Windsor Oaks Homes with Wake - Dillard Drive Middle Middle School

Welcome to Windsor Oaks, a charming and vibrant subdivision nestled in the heart of Cary, North Carolina. This delightful community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike. With its beautifully landscaped streets and friendly neighbors, Windsor Oaks embodies the warmth and charm of Southern living.

One of the standout features of this subdivision is its proximity to Wake - Dillard Drive Middle School, which is just a stone's throw away. Parents will appreciate the ease of access to quality education for their children, ensuring that they receive a top-notch learning experience. The school’s commitment to academic excellence and a supportive environment makes it a popular choice for families residing in the area.

Windsor Oaks boasts a variety of homes that cater to diverse tastes and lifestyles. From cozy single-family residences to spacious modern designs, there is something for everyone in this community. Many homes feature inviting outdoor spaces, perfect for entertaining or simply enjoying the beautiful North Carolina weather. Residents can also take advantage of nearby parks, walking trails, and recreational facilities, promoting an active and engaged lifestyle.

The location of Windsor Oaks is another significant advantage, with easy access to major highways, shopping centers, and dining options. Whether you’re looking for a quiet evening at home or a night out on the town, everything you need is just minutes away. Discover the charm of Windsor Oaks, where community spirit and convenience come together to create the perfect place to call home!

Newest Windsor Oaks Homes with Wake - Dillard Drive Middle Middle School

$749,900

4 Beds ⋅ 3 Baths ⋅ 10190542 MLS ⋅ ACTIVE Status

Welcome to 9701 Kingsford Drive, a warm, well-cared-for home tucked among mature trees in Cary's established Windsor Oaks neighborhood. The care shows where it counts most: a new roof and gutters with gutter guards (2025), two high-efficiency, filter-free HVAC systems with updated ductwork (2024), tankless water heater (2023), Tesla Universal Wall Connector EV charging station (2026), and backyard French drain system. Inside, more than 3,200 square feet offers plenty of room to spread out. Hardwood floors, a spacious kitchen with breakfast nook, a main-level bonus room ready to serve as an office, playroom or den, and multiple living and dining spaces create an easy flow for everyday life and entertaining. Upstairs you'll find four bedrooms, including the primary suite, along with a large bonus room, while the finished third-floor flex space offers even more room to make your own. Outside, a custom stone patio featuring the same materials and stonework found throughout Downtown Cary Park overlooks the wooded, fenced-in .27-acre backyard. A designated fire pit area adds another spot to gather and enjoy the outdoors, while an established vegetable and herb garden is ready for its next gardener. Approximately .50 acres of HOA-owned buffer along the front creates an added sense of space and privacy. With many of the big-ticket improvements already taken care of, 9701 Kingsford Drive is ready for its next chapter. Come see what makes this home so special!

9701 Kingsford Dr, Cary

$599,900

4 Beds ⋅ 3 Baths ⋅ 10186248 MLS ⋅ ACTIVE Status

Welcome to a Cary home where timeless character meets thoughtful updates and comfortable, spacious living. Imagine friends and family gathering around the handsome brick fireplace in the generous family room, or wandering into the kitchen designed with an abundance of cabinetry, counterspace, and convenience - including a breakfast island. The upstairs bedrooms include an exceptionally spacious flex bedroom that works equally well as a bonus room, home office or guest retreat. In the Primary Bedroom you'll relish your retreat to the beautifully updated Primary Bath, where distinctive marble mosaic flooring creates a zen-like escape with its wonderfully luxurious shower. Downstairs, hardwood floors, handsome millwork and wainscoting add warmth and distinction, with thoughtful details extending all the way to the graceful turnout of the balustrade staircase. Outside, the cul-de-sac setting offers something increasingly hard to find in Cary—a wonderful sense of openness and privacy. Unique common areas beyond the property create extra breathing room both front and back, giving this quarter-acre homesite a remarkably open feel The spacious kitchen overlooks an oversized (27' x 21') deck and private backyard complete with a charming custom playhouse/outbuilding. It's an inviting setting for morning coffee, weekend gatherings, playtime and evenings outdoors. The brick and fiber cement exterior pairs timeless curb appeal with low-maintenance durability, while upgraded windows and a sealed crawlspace enhance comfort, energy efficiency and quiet. A spacious 26' x 21' walk-up attic with permanent adds versatility for storage and future needs. Lastly, consider the location's convenience, which can only be expressed as exceptional. The neighborhood entrance is just three turns from anywhere on the Beltline, making this one of those rare locations that feels tucked away without feeling far away. Koka Booth Amphitheatre is just minutes from home, along with the shopping, dining, parks, greenways and recreation that give Cary its vibrant lifestyle. Cary continues to earn national recognition for its exceptional quality of life, and highly rated area schools, including an elementary school just a short drive away. It's a compelling combination of character, privacy, convenience and location in one of the Triangle's most sought-after communities. Schedule a showing at your convenience.

9712 Astor Ct, Cary

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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .