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For sale
£500,000Guide price

Upper High Street, Winchester, Hampshire, SO23 8UX

2bedrooms
1bathroom
Terracedtype
Freeholdtenure

Listed 27 Aug 2026 · Winchester

How the price compares

This home£500,000
Median 2 bed in SO23£400k63 homes listed · £505 per sq ft
Difference+25%above the area median

Key features

  • Charming period cottage in a perfectly central location, offering stylish and convenient city living.
  • Lovely sitting room with wood-burning stove, stripped wooden floorboards and a charming dining room with cast-iron fireplace.
  • Well-appointed kitchen with white high-gloss units and solid worksurfaces, plus a modern bathroom.
  • Two generous double bedrooms, with the main bedroom benefiting from a newly installed separate WC.
  • Wonderful cellar providing excellent additional storage, alongside a surprisingly spacious private garden with mature planting.
  • Ideally positioned close to Winchester city centre and mainline railway station with excellent M3 access. Included in the competitive Westgate and Western school catchments

About this home

A charming period cottage occupying a highly central and convenient position, combining beautifully presented accommodation with stylish city living and a wealth of original character.

The welcoming sitting room features a wonderful wood-burning stove set within a brick-lined chimney, while stripped wooden floorboards continue through to the dining room. This charming space includes a painted cast-iron fireplace and fitted cupboards. The kitchen is fitted with contemporary units, complemented by solid worksurfaces, with the modern bathroom located beyond. Planning permission is also in place for a kitchen extension, should additional space be desired.

The fully tanked basement provides excellent additional accommodation and is currently used as a utility and storage space. A built-in humidifier keeps the room exceptionally dry, while underfloor heating makes it warm and cosy in winter and pleasantly cool in summer. The basement stairs and handrail are constructed from solid oak, and the original beams have been carefully exposed. The former coal-chute window has been retained, now double glazed and opening easily from within, while the original fireplace shape has also been preserved as a nod to the room's history. The first floor offers two generous double bedrooms. The principal bedroom benefits from a recently installed separate WC, created from what was previously a cupboard.

Original Georgian brickwork has been carefully exposed, revealing historic brick and mortar, along with remnants of horsehair, leaves and timber from the property's earlier construction. The second bedroom enjoys views towards the garden office and its sedum roof. The surprisingly generous private garden is beautifully planted with mature roses, shrubs and established fig trees, which have been carefully trained to intertwine and create a wonderful summer canopy. A patio laid with hand-cut Honey Cathedral limestone provides an idyllic setting for outdoor dining, creating a peaceful oasis in the heart of the city. At the end of the garden is a spacious, purpose-built home office and recording studio.

Originally designed as a recording studio for Ben, a filmmaker, it has been thoughtfully constructed with natural cork flooring, chosen for its acoustic qualities, together with wood panelling, electricity, internet and heating. The generous proportions allow space for a double bed, and the room has also been used comfortably as a guest house. Its sedum roof provides an attractive seasonal outlook from the second bedroom.

ADDITIONAL INFORMATION

Has conservation area

Materials used in construction: Ask Agent

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Upper High Street enjoys an elevated and exceptionally convenient position, equidistant from Winchester's mainline railway station and the principal high street, placing the thriving city centre within easy walking distance. Winchester offers an eclectic selection of independent shops, bars and restaurants, together with the regular Hampshire Farmers' Market. The River Park Leisure Centre and Recreation Ground, St Giles' Hill, St Catherine's Hill and the Water Meadows are all close by, providing excellent opportunities for recreation and walks. Also located in Westgate and Western school catchments. Winchester's mainline station offers direct and convenient access to London and beyond, while the M3 is readily accessible, with Junction 10 to the south and Junction 9 to the north. Residents are also able to apply for on-street parking.

Property details

Property type
Terraced
Council tax band
D
Tenure
Freehold
Parking
On street, Permit
Garden
Yes
Heating
Gas
Broadband
FTTP (fibre to the premises)
Electricity
Mains supply
Water
Mains supply

Floorplan

1511866 L.jpg

Location

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  • Winchester Station0.2 mi
  • Shawford Station3.0 mi

What nearby homes sold for

Median sold prices in SO23 over the last 12 months: terraced £518k · flat £270k · semi-detached £505k · detached £850k.

AddressTypeSoldPrice
Flat 5, Chancery House, 11, Upper High Street
Winchester SO23 8UT
Flat
Leasehold
8 Jun 2026£375,000
9 Upper High Street
Winchester SO23 8UT
Semi-detached
Freehold
15 May 2026£430,000
17 Upper High Street
Winchester SO23 8UT
Terraced
Freehold
28 Apr 2026£605,000
Flat 3, Wessex Court, 4a, Upper High Street
Winchester SO23 8UT
Flat
Leasehold
27 Feb 2026£510,000
Flat 4, Chancery House, 11, Upper High Street
Winchester SO23 8UT
Flat
Leasehold
12 Dec 2025£208,500
31 Upper High Street
Winchester SO23 8UX
Terraced
Freehold
31 Oct 2025£450,000
Flat 3, Chancery House, 11, Upper High Street
Winchester SO23 8UT
Flat
Leasehold
12 Sept 2025£200,000
Sherwood House 2, 8a, Upper High Street
Winchester SO23 8UT
Other
Freehold
2 Dec 2024£1,500,000
8 Upper High Street
Winchester SO23 8UT
Terraced
Freehold
19 Nov 2024£465,000
Monument House, 5, Upper High Street
Winchester SO23 8UT
Terraced
Freehold
30 Aug 2024£800,000

Contains HM Land Registry data © Crown copyright and database right 2026. Licensed under the Open Government Licence v3.0. All sales in SO23

Buying costs

Monthly repayment£2,501£50,000 deposit · £450,000 loan
Stamp Duty£15,000England rates

Estimates only, using rates in force from April 2025. Check GOV.UK, Revenue Scotland or the Welsh Revenue Authority and speak to a mortgage adviser before you offer.

Listed by Charters, Winchester on Rightmove (original listing). First listed 27 Aug 2026; details checked 7 Nov 2026. Latest change: added on 27/08/2026.

Agent disclaimer

Disclaimer - Property reference WIN240852. The information displayed about this property comprises a property advertisement. Rightmove.co.uk makes no warranty as to the accuracy or completeness of the advertisement or any linked or associated information, and Rightmove has no control over the content. This property advertisement does not constitute property particulars. The information is provided and maintained by Charters, Winchester. Please contact the selling agent or developer directly to obtain any information which may be available under the terms of The Energy Performance of Buildings (Certificates and Inspections) (England and Wales) Regulations 2007 or the Home Report if in relation to a residential property in Scotland.

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