Refine Search
Map
Sort by
$250,000
3252167 MLS ⋅ ACTIVE Status ⋅ 3.724 Acres ⋅ 37398 Zip Code
Prime Commercial Opportunity – High-Traffic Location. Don’t miss this exceptional opportunity to own vacant commercial land in a highly visible, high-traffic area. Positioned for maximum exposure, this property offers endless potential for a wide range of business ventures. With continued growth in the surrounding area, this is your chance to secure a strategic location. Both Tracts 3 and 4 sale together

AEDC Rd, Winchester
$159,000
3243837 MLS ⋅ ACTIVE Status ⋅ 2.19 Acres ⋅ 37398 Zip Code
Discover the possibilities on this beautiful 2.19-acre property, ready for your next project. Whether you're envisioning a mini farm, a custom dream home, or an investment opportunity, this versatile tract offers exceptional potential. A preliminary soil test supports a 4-bedroom home site, making it easier to start planning your build. Zoned R-2, the property may also accommodate duplex development, offering flexibility for homeowners, investors, or builders seeking income-producing opportunities. Enjoy the space and freedom of country-style living while maintaining convenient access to nearby amenities. With ample room for gardens, animals, workshops, recreational space, or multiple residential units, this property is a rare find with endless possibilities! Soil sample attached

Metcalf Road, Winchester
$319,900
2 Beds ⋅ 2 Baths ⋅ 3234828 MLS ⋅ ACTIVE Status ⋅ 2.5 Acres ⋅ 37398 Zip Code
Charming 2 bed, 2 bath home situated on 2.4 acres, offering the perfect blend of modern comfort and peaceful country living. This 1,080 sqft home features high ceilings, updated finishes, and a beautifully renovated primary bathroom. Enjoy year-round relaxation in the Florida room, or step outside to take in the scenic surroundings. The newly built shop provides excellent space for storage, hobbies, or projects. Conveniently located just 10 minutes from town, this property delivers both privacy and accessibility in a truly storybook setting.

1687 Georgia Crossing Rd, Winchester
$689,600
3230781 MLS ⋅ ACTIVE Status ⋅ 34.48 Acres ⋅ 37388 Zip Code
34.48-Acre Private Retreat on Fergus Ln- Tullahoma, TN. Discover your perfect canvas for your dream home on this stunning 34.48 acre parcel located at 0 Fergus Ln in Tullahoma, TN. Offering rolling terrain, mature timber, and breathtaking water features, this property delivers the ultimate blend of privacy, natural beauty, and recreational potential. The land features gentle rolls and pockets of mature hardwood timber that provide a serene, wooded backdrop and excellent privacy. A highlight of the property is direct access to Rocky Branch Creek- a beautiful cascading waterway with picturesque waterfalls that create a soothing soundtrack and stunning visual appeal year- round. Complementing this is an additional spring-fed creek flowing across the property, ensuring fresh, reliable water resources and enhancing the overall ecosystem. Whether you're looking to build a custom home, establish a family compound, or create a weekend getaway, this acreage is ideally suited for it. The topography offers several potential build sites with natural elevation changes that could provide long-range views of the surrounding countryside and creeks. Access is convenient yet private, with legal easements from both Fergus Ln and Rackler Ln, giving you flexible entry options. This is a rare opportunity to own a substantial, water-rich tract in a desirable area. Whether you're an outdoor enthusiast, or someone seeking a peaceful homestead, this property checks every box. Don't miss your chance to own this slice of Tennessee paradise. Contact the listing agent today for more details or to schedule a private showing.

Fergus Ln, Tullahoma
$1,849,999
6 Beds ⋅ 4 Baths ⋅ 3226482 MLS ⋅ ACTIVE Status ⋅ 10.55 Acres ⋅ 37398 Zip Code
Exceptional property on 10.5 sprawling acres offering the perfect blend of space, comfort, and resort style outdoor living. The main residence features 3,617 sq. ft. with 6 bed, 3.5 baths, providing ample room for family, guests, and entertaining. The well appointed kitchen showcases beautiful hickory cabinetry, black stainless steel appliances, quartz countertops, abundant storage and generous workspace. The home also as an Electrolux vacuum system built into it. A standout feature of this property is the impressive 2,840 sq. ft. Pool House, thoughtfully designed with stunning tongue and groove ceilings, real hardwood floors, and a full kitchen equipped with stainless steel appliances and granite countertops. Whether used for entertaining, extended family accommodations, a game room, or private retreat, this building offers endless possibilities. Step outside to your own private oasis centered around a spectacular 24x40 custom in-ground pool featuring 2 swim-outs. The expansive outdoor setting creates the ideal environment for relaxing, hosting gatherings, and enjoying year round recreation. With over 6,400 square feet of combined living space between the main home and pool house, premium finishes throughout, and exceptional indoor-outdoor amenities, this one-of-a-kind property presents a rare opportunity to own a true entertainers dream.

3539 Liberty Rd, Winchester
$429,900
3 Beds ⋅ 3 Baths ⋅ 3221346 MLS ⋅ ACTIVE Status ⋅ 2.64 Acres ⋅ 37398 Zip Code
Located near Tims Ford Lake with deeded lake access, this well-built all brick home offers privacy, space, and plenty of potential on 2.64 wooded acres. With 2,431 sq ft, the home features 3 bedrooms, 2.5 bathrooms, a sunroom, large basement, garage, and attached carport. Mature trees provide a peaceful setting with room to enjoy the outdoors while still being just minutes from Tims Ford State Park and the shopping, dining, and conveniences of Downtown Winchester. The home has been well maintained and is in great overall condition, while offering an opportunity for cosmetic updates to match today’s style and make it your own. A rare combination of space, privacy, and lake-area living in one of Middle Tennessee’s most desirable locations.

90 Owl Hollow Ln, Winchester
$69,900
3217771 MLS ⋅ ACTIVE Status ⋅ 0.5680000000000001 Acres ⋅ 37398 Zip Code
Construction will start once we have an agreement for land purchase. Builder offering financing!! Build your dream home right here on this beautiful lot. Buyers have the opportunity to choose finishes and adjust the floor plan to fit their lifestyle. Standard features include luxury vinyl plank flooring throughout, beautiful granite countertops, soft-close cabinetry, a durable hardboard exterior and a concrete driveway. Experience the benefits of new construction in a desirable location near Tim’s Ford Lake. Let's make this one yours!

Mansford Rd, Winchester
$209,900
3 Beds ⋅ 1 Baths ⋅ 3217503 MLS ⋅ ACTIVE Status ⋅ 0.48 Acres ⋅ 37398 Zip Code
LARGE PRICE REDUCTION! Welcome home to this charming rambler in the City of Winchester. This home is bursting with character and sits on a large +/- 0.48-acre lot on a quiet street. Walking distance to the historic Winchester Square and Tim’s Ford Lake. Hardwood floors, new kitchen counters, and a fully fenced back yard for your four-legged friends. Mature trees line the back and side yard. Detached, single car garage with concrete floor. Single car attached carport. Roof replaced +/- 2 years ago. Great starter home or investment property. Close to it all, but with the benefits of country life.

208 Lillian St, Winchester
$450,000
3 Beds ⋅ 3 Baths ⋅ 3211510 MLS ⋅ ACTIVE Status ⋅ 0.55 Acres ⋅ 37398 Zip Code
Charming Southern Elegance Awaits You! Step into a world of timeless beauty and modern luxury with this stunning turn-of-the-century home, meticulously renovated to blend classic charm with contemporary comfort. The heart of the home is the spacious kitchen, featuring exquisite quartz and granite countertops that will inspire your culinary adventures. Whether hosting intimate dinners or grand celebrations, the classic dining room, adorned with original built-in china cabinets, provides the perfect backdrop for memorable gatherings. Retreat to your serene master suite, a luxurious haven offering not one, but two matching closets along with an expansive walk-in closet. The spa-like master bath is a true delight, boasting a twin vanity and a large walk-in shower, all complemented by a stunning white marble floor that adds a touch of sophistication. This Southern gem is not just about beauty; it's about functionality too! A generous 2-4 car garage (depending on your vehicles) and a spacious workshop provide ample storage and workspace for all your needs. The garage doors measure a convenient 9x9 in this 30X40 shop/garage, making access a breeze. Experience peace of mind with modern efficiencies, including a gas water heater and a gas furnace, ensuring your comfort year-round. Ask for the short list of wonderful renovations! Don't miss the chance to call this exquisite property your home. Live in elegance, entertain in style, and create cherished memories in a space that truly reflects the best of Southern charm. Schedule your private showing today and take the first step toward your dream home! https://youtu.be/Qn4Cg1jGLgQ (copy paste video link)

314 NW 4th Ave, Winchester
$695,000
5 Beds ⋅ 4 Baths ⋅ 3208025 MLS ⋅ ACTIVE Status ⋅ 0.62 Acres ⋅ 37398 Zip Code
This captivating property, beautifully blending residential charm with commercial potential, is now on the market and ready to redefine your living or working experience. Whether you're looking for a family home or an investiment property, this mixed-use gem offers unparalleled flexibility. Nestled in a vibrant historic district, this property offers superb visibility and accessibility. With a mix of residential and commercial spaces surrounding it, just steps away from local shops, restaurants, and cultural attractions. The formal living room welcomes you with its elegant built-in bookshelves framing a stunning gas log fireplace, perfect for cozy evenings. The beautifully finished wood floors enhance the home's warmth and character, making it an inviting space for both family gatherings or professional meetings. The separate study/office, featuring a private entrance and a second gas log fireplace is ideal for those who work from home or need a quiet space for client meetings. Built-in shelves enhance this versatile room's functionality. The downstairs layout features large bedrooms that share a well appointed jack-and-jill style full bath, offering convenience and privacy. Upstairs, Bedroom 3 includes its own full bath, while Bedroom 4 boasts a separate heat and air unit for personalized climate control. The private suite above the garage is perfect for guests, comlete with its own shower-only full bathroom. This property includes a basement that offers possibilities for storage, or a creative studio. Enjoy extra yard space that fronts S Porter St, presenting unique opportunities for outdoor seating framed by the unique stone bench at the edge of the property. The flexible outdoor area is perfect for a potential cafe outdoor dining, garden or additional parking for a retail business. You have the flexibility to continue using it as a home or convert it into a commercial space to host your business endeavors. (copy video link) https://youtu.be/HU5RftclNE8

110 S Porter St, Winchester
$475,000
3206894 MLS ⋅ ACTIVE Status ⋅ 1.27 Acres ⋅ 37398 Zip Code
Rare opportunity to acquire development-ready waterfront land for sale in Winchester, TN with flexible R3A zoning, dual road access, and strong residential development potential on Boiling Fork Creek with access to Tims Ford Lake. This 1.27-acre tract in Franklin County offers level topography, scenic water views, and a highly desirable location just minutes from downtown Winchester and the Winchester square. The property’s zoning supports multiple residential possibilities, including single-family homes, duplexes, and multifamily configurations, providing flexibility for developers seeking a future residential project. The level buildable area and access on two roads create added site-planning options and convenient access points. Located near Hwy 41A, shopping, dining, schools, healthcare, parks, and lake recreation, the property combines accessibility with waterfront appeal. Tims Ford Lake remains one of Middle Tennessee’s most sought-after destinations for residential and recreational development, adding long-term desirability to the location. Buyer to verify all information.

SE 2nd Ave, Winchester
$475,000
5 Beds ⋅ 2 Baths ⋅ 3205990 MLS ⋅ ACTIVE Status ⋅ 0.34 Acres ⋅ 37398 Zip Code
SELLER OFFERING OWNER FINANCING AT 5.75% — This income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with immediate rental income and future flexibility. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence generates approximately $2,000/month in rental income and includes approximately 3,922 sq ft on a .34-acre lot in the heart of Winchester. The property features original hardwood floors, spacious living areas, and a covered front porch that adds character and tenant appeal. A detached 1-car garage and driveway parking provide additional functionality. Located seconds from the Winchester square and Hwy 41A, the property is conveniently positioned within the community. Currently office space with a long-term tenant of 7 years, the layout and location support multiple potential uses, including long-term rental hold, mixed-use potential, or future repositioning within a growing downtown area. Convenient access to local amenities and a strong occupancy history contribute to the property's appeal for investors seeking a centrally located asset in a developing corridor. Buyer to verify all information.

309 NW 2nd Ave, Winchester
$1,475,000
3 Beds ⋅ 5 Baths ⋅ 3183871 MLS ⋅ ACTIVE Status ⋅ 12.19 Acres ⋅ 37398 Zip Code
We are introducing this breath taking home crafted on a beautifully wooded 12.1 acres in one of the most desired locations. Meticulously designed and constructed this remarkable traditional residence spans 4000 square feet, offering a seamless concept of traditional and modern floor plan. This home presents 3 bedrooms with 3 ensuite bathrooms and an additional guest half bath, a library, and a versatile Florida style room. Hardwood floors throughout. Over a 1,000 Sq feet master suite is by itself a masterpiece featuring cathedral 20 feet ceiling with decorative wooden beams. A gas fireplace with a custom precast stone creates a cozy ambiance. Spacious walk-in closet with custom build- ins & van extra-large master bath with Jacuzzi 12 jet tub, large jetted frameless glass walk-in shower & a dual sink vanity complete this very comfortable private space. Large newly remodeled kitchen with granite countertops and sprawling central island opens to a formal dining room. Plenty of traditional cabinetry provides a lot of storage. Living room with a 20-foot ceiling & wood burning fireplace give plenty of entertaining space. Upper deck is species and recently remodeled including natural oak rails and composite deck. Lower deck surrounds a newly constructed 18x35 resin saltwater pool. Energy efficiency takes center stage in this home. Tankless hot water heater for showers & tubs & high efficiency fiberglass 55-gal tank take care of all your demands. HVAC consists of 3 high-efficiency heating and cooling dual fuel system units. All windows were replaced with high efficiency 400 series Anderson windows. 4 car garage with additional, completely underground, large basement provides an exceptional shelter for family during potential weather crises. Newley build detached 24x40 double door garage is convenient for a workshop or just a storage place for your equipment and your boat. Property is surrounded by an array of flower gardens, shrubbery, fruit trees & cedar raised beds.

1485 Water Tank Rd, Winchester
$668,500
3 Beds ⋅ 2 Baths ⋅ 3181622 MLS ⋅ ACTIVE Status ⋅ 5.88 Acres ⋅ 37388 Zip Code
Lake life time! An amazing find with golf cart access to the LAKE! This secluded home is on approximately 6 acres featuring mature shade trees, oval in-ground pool measuring 20x40 feet, three-stall barn, and fenced pasture ideal for any type livestock. This peaceful country property is in an ideal location! It offers convenient walking or a short drive on a golf cart to Holiday Landing with easy boat dock access and good food at the Bluegill Grill restaurant. The first floor consists of authentic red and white oak hardwood flooring throughout main living areas, a large living room with a gas fireplace, a sunroom perfect for relaxation, a spacious bedroom with a walk-in closet, a roomy utility room, full bathroom, and two-car attached garage with an additional storage room! And that is only the downstairs! The upstairs features two extremely large bedrooms with large closet space and a second full sized bathroom. Property includes fiber internet, natural gas access, a storage shed, and a charming garden area. In addition to being within walking distance of the lake, this home is located minutes from Tim's Ford State Park and Bear Trace Golf Course, offering excellent recreational opportunities for boating, fishing, golfing, and hiking. There is abundant wildlife viewing on the property itself from the luxury of your own sunroom and the well-established shade trees create a private sanctuary while maintaining proximity to modern-day amenities and conveniences. This rare find combines rural tranquility with accessibility to waterfront activities and local dining. Just think, no HOA, unrestricted property, great location! And your own private oasis!

120 Evans Dr, Tullahoma
$79,000
3180680 MLS ⋅ ACTIVE Status ⋅ 0.61 Acres ⋅ 37398 Zip Code
Peaceful County Lot With Beautiful Mountain Views!! Discover the perfect place to build your dream home on this stunning vacant lot nestled in the quiet countryside. Surrounded by natural beauty this lot offers wide open space, fresh air, and lovely mountain views that change with the seasons. With ample space for your custom build, a garden, or small hobbies, the possibilities are endless. Soil study has been done and waiting for it to come back. No barndo's, no mobile homes, and a 1500 sq ft. minimum.

Old Holders Cove Rd, Winchester
$118,000
3180497 MLS ⋅ ACTIVE Status ⋅ 2.32 Acres ⋅ 37398 Zip Code
An incredible opportunity to design and build your dream home or a weekend gateway nestled in a peaceful and well established neighborhood tin Winchester, TN. This spacious lot offers the perfect balance of peaceful country setting, privacy, convenience, and natural beauty.

Old Estill Springs Rd, Winchester
$159,000
3177894 MLS ⋅ ACTIVE Status ⋅ 0.889 Acres ⋅ 37398 Zip Code
Prime Commercial Opportunity – High-Traffic Location. Don’t miss this exceptional opportunity to own vacant commercial land in a highly visible, high-traffic area. Positioned for maximum exposure, this property offers endless potential for a wide range of business ventures. With continued growth in the surrounding area, this is your chance to secure a strategic location. Tracts 3 and 4 available for purchase.

AEDC Rd, Winchester
$275,000
3171237 MLS ⋅ ACTIVE Status ⋅ 9.42 Acres ⋅ 37398 Zip Code
PREMIUM and RARE investment opportunity to own 9+ acres on Hwy 41A! Positioned in a high-traffic area with excellent visibility, it’s perfectly suited for future development. Opportunities like this are hard to find—don’t miss your chance!

Tullahoma Hwy, Winchester
$429,900
3 Beds ⋅ 2 Baths ⋅ 3155736 MLS ⋅ ACTIVE Status ⋅ 0.5680000000000001 Acres ⋅ 37398 Zip Code
Construction will start once we have an agreement for purchase. Builder offering financing!! This is a brand-new, customizable 3-bedroom, 2-bath home featuring an open floor plan. Buyers have the opportunity to choose finishes and adjust the floor plan to fit their lifestyle. Standard features include luxury vinyl plank flooring throughout, beautiful granite countertops, soft-close cabinetry, a durable hardboard exterior, and a concrete driveway. Experience the benefits of new construction in a desirable location near Tim’s Ford Lake. Don’t miss the chance to make this one yours!

Mansford Rd, Winchester
$1,100,000
4 Beds ⋅ 5 Baths ⋅ 3152557 MLS ⋅ ACTIVE Status ⋅ 2 Acres ⋅ 37398 Zip Code
This fantastic large custom home is located upon entering picturesque Tims Ford State Park. This home offers endless opportunities for outdoor enthusiasts.Spend your weekends golfing,hiking,boating or cycling through stunning trails,or enjoy a day on or by the lake. This property is horse-friendly & ideal for those who love the outdoors. As you explore the nearby walking trails, enjoy wildlife sightings, or simply enjoy relaxing in the expansive yard. Blink security stays, washer, dryer & 2nd refrig. stays.The approx. 30x50 detached garage/building allows plenty of room for parking or a workshop/hobby shop. There is also plenty of room for office space in the detached garage/building. Currently the detached garage/building can be used as offices. Potential for in-law quarters. The building has its own electric & half bath. If you're looking for a property that offers many options & opportunities, then look no further. This home has so much to offer, schedule your showing today. Listing broker is related to seller/builder.

236 Tims Ford Dr, Winchester
$72,000
3152479 MLS ⋅ ACTIVE Status ⋅ 0.91 Acres ⋅ 37398 Zip Code
Beautiful! Just under an acre residential lot is partially cleared and partially wooded. 5 Minutes to Winchester City Park & Public Boat Ramp, 8 Minutes to Winchester Courthouse Square' shopping, theater, restaurants and more. Must See!

Cooper Ln, Winchester
$89,000
3124566 MLS ⋅ ACTIVE Status ⋅ 0.27 Acres ⋅ 37398 Zip Code
Corner residential building lot just a stone's throw from Tims Ford Lake and the adorable downtown district of Winchester, TN! This lot is just 7 blocks from the public square and 1 mile from the nearest boat launching ramp which is located in the Winchester City Park. This lot also benefits from a variance that was granted to allow for a larger building footprint. This blank canvas is filled with possibilities!

612 N Jefferson St, Winchester
$999,500
4 Beds ⋅ 4 Baths ⋅ 2990003 MLS ⋅ ACTIVE Status ⋅ 2.6 Acres ⋅ 37398 Zip Code
BRAND NEW ROOF!* W/ Transferable Warranty. Ask Me About Our 1% Preferred Lender Credit To Be Used For Closing Costs Or Rate Buydown* *COMPLIMENTARY Home Warranty*Just MINUTES from Tim's Ford Lake! When Your Custom-Built Home Is Masterfully Crafted By A Brilliant Engineer, You’re Investing In A Home Designed For Generations. Set On An Expansive 2.6-Acre Estate, This Property Combines Uncompromising Quality With Thoughtful Functionality At Every Turn. Upstairs You Will Find The Primary Suite, Spacious Kitchen, Guest Bedrooms, Tranquil Sunroom, And A Relaxing Outdoor Back Deck. Downstairs, This Exceptional Home Also Features A Dedicated Woodworking And Craft Studio—Ideal For Passion Projects Or Hobbyists—Along With Expansive Open Space Ready To Be Transformed Into A Private Gym Or Wellness Sanctuary. Downstairs, The Fully Finished Basement Boasts An Entertainment Room Designed For Hosting Game Days Or Social Gatherings, While A Below Ground, Built-In, Reinforced Concrete Storm Shelter With A Steel Door Offers Peace Of Mind During Unexpected Weather Events. The Oversized Three-Car Garage Is As Functional As It Is Immaculate, Featuring A Polyurea-Sealed Floor With A High-Gloss Clearcoat For Unmatched Durability. Enjoy The Benefits Of Both A Private Well And City Water—Perfect For Personal Use Or Feeding Your Landscaped Irrigation System. A Subsurface 1,000-Gallon Propane Tank Fuels Multiple Fireplaces Throughout The Home, In Addition To State-Of-The-Art Tankless, On-Demand Water Heaters That Deliver Instant And Endless Hot Water. With Tim’s Ford Lake Just Five Minutes Away, You’ll Have Seamless Access To Boating, Fishing, Or A Relaxed Lunch At A Local Marina. And When You’re Ready For A Change Of Scenery, A Quick Drive Puts You In Downtown Chattanooga In Just Over An Hour. This Isn’t Just A Home. It’s A Legacy—Built For Those Who Demand The Finest!

2124 Boswell Rd, Winchester
$699,000
4 Beds ⋅ 2 Baths ⋅ 2922799 MLS ⋅ ACTIVE Status ⋅ 7.77 Acres ⋅ 37398 Zip Code
Charming 2-Story Country Home on 7.77 Acres in Winchester, TN! This beautiful 3-bedroom + bonus room, 2-bath home offers the perfect blend of comfort, privacy, and space. Enjoy an open-concept kitchen/living/dining area with a cozy gas fireplace, ideal for entertaining. Take in stunning mountain views from your peaceful retreat, complete with a fenced and gated driveway, attached garage, detached garage, and 3 metal carports. A storm shelter adds peace of mind. Whether you need extra bedrooms, a bonus room, or dedicated office space—this home has the flexibility to fit your lifestyle. Plenty of room to roam and relax!

379 Hooper Rd, Winchester
board logo

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.