Winchester Homes under $1 million

Welcome to Winchester, Tennessee—a charming city nestled in the heart of Franklin County. Known for its picturesque landscapes and vibrant community spirit, Winchester offers a delightful blend of small-town charm and modern conveniences. With its rich history and scenic surroundings, this city is an ideal place for families, retirees, and anyone seeking a peaceful yet engaging lifestyle.

Winchester boasts a variety of recreational opportunities, from exploring the beautiful Tims Ford Lake to enjoying the lush parks and trails that dot the area. The city's commitment to community events, such as the annual Franklin County Fair, fosters a strong sense of belonging among residents. Winchester’s welcoming atmosphere is complemented by its friendly local businesses, quaint shops, and delectable dining options that cater to every palate.

For those considering a move to this enchanting city, Winchester offers an impressive selection of homes under $1 million. Whether you’re looking for a cozy cottage with character, a spacious family home, or a modern new build, the real estate market here has something for everyone. With affordable pricing and diverse architectural styles, you can find the perfect property that suits your lifestyle and budget.

Living in Winchester means enjoying a slower pace of life without sacrificing access to urban amenities. With its strong sense of community, beautiful surroundings, and a range of affordable housing options, Winchester is a hidden gem waiting to be discovered. Come and explore all that this delightful city has to offer—you may just find your dream home here!

Newest Winchester Homes under $1 million

$209,900

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

Investor Special! Situated on approximately 1 acre in Winchester, just minutes from the downtown square! This 3-bedroom, 2-bath home offers 1,700 square feet of living space, including a bonus room. With plenty of potential and room to make it your own, this property is a great opportunity for investors or buyers looking for a renovation project. 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

$350,000

3 Beds ⋅ 2 Baths ⋅ 3623620 MLS ⋅ ACTIVE Status ⋅ 0.57 Acres ⋅ 37398 Zip Code

Welcome home to this charming 3-bedroom, 2-bath property offering the perfect combination of comfort, style, and versatility! Step inside to discover an inviting open floor plan featuring beautiful LVP flooring throughout, stylish accent walls, and a spacious kitchen complete with quartz countertops and a large island perfect for gathering and entertaining. Need additional living space? The recreation room offers endless possibilities for a second living area, game room, or entertainment space! Outside, enjoy a spacious front yard and a fenced backyard with plenty of room to relax, entertain, or enjoy the outdoors. An added bonus is the separate mother-in-law quarters located in the backyard, providing flexible space for guests or extended family. Conveniently located near beautiful Tims Ford Lake, where boating, fishing, kayaking, and outdoor adventures await! Whether you’re entertaining friends, hosting family, or simply enjoying the comforts of home, this Winchester property has so much to offer. Don’t miss your chance to pick this one! Schedule your private showing today!

19 Carol Cir, Winchester

$749,900

3 Beds ⋅ 3 Baths ⋅ 3623330 MLS ⋅ ACTIVE Status ⋅ 0.61 Acres ⋅ 37398 Zip Code

Welcome to Lake & Leisure, a beautifully renovated, fully furnished retreat offering exceptional value at Tims Ford Lake! Professionally designed interiors and extensive renovation upgrades make this turnkey short-term rental as inviting as it is convenient. Enjoy all-new furnishings, new HVAC and septic systems, and an 800-square-foot heated and cooled detached garage. Your brand-new dock is just a 60-second ride away in the new six-seater golf cart—included with the property! Whether you’re looking for a personal lake escape, an investment property, or the opportunity to enjoy both, Lake & Leisure is ready for you. With Freedom Property Management already in place and projected gross rental revenue of up to $70,000 for 2027, this thoughtfully updated retreat pairs the lake lifestyle with the convenience of an established management team.

96 Maple Dr, Winchester

$889,000

3 Beds ⋅ 1 Baths ⋅ 3622479 MLS ⋅ ACTIVE Status ⋅ 34 Acres ⋅ 37398 Zip Code

Charming brick residence situated on over 34 acres of tranquil countryside, bordered by pastureland. This property combines traditional brick architecture with spacious rural living, making it an excellent option for first-time homebuyers. The home is partially furnished and includes a plumbed garage, which has the potential to be converted into a primary suite with a full bathroom. The 34+ acres of greenbelt land offer ample space for custom home development, as well as the construction of a personal workshop or other outbuildings. Conveniently located approximately a quarter mile from Tims Ford State Park, Bear Trace Golf Course, and within ten minutes of multiple marinas. The property features a three-bedroom farmhouse suitable for occupancy or rental income. The land includes gently rolling pastures, a nine-stall pole barn with tack and wash areas, birthing stalls, a lean-to, hayloft, a four-bay gated implement shed, and a stocked pond. Please note that subdivision into parcels of less than five acres is not permitted.

5630 Mansford Rd, Winchester

$350,200

3 Beds ⋅ 3 Baths ⋅ 3620871 MLS ⋅ ACTIVE Status ⋅ 0.71 Acres ⋅ 37398 Zip Code

Lake life, flexible living, and potential rental income—all at 204 Homeward Ave! This updated 3-bedroom, 3-bath home offers nearly 2,000 square feet on a generous 0.71-acre lot, within walking distance of Tims Ford Lake and minutes from downtown Winchester’s square. A gorgeous sunroom provides a bright, inviting place to unwind, while the covered patio and spacious backyard offer room for entertaining, gardening, and enjoying the outdoors. The versatile layout creates options for an in-law or children’s suite, and the detached garage includes plumbing and additional living space previously rented as an apartment. The additional in-law suite is handicapped accessible, along with the step-in shower. Explore the potential for multigenerational living, guest accommodations, or short- and long-term rentals, subject to applicable requirements and approvals. Covered boat or RV parking adds convenience for your next lake adventure.

204 Homeward Ave, Winchester

$369,000

3 Beds ⋅ 2 Baths ⋅ 3620482 MLS ⋅ ACTIVE Status ⋅ 1.97 Acres ⋅ 37398 Zip Code

Stunning New Construction on 1.97 acres!! Experience the perfect blend of modern elegance and peaceful county living in this beautiful new construction home. Step inside and fall in love with the inviting open floor plan, designed for both everyday comfort and effortless entertaining. Gorgeous hardwood and tile flooring add warmth and sophistication throughout while the beautifully tiled shower offers a touch of luxury. Enjoy the convenience of a tankless water heater providing endless hot water and an oversized garage offering plenty of room for vehicles, storage, and more!

Sisk Rd, 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

$364,900

3 Beds ⋅ 2 Baths ⋅ 3620099 MLS ⋅ ACTIVE Status ⋅ 0.5 Acres ⋅ 37398 Zip Code

Stunning new construction with country charm and modern elegance!! This gorgeous home nestled on a beautiful half-acre lot, offering the perfect blend of modern style, comfort, and peaceful country living! Step inside to discover beautiful finishes and thoughtful details throughout, including lovely granite countertops and custom closet shelving designed for style and organization. Luxurious vinyl flooring runs throughout the home and enhances the spacious open floor plan. Step outside onto an oversized deck, perfect for entertaining family and friends, grilling out, or simply relaxing and enjoying the fresh country air. The attached two-car garage and concrete driveway add convenience and curb appeal to this beautiful property. Outdoor enthusiasts will love the location! Just minutes from Circle E Guest Ranch, where adventure awaits with horseback trail riding, camping, and plenty of outdoor recreation.

1579 Rowe Gap Rd, Winchester

$469,000

3 Beds ⋅ 3 Baths ⋅ 3619053 MLS ⋅ ACTIVE Status ⋅ 0.32 Acres ⋅ 37398 Zip Code

Its in the details - this home was meticulously designed for luxury and comfort! ** Get 1% towards closing costs + a free appraisal when you use our preferred lender! ** This home has so many details that make it special, from the beautifully crafted coffered ceiling and statement lighting to the thoughtfully selected finishes throughout. The open living area features a cozy fireplace and flows into a spacious kitchen with a large island, perfect for everyday living and entertaining. All three bedrooms are on the main level, with an upstairs bonus room and half bath offering extra flexibility. Located just minutes from Tims Ford Lake and downtown Winchester, with easy access to boating, fishing, local restaurants, and shopping. A beautiful home in a great location with plenty to enjoy both inside and out!

201 Lookout Dr, 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

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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.

Winchester Homes under $1 million

Newest Winchester Homes under $1 million

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