Windsor Oaks Homes with Wake - Dillard Drive Middle Middle School

Welcome to Windsor Oaks, a charming subdivision nestled in the heart of Cary, North Carolina, within the vibrant Wake County. Known for its picturesque landscapes and friendly atmosphere, Windsor Oaks offers a serene retreat just moments away from the bustling city life. This delightful community is perfect for families, professionals, and retirees alike, providing a perfect blend of comfort and convenience.

Windsor Oaks features an array of beautifully designed homes that cater to diverse tastes and lifestyles. From cozy single-family residences to spacious modern designs, there's something for everyone. Each home is thoughtfully constructed, boasting contemporary amenities, open floor plans, and lush outdoor spaces, making it an ideal setting for relaxation and entertaining.

One of the standout features of Windsor Oaks is its proximity to Wake - Dillard Drive Middle School, which is highly regarded for its commitment to academic excellence and community involvement. Families with school-aged children will appreciate the convenience of having such a reputable institution nearby, ensuring a quality education just a stone’s throw away.

Residents of Windsor Oaks enjoy easy access to a variety of local parks, shopping centers, and dining options, making it simple to embrace the vibrant lifestyle that Cary has to offer. Whether you're strolling through the neighborhood or taking advantage of the numerous recreational opportunities, you'll find that Windsor Oaks is more than just a place to live—it's a community where memories are made and friendships flourish. Come discover the charm of Windsor Oaks, where your dream home awaits!

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

$774,900

4 Beds ⋅ 3 Baths ⋅ 10190542 MLS ⋅ ACTIVE Status

Welcome to 9701 Kingsford Drive, a warm and inviting home tucked among mature trees in the established Windsor Oaks neighborhood in Cary! With more than 3,200 square feet, this home offers plenty of room to spread out while still feeling comfortable and connected. The main level features beautiful hardwood floors, a spacious kitchen, breakfast nook, dedicated office and multiple living and dining spaces that make everyday life and entertaining easy. Upstairs you'll find four bedrooms, including the primary suite, along with a large bonus room, while the finished third-floor flex room offers even more space to make your own. Outside, the wooded .27-acre lot is complemented by approximately .50 acres of HOA-owned buffer along the front, creating an added sense of space and privacy. The peaceful backyard features a generous patio, mature trees and an established vegetable and herb garden ready for its next gardener. With a two-car garage, flexible spaces throughout and a location convenient to all that Cary has to offer, 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

Start Your Search

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 .