Winston Drive, Skegness house prices are built from 141 sales lodged with HM Land Registry, the oldest in 2002 and the most recent on 9 Oct 2025. The median price paid across the whole record is £112,500. Across the 12 years from 2009 to 2021 the median moved -16.8% in cash — but once inflation is taken out, the change in 2026 money is -36.1%.
Median price paid
£112,500
Change in cash, 2009–2021
-16.8%
Change in real terms
-36.1%
Median per m²
£1,463
HM Land Registry141 sales34 with floor areaLatest sale 9 Oct 2025
Section 01
How Winston Drive, Skegness prices moved
The chart tracks the median Winston Drive, Skegness house price for every year with a recorded sale, from 2002 to 2021. The dashed line restates each year in 2026 money, so the two lines separate exactly as much as inflation has eroded the cash figure.
| Decade | Years with sales | Median paid | In today's money |
|---|---|---|---|
| 2000s | 8 | £115,000 | £209,496 |
| 2010s | 1 | £123,000 | £173,430 |
| 2020s | 1 | £98,950 | £101,101 |
The highest yearly median on record for Winston Drive, Skegness is £135,500 in 2007; the lowest is £89,950 in 2002. Across the full 20-year record the cash median has moved from £89,950 to £98,950.
In 2026 money that first median is worth £173,501, so the real change over the whole record is -27.9% — about -1.71% a year after inflation. Cash growth and real growth are not the same story, and the gap is the part most price reports leave out.
Over the last decade alone the difference is stark: -16.8% in cash against -36.1% once inflation is removed. A buyer who sold at the end of that decade would have needed the real figure, not the headline one, to know whether they had actually gained.
Section 02
The most recent sales
Every row is a completed sale as lodged with HM Land Registry. The right-hand column restates the price in 2026 money, which is the only fair way to compare a sale from the 1990s with one from last year.
| Address | Sold | Type | Price paid | In today's money |
|---|---|---|---|---|
| 65 | 9 Oct 2025 | Flat or maisonette | £114,000 | £116,478 |
| 57 | 8 Oct 2025 | Flat or maisonette | £95,000 | £97,065 |
| 82 | 22 Aug 2025 | Terraced | £178,500 | £182,380 |
| 59 | 28 Sep 2023 | Flat or maisonette | £99,000 | £106,966 |
| 49 | 14 Jul 2022 | Flat or maisonette | £105,000 | £121,652 |
| 68 | 28 Mar 2022 | Terraced | £175,000 | £202,753 |
| 78 | 16 Dec 2021 | Terraced | £177,500 | £224,261 |
| 65 | 16 Dec 2021 | Flat or maisonette | £95,000 | £120,027 |
| 51 | 30 Sep 2021 | Flat or maisonette | £98,950 | £125,017 |
| 55 | 23 Aug 2021 | Flat or maisonette | £93,000 | £117,500 |
| 11 | 10 Aug 2021 | Detached | £200,000 | £252,688 |
| 52 | 30 Apr 2021 | Terraced | £128,000 | £161,720 |
| 53 | 26 Feb 2021 | Flat or maisonette | £95,000 | £120,027 |
| 23 | 18 Dec 2020 | Semi-detached | £168,000 | £217,521 |
| 12 | 1 Dec 2020 | Detached | £215,000 | £278,375 |
| 35 | 19 Dec 2019 | Detached | £243,000 | £317,839 |
| 5 | 6 Nov 2019 | Detached | £210,000 | £274,675 |
| 30 | 7 Jun 2019 | Detached | £235,000 | £307,375 |
| 88 | 18 Dec 2018 | Semi-detached | £155,000 | £206,569 |
| 57 | 23 Nov 2018 | Flat or maisonette | £87,000 | £115,945 |
| 54 | 2 Nov 2018 | Terraced | £123,000 | £163,922 |
| 21 | 5 Oct 2018 | Detached | £144,500 | £192,576 |
| 63 | 17 Aug 2018 | Flat or maisonette | £80,000 | £106,616 |
| 61 | 28 Apr 2017 | Semi-detached | £77,500 | £105,478 |
| 72 | 27 Feb 2017 | Terraced | £137,995 | £187,812 |
Section 03
Homes that sold twice
These addresses appear in the register more than once, so the same bricks are being priced twice. That makes them the strongest evidence of what actually happened to Winston Drive, Skegness values — no mix of property types can flatter the number.
| Address | First recorded sale | Most recent sale | Cash a year | Real a year |
|---|---|---|---|---|
| 65 Winston Drive | £97,500 (2004) | £114,000 (2025) | +0.7% | -2.1% |
| 57 Winston Drive | £90,500 (2005) | £95,000 (2025) | +0.2% | -2.6% |
| 82 Winston Drive | £119,950 (2004) | £178,500 (2025) | +1.9% | -0.9% |
| 49 Winston Drive | £92,500 (2004) | £105,000 (2022) | +0.7% | -1.9% |
| 68 Winston Drive | £110,000 (2004) | £175,000 (2022) | +2.6% | 0.0% |
| 78 Winston Drive | £119,950 (2005) | £177,500 (2021) | +2.5% | +0.2% |
| 51 Winston Drive | £50,000 (2004) | £98,950 (2021) | +4.1% | +1.8% |
| 11 Winston Drive | £125,000 (2003) | £200,000 (2021) | +2.6% | +0.4% |
| 52 Winston Drive | £85,000 (2003) | £128,000 (2021) | +2.3% | +0.0% |
| 53 Winston Drive | £50,000 (2004) | £95,000 (2021) | +3.8% | +1.5% |
| 23 Winston Drive | £92,500 (2003) | £168,000 (2020) | +3.6% | +1.3% |
| 12 Winston Drive | £99,000 (2002) | £215,000 (2020) | +4.4% | +2.1% |
Section 04
What sells here
The mix of property types explains a large part of any area's median. Winston Drive, Skegness is dominated by the type at the top of this table, so its overall median leans that way.
| Property type | Sales | Share | Median paid | Range |
|---|---|---|---|---|
| Detached | 54 | 38.3% | £135,000 | £75,000 – £243,000 |
| Terraced | 47 | 33.3% | £115,000 | £80,000 – £178,500 |
| Flat or maisonette | 25 | 17.7% | £95,000 | £50,000 – £114,000 |
| Semi-detached | 15 | 10.6% | £97,950 | £50,000 – £168,000 |
Section 06
Ownership and new build in Winston Drive, Skegness
27 of the sales on record are leasehold and 114 freehold — 19.1% of the market. Tenure is not a detail: a leasehold flat and a freehold house are different assets, and mixing them into one median hides the difference.
The median leasehold sale is £95,000 and the median freehold sale £119,975 — a gap of +26.3%. Most of that gap is property type rather than tenure itself: leasehold here is largely flats, freehold largely houses.
| Category | Sales | Share | Median paid |
|---|---|---|---|
| Leasehold | 27 | 19.1% | £95,000 |
| Freehold | 114 | 80.9% | £119,975 |
| New build | 58 | 41.1% | £92,500 |
| Existing home | 83 | 58.9% | £125,000 |
New builds sold for less than the median existing home — -26.0%. A new-build premium is normal: the buyer gets a warranty and nothing to fix, and the price is set by a developer rather than negotiated between two households.
A further 11 transfers for this area are on the register but are left out of every figure above. HM Land Registry marks them as additional price paid entries: repossessions, buy-to-let portfolio moves, transfers between companies or family, and sales at a discount such as right to buy. They are real records but they are not open-market prices, and including them would drag the median somewhere no buyer ever paid.
Section 09
How Winston Drive, Skegness compares
The median across the whole archive is £157,500. Winston Drive, Skegness sits below that national figure — -28.6%.
Within Skegness the street ranks 282 of 489 by median price, and its median is below the town figure of £114,000 (-1.3%).
Where an EPC floor area could be matched to the sale, the median works out at £1,463 per square metre, across 34 of the 141 sales on record. Price per square metre is the only figure that compares a two-bed flat with a four-bed house honestly.
The full range on record runs from £50,000 to £243,000. Extremes usually mean something unusual — a plot sold without a house on it, a transfer between family members, or a very large property — so the median is the number to trust.
Section 10
Nearby on the record
Streets nearby
- Roman Bank£84,250 median
- Drummond Road£139,875 median
- Burgh Road£123,000 median
- Sunningdale Drive£136,500 median
- Richmond Drive£120,000 median
- Beacon Park Drive£109,950 median
- Park Avenue£88,000 median
- Hoylake Drive£127,500 median
- Beresford Avenue£137,250 median
- Lincoln Road£103,000 median
- Beacon Way£105,000 median
- St Andrews Drive£170,000 median
- Grosvenor Road£78,000 median
- Firbeck Avenue£132,500 median
- Gleneagles Drive£140,000 median
- Queens Road£78,000 median
Addresses with more than one recorded sale
- 12 Winston Drive5 sales
- 65 Winston Drive4 sales
- 57 Winston Drive4 sales
- 54 Winston Drive4 sales
- 14 Winston Drive4 sales
- 44 Winston Drive4 sales
- 74 Winston Drive4 sales
- 68 Winston Drive3 sales
- 52 Winston Drive3 sales
- 23 Winston Drive3 sales
- 5 Winston Drive3 sales
- 88 Winston Drive3 sales
- 21 Winston Drive3 sales
- 61 Winston Drive3 sales
- 34 Winston Drive3 sales
- 33 Winston Drive3 sales
- 36 Winston Drive3 sales
- 40 Winston Drive3 sales
- 38 Winston Drive3 sales
- 42 Winston Drive3 sales
- 82 Winston Drive2 sales
- 49 Winston Drive2 sales
- 78 Winston Drive2 sales
- 51 Winston Drive2 sales
Back to Skegness house prices.
Quick answers
Common questions about this data
What is the average house price in Winston Drive, Skegness?
The median price paid in Winston Drive, Skegness across every sale on the register is £112,500. The median is used rather than the mean because a handful of very large sales would otherwise drag the average away from what a typical buyer paid.
How many homes have sold in Winston Drive, Skegness?
141 sales are on record for Winston Drive, Skegness, the most recent completing on 9 Oct 2025. Every one is a completed transfer lodged with HM Land Registry, not an asking price or an estimate.
Have Winston Drive, Skegness house prices actually risen?
In cash, the median rose -16.8% between 2009 and 2021. In 2026 money — that is, after inflation — the change is -36.1%. Both numbers are true; only the second one tells you whether buying here preserved value.
When were Winston Drive, Skegness house prices at their highest?
The highest yearly median on record is £135,500, set in 2007. That is the cash figure; measured in 2026 money the peak may fall in a different year, because inflation reshapes the series.
What is the price per square metre in Winston Drive, Skegness?
£1,463 per square metre, from the 34 sales where an EPC floor area could be matched to the address. Price per square metre strips out size, so a flat and a house can be compared on the same basis.
How current is this data?
The latest sale shown here completed on 9 Oct 2025. HM Land Registry publishes Price Paid Data monthly and a sale can take a month or two to appear after completion, so the most recent weeks are always incomplete.
Cite this page: Sold Price History, “Winston Drive, Skegness house prices”, 2026. Source: HM Land Registry Price Paid Data © Crown copyright and database right, used under the Open Government Licence v3.0. Inflation adjustment: ONS CPIH.