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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.

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

$649,000

New construction unfinished on 13.28+/- acres that joins TVA. Lots of detailed wood work see photos.

3 Beds ⋅ 2 Baths ⋅ 3596642 MLS ⋅ ACTIVE Status ⋅ 13.28 Acres ⋅ 37398 Zip Code

New construction unfinished on 13.28+/- acres that joins TVA. Lots of detailed wood work see photos.

432 Meadowood Lane, Winchester

$239,000

PERFECT LOCATION right in the heart of Winchester located adjacent to the new Twin Creeks subdivision. Come and experience everything Winchester has to offer! Welcome to this awesome new construction ONE LEVEL home. This residence features LVP flooring throughout, providing durability and a modern, fresh look. Large living room and combo kitchen area complete with stainless steel appliances and custom cabinets. 3 bedrooms and 2 full baths. Easy access to shopping, within walking distance to Twin Creeks Marina and downtown restaurants. Just a short drive to Sewanee or Monteagle mountain, minutes from Tims Ford Lake boat ramps and Tullahoma. Excellent area for short term rentals! Ask agent about the Builder's preferred lender incentives. Owner is Agent and related to builder.

3 Beds ⋅ 2 Baths ⋅ 3543144 MLS ⋅ ACTIVE Status ⋅ 37398 Zip Code

PERFECT LOCATION right in the heart of Winchester located adjacent to the new Twin Creeks subdivision. Come and experience everything Winchester has to offer! Welcome to this awesome new construction ONE LEVEL home. This residence features LVP flooring throughout, providing durability and a modern, fresh look. Large living room and combo kitchen area complete with stainless steel appliances and custom cabinets. 3 bedrooms and 2 full baths. Easy access to shopping, within walking distance to Twin Creeks Marina and downtown restaurants. Just a short drive to Sewanee or Monteagle mountain, minutes from Tims Ford Lake boat ramps and Tullahoma. Excellent area for short term rentals! Ask agent about the Builder's preferred lender incentives. Owner is Agent and related to builder.

602 Style St, Winchester

$350,000

Discover this inviting home on 1.28+/- acres just outside city limits, only minutes from Tims Ford Lake. Bask in natural light from the Florida Sunroom, sip coffee on the spacious front porch, and enjoy plenty of room to play in the large yard. Pecan trees, roses, Yucca plants, muscadine vine (golden and blue varieties) is mature for making wine, jams & jellies to name a few of the beautiful landscaping touches. From the tall crepe myrtles to the shady driveway this home has potential. The attached 2-car garage, plus a detached shop and carport, offers abundant space for vehicles, hobbies, storage, or a workshop. With endless potential and a peaceful, convenient location, this property is ready for your personal touch. Don’t miss this rare opportunity - schedule your showing today!

4 Beds ⋅ 3 Baths ⋅ 3510726 MLS ⋅ ACTIVE Status ⋅ 1.3 Acres ⋅ 37330 Zip Code

Discover this inviting home on 1.28+/- acres just outside city limits, only minutes from Tims Ford Lake. Bask in natural light from the Florida Sunroom, sip coffee on the spacious front porch, and enjoy plenty of room to play in the large yard. Pecan trees, roses, Yucca plants, muscadine vine (golden and blue varieties) is mature for making wine, jams & jellies to name a few of the beautiful landscaping touches. From the tall crepe myrtles to the shady driveway this home has potential. The attached 2-car garage, plus a detached shop and carport, offers abundant space for vehicles, hobbies, storage, or a workshop. With endless potential and a peaceful, convenient location, this property is ready for your personal touch. Don’t miss this rare opportunity - schedule your showing today!

312 Harris Chapel Rd, Estill Springs

$659,000

This picturesque Historic home right off the square in Winchester offers 5 bedrooms 3.5 baths and old world charm. Tons of elegant built ins, gas log FP, an amazing office, Very large bedrooms on the 1st floor, 2 car garage, and much more. This property could also be a great spot for an office or other Commercial usages

8 Beds ⋅ 4 Baths ⋅ 3508033 MLS ⋅ ACTIVE Status ⋅ 0.62 Acres ⋅ 37398 Zip Code

This picturesque Historic home right off the square in Winchester offers 5 bedrooms 3.5 baths and old world charm. Tons of elegant built ins, gas log FP, an amazing office, Very large bedrooms on the 1st floor, 2 car garage, and much more. This property could also be a great spot for an office or other Commercial usages

110 S Porter St, Winchester

$125,000

Here's your chance to grab a renovation-ready property in one of Winchester's most desirable pockets. This home is perfect for an investor or hands-on buyer looking to build sweat equity, complete with a 1-car garage and a cellar for added storage. Tucked within walking distance of historic Winchester Square and just minutes from Tims Ford Lake, it's a location that blends small-town charm with everyday convenience. Bring your vision, this one has real upside for the right buyer.

3 Beds ⋅ 1 Baths ⋅ 3506512 MLS ⋅ ACTIVE Status ⋅ 0.39 Acres ⋅ 37398 Zip Code

Here's your chance to grab a renovation-ready property in one of Winchester's most desirable pockets. This home is perfect for an investor or hands-on buyer looking to build sweat equity, complete with a 1-car garage and a cellar for added storage. Tucked within walking distance of historic Winchester Square and just minutes from Tims Ford Lake, it's a location that blends small-town charm with everyday convenience. Bring your vision, this one has real upside for the right buyer.

406 NW 2nd Ave, Winchester

$220,000

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.

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

$1,775,000

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.

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

$450,000

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)

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

$475,000

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.

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

$470,000

SELLER OFFERING OWNER FINANCING AT 5.75% — An ideal income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with flexibility for different uses. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence 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. Previously office space with a long-term tenant, 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.

5 Beds ⋅ 2 Baths ⋅ 3205990 MLS ⋅ ACTIVE Status ⋅ 0.34 Acres ⋅ 37398 Zip Code

SELLER OFFERING OWNER FINANCING AT 5.75% — An ideal income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with flexibility for different uses. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence 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. Previously office space with a long-term tenant, 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

3287 Keith Springs Mountain Rd, Belvidere

$564,900

Nestled on 5.71 private acres, this property offers endless potential for the right buyer! This home is fully livable and functioning but needs a few finishing touches. The home was in the middle of a remodel when plans changed, giving the next owner a chance to add those finishing touches and truly make it their own. This place has so much to offer: Home has new windows, new skylights and interior doors. Dual fuel HVAC, 500 gallon propane tank on property, Central Vac system, New gutters with screens, 2 wells (1 well is inactive), Pelican water filtration system and more! Crawlspace has all vents sealed off and dehumidifier that kicks on when needed. Wet weather spring on property. Too much to mention! Half bath is off garage and plumbed for vanity and toilet. Bring your ideas and turn this secluded property into something special!

4 Beds ⋅ 3 Baths ⋅ 3205583 MLS ⋅ ACTIVE Status ⋅ 5.71 Acres ⋅ 37306 Zip Code

Nestled on 5.71 private acres, this property offers endless potential for the right buyer! This home is fully livable and functioning but needs a few finishing touches. The home was in the middle of a remodel when plans changed, giving the next owner a chance to add those finishing touches and truly make it their own. This place has so much to offer: Home has new windows, new skylights and interior doors. Dual fuel HVAC, 500 gallon propane tank on property, Central Vac system, New gutters with screens, 2 wells (1 well is inactive), Pelican water filtration system and more! Crawlspace has all vents sealed off and dehumidifier that kicks on when needed. Wet weather spring on property. Too much to mention! Half bath is off garage and plumbed for vanity and toilet. Bring your ideas and turn this secluded property into something special!

3287 Keith Springs Mountain Rd, Belvidere

$79,000

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.

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

$89,000

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!

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