Be the first Estate
Agent here!

Cheapside Road

Cheapside RoadHouse Prices / South East, Windsor and Maidenhead

Last updated May 2026

Key Street Insights

Cheapside Road is a residential street with 87 addresses.

It ranks as the 365th largest and 208th most expensive of the 390 streets in the SL5 area. The dominant property type is a period house built between 1800 and 1911.

The street contains a total of 87 properties: 81 houses and 6 flats.

87
Properties
  • Houses
  • Flats

Our partners and
data sources

Get a Fast Offer
for your property
Blog header image

House Priceson Cheapside Road

Sale prices range from £340,044 for 2 bedroom freehold houses with a garden (635 ft2) to £2,879,737 for 6 bedroom freehold houses with a garden (6,070 ft2) .

Monthly rental prices range from £1,561 pcm for 2 bed houses to £7,236 pcm for 6 bed houses.

The gross rental yield is between 3.0% and 5.5%.

The average value per square foot is £560.

Average Sale Value
£944,534
Average Rental Value
£3,195 pcm
Average Rental Yield
4.1% /year
Average Value Per Sqft
£560 /ft2
Prices last updated 1st May 2026
Blog header image
Blog header image
Properties list background

Properties and Buildingson Cheapside Road, Ascot, SL5

properties list title title

Sales History
on Cheapside Road, Ascot, SL5

The last sale was on 24th November 2025 for £18,000,000 and since then the market in the area has decreased by 1.6%. The street has had a total of 109 sales since 1995.

Cheapside Road, Ascot, SL5 has seen 10 sales in the last three years and 1 sale in the last twelve months.

properties list title title
properties list title title

Nearby Streetsto Cheapside Road, Ascot, SL5

Cheapside Road, Ascot, SL5 is the 365th largest and the 208th most expensive street in the SL5 area.

properties list title title

Postcodeson Cheapside Road, Ascot, SL5

There are 10 postcodes on Cheapside Road, Ascot, SL5.

properties list title title

Property Typesin Cheapside Road

  • 24 period houses built between 1800 and 1911
  • 11 period flats built between 1800 and 1911
  • 10 modern houses built after 1980
  • 6 mid-century houses built between 1936 and 1979
  • 7 houses of an unknown age
  • 29 other addresses of unknown type
  • period house (24)
  • period flat (11)
  • modern house (10)
  • mid-century house (6)
  • house (7)
  • Unknown (29)
Energy Efficiency

Energy Efficiencyof properties on Cheapside Road

  • Energy Performance Certificate (EPC) surveys conducted for 46 properties.
  • The dominant rating is D.
  • A (0)
  • E (7)
  • B (7)
  • F (1)
  • C (8)
  • G (0)
  • D (23)
  • No EPC (41)
Schools Nearby

Schools Nearbyto Cheapside Road, Ascot, SL5

The nearest primary school to Cheapside Road, Ascot, SL5 is Cheapside CofE Primary School which is 95 metres away.
  • 95
    m
    Cheapside CofE Primary School
  • 1.8
    km
    St Michael's CofE Primary School, Sunninghill
  • 2.3
    km
    Holy Trinity CofE Primary School, Sunningdale
The nearest secondary school is Charters School which is 2.8 kilometres away.
  • 2.8
    km
    Charters School
  • 6.1
    km
    Windsor Girls' School
  • 7.0
    km
    Ranelagh School
More reading links
Source: Ofsted 2026
Public Transport Nearby

Public Transport Nearbyto Cheapside Road, Ascot, SL5

The closest station to Cheapside Road, Ascot, SL5 is Ascot (Berks) station which is 2.4 kilometres away.

  • 2.4
    km
    Ascot (Berks)
  • 3.0
    km
    Sunningdale
  • 5.1
    km
    Longcross
Loading...
Loading...
Loading...
Loading...