A rare opportunity to be the next caretakers of a very special century home embodying the majestic history of Webster Groves. This is the quintessential Webster home you've been holding out for! This home is featured on the 32nd Annual Webster Groves Holiday House Tour. Located a block away from beautiful Blackburn Park, The Matthew T. Chestnut home is the original farmhouse that sat on 80 plus original acres in Webster Groves. The Chestnut family holds the namesake for many of the surrounding Street names in the neighborhood, and the home boasts it's very own feature in Marilynne Bradley's book, A City of Century Homes: A Centennial History of Webster Groves Missouri. The current owners have extensive historical information and photos of the original family history they'd love to share. This 5 bedroom 2 bath home is a stunner with original period millwork - much of it untouched - 4 pairs of 8 ft walnut pocket doors, 4 of the 5 original fireplaces, restored original hardwood floors and almost .75 acre of park-like grounds with unlimited possibilities for beautiful gardens. The huge driveway will come in handy for your large gatherings. The dramatic deep front yard with mature trees leads to a large and welcoming covered porch. Step through the original double doors into the a grand foyer and admire the gorgeous original front staircase, original stained glass and one of 4 original fireplaces, each an ode to specific tree varieties once on the property. To the left is the quintessential library, so warm and inviting, that beckons curling up with your favorite drink and a good book. The 2nd original fireplace with hand carved mantle is a beautiful focal point, along with the Restoration Hardware lighting. Through the library to the living room you will find more beautiful original woodwork, remarkable carved oak mantel and gas insert for cozy fire nights. Look up to find a stunning carved ceiling medallion and designer lighting, elegant curved walls, black Jeld-Wen windows and display nook. The large dining room will hold a table for 12+, contains a roomy coat closet and is anchored by a stunning Ralph Lauren 9-Light chandelier. The main level has great flow for entertaining! The darling cottagecore kitchen with designer appliances, quartz sink and an abundance of natural light is sure to delight any home chef. An updated full bath and bonus main floor laundry room rounds out the main floor. A second staircase takes you upstairs past more original stained glass to the 2nd floor where you'll find another full bathroom clad with marble tile and designer details, plenty of bedrooms for a growing family, and elegant owners suite with the 4th decorative fireplace in rich wood and an attached 5th bedroom that leads to a huge enclosed sunporch. The cutest staircase leads you up to a breathtaking 3rd floor bathed in light. The options upstairs are endless - family room, playroom, office, or an another bedroom, the flexibility of this 3rd floor space is just icing on the cake after touring this home. The current owners worked with well-known award winning architects to produce 2 sets of Webster approved plans, one for a luxurious kitchen and mudroom addition and the other for a custom primary bathroom and luxury closet room in place of the 5th bedroom. Plans are already approved and will be available for viewing. Webster has also approved a pool on the property and the contract may be negotiated, though there is no pool installed yet. Important brand new updates include new Owens Corning architectural 30 yr roof, all new high efficiency HVAC, refinished hardwoods, new premium carpet in upstairs hallway, new 50g water heater, new copper water line from street service. Walk to gorgeous parks, award winning schools and restaurants, the Webster Rec center and the booming Old Orchard district from this amazing location. This is the perfect Webster Groves life!