Chesapeake Estates Homes for Sale

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

Chesapeake Estates features a variety of beautifully designed homes that cater to diverse lifestyles and preferences. Whether you're searching for a cozy single-family residence or a spacious two-story home, you're sure to find something that suits your needs. The properties in this community boast contemporary architecture, well-manicured lawns, and inviting outdoor spaces perfect for entertaining or simply enjoying a quiet evening under the stars.

Residents of Chesapeake Estates enjoy the benefits of a close-knit community, where neighbors become friends and memories are made. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, ensuring that everything you need is just a short drive away. Outdoor enthusiasts will appreciate the nearby parks and nature trails, offering ample opportunities for hiking, biking, and family picnics.

With homes for sale in Chesapeake Estates, now is the perfect time to discover your dream home in this vibrant community. Experience the warmth and charm of Clarksville living while enjoying the modern amenities that Chesapeake Estates has to offer. Don’t miss out on the chance to become a part of this wonderful neighborhood—explore the available listings today and take the first step toward your new life in Chesapeake Estates!

Newest Chesapeake Estates Homes for Sale

$389,000

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

New roof & HVAC! Seller offering 5k to vendor of buyers choice! Located in the well desired Rossview district, This home has been 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!Immediate occupancy now available! 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.