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$1,799,000
4 Beds 5 Baths 3512410 MLS ACTIVE Status 0.37 Acres 37398 Zip Code
Elevated Lake Living. Lakeside Luxury at the Finest! 3 Level Home that Has It All and More. In Gated Boutique Community Close to Downtown Winchester. HOA incl Lawn Mowing, Gate Maintenance, Common Area and Dock Maintenance/Insurance. Entertainer's Dream Lake House. Luxury Awaits. Shared Community Dock and Exclusive Boat Slip #6. Built Ready for a Hot Tub, and Sauna. 3 Car Garage. Basement Level has 2 Full Bedrooms with 2 Full Bathrooms, Living Room, and Kitchenette/Bar. Slight Variations made to plans, there is no jack and jill bathroom any longer, it is a private bathroom for 1 Bedroom. Main Level built to plan, and Top Level has an additional Bathroom not seen on plans. Come tour to see all the improvements and upgrades for yourself!

322 N Porter St, Winchester

$355,000
3 Beds 3 Baths 3510602 MLS ACTIVE Status 0.71 Acres 37398 Zip Code
Enjoy the best of Winchester living in this well-maintained 3-bedroom, 3-bath home on a spacious 0.71-acre lot. Offering nearly 2,000 square feet, the home features comfortable living spaces, a bright sunroom, and a covered patio overlooking a large backyard with plenty of room for gardening, entertaining, pets, or simply enjoying the outdoors. The detached garage adds exceptional flexibility with plumbing and a space previously used as an apartment—ideal for a guest suite, home office, workshop, hobby room, or potential rental opportunity. Covered parking for your boat or RV makes it easy to take advantage of everything the area has to offer. Just a short walk from Tim's Ford Lake and only minutes from downtown Winchester, you’ll enjoy convenient access to boating, fishing, local restaurants, shopping, and everyday amenities. With its generous outdoor space, versatile detached building, and sought-after location, this property is ready to fit your lifestyle.

204 Homeward Ave, Winchester

$124,900
3510249 MLS ACTIVE Status 1.04 Acres 37398 Zip Code
Discover the perfect setting for your future home on this spacious 1.04 acre homesite in Stone Field Heights. Positioned along the front of the neighborhood and backing to picturesque horse farm acreage, Lot 9 offers a peaceful sense of openness, beautiful sunset views, and added privacy with no subdivision lots directly behind it. The gently sloping terrain offers exciting potential for a walk out basement design, giving you flexibility to create additional living, recreation, or storage space while making the most of the property’s natural grade. Enjoy the best of Southern Middle Tennessee living just minutes from Tims Ford Lake, where boating, fishing, kayaking, and relaxed days on the water can become part of everyday life. Tims Ford State Park, area marinas, boat ramps, trails, camping, and the Bear Trace golf course are all within easy reach. Historic Downtown Winchester is also nearby, offering local shopping, dining, community events, and small town charm. For a scenic day trip, the mountain community of Sewanee and the University of the South are only a quick drive away. With city water, electricity, and public sewer available at the street, much of the essential infrastructure is conveniently accessible as you begin planning your build. Whether you envision a full time residence, a lake area retreat, or a home designed for gathering with family and friends, Lot 9 combines space, scenery, convenience, and access to the Tims Ford lifestyle in one exceptional homesite. Bring your plans and make your vision a reality!

Cascade Dr, Winchester

$325,000
3509952 MLS ACTIVE Status 37398 Zip Code
Investors, take notice! 1012/1014 Hunt St, Winchester, TN! This new-construction duplex offers an excellent opportunity to add a modern, low-maintenance property to your portfolio in a convenient Winchester location. Each unit features 2 bedrooms and 2 full bathrooms, an attractive floor plan for renters seeking comfortable, functional living space. Both units offer desirable modern finishes, including LVP flooring, custom cabinets, and private patios. New construction means today's finishes and fewer immediate maintenance concerns, making this property an appealing option for both seasoned investors and those looking to expand their rental portfolio. Conveniently located just minutes from downtown Winchester, Nissan, shopping, dining, and other everyday amenities, the property offers easy access to Nissan and other lifestyle destinations—an important advantage for attracting and retaining tenants. With two separate units, modern construction, desirable 2BR/2BA layouts, and a convenient location, this duplex presents a strong opportunity for investors seeking a turnkey-style rental property in the Winchester market. Some photos have been virtually enhanced to completion for illustrative purposes only. Actual photos are also included. Final finishes and details may vary. Buyer/buyer’s agent to verify all pertinent information.

1012 Hunt St, Winchester

$310,500
3509953 MLS ACTIVE Status 37398 Zip Code
Investors, take notice! 112/114 Short St Winchester, TN! This new-construction duplex offers an excellent opportunity to add a modern, low-maintenance property to your portfolio in a convenient Winchester location. Each unit features 2 bedrooms and 2 full bathrooms, an attractive floor plan for renters seeking comfortable, functional living space. Both units offer desirable modern finishes, including LVP flooring, custom cabinets, and private patios. New construction means today's finishes and fewer immediate maintenance concerns, making this property an appealing option for both seasoned investors and those looking to expand their rental portfolio. Conveniently located just minutes from downtown Winchester, Nissan, shopping, dining, and other everyday amenities, the property offers easy access to Nissan and other lifestyle destinations—an important advantage for attracting and retaining tenants. With two separate units, modern construction, desirable 2BR/2BA layouts, and a convenient location, this duplex presents a strong opportunity for investors seeking a turnkey-style rental property in the Winchester market. Some photos have been virtually enhanced to completion for illustrative purposes only. Actual photos are also included. Final finishes and details may vary. Buyer/buyer’s agent to verify all pertinent information.

112 Short St, Winchester

$685,700
4 Beds 4 Baths 3508025 MLS ACTIVE Status 0.92 Acres 37398 Zip Code
Step into this magnificent 3,705 square foot home, an absolute gem in the highly sought-after Franklin Hills Subdivision. Designed for both grand entertaining and comfortable family living, this residence offers 4 bedrooms and 3.5 baths across two levels. You will immediately notice the architectural elegance, highlighted by premier trim work and stunning tray ceilings. The entryway is graced by a stunning staircase, one of the home's beautiful architectural features, complemented by a gas fireplace that serves as a warm, artistic centerpiece. The main floor features an array of gathering spaces: a gracious Formal Dining Room, a dedicated Sitting Room, and a cozy Living Room warmed by a gas fireplace. The heart of the home is the Kitchen, featuring premium granite countertops and a suite of stainless steel appliances, highlighted by a new oven installed in 2025 , perfect for the home chef, along with a sunny Breakfast Nook. Retreat to the private master bedroom on the main floor, complete with a luxurious full bath. Flooring is a mix of high-quality hardwood, tile, and carpeting. Upstairs, you'll find the additional bedrooms and a spacious Loft. Enjoy outdoor living on the large, covered front porch or relax on the back patio by the warmth of the brick fireplace. Storage and parking are plentiful with the oversized 3-car garage. The washer and dryer, all bedroom furniture, and potentially select living room items convey with acceptable offer.

356 Ridgecrest Dr, Winchester

$140,000
3506562 MLS ACTIVE Status 0.31 Acres 37398 Zip Code
Lake View Lot- Very RARE! Beautiful and spacious lot on the end of Suntan Court, in a coveted cul-de-sac. LAKE VIEW LOT on the TWIN CREEKS MARINA SIDE. Come build your dream home! HOA cuts the grass, even after you build a home. Lake Life Made Easy and Convenient! Not 1, not 2, but WOW- 3 Community Pools!!! Gated Neighborhood, Golf Cart Friendly, Adjacent to Twin Creeks Marina via private golf cart path with gate- code only given to Twin Creeks Residents and Guests. Great for an Investment. No Build Out Times- Buy and Hold to Build When You're Ready. Twin Creeks offers a wonderful community to part time residents, full time residents, and lot owners with a wide array of social activities on their calendar. Boat slips currently available at Twin Creeks Marina. Complimentary boat and boat trailer storage inside the gate at the boat trailer parking areas in neighborhood as availability allows. Neighborhood managed by Ghertner. Lot owners still have full use of pools whether they have a house or not. Come dip your toe in the lake life!

Suntan Court, Winchester

$644,900
3 Beds 3 Baths 3506107 MLS ACTIVE Status 1 Acres 37398 Zip Code
Gorgeous new construction located in the desirable Whispering Pines subdivision! This home offers 3 bedrooms, 2 full baths, 1 half bath, bonus room, spaciously laid out and designed for comfortable living. The great room features a stunning double-tray vaulted ceiling. Luxury vinyl plank flooring runs throughout the home for style and durability. The kitchen comes fully equipped with stainless steel appliances, including a refrigerator. Enjoy the convenience of a 2-car garage, concrete driveway, along with durable Hardie board siding for lasting curb appeal. Unwind or entertain outdoors on the front or sprawling back covered porches. Home is conveniently located with easy access to Winchester and Tullahoma retail, grocery, entertainment, healthcare options, and only minutes from beautiful Tims Ford Lake, where boating, fishing, and recreation can be explored! All measurements are approximate and not guaranteed, if important please remeasure.

90 Pine Bluff Ct, Winchester

$510,000
4 Beds 3 Baths 3501421 MLS ACTIVE Status 0.46 Acres 37398 Zip Code
Beautifully Maintained Home With Space, Comfort, and Incredible Extras! Pride of ownership shines throughout this very-well maintain 4-bedroom, 3-bath home located in a wonderful, established neighborhood. Offering a thoughtfully designed layout with plenty of space and flexibility, this home features a main level primary suite, plus an additional upstairs primary suite/bonus room. Perfect for guests, extended family, or multi-generational living. The spacious kitchen is made for those who love to cook and entertain featuring double ovens, a large gas range, a walk-in pantry, and an abundance of cabinetry. Charming details such as a clawfoot tub add character and personality. Step outside and enjoy the screened-back patio, an ideal spot for morning coffee or relaxing evenings. Car enthusiasts, hobbyists, and RV owners will appreciate both an attached and detached garage, along with 30 and 50 amp hookups and a dedicated septic connection for a motorhome. Major improvements and thoughtful upgrades add even more value, including a new roof in 2020, Leafguard gutter system, a new hot water heater, and automatic crawl space vents. With generous living space, excellent storage, multiple garage options, RV accommodations, and so many well-planned features, this home offers the perfect combination of comfort, convenience, and versatility.

218 Charlotte Dr, Winchester

$400,000
3 Beds 2 Baths 3501390 MLS ACTIVE Status 1.45 Acres 37398 Zip Code
Welcome to 1522 Holders Cove Road, a truly unique, fully updated, single-level ranch offering a backyard paradise that embodies the American dream. Situated on nearly 1.5 private acres, this move-in-ready home offers the ideal blend of peaceful privacy and everyday convenience, located just minutes from downtown Winchester's shopping, dining, and local attractions. Inside, you will discover a thoughtful and efficient layout designed for modern living. The bright, open living area welcomes you with abundant natural light and flows seamlessly into a tastefully updated kitchen with new appliances. A dedicated home office and a separate laundry room provide a rare level of everyday functionality. The primary suite serves as a true retreat, complete with a spa-like ensuite bathroom, while two additional bedrooms and a stylish full guest bath ensure everyone has plenty of room to spread out. Step through the back door into your personal outdoor paradise. The current owners spared no expense curating a beautifully landscaped backyard experience. You can entertain guests effortlessly on the expansive patio featuring a cozy fire pit, or follow the stone footpath to the custom raised garden beds. The back yard finale is the custom water feature and pristine koi pond, complete with its own private sun deck for relaxing afternoons. Don't miss your chance to own this extraordinary property in Winchester, TN. Call today to schedule your private tour.

1522 Holders Cove Road, Winchester

$999,000
2 Beds 2 Baths 3500985 MLS ACTIVE Status 0.5700000000000001 Acres 37398 Zip Code
Experience lakefront living at its finest in this immaculate 2-bedroom, 2-bath log home nestled in a peaceful cove. Meticulously maintained and full of rustic charm, this property offers exceptional access to the water with three points of entry, including a boathouse, floating dock, and standard dock—perfect for boating, fishing, swimming, or simply enjoying the lake lifestyle. The inviting interior features warm wood finishes and a comfortable, move-in-ready layout, while the tranquil setting provides the perfect place to relax and unwind. Unfinished basement offers endless options for expansion. Whether you’re searching for a full-time residence, weekend getaway, or vacation rental opportunity, this waterfront retreat is a rare find

52 Narrows Dr, Winchester

$99,900
3336266 MLS ACTIVE Status 1.09 Acres 37398 Zip Code
Are you ready for custom country living? This beautiful 1.09-acre buildable lot offers the perfect setting to create your dream home in Winchester, Tennessee. Situated on a private road with the convenience of being close to everything the small town of Winchester has to offer, this property gives you the space, freedom, and privacy you have been looking for. Water and electricity are already available at the lot, and a percolation site approved for up to a 4-bedroom home provides the opportunity to design a home that fits your lifestyle. Build the home, create the memories, and enjoy the country lifestyle you have always envisioned. A second build-ready tract is available on a separate listing for Lot #1.

Old Tullahoma Rd, Winchester

$1,750,000
3335281 MLS ACTIVE Status 47.5 Acres 37398 Zip Code
Exceptional 47.5± acre residential development opportunity in the heart of Winchester, TN. This predominantly level, well-drained farm offers frontage on Old Estill Springs Rd., Bible Crossing Rd., and Myers Rd., providing multiple access points for a future subdivision or master-planned community. Adjacent to Winchester City Park, the property presents a rare opportunity to create a deed-restricted neighborhood with the potential for sidewalk connections to the City's walking trail system (subject to City approval). A beautiful 2.5± acre spring-fed pond provides a stunning centerpiece for community green space or premium homesites. Public sewer, water, natural gas, fiber internet, and electric are available along Sharp Springs Rd. and Myers Rd., making this one of the area's most development-ready tracts. The property includes an approximately 2,800 sq. ft. residence that could be divided off and sold separately or incorporated into the development as a clubhouse, sales center, or community amenity. Located less than one mile from a public boat ramp on Tims Ford Lake, the property offers residents convenient access to boating, fishing, and outdoor recreation. Frontage along **Bible Crossing Rd.—one of Winchester's busiest corridors—**provides excellent visibility and accessibility. Winchester (population approximately 10,400) is one of Middle Tennessee's fastest-growing lake communities, located approximately 90 minutes from Nashville, 60 minutes from Chattanooga, and 60 minutes from Huntsville, AL. The combination of strong regional growth, available utilities, outstanding topography, and an exceptional location makes this a premier residential development opportunity.

903 Old Estill Springs Rd, Winchester

$449,000
3 Beds 2 Baths 3322405 MLS ACTIVE Status 0.6900000000000001 Acres 37398 Zip Code
Brick Ranch in Prime Winchester Location! Welcome home to this 3-bedroom, 2-full-bath brick home situated on a spacious 0.7-acre lot in a quiet, established subdivision. Featuring a desirable split-bedroom floor plan, this property offers the perfect blend of privacy, comfort, and convenience. The primary bedroom is a true sanctuary, featuring 252' sq ft of space with a large walk-in closet plus a convenient second closet for ample storage. For mealtime or entertaining guests the house features a separate dining room, bar space in the kitchen and an eat-in breakfast area right in the kitchen. Sunlit Florida Room: The large Florida room offers seamless indoor-outdoor transition with direct access from both the main living room and the primary bedroom. The expansive 0.7-acre yard provides a beautiful, serene backdrop perfect for outdoor gatherings, gardening, or weekend relaxation. Enjoy peace of mind knowing the roof is only 4 years old, and the HVAC system was replaced just 6 years ago. Winchester is positioned in a highly sought-after area of Southern Middle Tennessee, and you are just minutes away from everything Winchester has to offer: Historic downtown Winchester shopping and dining; Winchester City Park; local medical facilities; pristine waters and recreation at Tims Ford Lake. This move-in-ready gem truly is a must-see to fully appreciate all of its fine details. Schedule your private tour today before it's gone! (HVAC 2020; Roof 2022)

262 Crimson Dr, Winchester

$354,900
3 Beds 2 Baths 3320086 MLS ACTIVE Status 0.928 Acres 37398 Zip Code
**Double lot with large shop** This beautiful, well-maintained brick home is convenient to everywhere - less than 1.5 miles from downtown Winchester - a mile from the Country Club -1.2 miles from the Hospital and 2 miles from Food City! It's perfectly positioned on a desirable corner lot and includes a second lot as well! Offering 3 bedrooms and 1.5 baths, this home combines timeless charm with clear pride of ownership throughout. A sizeable living room with an eat-in kitchen or separate dining area and wonderful florida room ready for entertaining. The property includes a single car attached garage and carport and a 30 x 40 detached double door garage with it's own small carport..perfect for a woodworking shop or lake toys or whatever your heart desires. Both the shop and home have metal roofs and a circular drive enters both. This well cared for home is ready for the updates you desire or could be move-ready for the young buyer!

1111 Holders Cove Rd, Winchester

$209,900
3 Beds 2 Baths 3319920 MLS ACTIVE Status 3.11 Acres 37398 Zip Code
Opportunity Awaits! Situated on 3.12± acres spanning two lots, this 3-bedroom, 2-bath home offers a peaceful setting with plenty of room to enjoy country living or create your dream property. The home is nicely positioned on the land and features a spacious yard surrounded by mature trees. A standout feature is the large detached shop, complete with electricity and water, making it ideal for storage, hobbies, a workshop, or small business use. The property is being sold As-Is, presenting an excellent opportunity for investors, renovators, or buyers looking to add their personal touch. Please use caution when viewing the front deck, as it is in need of repair. With acreage, a functional shop, and endless possibilities, this property is ready for its next owner to unlock its full potential.

145 Edgewood Ln, Winchester

$230,000
2 Beds 2 Baths 3318900 MLS ACTIVE Status 0.43 Acres 37398 Zip Code
Whether you're buying your very first home, looking to simplify life with less maintenance, or searching for the perfect vacation retreat, this charming 2-bedroom, 2-bath home checks every box. Thoughtfully designed with comfortable living spaces and a functional layout, this home offers the perfect balance of convenience and comfort. Its unbeatable location near Tims Ford Lake and Twin Creeks Marina makes it easy to spend your weekends boating, fishing, dining, or simply enjoying everything lake life has to offer. For first-time homebuyers, it's an affordable opportunity to begin building equity in a desirable location. For those ready to downsize, it provides the ease of low-maintenance living without sacrificing comfort. And for investors, its proximity to one of Middle Tennessee's most sought-after lake destinations makes it an excellent opportunity as a short-term rental or weekend getaway. Whether you're looking for a place to call home or a smart investment with year-round appeal, this property offers endless possibilities in a location you'll love.

525 Sharp Springs Rd, Winchester

$774,900
4 Beds 4 Baths 3316017 MLS ACTIVE Status 0.13 Acres 37398 Zip Code
Lake life at its finest AND offered FULLY FURNISHED, saving you time and money! This turn-key home in Twin Creeks is a MUST SEE and features upgrades galore! From the inviting stone-accented exterior and charming covered front porch to the open and thoughtfully designed interior, every detail of this home exudes quality and comfort. It is rare to find a fully "high end" furnished home with all the bells and whistles at this price. The open floor plan features a spacious living room with a coffered ceiling, a gas fireplace and built-ins. Luxury vinyl plank floors flow seamlessly throughout this home. The kitchen and dining areas feature beautiful wooden beams, granite countertops, a 4-burner gas cooktop w/griddle and stainless steel appliances, creating a perfect mix of elegance and functionality. This area is an ideal focal point for family gatherings and entertaining. Just off the kitchen, a screened porch with a gas fireplace opens to expansive outdoor living spaces featuring a built-in grill, refrigerator, and pergola-covered entertaining area. The main-level primary suite boasts a coffered ceiling and direct access to a private covered patio. Upstairs, a second primary suite with an ensuite bath is joined by two additional bedrooms, a bonus room, a third full bath, and an impressive 16' x 13' balcony. Don’t miss the chance to experience this impeccably maintained, move-in-ready, turn-key home that blends luxury, functionality, and a true sense of community. But the true magic is in the lifestyle. Enjoy days on the water boating or kayaking, evenings at the community restaurant and bar, and weekends spent at the pools, clubhouse, and social events with neighbors who soon feel like family. Whether you’re looking for a primary home or a lake getaway, this home offers the best of both worlds — comfort, community, and a life that feels like vacation every day. his home has it all!

309 Campfire Ct, Winchester

$1,150,000
2 Beds 3 Baths 3314284 MLS ACTIVE Status 0.48 Acres 37398 Zip Code
Gorgeous 5 bedroom, 3 bath lakefront living at its best on Tims Ford Lake! Just in time for lake season! Experience the ultimate waterfront lifestyle in this stunning home perfectly situated in the highly sought-after Caney Hollow. With direct lake access from your backyard and your own covered boat slip featuring both a boat lift and jet ski lift with an adjacent floating dock, this property is fully equipped and ready for long days on the water. Wake up to breathtaking lake views from the spacious primary suite with private outdoor access—perfect for morning coffee overlooking the water. Designed for both relaxation and entertaining, the home features two fireplaces, including a stunning stacked-stone fireplace on the expansive covered back porch. Multiple access points create seamless indoor-outdoor living and effortless enjoyment of the views. The finished walk-out basement adds even more living space with a full bedroom, spacious bonus area, and large utility room—ideal for guests, a game room, or multi-generational living. A spacious garage provides plenty of room for your boat and lake toys, while newly added parking offers added convenience for guests. A gently sloped stone pathway with 30 steps lead directly to your private dock & boat house, making every lake day easy and accessible. Located just minutes from marinas, dining, and Tims Ford State Park, this home offers the perfect blend of comfort, convenience, and one of Tennessee’s most sought-after lake lifestyles. All SS appliances, including the washer and dryer, remain. Bathrooms have been updated and home freshly painted! Home warranty provided!

645 Wildwood Trce, 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.