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$399,500
3 Beds 3 Baths 3080607 MLS ACTIVE Status 0.76 Acres 37330 Zip Code
Nestled in desirable Estill Springs, 188 Trotters Circle offers space, functionality, and scenic beauty in one impressive package. This two-story home features 3 bedrooms, 3 bathrooms, and 2,697 sq ft., along with a garage, a double carport plus a single carport, and a 14x24 workshop ideal for storage or hobbies. 1339 square feet of partially finished basement with work area and garage space. Enjoy peaceful surroundings and beautiful views at Tims Ford Lake and a boat launch less than half a mile away, making this property perfect for those seeking both comfort and lifestyle. Located just minutes from the water, this home blends practicality with the charm of lakeside living in Estill Springs.

188 Trotters Cir, Estill Springs

$274,900
3078781 MLS ACTIVE Status 11.77 Acres 37330 Zip Code
NEW PRICE! Incredible value for turnkey acreage near Tims Ford Lake! This 11.77-acre unrestricted tract is minutes from the Pleasant Grove boat ramp and is shovel-ready. Much of the land has already been cleared, a gravel road and septic have been installed, and water has been run to the lot. Gas and utilities are available at the road, and there are no city taxes. Perfect for a home with acreage, a mini farm, small development, RV park, or weekend getaway — the groundwork has already been done, saving time and expense. Easy access to Winchester, Tullahoma, and Lynchburg. Bring your plans and imagination — the potential here is endless. Property located across the street from 7318 Old Tullahoma Rd Estill Springs.

Old Tullahoma Rd, Estill Springs

$464,900
4 Beds 2 Baths 3058511 MLS ACTIVE Status 1.3860000000000001 Acres 37398 Zip Code
Discover this beautiful home featuring custom-built cabinets, granite countertops, spacious walk-in closets, a welcoming covered front porch, and a back deck perfect for relaxing or entertaining. Sitting on 1.386 acres, the property boasts a huge, flat, and cleared backyard—ideal for kids, pets, and outdoor activities. Located in a peaceful and desirable new neighborhood, this home offers flexibility with a 4th bedroom that can easily serve as a bonus room, office, or playroom. You’ll love the convenience of being perfectly positioned between Winchester and Lynchburg—just about a mile from Tim's Ford Lake and 12 miles from Jack Daniel’s Distillery. Schedule your private tour today!

188 Wiseman Ln, Winchester

$1,500,000
3056561 MLS ACTIVE Status 19.58 Acres 37398 Zip Code
Prime Residential Development Tract – Inside the City Limits of Winchester. This exceptional 19.5± acre development tract presents a rare, in-town opportunity for residential builders and developers seeking scale, location, and long-term upside. The property is strategically located behind Watson North Funeral Home and directly adjacent to the established lakefront community of Winchester Village, placing it in one of Winchester’s most desirable growth corridors. With gently rolling topography, wide open pastureland, and excellent natural drainage, the tract offers multiple efficient layout options for single-family homes, cottage-style development, or low-density luxury residences. The property’s size and shape allow for creative subdivision design, including interior streets, green space, and potential home sites with lake proximity. Key Development Advantages: (1) Inside city limits – access to municipal utilities and services (2) Immediate proximity to established neighborhoods – minimizes entitlement resistance (3) Adjacent to Winchester Village – proven demand for nearby residential housing, (4) Minutes from downtown Winchester & Tim’s Ford Lake – ideal for full-time residents or second-home buyers. (5) Nearly 20 acres of contiguous, buildable land – rare at this scale in-town, (6) Multiple access points & road frontage potential for phased development. Opportunities like this—large, buildable acreage inside the city limits and adjacent to a successful lakefront community—are becoming increasingly scarce. This tract offers the perfect blend of location, scale, infrastructure access, and long-term investment security.

405 Sharp Springs Rd, Winchester

$264,900
2 Beds 1 Baths 3049262 MLS ACTIVE Status 1.7000000000000002 Acres 37330 Zip Code
The foundation is complete and the home is ready to be framed, with full construction to continue once an agreement is accepted, allowing buyers to select finishes and even modify floor plans to suit their needs. On almost two acres you could have a brand new, customizable open floor plan home. Located in the desirable area near Tims Ford Lake. Imagine this being your primary home, second home or even an investment property to store your boat and toys. There is space for a detached building, large fire pit and even a pool. Standard features include luxury vinyl plank flooring throughout, granite countertops, soft-close drawers, custom tile shower and fans in all the bedrooms. Enjoy the advantages of an energy efficient new construction. Financing available. Note: Completed photos are for reference only and do not depict the actual home. Final details subject to change based on buyer selections.

Pleasant Grove Road, Estill Springs

$79,900
3042947 MLS ACTIVE Status 0.146 Acres 37398 Zip Code
Motivated Sellers! All reasonable offers considered. Come enjoy all the amenities this Summer ! And the 4th of July fireworks - at Twin Creeks Marina. This level lot is ready for your dream home! Bring the house plans. (The lot next door *364, MLS * is also for sale so you could build on both lots. Located in family-friendly, gated lakeside community, Twin Creeks offers everything you need for year-round living or the perfect summer getaway. Community Highlights: -Spacious clubhouse and three pools (including one heated pool) -Poolside putting green, walking trails, pavilion, and event venue -Summer concerts at the amphitheater -City sewer, high speed fiber internet and underground utilities -Easy golf cart access to everything- marina, cabins, campground The lakeside area features a restaurant, full service marina, general store and boat ramp, making life easy and enjoyable. HOA includes mowing and access to all community amenities. Build your dream home and relax where everyday feels like a vacation.

River Watch Way, Winchester

$79,900
3042948 MLS ACTIVE Status 0.146 Acres 37398 Zip Code
Motivated Sellers! All reasonable offers considered. Come enjoy this Summer ! Get access to all the amenities and enjoy your weekends at the lake This level lot is ready for your dream home! Bring the house plans. (The lot next door *365, MLS * is also for sale so you could build on both lots. Located in family-friendly, gated lakeside community, Twin Creeks offers everything you need for year-round living or the perfect summer getaway. Community Highlights: -Spacious clubhouse and three pools (including one heated pool) -Poolside putting green, walking trails, pavilion, and event venue -Summer concerts at the amphitheater -City sewer, high speed fiber internet and underground utilities -Easy golf cart access to everything- marina, cabins, campground The lakeside area features a restaurant, full service marina, general store and boat ramp, making life easy and enjoyable. HOA includes mowing and access to all community amenities. Build your dream home and relax where everyday feels like a vacation.

River Watch Way, Winchester

$307,900
3 Beds 2 Baths 3042038 MLS ACTIVE Status 37398 Zip Code
Welcome home to “A Whiter Shade of Pale,” a home that beautifully blends classic character with modern comfort. Perfectly situated within walking distance of downtown Winchester and just 1.5 miles from stunning Tims Ford Lake, this home offers the best of small-town living and outdoor adventure. Step inside to discover an inviting open-concept main level designed for both everyday living and entertaining. The chef’s kitchen features a spacious island, sleek finishes, and plenty of room to gather with friends and family. Two generous bedrooms and a full bath complete the first floor, offering comfort and convenience for guests or family. Upstairs, your private primary suite awaits—a peaceful retreat occupying the entire second level. Enjoy your own en suite bathroom and plenty of space to unwind at the end of the day. Outside, choose your favorite spot to relax: the welcoming front porch, perfect for morning coffee, or the back deck, ideal for evening get-togethers. A detached one-car garage provides extra storage or secure parking.

103 N Shephard St, Winchester

$146,000
3039225 MLS ACTIVE Status 0.5 Acres 37398 Zip Code
*MOTIVATED SELLER* Experience lake living at its finest on this spacious 0.5-acre corner lot in the prestigious Twin Creeks Village of Winchester, TN. Backing up to a lush tree line, Lot 531 offers privacy and flexibility with its generous size. Located within a gated community that leaves nothing to be desired, you’ll enjoy underground utilities, city sewer, and high-speed internet. Neighborhood amenities include a full service marina, boat slip rentals, boat storage lot, clubhouse, on-site restaurant and bar, fire pit, as well as walking trails and golf cart paths that connect you to all the community’s highlights. Spend your days at the pools, work on your short game at the putting green, and enjoy year-round entertainment at the community venues. Guests can even stay nearby at the Twin Creeks RV Resort or rental cottages! The HOA maintains lawn and pool care, so you can relax and fully embrace the Tims Ford Lake lifestyle, where every day feels like a vacation.

River Watch Way, Winchester

$230,000
3033545 MLS ACTIVE Status 0.25 Acres 37398 Zip Code
LAKE VIEW LOT with water access! Don’t miss this highly sought-after lake view lot in the Twin Creeks Development. This is an excellent opportunity to build your dream home in a resort-style, golf cart friendly community. This lot is just a short ride to the marina, beach, hiking trails, fishing ponds, cabins, and campground. HOA includes mowing, access to 3 swimming pools, and use of the clubhouse. THE PROPERTY OFFERS access to the water across TVA land — spend the day walking straight out from your back yard to the water and enjoy kayaking, canoeing, or fishing right at your doorstep. One of the last available lots on this desirable street. Picture your mornings waking up to peaceful lake views, and your evenings on the back porch with a fire, hot cocoa in hand, watching the sun set over the water. Come live the Twin Creeks lifestyle.

W Kayak Way, Winchester

$1,538,000
4 Beds 3 Baths 3032681 MLS ACTIVE Status 4.28 Acres 37356 Zip Code
Two of a kind with this brand new home and its sister home down the wooded road. Both homes are loaded with amenities, cathedral ceilings, open floor plan, the utmost in quality construction, detail, and character. Private settings with cozy, inviting porches with stone fireplaces and eze-breeze custom windows for the screened porch feel when the weather calls for it. Central vacuuming systems, Fireplaces in the main houses are Monteagle stone, and kiln dried, 2x6 hardwoods throughout. Kitchens include six burner gas stoves with double ovens, and wine fridges. All utilities are underground. Andersen windows, custom blinds, LP Techshield radiant barrier. Primary bedroom on first floor, two car garage, tankless water heaters with pumps. Heavily wooded lots with outdoor gathering areas.

1863 Lake Louisa Loop, Monteagle

$329,900
2 Beds 2 Baths 3015718 MLS ACTIVE Status 1.4 Acres 37306 Zip Code
Dreaming of getting away to a Country Lifestyle? On 1.4 +/- of an acre corner lot surrounded by trees and farms... this 2 BDR, 2 Bath house features a large Den with side entry, Living Room/Dining Area with propane rock Fireplace. Huge Den could be used as a 3rd BDR, if needed. If you like the outdoors... there's a large, covered front and back porch, a deck with Privacy Fencing around a 32’ AG Pool with a Gazebo, a detached 2 car garage with a huge storage room, a detached 1 car garage is great for a workshop, and a Huge 24 x 50 Drive-thru SHOP with 4 Bay doors for easy storage of trailers, boats, etc. with Tims Ford Dam just minutes down the road. The backyard offers privacy. Large utility room. Selling AS IS with right to inspect.

26 Water Cure Rd, Belvidere

$225,000
3014968 MLS ACTIVE Status 3 Acres 37398 Zip Code
Discover the perfect blend of convenience and freedom with this rare 3-acre parcel inside Winchester city limits. If you’ve been searching for a few acres to build your dream home—just minutes from downtown—this one checks every box. Located just beyond a neatly maintained grass-lined fence row at the edge of Winchester Village Phase II, the property offers the benefits of subdivision proximity without the restrictions. You’ll enjoy easy access, a flat and build-ready landscape, and beautiful natural surroundings that include mature trees and a bamboo-lined border offering privacy and charm. With city utilities nearby, this land is unrestricted except for standard city requirements, allowing flexibility for a custom home, barndominium, or peaceful retreat. The location provides that tucked-away feel while remaining close to schools, shopping, dining, and Tim’s Ford Lake. Opportunities like this don’t come around often—unrestricted land within the city limits is a true find. Whether you’re ready to break ground or planning for the future, this property is ready to make your dream home a reality.

Spring Hill Dr Off, 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

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