Highlands Homes with Gated Community Features

Welcome to Highlands, a stunning gated community nestled in the heart of Winchester, Tennessee, within the picturesque Franklin County. This charming subdivision is a hidden gem that offers a perfect blend of tranquility and modern living, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle amidst nature’s beauty.

Highlands boasts a collection of beautifully designed homes that cater to a variety of tastes and preferences. Each residence is thoughtfully crafted with high-quality materials, spacious layouts, and modern amenities, ensuring comfort and style. The community is characterized by its manicured landscapes, tree-lined streets, and a sense of safety and privacy that only a gated community can provide.

Living in Highlands means enjoying a peaceful environment while being just minutes away from Winchester’s vibrant downtown area. Residents can explore local shops, delightful eateries, and recreational activities that the city has to offer. For outdoor enthusiasts, the nearby parks and lakes provide ample opportunities for hiking, fishing, and enjoying the great Tennessee outdoors.

In addition to the stunning homes and beautiful surroundings, Highlands fosters a strong sense of community. Neighbors often come together for social events, creating lasting friendships and a supportive atmosphere. Whether you’re looking for a place to raise a family or a peaceful retreat to enjoy your golden years, Highlands in Winchester, TN, is the perfect destination to call home. Come discover the charm and elegance of this remarkable community today!

Newest Highlands Homes with Gated Community Features

$649,000

4 Beds ⋅ 3 Baths ⋅ 3214337 MLS ⋅ ACTIVE Status ⋅ 0.30000000000000004 Acres ⋅ 37398 Zip Code

Welcome to one of the premier homes in The Highlands of Winchester. Offering over 3,100 square feet of thoughtfully designed living space, this custom-built home combines quality craftsmanship, timeless finishes, and the security of a gated community just minutes from downtown Winchester and beautiful Tims Ford Lake. High-end finishes, spacious rooms, and carefully selected details create a home that feels both elegant and comfortable. The heart of the home is a beautifully appointed kitchen that opens to the main living area. An oversized two-car garage includes additional space for a golf cart, making it easy to enjoy the neighborhood and nearby amenities. If you're searching for a home that offers more space, superior quality, and custom details beyond typical new construction, 260 Lookout Drive delivers an exceptional opportunity to enjoy upscale living. Buyer and/or buyers agent to confirm all important information.

260 Lookout Dr, Winchester

$469,900

3 Beds ⋅ 2 Baths ⋅ 3189545 MLS ⋅ ACTIVE Status ⋅ 0.29 Acres ⋅ 37398 Zip Code

Better than new with tons of builder and seller upgrades in a beautiful, gated community! This gem is located only 1/2 mile from a public boat ramp on the ever-popular Tims Ford Lake. You'll love the grand entrance with soaring ceilings, 8 foot doors throughout, tons of natural light, quartz countertops, and the huge custom pantry. The laundry room, with custom cabinets and folding station, connects to the primary suite. The primary bath includes a separate soaking tub, walk-in tile shower, and double vanities. And the primary closet has custom shelving, by Closets By Design. This gorgeous home has an open floor plan, custom blinds, some new lighting, and tons of storage. The relaxing back porch is a must see. It includes a high ceiling, hanging flower boxes, patio lighting, and a propane heater that conveys with the property. And the extended patio, professional landscaping, and fenced back yard make outdoor entertaining a breeze. Preferred lender is offering 1% of purchase price towards closing costs or rate buy down. Ask me for details. Home is currently under contract, with a Buyer's First Right of Refusal in place, due to a home-sale contingency. Sellers are still accepting showings and entertaining offers!

172 Lookout Dr, Winchester

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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.