Today's Winchelsea was the result of the old town's population moving to the present site, when in 1281 King Edward I ordered a planned town, based on a grid, to be built.
The names of the town planners are recorded as Henry le Waleys and Thomas Alard.
The new town inherited the title of "Antient Town" from Old Winchelsea and retained its affiliation to the Cinque Ports confederation together with Rye and the five head-ports.

Winchelsea was greatly involved in the wine trade with Guyenne and the extensive wine cellars under the town may still be visited on open days.

The town had a tidal harbour on the River Brede.
It flourished until the middle of the 14th century.
It then suffered French and Spanish raids during the Hundred Years' War until the 15th century and was hit by the Black Death.
In 1350, the Battle of Les Espagnols sur Mer was fought nearby.
In 1360 the town was sacked and burnt by a French expeditionary force, sent in an unsuccessful attempt to retrieve their King John II of France captured at the Battle of Poitiers four years earlier.
The town remained prosperous, although reduced in size until the 1520s.
The silting of the harbour ultimately destroyed its prosperity.
Camber Castle was built by Henry VIII in the early 16th century halfway between Winchelsea and Rye to guard the approach to the Camber.
Much of the stone used in its construction may have been taken from the demolition of the Franciscan monastery of Greyfriars.

Winchelsea retains its medieval setting on a hill surrounded by largely empty marsh, the original layout of the planned town and the largest collection of medieval wine cellars in the country with the possible exception of Norwich and Southampton.
It also retains three of the four town gates and several original buildings, including the parish church, which is dedicated to St Thomas the Martyr.
Another church, St Leonard's, was later the site of a windmill, which was blown down in the Great Storm of 1987.
Some of the original 13th/14th-century fortifications can still be seen at the Strand Gate and Pipewell or Ferry Gate.
The scale of the original plan for New Winchelsea can be judged by the site of the "New Gate", over half a mile outside the current town.

Across the road from the churchyard stands the Court Hall, one of Winchelsea's oldest buildings, the lower floor once being the gaol.
The first floor is now a museum, full of relics of the history of Winchelsea, the Corporation, and a model of the town.
Nearby is the town well, dug in 1851 to save water being carried up the hill.
It is thought to be 80 feet deep.
At the foot of Strand Hill stands the town workhouse Strand House just behind the port area of Winchelsea which runs along the river bank on the far side of the main road.
This area contains the remains of several old buildings, such as the Old Malt House and Appletree Wick while Strand House itself was built around 1425 according to dendrochronology.
These buildings made up the workhouse of the parish of Winchelsea being known as "The Old Poor Houses".
The area was a subject of archaeological investigation in 2013 which found the remains of the medieval wharf and a medieval boat next to the Bridge Inn.

Winchelsea stands on the main south coast road, the A259.
The Royal Military Canal built in the early 19th century as a defence-line against the highly anticipated invasion by Napoleon Bonaparte passes the eastern side of the town and connects to the river Brede.

The town lends its name to the nearby seaside village of Winchelsea Beach.
Today's Winchelsea was the result of the old town's population moving to the present site, when in 1281 King Edward I ordered a planned town, based on a grid, to be built. The names of the town planners are recorded as Henry le Waleys and Thomas Alard. The new town inherited the title of "Antient Town" from Old Winchelsea and retained its affiliation to the Cinque Ports confederation together with Rye and the five head-ports.
Winchelsea was greatly involved in the wine trade with Guyenne and the extensive wine cellars under the town may still be visited on open days.
The town had a tidal harbour on the River Brede. It flourished until the middle of the 14th century. It then suffered French and Spanish raids during the Hundred Years' War until the 15th century and was hit by the Black Death. In 1350, the Battle of Les Espagnols sur Mer was fought nearby. In 1360 the town was sacked and burnt by a French expeditionary force, sent in an unsuccessful attempt to retrieve their King John II of France captured at the Battle of Poitiers four years earlier. The town remained prosperous, although reduced in size until the 1520s. The silting of the harbour ultimately destroyed its prosperity. Camber Castle was built by Henry VIII in the early 16th century halfway between Winchelsea and Rye to guard the approach to the Camber. Much of the stone used in its construction may have been taken from the demolition of the Franciscan monastery of Greyfriars.
Winchelsea retains its medieval setting on a hill surrounded by largely empty marsh, the original layout of the planned town and the largest collection of medieval wine cellars in the country with the possible exception of Norwich and Southampton. It also retains three of the four town gates and several original buildings, including the parish church, which is dedicated to St Thomas the Martyr. Another church, St Leonard's, was later the site of a windmill, which was blown down in the Great Storm of 1987. Some of the original 13th/14th-century fortifications can still be seen at the Strand Gate and Pipewell or Ferry Gate. The scale of the original plan for New Winchelsea can be judged by the site of the "New Gate", over half a mile outside the current town.
Across the road from the churchyard stands the Court Hall, one of Winchelsea's oldest buildings, the lower floor once being the gaol. The first floor is now a museum, full of relics of the history of Winchelsea, the Corporation, and a model of the town. Nearby is the town well, dug in 1851 to save water being carried up the hill. It is thought to be 80 feet deep. At the foot of Strand Hill stands the town workhouse Strand House just behind the port area of Winchelsea which runs along the river bank on the far side of the main road. This area contains the remains of several old buildings, such as the Old Malt House and Appletree Wick while Strand House itself was built around 1425 according to dendrochronology. These buildings made up the workhouse of the parish of Winchelsea being known as "The Old Poor Houses". The area was a subject of archaeological investigation in 2013 which found the remains of the medieval wharf and a medieval boat next to the Bridge Inn.
Winchelsea stands on the main south coast road, the A259. The Royal Military Canal built in the early 19th century as a defence-line against the highly anticipated invasion by Napoleon Bonaparte passes the eastern side of the town and connects to the river Brede.
The town lends its name to the nearby seaside village of Winchelsea Beach.
Winchelsea