5 bed detached house for sale

Chestnut Drive, Windsor SL4

Spacious Five Bedroom Home With Annex & Large Gardens Just Off The Prestigious St. Leonard’s Hill

Located in the heart of one of Windsor’s most exclusive and sought-after residential addresses, this distinguished five bedroom detached home on Chestnut Drive, just off St. Leonard’s Hill, offers an exceptional blend of space, seclusion and lifestyle potential.

Occupying one of the largest and most private plots on the road, the property is set within magnificent, landscaped gardens extending to just under 0.4 acre, with mature trees, sun-drenched terraces and sweeping lawns that create an idyllic retreat.

This rare and versatile home includes a self-contained one-bedroom annex, seamlessly integrated into the main house—perfect for extended family, an au pair suite, guests, or even rental potential. The main accommodation is thoughtfully arranged, featuring four generously sized bedrooms on the first floor, three well-appointed bathrooms and spacious, light-filled living areas that overlook and open onto the stunning garden.

The elegant exterior is matched by the substantial frontage, offering extensive driveway parking for multiple vehicles, with ample space remaining for further extension, reconfiguration, or complete redevelopment, subject to the necessary consents. This unique opportunity is ideal for those seeking to create a dream family home in a location where space and privacy are becoming increasingly rare.

Set on a tranquil, tree-lined road and surrounded by some of Windsor’s most prestigious homes, this property offers a wonderful balance of countryside charm and urban convenience. Windsor’s historic town centre, renowned schools, boutique shops, restaurants, and transport links (including direct trains to London) are all within easy reach, while local walks and green spaces, including Windsor Great Park, are just moments away.

Whether you're drawn by the generous plot, the lifestyle flexibility of the annex, the future development possibilities, or simply the serenity and status of St. Leonard’s Hill, this home presents a truly rare offering.