Glenwood Real Estate

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

Glenwood boasts a variety of beautifully designed homes, each reflecting the warmth and character of the neighborhood. With tree-lined streets and well-maintained yards, the subdivision exudes a welcoming atmosphere that encourages outdoor living and community interaction. Residents enjoy spacious lots, modern amenities, and a range of architectural styles that cater to diverse tastes.

One of the standout features of Glenwood is its prime location. Situated just minutes from downtown Clarksville, residents have easy access to a plethora of shopping, dining, and entertainment options. Whether you're exploring local boutiques or indulging in a meal at one of the area's popular restaurants, the vibrant city life is right at your doorstep. For those who appreciate nature, the nearby parks and recreational areas offer ample opportunities for hiking, biking, and family picnics.

Families with children will appreciate the highly-rated schools in the area, ensuring a quality education for young residents. The community spirit in Glenwood is palpable, with neighborhood events and gatherings that foster connections among neighbors.

In Glenwood, you’ll find not just a home, but a lifestyle rich in comfort, community, and convenience. Come discover why this subdivision is one of Clarksville's best-kept secrets!

Newest Listings in Glenwood

$385,000

4 Beds ⋅ 3 Baths ⋅ 3531862 MLS ⋅ ACTIVE Status ⋅ 0.24 Acres ⋅ 37040 Zip Code

Welcome to 165 E Glenwood Dr, one of Clarksville’s genuine historic gems. This renovated 4 bedroom 2.5 bathroom home perfectly balances timeless character with the modern comforts you crave, all while sitting just five minutes from the vibrant energy of downtown Clarksville. From the street, the inviting curb appeal hints at the thoughtful updates waiting inside, offering a rare opportunity to own a piece of local history without sacrificing contemporary style. The moment you step through the front door, you’ll notice how natural light pours across the open living spaces, highlighting the rich, real hardwood flooring that runs throughout. The heart of the home features a kitchen designed for both style and function, flowing effortlessly into dining and living areas anchored by a cozy fireplace. For a change of pace, the sunroom offers a bright and airy sanctuary, perfect for enjoying your morning coffee while surrounded by views of the property. For those looking for even more room to roam, the full finished basement offers incredible versatility. It’s the perfect spot for a media lounge, a home gym, or a creative studio, the possibilities are endless. The main level primary suite serves as a true retreat, providing a peaceful spot to unwind at the end of the day. Step outside to discover a generous backyard just waiting for your personal touch. Whether you’re dreaming of a lush garden, a space for weekend BBQs, or simply a spot to enjoy the Tennessee breeze, this outdoor area offers the privacy and room you’ve been looking for. With its proximity to the best shopping and dining in the city, this property isn’t just a house, it’s a place to truly plant roots. Come see for yourself why this historic beauty feels like home the second you walk in.

165 E Glenwood Dr, Clarksville

$325,000

3 Beds ⋅ 2 Baths ⋅ 3525597 MLS ⋅ ACTIVE Status ⋅ 0.24 Acres ⋅ 37323 Zip Code

This beautifully updated 3-bedroom, 2-bath brick ranch blends a warm modern farmhouse style with a functional layout and plenty of thoughtful details. The split-bedroom floor plan offers added privacy, while the main living room and separate den provide flexible space for everyday living, entertaining, or a home office. Inside, you'll find barn doors, shiplap walls, custom tile flooring, updated vanities and light fixtures, a custom backsplash, farmhouse sink, and a walk-in shower. The home also includes a dedicated laundry room and an attached one-car garage. Out back, the flat lot features a patio, wooden privacy fence, and storage shed, creating a comfortable and private outdoor space to enjoy. A rail line runs behind the property, with only occasional train traffic. Full of character, nicely updated, and move-in ready, this Cleveland home offers a lot to love inside and out.

2660 SE Rogers Drive, Cleveland

$252,700

3 Beds ⋅ 1 Baths ⋅ 3518824 MLS ⋅ ACTIVE Status ⋅ 0.03 Acres ⋅ 37404 Zip Code

Don't miss this charming historic bungalow offering an exceptional combination of character, convenience, and value! Ideally located within easy reach of Downtown Chattanooga, this home puts you close to the city's restaurants, shopping, entertainment, parks, and attractions while offering the warmth and appeal of an established neighborhood. The seller has just invested twenty four thousand dollars in upgrades and repairs, giving the next owner added peace of mind and tremendous value. Recent improvements include a brand-new concrete floor on the front porch, a brand-new water heater, and fresh paint on the entire exterior, along with much more. These substantial improvements make this home an especially attractive opportunity for buyers looking for a property where significant work has already been completed. With its historic charm, comfortable size, convenient location, and substantial recent investment, this home offers an outstanding amount of house for the price. Opportunities to own a home of this size and character this close to Downtown Chattanooga at this price point are increasingly hard to find. Whether you're looking for a primary residence, investment opportunity, or a home close to all that Chattanooga has to offer, this bungalow deserves a closer look. Historic charm. Recent improvements. Prime convenience. Exceptional value. Come see why this one is such a great opportunity!

2422 Vine Street, Chattanooga

$415,000

4 Beds ⋅ 3 Baths ⋅ 3509995 MLS ⋅ ACTIVE Status ⋅ 0.27 Acres ⋅ 37040 Zip Code

PRESTIGIOUS GLENWOOD LOCATION ON A PRIVATE HILLTOP LOT! Experience true historic luxury on one of Clarksville’s most beautiful streets. Tucked away on a sun-filled, private 0.27-acre hilltop lot away from busy commercial roads, this beautifully preserved 1941 residence offers 4 spacious bedrooms and 2.5 bathrooms, flawlessly blending amazing original details with extensive high-end improvements from 2022-2026. The main-floor primary bedroom suite features a private porch and a brand-new custom bathroom completed this September. Charming brick steps lead to a welcoming foyer with a coat closet, opening to rich oak hardwood flooring that flows throughout, complemented by classic subway tile in the original bathroom. The inviting living room features a cozy fireplace, while the formal dining room provides an elegant space for gatherings. The gourmet kitchen is equipped with floor-to-ceiling custom cabinetry, a Fisher & Paykel drawer dishwasher, and ample stone countertop space. A unique spiral staircase adds immense character while leading to the second level. Outside, a peaceful backyard with a charming gazebo is surrounded by mature trees, pairing perfectly with a detached garage with a remote-controlled door and 2 dedicated storage rooms. Combining classic character, a thoughtful layout, and convenient access to Sango, downtown, APSU, and I-24, this premier home offers a wonderful opportunity to enjoy timeless charm, unmatched convenience, and a private setting.

164 W Glenwood Dr, Clarksville

$1,600,000

4 Beds ⋅ 6 Baths ⋅ 3206921 MLS ⋅ ACTIVE Status ⋅ 0.45 Acres ⋅ 37040 Zip Code

Nestled in Historic Glenwood, one of downtown Clarksville's historic district, this fully custom estate is a rare offering that checks every box. Every major system has been replaced to include a new roof, new copper plumbing, new electrical, and new windows, all wrapped in durable Hardie siding with superior insulation throughout. Inside, heated tile floors and solid hardwood carry you through a layout built for entertaining and everyday living. The marble primary retreat is a true sanctuary, while the mother-in-law suite with private entrance, deck, and morning bar offers unmatched flexibility. The large eat-in kitchen with pantry, formal living and dining rooms, sunroom opening to a covered porch with natural gas grill, private office, and main-floor laundry complete the main level. The finished basement adds a game room, theater, gym, full bath, and another laundry. Outside enjoy professional landscaping, a new paved driveway, sprinkler system, and a 3-car garage with shop space. Additional highlights include central vacuum, video surveillance, concrete/steel storm shelter, tankless water heater, and generator wiring. Three contiguous lots with separate addresses included. A home of this caliber in a neighborhood of this character simply does not come along often. With a full offer, this property conveys as a full private acre in the heart of downtown Clarksville. INTERIOR PHOTOS COMING SOON

171 W Glenwood 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.