Happy Hollow Real Estate

Welcome to Happy Hollow, a charming subdivision nestled in the heart of Clarksville, Tennessee, within the scenic Montgomery County. This delightful community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and everyone in between.

Happy Hollow boasts beautifully landscaped streets lined with stunning homes, each exuding character and warmth. The architecture reflects a variety of styles, ensuring that there’s something for everyone. Residents enjoy spacious lots, providing ample room for outdoor activities and personal gardens. The community is known for its friendly atmosphere, where neighbors become friends and gatherings are a common occurrence.

One of the standout features of Happy Hollow is its proximity to essential amenities. Just a short drive away, you’ll find top-rated schools, shopping centers, and dining options that cater to every palate. Outdoor enthusiasts will appreciate the nearby parks and recreational areas, perfect for hiking, picnicking, or simply enjoying the natural beauty of Tennessee.

For those commuting to work or seeking adventure, Happy Hollow is conveniently located near major highways, offering easy access to Nashville and beyond. Whether you’re looking to explore the vibrant music scene of the city or enjoy a quiet evening in your backyard, this subdivision provides the best of both worlds.

In Happy Hollow, you’re not just buying a home; you’re investing in a lifestyle filled with community spirit, comfort, and convenience. Come discover why so many have chosen to call this enchanting neighborhood their home!

Newest Listings in Happy Hollow

$224,900

3530767 MLS ⋅ ACTIVE Status ⋅ 37040 Zip Code

Turn-key, income-producing duplex with both units currently leased and generating consistent cash flow. Each unit is equipped with a stove, refrigerator, and microwave, offering tenant convenience and strong rental appeal. The property was renovated by the seller at the time of purchase, providing updated interiors and minimizing immediate capital expenses! **CAN BE PURCHASED AS A PACKAGE DEAL WITH 924 & 926 WOODY HILLS DR.*CALLING ALL VA or FHA BUYERS!! VACANT UNIT READY FOR IMMEDIATE MOVE-IN. PLEASE DO NOT DISTURB TENANT!

928 Woody Hills Dr, Clarksville

$224,900

3530762 MLS ⋅ ACTIVE Status ⋅ 37040 Zip Code

Turn-key, income-producing duplex with both units currently leased and generating consistent cash flow. Each unit is equipped with a stove, refrigerator, and microwave, offering tenant convenience and strong rental appeal. The property was renovated by the seller at the time of purchase, providing updated interiors and minimizing immediate capital expenses! **CAN BE PURCHASED AS A PACKAGE DEAL WITH 928 & 930 WOODY HILLS DR.** Please note: property is fully occupied but one unit to remain month-to-month so property qualifies for VA or FHA financing! PLEASE DO NOT DISTURB TENANTS!

924 Woody Hills Dr, Clarksville

$182,500

2 Beds ⋅ 1 Baths ⋅ 3520775 MLS ⋅ ACTIVE Status ⋅ 0.21 Acres ⋅ 37040 Zip Code

**Recently Appraised at $206,000 — Competitively Priced!** Located in the Happy Hollow neighborhood, this renovated 1950s one-story home is minutes from the Montgomery County Public Library and APSU. The home features updated flooring, light gray walls with white trim, updated fixtures and lighting, and a separate front room with an oversized window for plenty of natural light. The eat-in kitchen opens to the backyard, providing easy access to the outdoor space. The exterior has also been freshly painted. With the major updates already completed, this is a great opportunity for a first-time buyer looking for an affordable, move-in-ready home in a convenient location.

914 W Happy Hollow Dr, Clarksville

$299,900

3 Beds ⋅ 2 Baths ⋅ 3297880 MLS ⋅ ACTIVE Status ⋅ 1.3900000000000001 Acres ⋅ 37040 Zip Code

$15,000 IN CONCESSIONS TO BUYER!!! Brand-new construction meets peaceful privacy. This stunning 1-story modern home features 3 bedrooms, 2 bathrooms, and 1,360 square feet of open-concept living space. High-end finishes elevate the interior, including durable laminate hardwood flooring and a chef-inspired kitchen complete with sleek quartz countertops, stainless steel appliances, and a functional center island. Nestled on a premium 1.39-acre cul-de-sac lot with no backyard neighbors, this move-in-ready property offers the perfect blend of style, quality, and serene seclusion.

613 Hill Rd, Clarksville

$445,000

3247947 MLS ⋅ ACTIVE Status ⋅ 37040 Zip Code

Great opportunity to own a full duplex in Clarksville’s Happy Hollow subdivision, with both units included in the sale. Each side offers 3 bedrooms, 2 bathrooms, and a well designed floor plan with modern finishes and comfortable living spaces throughout. The main level features an open living, dining, and kitchen area with durable wood look flooring, neutral colors, and plenty of natural light. Each kitchen is finished with white cabinetry, granite countertops, black appliances, and a large center island with bar seating, making the space both stylish and functional. The primary bedroom is located on the main floor in each unit and includes a walk in closet and private bath with granite countertops and a tub/shower combo. Upstairs, you'll find two additional bedrooms, a full bath, and a dedicated laundry room complete with washer and dryer. Each unit also features a back deck overlooking the surrounding greenery, offering a peaceful outdoor space to unwind. An oversized parking pad provides generous off street parking for residents and guests. Whether you're searching for an investment property, a multi generational setup, or the chance to live in one unit while renting the other, this duplex offers flexibility, space, and strong potential in a convenient Clarksville location.

906 E Happy Hollow 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.