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Many older parts of Hailsham have been lost to redevelopment prior to preservation orders being introduced, so in spite of its historic age, the present town retains few buildings, which display any evidence of antiquity. The houses are mainly Victorian in character with more modern residential developments around the original town centre.

Some facades, however, hide the real age of the structures behind them. Various buildings in the High Street preserve evidence of 16th or 17th century timber framing. St. Mary's Parish Church (in Vicarage Field) dates back to the early 15th century, although there is evidence of a church on this site in the early 13th century.

The oldest house is probably “The Stone” (Vicarage Road/ Marshfoot Lane), likely named after an old boundary stone in the grounds, and originally built about 1320, in the style of the old Wealden Hall houses.

Featuring inglenook fireplaces, a bread oven, a priest hide, and with evidence of early sliding shuttered windows, it was once owned by Cardinal Wolsley.

Of a slightly later period, are the timber-framed buildings in the High Street, now occupied by Haywards Carpets, Paydens (Chemist), and the “Homely Maid” (Café and Patisserie) - which was once an inn called “The Good Intent”.

The “Fleur-de-Lys” and “Inglenook” (Market Square/Market Street) - one building divided in two in the late 19th century, but now reinstated as one - was originally built in the reign of Elizabeth I (1542) as part of the original hostelry of the town. From here the London coach started and people from outlying villages such as Bourne (Eastbourne) or Alfriston had to make their way to HaiIsham as best they could.

Later to become the Workhouse, after which it was converted to shops and residential dwellings, it is now the Hailsham Town Council’s offices and meeting room.

More recent buildings with significant historical backgrounds are, “The Grenadier Inn “(High Street/London Road - c. 1803); “The Crown Inn” and “Corn Exchange” (central High Street); “Cortlandt” (George Street - 1793). The latter ceased to be a residence in 1932 when it was bought by the Hailsham Rural District Council for offices.

The Old Vicarage - now “The Grange” (Vicarage Road) is an early 18th century residence. Built of red and grey bricks with pediments and classic pilasters, it contains an attractive period staircase with carved tread ends and twisted balusters.

Other than the town centre, there are also various late period residences and characteristic old Sussex farmhouses elsewhere in, or close to, the Parish, including an interesting building at Amberstone Corner, parts of which date from the 15th century.

“WiIlowhyrst” which dates back to the Tudor period; and “Carters Corner Place”, once the home of the Right Hon. Lord Hailsham, Quintin Hogg, and which bears the date 1602.