1. St. Thomas the Martyr Church: A historic gem, St. Thomas the Martyr Church features beautiful medieval stained glass windows and a remarkable 14th-century stone pulpit. Take a moment to admire the intricate craftsmanship and soak in the atmosphere of this ancient place of worship.

2. Winchelsea Court Hall Museum: Delve into Winchelsea's rich history at the Court Hall Museum, housed in a 15th-century building. Explore a fascinating collection of artefacts, including the original town seals, and learn about the area's past, from its medieval origins to the present day.

3. Winchelsea Cellars: A unique experience awaits you in the medieval cellars beneath Winchelsea's charming streets. Join a guided tour and uncover the secrets of these atmospheric, vaulted spaces that once stored goods and contributed to the prosperity of the ancient town.

4. Winchelsea Beach: Enjoy a leisurely stroll along the shingle beach, taking in the stunning views of the English Channel. Perfect for a family day out, Winchelsea Beach offers a tranquil setting for picnics, beachcombing, birdwatching, and simply appreciating the beauty of the East Sussex coast.

5. Smugglers Walk: Immerse yourself in the intriguing history of smuggling in Winchelsea by following the Smugglers Walk. This self-guided trail will lead you through picturesque streets and lanes, revealing the town's hidden connections to the notorious Hawkhurst Gang and other smuggling tales.

1. High Street: The charming High Street offers a delightful blend of historic properties, local shops, and cosy cafes. This central location is perfect for those who appreciate the convenience of being close to essential amenities.

2. Castle Street: Lined with picturesque cottages and period homes, Castle Street is ideal for those seeking a tranquil setting steeped in history. This charming street is also close to Winchelsea's medieval landmarks.

3. Rectory Lane: Known for its beautiful houses and peaceful atmosphere, Rectory Lane is a highly sought-after area in Winchelsea. Its proximity to the ancient St Thomas' Church adds to the appeal for those interested in the town's rich heritage.

4. Mill Road: Situated near the stunning Winchelsea Beach, Mill Road is perfect for nature lovers and those who enjoy coastal living. The nearby nature reserve offers ample opportunities for birdwatching and leisurely walks.

5. Sea Road: Boasting stunning sea views, Sea Road is an idyllic location for individuals and families who appreciate the beauty and serenity of coastal living. The nearby Winchelsea Beach provides a perfect backdrop for leisure activities and relaxation.

6. German Street: German Street is a quaint and historic location, featuring a mix of charming cottages and period homes. Its close proximity to the town centre and local attractions makes it an ideal spot for those seeking convenience and character.

7. Pett Level Road: Offering a blend of countryside living and coastal charm, Pett Level Road is a desirable area for those who enjoy the best of both worlds. With easy access to Winchelsea Beach and the surrounding countryside, residents can enjoy a range of outdoor pursuits.

8. Friars Road: Known for its attractive period properties and peaceful atmosphere, Friars Road is a popular choice for families and individuals seeking a quiet, residential area with a strong sense of community.

9. Ferry Hill: Overlooking the River Brede, Ferry Hill offers stunning views and a serene environment for those who appreciate natural beauty. The nearby Strand Quay is perfect for leisurely strolls and enjoying the scenery.

10. South Undercliff: South Undercliff boasts a collection of beautiful homes, many offering wonderful sea views. This desirable area provides a tranquil setting for those who value a peaceful lifestyle, while still being close to local amenities.

1. Rich Historical Heritage: Winchelsea boasts a fascinating history dating back to the 13th century. With well-preserved historical sites, such as the medieval town gate, the Church of St. Thomas the Martyr, and several ancient wine cellars, residents and visitors alike can immerse themselves in the town's intriguing past.

2. Stunning Natural Beauty: Surrounded by rolling hills, lush countryside, and picturesque landscapes, Winchelsea provides an idyllic setting for individuals seeking tranquillity. The nearby Winchelsea Beach, Pett Level, and the High Weald Area of Outstanding Natural Beauty offer ample opportunities for outdoor enthusiasts to explore and enjoy.

3. Friendly Community Spirit: Known for its warm and welcoming residents, Winchelsea fosters a strong sense of community spirit. Various local events, such as the annual Winchelsea Arts Festival and the Mayor-Making ceremony, encourage social interaction and create lasting memories for those living in the town.

4. Convenient Location: Situated in the heart of Rother, Winchelsea enjoys excellent transport links, making it easily accessible to nearby towns and cities. The town is just a short drive from Hastings, Rye, and Battle, offering residents the convenience of urban amenities within a serene and picturesque setting.

5. Unique Arts and Crafts Scene: Winchelsea is home to a thriving arts and crafts community, with numerous artists, artisans, and craftspeople residing in the area. The town boasts several galleries and studios, where local artists showcase their work, and hosts workshops, allowing residents to learn and develop new skills in various art forms.

1. Limited Amenities: Winchelsea is a small, historic town which may not cater to all the modern conveniences and amenities that one might be accustomed to in larger cities. This includes a limited number of shops, restaurants, and entertainment options, which may require residents to travel to nearby towns for a wider variety of services.

2. Public Transportation: The public transport connections in Winchelsea can be sparse, with infrequent bus services and the nearest train station being in the adjacent village of Winchelsea Beach. This can make it challenging for those without personal vehicles to travel to nearby towns and cities for work or leisure purposes.

3. Employment Opportunities: As a small town, employment opportunities within Winchelsea itself may be limited, particularly in specialised fields. Residents may need to commute to nearby towns or cities for a wider range of job prospects, which can be time-consuming and costly.

4. Tourist Crowds: Winchelsea is a popular destination for tourists due to its rich history and picturesque setting. While this can bring a vibrant atmosphere to the town, it can also lead to overcrowded streets and attractions during peak seasons, which may be a drawback for some residents who prefer a quieter lifestyle.

5. Property Prices: The desirability of Winchelsea as a place to live, combined with its historic charm and limited housing stock, can lead to relatively high property prices. This may make it challenging for first-time buyers or those on a lower budget to find affordable housing in the area.