Property Snakes & Ladders in Winchester
The biggest price drops and jumps on homes sold in the last year, compared with their previous Land Registry sale - curiosity, not analysis.
Rankings from Land Registry resales, last calculated 05 June 2026.
Snakes — biggest house price falls in Winchester
The top-ranked Winchester properties with the largest house price falls on resale. Go beyond house price indices with specific examples.
No. 1
15 Dempsey Close
SO19 8JZ · Flat · 2 bed
Was
£150,000 (May 2023)
Now
£90,000 (Aug 2025)
Price change
-£60,000 over 2.3 yrs
Total %
-40.0%
Annualised %
↓ 20.1%
No. 2
38 Knights Lodge North Close
SO41 9PB · Flat
Was
£492,950 (Jun 2019)
Now
£250,000 (Nov 2025)
Price change
-£242,950 over 6.4 yrs
Total %
-49.3%
Annualised %
↓ 10.1%
No. 3
Flat 5 Homeborough House Brinton Lane
SO45 6EE · Flat · 1 bed
Was
£150,000 (Nov 2022)
Now
£110,000 (Feb 2026)
Price change
-£40,000 over 3.3 yrs
Total %
-26.7%
Annualised %
↓ 9.0%
No. 4
Chalkhill House, 133 Olivers Battery Road South
SO22 4HB · Detached · 3 bed
Was
£1,195,000 (Aug 2023)
Now
£1,000,000 (Nov 2025)
Price change
-£195,000 over 2.2 yrs
Total %
-16.3%
Annualised %
↓ 7.7%
No. 5
25 Cleveland Road
SO18 2AP · Terrace · 3 bed
Was
£277,500 (Aug 2018)
Now
£159,950 (Nov 2025)
Price change
-£117,550 over 7.2 yrs
Total %
-42.4%
Annualised %
↓ 7.3%
No. 6
Flat 25 Oakley Court, 1 Oakley Road
SO16 4FA · Flat · 1 bed
Was
£140,000 (Apr 2019)
Now
£85,000 (Nov 2025)
Price change
-£55,000 over 6.6 yrs
Total %
-39.3%
Annualised %
↓ 7.3%
No. 7
Flat 1 49 Bevois Valley Road
SO14 0TD · Flat
Was
£219,900 (Feb 2020)
Now
£145,000 (Dec 2025)
Price change
-£74,900 over 5.9 yrs
Total %
-34.1%
Annualised %
↓ 6.9%
No. 8
5 Melrose Road
SO15 7PB · Detached · 3 bed
Was
£620,000 (Mar 2023)
Now
£525,000 (Sep 2025)
Price change
-£95,000 over 2.5 yrs
Total %
-15.3%
Annualised %
↓ 6.5%
No. 9
16 Saxon Gate
SO14 3HA · Flat
Was
£160,000 (Jun 2022)
Now
£129,000 (Mar 2026)
Price change
-£31,000 over 3.8 yrs
Total %
-19.4%
Annualised %
↓ 5.6%
No. 10
Flat 14 Heathlands Court Beaulieu Road
SO45 4BB · Flat · 1 bed
Was
£186,000 (Jul 2016)
Now
£107,500 (Apr 2026)
Price change
-£78,500 over 9.7 yrs
Total %
-42.2%
Annualised %
↓ 5.5%
No. 11
19 Moorlands Road
SO32 2QL · Semi-D · 3 bed
Was
£507,000 (Feb 2022)
Now
£410,000 (Dec 2025)
Price change
-£97,000 over 3.8 yrs
Total %
-19.1%
Annualised %
↓ 5.4%
No. 12
85 Midlands Estate
SO30 3AD · Semi-D · 3 bed
Was
£282,500 (Jan 2020)
Now
£207,000 (Sep 2025)
Price change
-£75,500 over 5.6 yrs
Total %
-26.7%
Annualised %
↓ 5.4%
No. 13
1 Dunwood Court Salisbury Road
SO51 6GR · Flat
Was
£280,000 (Jan 2016)
Now
£164,000 (Feb 2026)
Price change
-£116,000 over 10.1 yrs
Total %
-41.4%
Annualised %
↓ 5.2%
No. 14
Flat 28 Homepoint House Mersham Gardens
SO18 6TX · Flat · 1 bed
Was
£82,500 (Dec 2017)
Now
£55,000 (Nov 2025)
Price change
-£27,500 over 7.9 yrs
Total %
-33.3%
Annualised %
↓ 5.0%
No. 15
7 Abbey Lodge Bridge Road
SO51 8LJ · Flat
Was
£218,000 (Jul 2020)
Now
£165,000 (Jan 2026)
Price change
-£53,000 over 5.5 yrs
Total %
-24.3%
Annualised %
↓ 5.0%
Ladders — largest house price rises in Winchester
The top-ranked Winchester properties with the biggest house price rises on resale. Go beyond house price indices with specific examples.
No. 1
Flat 14 Brampton Tower Bassett Avenue
SO16 7FB · Flat · 2 bed
Was
£100,000 (Mar 2024)
Now
£275,000 (Apr 2026)
Price change
+£175,000 over 2.0 yrs
Total %
175.0%
Annualised %
↑ 64.8%
No. 2
78 Glenfield Avenue
SO18 4EU · Semi-D · 3 bed
Was
£230,500 (Apr 2023)
Now
£550,000 (Dec 2025)
Price change
+£319,500 over 2.6 yrs
Total %
138.6%
Annualised %
↑ 38.9%
No. 3
Oak Cottage Winchester Road
SO32 2DH · Semi-D · 3 bed
Was
£222,500 (Dec 2023)
Now
£397,000 (Feb 2026)
Price change
+£174,500 over 2.2 yrs
Total %
78.4%
Annualised %
↑ 30.6%
No. 4
20 Macnaghten Road
SO18 1GJ · Semi-D · 3 bed
Was
£202,000 (Sep 2023)
Now
£365,000 (Dec 2025)
Price change
+£163,000 over 2.3 yrs
Total %
80.7%
Annualised %
↑ 29.9%
No. 5
35a Canon Street
SO23 9JJ · Terrace · 2 bed
Was
£487,500 (Dec 2022)
Now
£850,000 (Jul 2025)
Price change
+£362,500 over 2.6 yrs
Total %
74.4%
Annualised %
↑ 23.7%
No. 6
28 Church Road
SO19 9FS · Terrace · 3 bed
Was
£191,500 (Mar 2023)
Now
£305,000 (Jul 2025)
Price change
+£113,500 over 2.3 yrs
Total %
59.3%
Annualised %
↑ 22.1%
No. 7
6 Buckstone Close
SO41 0UE · Detached
Was
£580,000 (Sep 2022)
Now
£980,000 (Jun 2025)
Price change
+£400,000 over 2.7 yrs
Total %
69.0%
Annualised %
↑ 21.1%
No. 8
185 Hursley Road
SO53 1JH · Detached · 2 bed
Was
£230,000 (Jun 2019)
Now
£745,000 (Oct 2025)
Price change
+£515,000 over 6.3 yrs
Total %
223.9%
Annualised %
↑ 20.4%
No. 9
Newlands Hawthorn Close
SO21 3DQ · Detached · 4 bed
Was
£560,000 (Jan 2021)
Now
£1,250,000 (Aug 2025)
Price change
+£690,000 over 4.6 yrs
Total %
123.2%
Annualised %
↑ 19.0%
No. 10
37 Rownhams Lane
SO52 9HR · Detached · 2 bed
Was
£425,000 (Nov 2022)
Now
£700,000 (Feb 2026)
Price change
+£275,000 over 3.2 yrs
Total %
64.7%
Annualised %
↑ 16.8%
No. 11
46 Canon Street
SO23 9JW · Terrace · 3 bed
Was
£730,000 (Jun 2021)
Now
£1,400,000 (Sep 2025)
Price change
+£670,000 over 4.2 yrs
Total %
91.8%
Annualised %
↑ 16.8%
No. 12
48 Arnold Road
SO17 1TG · Terrace · 3 bed
Was
£115,000 (Mar 2020)
Now
£260,000 (Jun 2025)
Price change
+£145,000 over 5.3 yrs
Total %
126.1%
Annualised %
↑ 16.7%
No. 13
286 Orpen Road
SO19 0ED · Terrace · 3 bed
Was
£105,000 (Nov 2020)
Now
£225,000 (Oct 2025)
Price change
+£120,000 over 5.0 yrs
Total %
114.3%
Annualised %
↑ 16.7%
No. 14
2 Meadow Flats New Road
SO45 6BP · Flat · 1 bed
Was
£123,000 (Oct 2020)
Now
£245,000 (Jul 2025)
Price change
+£122,000 over 4.7 yrs
Total %
99.2%
Annualised %
↑ 15.9%
No. 15
Flat 2 Lynwood Court Priestlands Place
SO41 9GA · Flat · 2 bed
Was
£125,000 (Dec 2020)
Now
£255,000 (Oct 2025)
Price change
+£130,000 over 4.9 yrs
Total %
104.0%
Annualised %
↑ 15.6%
Frequently asked questions
Each entry links sales by the address and property type from Land Registry, with two registered sales at least two years apart.
The latest sale was in the last 12 months. Prices are nominal — not adjusted for extensions, condition, or inflation.
We show listings with archived photos and floorplans where available (15 snakes, 15 ladders).
A fall is not always a market crash story. Land Registry data input errors, Lease or title changes, part ownership, mis-matched addresses can all influence the numbers.
This is not analysis nor is it investment advice, just a bit of fun.
We link sales based on the address and property type provided by Land Registry. We then compare the latest sale to the immediately previous registered sale on that address.