Milton Overlook Homes with Two Stories

Welcome to Milton Overlook, a stunning subdivision nestled in the heart of Woodstock, Georgia, within the picturesque Cherokee County. This charming community is designed for those who appreciate elegance and comfort, featuring a collection of exquisite two-story homes that perfectly blend modern amenities with timeless design.

Milton Overlook is renowned for its spacious layouts and thoughtful craftsmanship, making it an ideal choice for families and individuals alike. Each home boasts an impressive two-story design, offering ample living space, high ceilings, and an abundance of natural light. These residences are thoughtfully designed to create an inviting atmosphere, perfect for both entertaining guests and enjoying quiet evenings at home.

The community is strategically located near Woodstock’s vibrant downtown area, where you can explore a variety of boutique shops, delightful eateries, and local parks. Enjoy the convenience of nearby schools, recreational facilities, and easy access to major highways, making commuting a breeze. The serene surroundings and friendly neighborhood vibe make Milton Overlook an oasis of tranquility, allowing residents to escape the hustle and bustle while still being close to urban conveniences.

Outdoor enthusiasts will appreciate the nearby hiking trails and green spaces, perfect for weekend adventures with family and friends. Whether you’re looking to relax in your beautifully landscaped backyard or take a stroll through the community, Milton Overlook offers a lifestyle that combines comfort, convenience, and charm.

Discover your dream home in Milton Overlook today, where every two-story residence tells a story of elegance and warmth, waiting to welcome you home.

Newest Milton Overlook Homes with Two Stories

$1,299,900

7 Beds ⋅ 7 Baths ⋅ 7809362 MLS

Luxury, privacy, and exceptional value converge in this remarkable Toll Brothers residence, offering a rare opportunity to own a nearly new custom quality home below market value. Perfectly positioned just minutes from Milton and Crabapple, this impressive house showcases more than 5,400 square feet of impeccably designed living space, designer-selected finishes, a beautifully finished terrace level, and tranquil wooded views that create a true private retreat. From the moment you enter, you’ll appreciate the soaring ceilings, abundant natural light, designer finishes, and open-concept floor plan created for both everyday living and effortless entertaining. The chef’s kitchen is the heart of the home, featuring premium appliances, an oversized island, abundant cabinetry, and seamless flow into the spacious family room and dining areas. You will fall in love with the walk in pantry, the mudroom storage for coats, shoes and anything else you want to place behind custom cabinets along with a space for your family calendar and drop zone. The luxurious owner’s suite provides a private retreat with a spa inspired bath, and expansive walk-in closets, while the additional bedrooms offer generous space and privacy for family and guests. A dedicated home office, flexible living areas, and a professionally finished terrace level create endless possibilities for entertaining, a home gym, media room, playroom, home school, or multigenerational living. In addition, expansive heated & cooled storage space making exceptional organization in this home. Situated on .74 acres, step outside to enjoy the covered back porch overlooking large backyard plus a wooded area behind the house offering peaceful views and exceptional privacy including a nature buffer. With ample room to create your dream outdoor oasis, including a future pool, outdoor kitchen, or entertaining area, the possibilities are endless. Neighborhood boasts a community pool, playground, and lighted tennis and pickle ball courts and just down the street from the home. Located just minutes from Milton and Alpharetta, this home offers the rare opportunity to enjoy luxury living with the added benefit of lower Cherokee County taxes while remaining close to award-winning dining, Avalon shopping, parks, nearby golf, and top-rated schools. In addition, residents of Cherokee County love the lower taxes compared to neighboring counties, Schedule your private showing today and experience everything this exceptional home has to offer. Note the property line goes far beyond the fence line, as one of the larger lots in this community.

419b Oakleigh Avenue, Woodstock

$1,750,000

6 Beds ⋅ 6 Baths ⋅ 7791009 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 ⋅ 7783780 MLS

NOW OFFERING $10,000 TO USE TOWARD YOUR INTEREST RATE BUY-DOWN OR CLOSING COSTS! 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

$1,262,500

5 Beds ⋅ 6 Baths ⋅ 7740975 MLS

What A PRICE for luxury on a grand scale for your like-new home in Milton Overlook: come see why discerning buyers are flocking to bucolic and convenient Woodstock! From the moment you step into the foyer, your eye is drawn through sun-drenched living spaces framed by a dramatic wall of windows overlooking a tranquil wooded backdrop. An exquisitely appointed chef's kitchen balances beauty and function with premium finishes, abundant cabinetry, an oversized walk-in pantry, and the best in appliances. A dedicated main-level office provides a quiet place to work or create, while a private guest suite offers flexibility for visitors, or extended family. Upstairs, the primary suite serves as a peaceful retreat, thoughtfully designed for renewal. An expansive media room creates a natural hub, while three additional bedrooms each feature ensuite baths and generous closets. An upgraded laundry room adds convenience. Outside, a spacious deck overlooks a level, private backyard—an inviting setting. Additional features include a three-car garage with epoxy flooring, tankless water heater, exceptional storage, and a desirable northeast-facing orientation. Located in a coveted newer community offering resort-style amenities including a pool, clubhouse, courts, and playground, and served by highly regarded schools, this home delivers an enviable lifestyle. Just minutes from the boutiques, restaurants, and community events of Milton and Crabapple, with convenient access to downtown Woodstock, this remarkable property offers the rare combination of luxury, comfort, and connection in one unforgettable address. Be sure to experience the virtual tour.

512 Cedar Crest Circle, Woodstock

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