Milton Overlook Homes with Two Levels

Welcome to Milton Overlook, an enchanting subdivision nestled in the heart of Woodstock, Georgia, within Cherokee County. This picturesque community is a hidden gem, offering residents the perfect blend of suburban tranquility and vibrant city life. With its lush landscapes and charming architecture, Milton Overlook invites you to experience a lifestyle that feels both upscale and welcoming.

One of the standout features of this community is the exquisite two-level homes that grace its streets. Perfectly designed for modern living, these residences boast spacious layouts that cater to families of all sizes. Imagine hosting gatherings in your expansive living room, cooking up culinary delights in a gourmet kitchen, and retreating to your serene master suite at the end of a busy day. With ample space for both relaxation and entertainment, these homes are truly a sanctuary.

Milton Overlook is ideally located, providing easy access to Woodstock's vibrant downtown area, where you can explore an array of shops, restaurants, and recreational activities. The nearby parks and nature trails offer opportunities for outdoor adventures, making it easy to enjoy the beautiful Georgia weather. Additionally, the community is served by highly-rated schools, ensuring that families have access to quality education.

Whether you’re a first-time homebuyer or looking to upgrade, Milton Overlook presents an exceptional opportunity to embrace a lifestyle of comfort, convenience, and community. Come discover your dream home in this delightful subdivision, where every day feels like a getaway!

Newest Milton Overlook Homes with Two Levels

$1,750,000

6 Beds ⋅ 6 Baths ⋅ 10788927 MLS

Welcome to this Extraordinary Custom Estate in the prestigious Milton Overlook community, where timeless architecture, luxury finishes, and exceptional craftsmanship combine to create a truly one-of-a-kind residence. Perfectly positioned on a beautifully landscaped homesite in one of Woodstock's most sought-after neighborhoods, this remarkable home offers convenient access to Downtown Woodstock, Crabapple, Milton, Roswell, top-rated schools, premier golf clubs, upscale dining, shopping, and entertainment while maintaining a peaceful, private setting. A sprawling Covered Front Porch and Grand Foyer Entrance create an unforgettable first impression, opening to elegant living spaces designed for both everyday living and large-scale entertaining. The Main Level features a private Home Office, Formal Dining Room, and an expansive Fireside Family Room that seamlessly connects to the heart of the home. The Chef's Kitchen is a showpiece, offering an Oversized Center Island, Premium Appliances, Custom Cabinetry, abundant storage, and exceptional workspace, while the adjoining Scullery elevates functionality with an Additional Refrigerator, Gas Oven, Dishwasher, extensive Cabinetry, and generous Prep Space. A convenient Half Bath completes the Main Level. Upstairs, the Luxurious Primary Suite serves as a true private retreat, featuring a Sitting Area with Fireplace and an extraordinary Spa-Inspired Ensuite Bath that rivals those found in high-end custom homes. Thoughtfully designed with striking Designer Finishes throughout, the space showcases Dual Furniture-Style Vanities with Vessel Sinks, Quartz Countertops, Backlit Mirrors, a Freestanding Soaking Tub, and a spectacular Oversized Walk-In Shower wrapped in Floor-to-Ceiling Marble-Look Tile. The shower features Dual Rainfall Showerheads, Multiple Body Sprays, Built-In Niches, a Frameless Glass Enclosure, and a spacious Bench Seating Area, creating a true resort-style experience. The expansive Walk-In Closet is equally impressive, featuring Custom Built-Ins designed for both luxury and organization. Additional Bedrooms are generously sized and well-appointed, each offering access to beautifully finished Bathrooms. The Finished Terrace Level provides incredible flexibility with expansive Recreation and Living Spaces, an Additional Bedroom and Full Bathroom, a Kitchen Area, Fitness Room, and abundant Storage. Highlights include a Bar Area, Dedicated Pool Table Room, and a hidden room concealed behind a Murphy Door, creating the perfect space for entertaining, hobbies, or additional storage. Outdoor living is equally impressive with Covered Porches enhanced by Retractable Screens, allowing for year-round enjoyment and seamless Indoor-Outdoor Living, overlooking the private backyard. The Garage has been thoughtfully upgraded with Epoxy Floors, a Workshop Area, and a Mini-Split System, making it ideal for projects, storage, or climate-controlled workspace. Additional premium features include a Whole-House Water Filtration System and professionally tinted windows designed to provide UV Protection while improving energy efficiency and comfort. Combining Luxury Design, Functional Living, and an unbeatable location in Milton Overlook, this exceptional home offers a rare opportunity to enjoy elevated living at its finest.

423 Oakleigh Avenue, Woodstock

$1,299,000

5 Beds ⋅ 4 Baths ⋅ 10782008 MLS

Tucked away on a premier cul-de-sac lot in Milton Overlook, this stunning home sits on a full acre backing to protected greenspace. No homes behind you. No traffic noise. Just peaceful wooded views, visiting deer, and the kind of backyard privacy that's becoming harder and harder to find. This 5 bedroom, 4 bath home offers over 4,200 square feet of thoughtfully designed living space, plus an unfinished daylight basement already framed and stubbed for future expansion. Whether you envision a home theater, gym, golf simulator, in-law suite, you've got the space to make it happen. Inside, soaring 10 foot ceilings and a dramatic wall of floor-to-ceiling windows showcase the breathtaking backyard views. The open-concept layout centers around an incredible chef's kitchen featuring an oversized island, KitchenAid appliances, double ovens, wine bar, quartz countertops, and a walk-in pantry large enough to survive a Costco run. The thoughtful floor plan offers space for every stage of life, including a private main-level guest suite with a full bath, an oversized office with French doors, an elegant dining room, and a practical mudroom that keeps everyday life running smoothly. Upstairs, one of the home's standout features is the oversized loft-flexible living space that can serve as a media room, playroom, or teen retreat. In other words, a place for the kids to disappear without actually leaving the house. The primary suite is its own retreat, complete with a sitting area, newly added designer ceiling beams, spa-inspired bath with soaking tub, oversized shower, dual vanities, and an impressive walk-in closet. Three additional bedrooms are generously sized, with ensuite and Jack-and-Jill bathroom. Outside, the flat backyard offers plenty of room for the pool you've already started pinning on Pinterest, while still preserving the private, park-like setting that makes this property so special. Enjoy morning coffee from the front porch overlooking beautiful treetop views-because coffee simply tastes better with a view like this. The location is equally impressive, placing you within easy reach of some of North Atlanta's most sought-after destinations. Enjoy the restaurants, boutiques, and charm of Downtown Crabapple in about 10 minutes, the vibrant dining and entertainment scene of Downtown Woodstock in roughly 15 minutes, and both Downtown Alpharetta and Avalon in about 20 minutes. Private. Peaceful. Move-in ready! This isn't just another house in the neighborhood. It's the lot everyone wishes they had - and the home everyone hopes they'll find.

401 Oakleigh Avenue, Woodstock

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