Pleasantville Real Estate

Welcome to Pleasantville, Tennessee—a charming gem nestled in the heart of Perry County. This idyllic town is a perfect blend of small-town charm and natural beauty, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Pleasantville boasts a rich history that is reflected in its well-preserved architecture and friendly community atmosphere. The town is surrounded by the stunning landscapes of Tennessee, with lush rolling hills and serene waterways that invite outdoor enthusiasts to explore. Whether you enjoy hiking, fishing, or simply taking a leisurely stroll through the picturesque parks, Pleasantville offers an abundance of recreational opportunities.

The community is known for its strong sense of belonging, where neighbors become friends and local events bring everyone together. Residents can enjoy seasonal festivals, farmers' markets, and a variety of local shops and eateries that celebrate the unique flavors and crafts of the region. The strong community spirit is palpable, making it a welcoming place for newcomers.

Education is a priority in Pleasantville, with well-regarded schools that foster a nurturing environment for children. Families will appreciate the dedication to providing quality education and extracurricular activities that help students thrive.

With its affordable housing options, beautiful surroundings, and a welcoming community, Pleasantville is not just a place to live—it's a place to call home. Discover the charm of this delightful Tennessee town and envision your future in Pleasantville, where every day feels like a breath of fresh air.

Newest Listings in Pleasantville

$750,000

3613257 MLS ⋅ ACTIVE Status ⋅ 73.5 Acres ⋅ 37033 Zip Code

Rare opportunity to own 73 acres of versatile Tennessee land offering privacy, recreation, hunting, farming, and homesteading potential. The property features approximately 9 acres of open pasture, with the remaining acreage consisting of mature hardwood timber—providing excellent wildlife habitat, hunting opportunities, and a beautiful private setting. A natural spring is also near front of property. Access is provided by a private road that dead-ends directly into the property, offering an added level of privacy and seclusion. A 48x60 barndominium built in 2018 is already in place and features 1 bedroom, 1.5 baths, a kitchen, office, storage room and a large shop area. The shop includes an electric lift providing convenient access to additional attic storage. The property is serviced by a septic system that was approved for a 4-bedroom home. The septic tank and drain field are already installed, providing the opportunity to expand the existing barndominium with additional bedrooms or construct a separate 3-bedroom home, subject to applicable approvals. Whether you’re looking for a private hunting retreat, working farm, homestead, timberland investment, or a place to escape the everyday hustle, this property offers the land, infrastructure, and flexibility to make it your own. A true Tennessee getaway with room to hunt, farm, build, and enjoy the outdoors.

3600 Dee Oguin Rd, Pleasantville

$405,000

3 Beds ⋅ 2 Baths ⋅ 3599387 MLS ⋅ ACTIVE Status ⋅ 10 Acres ⋅ 37033 Zip Code

Escape to the peace and privacy of country living with this well-maintained 1,564 square foot manufactured home nestled on 10+/- picturesque acres. Surrounded by natural beauty, this property offers the perfect blend of comfort, functionality, and outdoor enjoyment. The home features a spacious layout with ample living space, making it ideal for families, hobby farmers, or anyone seeking room to spread out. Step outside and enjoy the scenic landscape, highlighted by a beautiful creek, creating a tranquil setting and attracting local wildlife. For those needing extra storage or workspace, the property includes a storage building and a carport. The expansive acreage offers plenty of room for gardening, horseback riding, hunting, or simply enjoying the great outdoors. Whether you're looking for a peaceful rural retreat, a hobby farm, or a property with room to grow, this unique acreage delivers the space, versatility, and natural beauty you've been searching for.

5898 W Highway 100, Pleasantville

$384,900

2 Beds ⋅ 3 Baths ⋅ 3526625 MLS ⋅ ACTIVE Status ⋅ 12.51 Acres ⋅ 37033 Zip Code

A little piece of Tennessee that's getting harder to find is currently available. Situated on approximately 12.5 acres in Pleasantville, this 4 bedroom, 2.5 bathroom home has 1,921 square feet of living space and a setting filled with character, privacy and natural beauty. The home was updated in 2021, with a metal roof, farmhouse inspired details, expansive covered porches and decking overlooking the surrounding countryside. An unfinished basement provides additional space for storage and workshop space. The home comes with a refrigerator, washer and dryer. The outdoors is where this property truly sets itself apart. Explore 12.5 acres of open pastures and wooded terrain featuring a natural spring, mature fruit trees, a chicken coop, striking rock formations and even a cave tucked into the hillside. The combination of usable pasture and wooded acreage creates opportunities for animals, gardening, recreation or simply enjoying the land. Whether envisioned as a homestead, hobby farm or private country retreat, this property offers the space and natural features to create something special. From fruit trees and grazing pasture to the spring and wooded trails, this isn't simply a home on acreage, it's a place to put down roots and enjoy a different pace of Tennessee living. Note: There are three additional hobby/office rooms that if Septic lines would be increased could easily be turned into a 4,5 bedroom home.

3344 Highway 438 E, Pleasantville

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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.