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Noted by Pevsner, prior to boundary changes in 1974, as 'without doubt the finest village street in East Sussex" containing at least thirty five buildings of ancient origin with about twelve surviving from the medieval period. The original linear settlement runs from the church in the north to the common in the south. The oldest part is undoubtedly around the church where the street, having ascended from the Ouse valley to the north, briefly diverts itself around the old churchyard then straightens then gently descends as it resumes its journey southwards initially to the junction with Lewes Road and the Town Pond then briefly beyond past the latter to the common before turning west once more as Black Hill and heads towards Haywards Heath.

The section to the south of the church was the first expansion of the settlement and is believed to have been planned by the then lords of the manor, the Canons of South Malling near Lewes, to accommodate a weekly market given approval in 1344. The street itself widens as it heads down to the junction with the old road to Lewes. Only one house, number 65, is believed to predate this grant. Thirteen houses survive from the period 1350-1500, these being numbers 36-38, 76, 84-86, 95, 107, 115, 122, 126, 135, 153, 171, the Thatched Cottage and Old Place. All these buildings are timber framed Wealden Hall types though many were refronted in the Georgian era. Beyond that era, 8 survive from the 16th century, 14 from the 17th, 12 from the 18th and 15 from the early 19th century. The latter tended to be located to the south around the common and the old pond.

With the arrival of the railway at Haywards Heath, Lindfield's development initially stalled in the short term as it lost much trade to its new neighbour as well the disappearance of a former London-Brighton coaching route that had operated through the settlement since the 1770s. However, the rapid growth of its neighbour led in the long run to the development of the town in the 20th century particularly off the High Street. This in turn has meant that the High Street still retains a number of services particularly at the southern end. There are still four pubs, a number of tea houses, a small Co-op, the Post Office still survives but has downsized and moved into a local newsagent, a butcher, toy shop and a couple of small boutiques amongst others.

Created: Mon, 31 Aug 2015, Updated: Tue, 1 Sep 2015