Happy Hollow Real Estate

Welcome to Happy Hollow, a charming subdivision nestled in the heart of Clarksville, Tennessee, within the picturesque Montgomery County. This delightful community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place to call home.

Happy Hollow is characterized by its beautifully landscaped streets, where mature trees provide shade and a sense of serenity. The homes here exude warmth and character, featuring a variety of architectural styles to suit diverse tastes. Whether you’re searching for a cozy single-family home or a spacious property for your growing family, Happy Hollow has something for everyone.

Residents of this inviting subdivision enjoy easy access to a wealth of amenities. Just a short drive away, you’ll find a variety of shopping centers, restaurants, and entertainment options to suit every lifestyle. Outdoor enthusiasts will appreciate the nearby parks and recreational areas, perfect for picnics, hiking, and family outings.

One of the standout features of Happy Hollow is its strong sense of community. Neighbors often come together for seasonal events and gatherings, fostering lasting friendships and a welcoming atmosphere. Families will also benefit from the highly-rated schools in the area, ensuring quality education for children of all ages.

With its ideal location, friendly neighbors, and a vibrant community spirit, Happy Hollow offers a lifestyle that balances comfort and convenience. Discover the charm of this wonderful subdivision and envision your future in a place where happiness truly thrives. Come and experience the warmth of Happy Hollow—your new home awaits!

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.