Windwood Hills Homes with North Side High School

Windwood Hills Homes with North Side High School

Welcome to Windwood Hills, an inviting subdivision nestled in the heart of Jackson, Tennessee. This charming community in Madison County is perfect for families, professionals, and anyone looking to enjoy the serene beauty of suburban living while still being close to the vibrant city life.

Windwood Hills boasts a variety of beautifully designed homes that cater to diverse tastes and lifestyles. From modern single-family residences to cozy townhomes, there’s something here for everyone. Many of the homes feature spacious yards, perfect for outdoor gatherings and playtime with children, while others offer stunning views of the surrounding landscape, making it a picturesque place to call home.

One of the standout features of Windwood Hills is its proximity to North Side High School, which is known for its strong academic programs and dedicated staff. Families with school-aged children will appreciate the convenience of having a quality educational institution just a short distance away, fostering a sense of community and providing easy access to extracurricular activities.

In addition to its excellent schools, Windwood Hills offers residents a welcoming atmosphere with well-maintained streets, friendly neighbors, and a strong sense of community pride. Enjoy leisurely strolls through the neighborhood, or take a short drive to explore Jackson's local parks, shopping centers, and dining options.

Whether you're searching for your first home or looking to settle down in a peaceful community, Windwood Hills in Jackson, TN, is the perfect place to create lasting memories. Come and discover the charm of Windwood Hills—where home is more than just a place; it’s a lifestyle!

Newest Windwood Hills Homes with North Side High School

9 Windwood Dr, Jackson
$1,775,000
5 Beds ⋅ 5 Baths ⋅ 3603652 MLS ⋅ ACTIVE Status ⋅ 6.29 Acres ⋅ 38305 Zip Code
Year-round swimming may not be what you expect to find in a private Tennessee estate—but this home is anything but ordinary. Set on 6.29 wooded acres in one of Jackson's premier gated communities, this exceptional home combines privacy, generous living spaces and remarkable flexibility. The indoor pool creates a four-season retreat, while multiple bedroom suites—including an upper-level suite with its own kitchenette and washer/dryer—make the home especially well suited for multigenerational living, extended guests or a live-in nanny. Soaring windows bring the wooded surroundings and natural light into the home, while expansive gathering spaces make entertaining easy. Luxury here means having room for everyone you love—and plenty of room to enjoy it. Minutes from Jackson's shopping, dining and healthcare.

9 Windwood Dr, Jackson
18 Windwood Dr, Jackson
$2,750,000
5 Beds ⋅ 7 Baths ⋅ 3546526 MLS ⋅ ACTIVE Status ⋅ 10 Acres ⋅ 38305 Zip Code
A Rare European- Country Inspired Estate of Extraordinary Scale & Craftsmanship. Welcome to a truly Iconic exceptional European-style estate nestled on approximately 10 private acres within a gated community, with an additional gated entry providing privacy at the property. Offering approximately 8,500 square feet of luxurious living space, this remarkable residence is a one-of-a-kind masterpiece showcasing extraordinary craftsmanship, imported architectural elements, and an impressive sense of scale. The home features 5 exceptionally spacious bedrooms and 5 full baths, and 2 1/2 baths, with grand proportions throughout. Every room is generously sized, creating an elegant yet comfortable environment designed for both refined entertaining and everyday living. Among the home's most distinctive features is its extraordinary craftsmanship, including a magnificent staircase and exquisite woodwork imported from Europe and other countries. These exceptional architectural details bring a sense of old-world character and authenticity rarely found in today's luxury homes. At the heart of the home is a spectacular chef's kitchen featuring double ovens and a 6-burner gas cooktop, perfectly suited for preparing intimate dinners or entertaining on a grand scale. The residence also offers multiple elegant living spaces, including a formal living room, dining room, private office, and sunroom. Five beautiful fireplaces, add warmth, character, and timeless elegance throughout the home, creating inviting spaces for gathering with family and friends. Outside, the estate transforms into a private resort-like retreat. Enjoy the in-ground gunite pool, surrounded by expansive grounds and beautiful landscaping. Three distinctive water fountains provide soothing water features and enhance the property's extraordinary outdoor setting. From the private gated entry and sprawling acreage to the imported European craftsmanship, grand-scale rooms,and five fireplaces

18 Windwood Dr, Jackson
Start Your Search
board logo

Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.

How much is your home worth?

Get instant property value now!