77 Maidstone Dr

Exceptional opportunity in the Town of Montgomery! Welcome to 77 Maidstone Drive, Walden, NY—a meticulously updated legal 2-family currently configured as a spacious single-family home, offering flexibility for multi-generational living, income potential, or future conversion.

Tucked away on a peaceful cul-de-sac, this property offers privacy, curb appeal, and a truly extraordinary setting. The grounds are a standout feature, showcasing beautifully curated gardens, specimen trees, professional landscaping, and timeless stone walls and hardscape, all thoughtfully designed to enhance the natural surroundings and create a rich, estate-like presence. A circular driveway completes the approach, setting the tone for what awaits. Enjoy the quiet rhythm of cul-de-sac living—perfect for daily strolls, walking the dog, or cycling along your peaceful street.

Pride of ownership is evident throughout with major upgrades including newer roof (2016), vinyl siding (2015), and a fully owned solar energy system for long-term efficiency and savings.

The home features a thoughtfully designed layout with a newer 1-bedroom living space on the main level and a 2-bedroom configuration below—ideal for extended family, guests, or potential rental use. Interior spaces are in pristine condition with updated kitchens, renovated baths, custom finishes, and abundant natural light. The newly renovated kitchen is a true centerpiece, featuring a gorgeous design with a chef’s oven and gas cooktop—while both kitchens are equipped with gas cooktops, a rare and highly desirable feature for the true chef. The current owners have thoughtfully completed extensive upgrades throughout, creating a truly turnkey, move-in-ready home where there is nothing to do but unpack and enjoy.

Outdoor living is where this home truly shines. Enjoy your morning coffee or evening unwind from the back porch with stunning mountain views creating a serene and scenic backdrop. A beautifully constructed three-season room, upper and lower decks, and thoughtfully designed outdoor living spaces make this property perfect for entertaining or quiet retreat.

Perfectly positioned to experience the best of the Hudson Valley lifestyle, you’re just minutes to Angry Orchard Cider House, scenic hiking and biking trails, and world-renowned destinations including Minnewaska State Park Preserve and the vibrant New Paltz area. Enjoy nearby wineries, orchards, breweries, and farm-to-table dining that make this region one of the most sought-after escapes from NYC.

Extensive improvements including Anderson windows, updated systems, and major infrastructure upgrades provide peace of mind for years to come.

Whether you're searching for a move-in-ready home with room to grow, a weekend retreat, or a smart investment opportunity, this property offers unmatched versatility, condition, and location.