1. Chepstow Castle: As the oldest surviving post-Roman stone fortification in Britain, Chepstow Castle boasts magnificent architecture and a rich history. Explore the castle's towers, halls, and courtyards while taking in stunning views of the River Wye.

2. Tintern Abbey: Founded in 1131, the awe-inspiring ruins of Tintern Abbey offer a glimpse into the lives of Cistercian monks. Immerse yourself in the serenity of the Wye Valley as you explore the well-preserved remains of the church, cloister, and other monastic buildings.

3. Old Wye Bridge: This iconic 19th-century cast iron bridge is a testament to the engineering prowess of the Industrial Revolution. Connecting Chepstow to the Forest of Dean, the Old Wye Bridge offers picturesque views of the town and its surroundings.

4. Chepstow Museum: Housed in a beautiful Georgian townhouse, the Chepstow Museum showcases the fascinating history of the town and its inhabitants. Learn about Chepstow's development, from its early days as a bustling port to its role in the Industrial Revolution and beyond.

5. Chepstow Racecourse: Home to the prestigious Welsh Grand National, Chepstow Racecourse offers thrilling horse racing events throughout the year. Enjoy a day at the races, complete with exceptional dining options and stunning views of the surrounding countryside.

1. St. Kingsmark Avenue: A tree-lined road situated near the Chepstow Racecourse, St. Kingsmark Avenue is perfect for families with its large detached homes and tranquil atmosphere.

2. Mathern Road: This desirable road boasts an array of beautiful properties, from period cottages to modern family homes, all within easy reach of local amenities and stunning countryside.

3. Bulwark Road: Located close to the town centre, Bulwark Road offers a mix of charming Victorian terraced houses and spacious family homes, with the added benefit of excellent transport links.

4. Sedbury Lane: Featuring a delightful selection of detached and semi-detached properties, Sedbury Lane is an ideal location for families and professionals, due to its proximity to both Chepstow and the M48 motorway.

5. Itton Road: Set in the picturesque village of Itton, this rural road is perfect for those seeking a peaceful retreat, surrounded by idyllic countryside and charming country cottages.

6. Mounton Road: With its impressive period properties and large gardens, Mounton Road is a popular choice for families and individuals seeking a prestigious address in Chepstow.

7. Pwllmeyric Hill: Offering stunning views of the Wye Valley and surrounding countryside, this sought-after road features a range of luxurious properties, including executive detached homes and stylish new builds.

8. Tutshill: A delightful village located on the outskirts of Chepstow, Tutshill is home to a variety of desirable roads, including Brockweir Road and Beachley Road, both offering a mix of attractive properties and rural charm.

9. Shirenewton: This picturesque village, nestled in the Monmouthshire countryside, boasts several appealing roads, such as The Smithy and Mynyddbach, providing a range of stunning properties and peaceful surroundings.

10. Bayfield Wood: This exclusive development, situated just outside Chepstow, offers a range of modern, high-specification homes set within a private, gated community, making it a highly desirable location for those seeking luxury and privacy.

1. Rich History and Heritage: Chepstow boasts a wealth of historical sites and attractions, including the impressive Chepstow Castle, the oldest surviving post-Roman stone fortification in Britain. Stroll through the charming town centre, which features many well-preserved Georgian and Victorian buildings, and delve into the area's past at the Chepstow Museum.

2. Proximity to Outstanding Natural Beauty: Nestled on the banks of the River Wye, Chepstow is the perfect base for exploring the Wye Valley Area of Outstanding Natural Beauty. Enjoy picturesque walks, cycling routes, and river activities such as canoeing and fishing, all surrounded by stunning landscapes and abundant wildlife.

3. Vibrant Community and Events: Throughout the year, Chepstow hosts numerous festivals, events, and markets, reflecting the town's strong sense of community and cultural diversity. Highlights include the annual Chepstow Show, the Wye Valley River Festival, and the popular Chepstow Racecourse, offering thrilling horse racing and live entertainment.

4. Excellent Transport Links: Chepstow benefits from excellent road and rail connections, making it easy to travel to nearby cities such as Bristol, Cardiff, and Gloucester. The M48 motorway provides direct access to the Severn Bridge, while the town's railway station offers regular services to Newport, Cardiff, and beyond. Additionally, Chepstow is just a short drive away from Bristol Airport for international travel.

5. Leisure and Sports Facilities: The town offers a wide variety of leisure and sports facilities to cater to all interests and ages. The Chepstow Leisure Centre provides a swimming pool, gym, and sports hall, while golf enthusiasts can enjoy the scenic courses at the nearby St. Pierre Golf & Country Club and Chepstow Golf Club. For outdoor pursuits, the National Diving & Activity Centre and Offa's Dyke Path provide thrilling adventures for all abilities.

1. Limited Employment Opportunities: Chepstow is a relatively small town, which means that job opportunities can be somewhat limited. Residents may need to commute to larger cities such as Bristol or Cardiff for a wider range of employment options.

2. Traffic Congestion: Chepstow is known for its traffic congestion, particularly around the M48 Severn Bridge and the A48. During peak hours and holiday seasons, residents may experience longer travel times and increased stress levels.

3. Limited Nightlife and Entertainment: As a small town, Chepstow lacks a vibrant nightlife scene. Residents seeking diverse entertainment options, such as theatres, live music venues or a wide range of restaurants, may need to travel to nearby cities.

4. Limited Public Transportation: While Chepstow has a train station and bus services, the public transportation options are not as extensive or frequent as those in larger cities. This can make it difficult for residents without private transportation to travel around the area.

5. Potential for Flooding: Chepstow is situated along the River Wye, which means that parts of the town are at risk of flooding during periods of heavy rainfall. This can lead to property damage and disruption of daily life for residents in affected areas.