Milton Overlook Homes with Two Stories

Welcome to Milton Overlook, a charming subdivision located in Woodstock, Georgia. Situated in Cherokee County, this community offers a tranquil and family-friendly environment for residents to call home.

Milton Overlook is renowned for its beautiful homes with two stories, providing ample space and comfort for families of all sizes. These two-story residences offer a perfect blend of functionality and style, allowing homeowners to enjoy the best of both worlds.

Whether you're looking for a cozy starter home or a spacious property to accommodate a growing family, Milton Overlook has a range of options to suit your needs. With well-designed floor plans and modern amenities, these homes are thoughtfully crafted to enhance your living experience.

In addition to the stunning homes, Milton Overlook boasts a convenient location. Woodstock, a vibrant city in Georgia, offers a variety of shopping, dining, and entertainment options. Residents can enjoy the nearby parks, recreational facilities, and excellent schools, making it an ideal place to raise a family.

If you're seeking a welcoming community with beautiful two-story homes, look no further than Milton Overlook in Woodstock, Georgia. Discover the perfect blend of comfort, convenience, and charm in this desirable subdivision.

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.

419 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

$1,285,000

5 Beds ⋅ 4 Baths ⋅ 7783780 MLS

4,282 SF FINISHED, 1,947 SF UNFINISHED BASEMENT, 6,229 SF OF POTENTIAL LIVING SPACE. NEARLY 1 ACRE ON A PRIVATE CUL-DE-SAC LOT IN MILTON OVERLOOK, WITH A VERY PRIVATE WOODED VIEW AND NO HOMES IN SIGHT. This 5 Bedroom, 4 Bath, 3 Car Garage home offers 4,282 square feet of finished living space plus an unfinished daylight basement, already framed and stubbed for future expansion. Inside, 10-foot ceilings and floor-to-ceiling windows take full advantage of the wooded views. The chef's kitchen features an oversized island, KitchenAid appliances, double ovens, wine bar, quartz countertops and walk-in pantry. The main level includes a private guest suite with full bath, oversized office, dining room and mudroom. Upstairs offers a large Loft, spacious primary suite with sitting area and spa-style bath, plus three additional bedrooms with ensuite and Jack-and-Jill baths. The unfinished basement gives the next owner the flexibility to create the space they want - home theater, gym, golf simulator, guest suite or additional living space. Already framed and stubbed for a 6th bedroom and 5th bathroom, with the opportunity to add nearly 2,000 square feet of finished space on your terms. Outside, the flat backyard has room for a pool and offers privacy and protected wooded views. With more finished square footage and a larger lot than many recent nearby sales, this property offers a combination that is increasingly difficult to find. Come see it in person. The lot, views and scale of this home are best appreciated firsthand.

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

Start Your Search

board logo Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work, please click here to review our DMCA policy and learn how to submit a takedown request. © 2026 FMLS. Last updated