37398 Homes under $300,000

Welcome to the charming community of Winchester, Tennessee, nestled in the heart of Franklin County, where the zip code 37398 opens the door to a world of possibilities. Known for its picturesque landscapes and friendly atmosphere, Winchester is a hidden gem that offers a perfect blend of small-town charm and modern conveniences.

For homebuyers seeking affordability without compromising on quality, the 37398 area boasts an impressive selection of homes priced under $300,000. This vibrant community features a variety of housing options, from cozy single-family homes to spacious townhouses, making it an ideal destination for first-time buyers, families, and retirees alike. With its reasonable property prices, Winchester allows residents to enjoy the comfort of homeownership while keeping their budget in check.

Beyond the homes, the Winchester area is rich in recreational opportunities and local amenities. Residents can take advantage of the stunning Tims Ford Lake, perfect for boating, fishing, and picnicking, or explore the scenic hiking trails that wind through the nearby mountains. The city also offers a variety of shops, restaurants, and community events that foster a strong sense of belonging and connection among neighbors.

With its welcoming spirit, beautiful surroundings, and affordable housing options, the 37398 zip code is a fantastic choice for anyone looking to plant their roots in a vibrant community. Discover the joys of living in Winchester, where your dream home awaits just around the corner!

Newest 37398 Homes under $300,000

$229,000

3 Beds ⋅ 1 Baths ⋅ 3626796 MLS ⋅ ACTIVE Status ⋅ 0.19 Acres ⋅ 37398 Zip Code

Charming 3 bed, 1 bath in the Heart of Winchester. Cute as a button and newly remodeled, this inviting home offers comfort, convenience, and an incredible bonus—an additional approximately 45'x207' lot included with the property. Inside, the home features fresh updates throughout and a concrete basement, perfect for storage or hobbies. The layout is cozy and efficient, ideal for anyone seeking an easy‑to‑maintain home with character. Located right in the heart of Winchester, you’re just moments from downtown shops, dining, and the historic town square. Enjoy walkable living with small‑town charm and room to breathe. Appliances have been ordered.

814 S High St, Winchester

$209,900

3 Beds ⋅ 2 Baths ⋅ 3626113 MLS ⋅ ACTIVE Status ⋅ 1.09 Acres ⋅ 37398 Zip Code

Situated on approximately 1 acre in Winchester, just minutes from the downtown square! This 3-bedroom, 2-bath home offers approximately 1,700 square feet of living space, including a bonus room. With a spacious lot, convenient location, and plenty of room to make it your own, this property has so much to offer! Whether you’re looking for your next home or an opportunity to add your personal touches, come see the possibilities! Property is being sold as-is.

205 Sells St, Winchester

$269,900

2 Beds ⋅ 1 Baths ⋅ 3623676 MLS ⋅ ACTIVE Status ⋅ 0.74 Acres ⋅ 37398 Zip Code

Make plans now to see this extensively renovated home with a FULL basement in the heart of Winchester! Sitting on a huge corner lot and surrounded by mature shade trees, there is still room to expand. Beautifully renovated inside and out, some of the major updates include a new roof, new Hardie Board siding, new heat/air system, new plumbing, new electric, new water heater, new windows, new gutters and downspouts. The newly renovated kitchen includes new cabinets, new quartz counters, new stainless steel appliance package, new faucets and light fixtures. Beautiful new LVP flooring throughout the main level. The renovated bathroom features a custom tiled shower. Updates also include new recessed lighting plus updated drywall, trim and paint. Original pine bedroom walls add character while the rest of the home offers modern finishes and an open, functional layout. Best of all, the FULL basement and oversized lot offer opportunities for additional living space, workshop, storage, garage, recreation area, or future expansion. This home is a great option for owner/occupants (especially if you operate a home-based business!), investors, long or short-term rentals (think AirBnb/VRBO opportunities)! Great location--roughly 1.5 miles to Downtown Winchester and so convenient to Tims Ford Lake, Nissan Decherd, AEDC, Tullahoma, Manchester, and Huntsville.

102 Oak Park, Winchester

$245,000

2 Beds ⋅ 1 Baths ⋅ 3620452 MLS ⋅ ACTIVE Status ⋅ 0.17 Acres ⋅ 37398 Zip Code

Just under a mile from the Winchester square, 1101 N High St is 1,292 square feet of character with a lot of updates. The living room is the showpiece, with a tongue-and-groove wood ceiling, warm wood accent walls, recessed lighting and a brick fireplace as its centerpiece. Big windows bring in light throughout, and dark wood-look floors run through the main living areas. The kitchen opens to the dining space and has white cabinetry, light stone-look counters, a wood-front peninsula with seating, a gas range and tile floors. There's a separate laundry room with its own door to the backyard, plus built-in shelving for pantry storage. Both bedrooms have ceiling fans and good closet space, and the bath has a subway-tile tub and shower. For storage, there's walk-up stair access to the attic and a basement below. Outside, the covered front porch has a wood ceiling and a swing. The back has a large privacy-fenced yard, a patio and a long gravel drive. It's a quick drive to shops and restaurants downtown and close to the lake for weekends on the water.

1101 High St N, Winchester

$250,000

3 Beds ⋅ 2 Baths ⋅ 3615203 MLS ⋅ ACTIVE Status ⋅ 0.54 Acres ⋅ 37398 Zip Code

Tims Ford Lake opportunity in Winchester! This 3-bedroom, 2-bath ranch offers approximately 1,552 sq. ft. on approximately 0.54 acres with plenty of potential for the buyer ready to make it their own. Features include hardwood flooring, spacious living areas, an attached garage/carport area, and a generous yard in the Rogers Haven community. Selling AS-IS. Buyer to independently verify any TVA dock/shoreline permit eligibility. Some listing photos have been digitally enhanced to remove personal belongings; the home’s permanent features and current condition should be verified in person.

300 Edgewater Dr, Winchester

$169,900

3 Beds ⋅ 2 Baths ⋅ 3613169 MLS ⋅ ACTIVE Status ⋅ 0.26 Acres ⋅ 37398 Zip Code

Charming three bedroom two bath plus bonus that could be used as a fourth bedroom! This home offers character, charm, and space! Located walking distance to the lake and only minutes from downtown.

1011 Massengill St, Winchester

$198,000

3 Beds ⋅ 2 Baths ⋅ 3602885 MLS ⋅ ACTIVE Status ⋅ 0.3 Acres ⋅ 37398 Zip Code

Priced to Sell! Welcome home to this spacious 2,040 sq ft double-wide manufactured home on a permanent foundation! This home features large bedrooms throughout, each with a walk in closets, offering plenty of space and storage. The kitchen offers an abundance of countertop space and cabinets, along with a large island - perfect for cooking, gathering, and entertaining. This home offers generous living space and wood burning fireplace. Retreat to to the oversized primary suite, complete with a huge walk in closet and a private bath featuring a soaking tub, an 8' vanity with a dedicated makeup area, and extra storage. Enjoy the outdoors from the large concrete front porch, and take advantage of the fully fenced backyard with a 24' above ground pool- ideal for summer fun! Extra storage provides added convivence.

1110 Hunt St, Winchester

$217,900

3 Beds ⋅ 2 Baths ⋅ 3602587 MLS ⋅ ACTIVE Status ⋅ 0.51 Acres ⋅ 37398 Zip Code

Complete Renovation in 2026! Cute 3 bed/1.5 bath home totally updated with LVP flooring throughout, SS appliances, washer & dryer and all new bathroom. Home has a complete cellar underneath with separate entry on back that could be finished at buyer's discretion or make a great storage. New vinyl windows. Large yard that is partially fenced. Property extends into the back treeline. Close to Winchester square, hospital, public library and more.

417 Laura Ave, Winchester

$179,900

2 Beds ⋅ 1 Baths ⋅ 3602546 MLS ⋅ ACTIVE UNDER CONTRACT Status ⋅ 0.14 Acres ⋅ 37398 Zip Code

Take A Look!! This adorable totally renovated 2-bedroom, 1-bath cottage that blends cozy charm with fresh modern updates! Step inside to find beautiful LVT flooring throughout, a bright and inviting interior, and an updated kitchen featuring stainless steel appliances. The bathroom has been refreshed with stylish tile surrounding the bathtub, adding a clean, modern touch. Outside you will appreciate the durability and low maintenance of the metal roof. Conveniently located close to town, shopping, dining, and everyday amenities, this charmer would make a wonderful starter home, downsizing option, or investment property.

407 Laura Ave, Winchester

$264,900

3 Beds ⋅ 2 Baths ⋅ 3599190 MLS ⋅ ACTIVE UNDER CONTRACT Status ⋅ 0.35 Acres ⋅ 37398 Zip Code

Welcome home to this beautiful 3br 2ba home located in a nice, established neighborhood! This home features beautiful HW flooring, a new roof, and a welcoming covered front porch for that morning coffee. Inside you will find a spacious layout with a huge kitchen offering plenty of room for entertainment, cooking, and gatherings of family and friends. The sunroom provides a wonderful added space to relax and enjoy natural light year round. This home is a must see!!

114 Hillcrest Dr, Winchester

$294,900

3 Beds ⋅ 2 Baths ⋅ 3598640 MLS ⋅ ACTIVE Status ⋅ 0.46 Acres ⋅ 37398 Zip Code

Beautiful updates, spacious living, and classic brick charm! Welcome to 371 Myers Rd in Winchester, offering 3 bedrooms, 2 baths, and over 1,800 square feet of comfortable living space. All-new windows and fresh paint throughout give the home a bright, refreshed feel, while beautiful original hardwood floors preserve its character. The generously sized kitchen offers plenty of room for preparing meals and gathering, with a newly added pantry providing outstanding storage. Located near Tims Ford Lake, you can enjoy easy access to boating, fishing, and days on the water, along with the everyday convenience of nearby shopping, dining, and downtown Winchester. Thoughtful renovations blend fresh finishes with timeless details, creating a welcoming space ready for its next chapter. Come see the updates, explore the space, and imagine making it your own. Schedule your private showing today!

371 Myers Rd, Winchester

$225,000

3 Beds ⋅ 2 Baths ⋅ 3597234 MLS ⋅ ACTIVE Status ⋅ 0.52 Acres ⋅ 37398 Zip Code

Welcome to this charming 1,344-square-foot brick ranch offering 3 bedrooms and 2 baths in a convenient Winchester location! This well-located home provides easy access to the activities and amenities that make the area so desirable, including Winchester City Park, beautiful Tims Ford Lake for boating and recreation, and historic Downtown Winchester with local dining, shopping, and the lively Square. Outside, you’ll find a spacious front and back yard with plenty of room for entertaining, relaxing, gardening, or enjoying time with family and friends. A detached metal shop/garage provides abundant space for parking, storage, hobbies, or a workshop, with plenty of room to work and create. The home also has an attached garage. With its classic brick exterior, functional floor plan, generous outdoor spaces, and detached shop/garage, this property offers both comfort and versatility in a great location close to everything Winchester has to offer! Property is Selling As Is.

222 Orchard Ln, Winchester

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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.

37398 Homes under $300,000

Newest 37398 Homes under $300,000

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