Milton Overlook Homes with Two Levels

Welcome to Milton Overlook, a charming subdivision nestled in the heart of Woodstock, Georgia, within the picturesque Cherokee County. This delightful community is known for its serene atmosphere, friendly neighbors, and beautiful landscapes, making it the perfect place to call home.

Milton Overlook features a stunning array of homes, many of which boast two levels, providing ample space for families to grow and thrive. These thoughtfully designed residences offer a blend of modern amenities and classic charm, ensuring that every family member feels right at home. With spacious floor plans, soaring ceilings, and large windows that flood the interiors with natural light, the two-level homes in Milton Overlook are perfect for entertaining guests or enjoying cozy family evenings.

The subdivision is conveniently located near a variety of shopping, dining, and recreational options, making it easy to enjoy the vibrant lifestyle that Woodstock has to offer. Residents can take advantage of nearby parks, hiking trails, and community events, fostering a sense of camaraderie among neighbors.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education. With its perfect blend of suburban tranquility and easy access to urban conveniences, Milton Overlook is an ideal choice for those seeking a peaceful yet connected lifestyle.

If you’re searching for a home that combines comfort, style, and a welcoming community, look no further than Milton Overlook. Discover your dream home today in this enchanting neighborhood!

Newest Milton Overlook Homes with Two Levels

$1,299,900

7 Beds ⋅ 7 Baths ⋅ 10813844 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.

419 Oakleigh Avenue, Woodstock

Listing courtesy of Keller Williams Realty.

$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

Listing courtesy of Bolst, Inc..

$1,299,000

5 Beds ⋅ 4 Baths ⋅ 10782008 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

Listing courtesy of Coldwell Banker Realty.

Start Your Search

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.