022 sqft	£4,578 £425	Terrace (3 bed)
34, Cheltenham Road, Winchcombe, GL54 5NF -	04 Jun 2021	£410,000	121 m² 1302 sqft	£3,388 £314	Terrace (3 bed)
4, Cheltenham Road, Winchcombe, GL54 5ND -	26 Feb 2021	£385,000	93 m² 1001 sqft	£4,139 £384	Detached (2 bed)
28, Cheltenham Road, Winchcombe, GL54 5NF -	23 Jul 2020	£490,000	117 m² 1259 sqft	£4,188 £389	Semi-D (4 bed)
48, Cheltenham Road, Winchcombe, GL54 5NF -	12 Jun 2019	£370,000	74 m² 796 sqft	£5,000 £464	Detached (2 bed)
37, Cheltenham Road, Winchcombe, GL54 5NF -	01 May 2019	£340,000	93 m² 1001 sqft	£3,655 £339	Terrace
45, Cheltenham Road, Winchcombe, GL54 5NQ -	21 Dec 2018	£270,000	89 m² 957 sqft	£3,033 £281	Terrace (3 bed)
8, Cheltenham Road, Winchcombe, GL54 5ND -	04 May 2018	£302,500	103 m² 1108 sqft	£2,936 £272	Semi-D (3 bed)
2, Cheltenham Road, Winchcombe, GL54 5ND -	18 Sep 2017	£615,000	213 m² 2292 sqft	£2,887 £268	Detached (4 bed)
43, Cheltenham Road, Winchcombe, GL54 5NQ -	20 Mar 2017	£270,000	101 m² 1087 sqft	£2,673 £248	Terrace (3 bed)
14, Cheltenham Road, Winchcombe, GL54 5ND -	17 Feb 2017	£215,000	94 m² 1011 sqft	£2,287 £212	Semi-D (3 bed)
20, Cheltenham Road, Winchcombe, GL54 5ND -	12 Feb 2016	£385,000	124 m² 1334 sqft	£3,104 £288	Semi-D (5 bed)
53, Cheltenham Road, Winchcombe, GL54 5NQ -	24 Apr 2015	£250,000	96 m² 1033 sqft	£2,604 £241	Terrace (3 bed)
10, Cheltenham Road, Winchcombe, GL54 5ND -	23 Feb 2015	£162,000	91 m² 979 sqft	£1,780 £165	Semi-D (3 bed)
Pear Tree Cottage, Cheltenham Road, Winchcombe, GL54 5NF -	01 Sep 2011	£272,500	100 m² 1076 sqft	£2,725 £253	Detached (2 bed)
31, Cheltenham Road, Winchcombe, GL54 5NF -	28 Feb 2011	£249,950	64 m² 688 sqft	£3,905 £362	Terrace (2 bed)
46, Cheltenham Road, Winchcombe, GL54 5NF -	19 Oct 2009	£235,000			Detached (2 bed)
51, Cheltenham Road, Winchcombe, GL54 5NQ -	27 May 2009	£138,000	97 m² 1044 sqft	£1,422 £132	Terrace (3 bed)
12, Cheltenham Road, Winchcombe, GL54 5ND	08 Oct 2007	£287,000			Semi-D
Hollyhock House, 50, Cheltenham Rd -	£1,290,000 B Nov-2025	288 3100	4,479 416
21, Cheltenham Rd -	£825,000 Oct-2025	170 1829	4,852 450
35, Cheltenham Rd -	£249,000 B Sep-2025	67 721	3,716 345
Orchard House, Cheltenham Rd	£1,250,000 Sep-2025	191 2055	6,544 607
39, Cheltenham Rd -	£400,000 Sep-2025	145 1560	2,758 256
9, Cheltenham Rd -	£60,000 B Aug-2025	122 1313	491 45
22, Cheltenham Rd -	£780,000 Aug-2025	167 1797	4,670 433
18, Cheltenham Rd -	£300,000 May-2024	76 818	3,947 366
27, Cheltenham Rd -	£319,000 Nov-2023	64 688	4,984 463
41, Cheltenham Rd -	£285,000 Feb-2023	107 1151	2,663 247
Humblebee View, 6, Cheltenham Rd -	£540,000 Jan-2023	113 1216	4,778 443
36, Cheltenham Rd -	£435,000 Sep-2022	95 1022	4,578 425
34, Cheltenham Rd -	£410,000 Jun-2021	121 1302	3,388 314
4, Cheltenham Rd -	£385,000 Feb-2021	93 1001	4,139 384
28, Cheltenham Rd -	£490,000 Jul-2020	117 1259	4,188 389
48, Cheltenham Rd -	£370,000 Jun-2019	74 796	5,000 464
37, Cheltenham Rd -	£340,000 May-2019	93 1001	3,655 339
45, Cheltenham Rd -	£270,000 Dec-2018	89 957	3,033 281
8, Cheltenham Rd -	£302,500 May-2018	103 1108	2,936 272
2, Cheltenham Rd -	£615,000 Sep-2017	213 2292	2,887 268
43, Cheltenham Rd -	£270,000 Mar-2017	101 1087	2,673 248
14, Cheltenham Rd -	£215,000 Feb-2017	94 1011	2,287 212
20, Cheltenham Rd -	£385,000 Feb-2016	124 1334	3,104 288
53, Cheltenham Rd -	£250,000 Apr-2015	96 1033	2,604 241
10, Cheltenham Rd -	£162,000 Feb-2015	91 979	1,780 165
Pear Tree Cottage, Cheltenham Rd -	£272,500 Sep-2011	100 1076	2,725 253
31, Cheltenham Rd -	£249,950 Feb-2011	64 688	3,905 362
46, Cheltenham Rd -	£235,000 Oct-2009
51, Cheltenham Rd -	£138,000 May-2009	97 1044	1,422 132
12, Cheltenham Rd	£287,000 Oct-2007

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

The average price per square metre (per square foot) in Cheltenham Road, Winchcombe is £4,551 sqm (£422 per sq ft), this is from the selling price of the 10 most recent sales.
The majority of homes in Winchcombe are now selling for between £3,390 and £4,920 per square metre (£314 and £457 per square foot) , find out more in this local analysis of GL54 5 (Winchcombe) house prices.
There are about 37 homes on Cheltenham Road, we would have expected about 5 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 10 property sales in Cheltenham Road, averaging roughly 2 home sales per year .
The average size of all the properties on Cheltenham Road is 119 m2 (1,280 sqft).