Windwood Hills Real Estate

Welcome to Windwood Hills, a charming subdivision nestled in the heart of Jackson, Tennessee, within the scenic Madison County. This delightful community combines the tranquility of suburban living with the vibrant energy of city life, making it an ideal place for families, professionals, and retirees alike.

Windwood Hills is characterized by its picturesque tree-lined streets and beautifully landscaped homes, each reflecting the unique charm of Southern architecture. The subdivision offers a variety of housing options, from cozy single-family homes to spacious modern residences, ensuring there’s a perfect fit for everyone. With well-maintained sidewalks and community parks, residents enjoy leisurely strolls, family picnics, and outdoor activities right at their doorstep.

One of the highlights of living in Windwood Hills is its proximity to local amenities. Just a short drive away, you’ll find a plethora of shopping, dining, and entertainment options. From quaint boutiques to popular restaurants, Jackson has something for every taste. Families will appreciate the highly-rated schools in the area, providing excellent educational opportunities for children of all ages.

Nature enthusiasts will love the nearby parks and recreational areas, perfect for hiking, biking, and enjoying the great outdoors. The community’s friendly atmosphere fosters a strong sense of belonging, making it easy to connect with neighbors and build lasting friendships.

Whether you’re looking to settle down or simply seeking a peaceful retreat, Windwood Hills offers the perfect blend of comfort, convenience, and community spirit. Discover your dream home in this idyllic subdivision and experience the best of Jackson living!

Newest Listings in Windwood Hills

$1,950,000

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

$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 Drive, Jackson

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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.