Chesapeake Estates Real Estate

Welcome to Chesapeake Estates, a hidden gem nestled in the heart of Clarksville, Tennessee. This charming subdivision in Montgomery County offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike.

Chesapeake Estates boasts an array of beautifully designed homes, each with unique architectural styles that reflect the warmth and character of the community. With spacious lots and meticulously landscaped yards, residents enjoy a serene environment that fosters a strong sense of community. The neighborhood is perfect for evening strolls, weekend barbecues, and building lasting friendships with neighbors.

One of the standout features of Chesapeake Estates is its prime location. Situated just a short drive from downtown Clarksville, residents have easy access to a vibrant array of shopping, dining, and entertainment options. Whether you’re looking to enjoy a cozy café, explore local boutiques, or indulge in a night out, everything you need is just around the corner. For outdoor enthusiasts, the nearby parks and recreational facilities offer ample opportunities for hiking, biking, and enjoying the stunning Tennessee landscape.

Families will appreciate the excellent school district serving Chesapeake Estates, ensuring that children receive a quality education in a nurturing environment. With a strong emphasis on community and family values, Chesapeake Estates is more than just a place to live; it’s a place to thrive.

Come discover the charm of Chesapeake Estates, where your dream home awaits amidst the beauty of Clarksville, TN!

Newest Listings in Chesapeake Estates

$394,000

3 Beds ⋅ 3 Baths ⋅ 3520199 MLS ⋅ ACTIVE Status ⋅ 0.45 Acres ⋅ 37043 Zip Code

Welcome to 1025 Hillshire, a charming and beautifully maintained home nestled in the desirable Rossview area! New roof & HVAC! Thoughtfully updated while preserving its warm, inviting character, this home is filled with timeless details throughout. The spacious kitchen is sure to impress with gorgeous cabinetry, quartz countertops, stainless steel appliances, and plenty of room to gather and entertain. The primary suite is conveniently located on the main level, while additional generously sized bedrooms and a beautifully updated full bathroom are located upstairs. Outside, enjoy an expansive backyard with a privacy fence, mature shade trees, and plenty of room to relax, play, or entertain. The washer and dryer convey, making this home truly move-in ready. With its charming character, thoughtful updates, desirable location, and generous outdoor space, 1025 Hillshire is a wonderful place to call home!

1025 Hillshire Dr, Clarksville

$650,000

5 Beds ⋅ 4 Baths ⋅ 3231576 MLS ⋅ ACTIVE Status ⋅ 3.4 Acres ⋅ 37043 Zip Code

$20,000 UPDATE ALLOWANCE! All Brick Cape Cod on 3.4 Acres with Shop, Pond & Basement What more could you ask for? This stunning all-brick Cape Cod home offers 5 bedrooms, 3.5 baths, a basement, a massive 60' x 36' shop, a stocked pond with its own pond house, and 3.4 beautiful acres—all in a convenient central location. The main level features 3 spacious bedrooms, while 2 additional bedrooms are located upstairs, providing plenty of room for family, guests, or a home office setup. The recently renovated eat-in kitchen is designed to impress with quartz countertops, a tiled backsplash, pantry, and stainless-steel appliances including a range/oven, microwave, dishwasher, and refrigerator. Enjoy gathering in the inviting great room with a gas fireplace, hosting meals in the formal dining room, and the convenience of a dedicated laundry room. The highlight of the home may be the spectacular sunroom/Florida room, where you'll enjoy breathtaking views of your private property year-round. The basement offers a huge recreation/bonus room and a half bath, creating the perfect space for entertainment, hobbies, or a home gym. The oversized basement garage features 23-foot and 27-foot-deep bays, providing ample space for full-size trucks, SUVs, and additional storage. Outside, hobbyists and enthusiasts will appreciate the impressive 60' x 36' shop, complete with a car lift and air compressor. Whether you're into woodworking, automotive projects, equipment storage, or other pursuits, this space is ready to accommodate your dreams. Would also make a perfect RV garage! Step outside to enjoy your stocked pond and charming pond house—your own private retreat that feels like a state park right in your backyard. Recent updates include: Main-level dual-fuel HVAC (2023) Gas water heater (2023) Roof (2022) This unique property combines space, functionality, recreation, and natural beauty in one exceptional package.

1030 Hillshire Dr, Clarksville

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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.