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109 Overhead Bridge Rd, Hampshire

Main House used as short term rental w/2 Bedrooms (3 actual Beds) + Caretaker's House w/ 1 Bedroom + Second Story Suite in Event Hall Building with 1 Bedroom. A wonderful opportunity to own 16 acres of rolling Tennessee countryside with two residences, expansive entertaining spaces, and an established winery and vineyard! Situated along the scenic Natchez Trace corridor, Natchez Hills Vineyard & Winery offers a unique combination of private country living, recreational opportunities, and income-producing potential. The property features a recently renovated 1,340-square-foot cottage, ideal as a primary residence, private retreat, or short-term rental. A separate 692-square-foot caretaker's house provides additional accommodations for guests, extended family, or on-site property management. Surrounded by picturesque countryside and an established vineyard, the setting offers privacy, natural beauty, and room to create a truly one-of-a-kind estate. Beyond the residences, the property offers an impressive collection of improvements designed for entertaining, hospitality, and agricultural use. A 4,832-square-foot event venue features a stage, bar, commercial kitchen, and former recording studio that could serve as additional overnight flex space with a full bathroom. Outdoor gathering areas provide beautiful views of the surrounding landscape, while a 728-square-foot maintenance shed offers additional storage and utility space. Also included is a fully equipped 6,050-square-foot winery production facility and tasting room, complete with wine production equipment and an established vineyard. With two residences, substantial existing infrastructure, ample parking, and versatile improvements across 16 acres, the possibilities extend far beyond a traditional residential property. Please do not visit the property without an agent.

2 Beds ⋅ 2 Baths ⋅ 3620479 MLS ⋅ ACTIVE Status ⋅ 16.35 Acres ⋅ 38461 Zip Code

Main House used as short term rental w/2 Bedrooms (3 actual Beds) + Caretaker's House w/ 1 Bedroom + Second Story Suite in Event Hall Building with 1 Bedroom. A wonderful opportunity to own 16 acres of rolling Tennessee countryside with two residences, expansive entertaining spaces, and an established winery and vineyard! Situated along the scenic Natchez Trace corridor, Natchez Hills Vineyard & Winery offers a unique combination of private country living, recreational opportunities, and income-producing potential. The property features a recently renovated 1,340-square-foot cottage, ideal as a primary residence, private retreat, or short-term rental. A separate 692-square-foot caretaker's house provides additional accommodations for guests, extended family, or on-site property management. Surrounded by picturesque countryside and an established vineyard, the setting offers privacy, natural beauty, and room to create a truly one-of-a-kind estate. Beyond the residences, the property offers an impressive collection of improvements designed for entertaining, hospitality, and agricultural use. A 4,832-square-foot event venue features a stage, bar, commercial kitchen, and former recording studio that could serve as additional overnight flex space with a full bathroom. Outdoor gathering areas provide beautiful views of the surrounding landscape, while a 728-square-foot maintenance shed offers additional storage and utility space. Also included is a fully equipped 6,050-square-foot winery production facility and tasting room, complete with wine production equipment and an established vineyard. With two residences, substantial existing infrastructure, ample parking, and versatile improvements across 16 acres, the possibilities extend far beyond a traditional residential property. Please do not visit the property without an agent.

109 Overhead Bridge Rd, Hampshire

4854 Dry Fork Rd, Hampshire

Escape to the rolling Hampshire countryside in this beautifully updated ranch home set on a picturesque 0.65-acre lot framed by mature trees. Perfect as a primary residence, artist’s retreat, or peaceful weekend getaway, this home offers modern convenience blended with scenic country living. The interior showcases fresh paint, refinished original hardwoods, new luxury vinyl plank (LVP) flooring, and charming tongue-and-groove accents. The updated kitchen features new cabinetry, butcher block countertops and SMART appliances—all of which remain, along with the washer and dryer and a NEST thermostat. Additional highlights include newer replacement windows, an attached storage room for tools and gear, and scenic countryside views. Enjoy the tranquility of rural life with easy access to the Natchez Trace Parkway and a convenient commute to both Columbia and Hohenwald. Move-in ready and full of charm!

2 Beds ⋅ 1 Baths ⋅ 3526008 MLS ⋅ ACTIVE Status ⋅ 0.65 Acres ⋅ 38461 Zip Code

Escape to the rolling Hampshire countryside in this beautifully updated ranch home set on a picturesque 0.65-acre lot framed by mature trees. Perfect as a primary residence, artist’s retreat, or peaceful weekend getaway, this home offers modern convenience blended with scenic country living. The interior showcases fresh paint, refinished original hardwoods, new luxury vinyl plank (LVP) flooring, and charming tongue-and-groove accents. The updated kitchen features new cabinetry, butcher block countertops and SMART appliances—all of which remain, along with the washer and dryer and a NEST thermostat. Additional highlights include newer replacement windows, an attached storage room for tools and gear, and scenic countryside views. Enjoy the tranquility of rural life with easy access to the Natchez Trace Parkway and a convenient commute to both Columbia and Hohenwald. Move-in ready and full of charm!

4854 Dry Fork Rd, Hampshire

3838 Old State Rd, Hampshire

Turnkey, Fully Furnished Tennessee Retreat with Proven Vacation Rental History! Welcome to Hampshire Estate – Songwriter's Escape, a beautifully maintained and highly rated retreat nestled in the peaceful countryside of Hampshire, Tennessee. With 10/10 Exceptional guest reviews, this fully furnished property offers a rare opportunity to own a move-in-ready home, private getaway, or established income-producing investment. The home features 2 spacious bedrooms, 3 full bathrooms, and accommodations for up to 8 guests. Every detail has been thoughtfully curated to create a warm, inviting atmosphere where family and friends can relax and reconnect. Step outside to enjoy the expansive outdoor living space featuring a private hot tub, scenic countryside and mountain views, and plenty of room to unwind under the Tennessee sky. The fully equipped kitchen, central HVAC, washer & dryer and ample parking, make this property as practical as it is charming. Located just a short drive from some of Middle Tennessee's favorite destinations, you'll enjoy convenient access to Natchez Hills Vineyard, Amber Falls Winery & Cellars, Keg Springs Winery, and downtown Nashville, making this an ideal location for both personal enjoyment and guest appeal. Property Highlights: Spacious deck and outdoor entertaining area All furnishings included with the sale! Fully equipped kitchen Central heating and air Ample parking Whether you're looking for a peaceful full-time residence, a weekend retreat, or a turnkey investment property with an established reputation, Hampshire Estate offers the perfect blend of comfort, convenience, and Tennessee charm. Simply bring your suitcase—everything else is already here!

2 Beds ⋅ 3 Baths ⋅ 3311659 MLS ⋅ ACTIVE Status ⋅ 3.01 Acres ⋅ 38461 Zip Code

Turnkey, Fully Furnished Tennessee Retreat with Proven Vacation Rental History! Welcome to Hampshire Estate – Songwriter's Escape, a beautifully maintained and highly rated retreat nestled in the peaceful countryside of Hampshire, Tennessee. With 10/10 Exceptional guest reviews, this fully furnished property offers a rare opportunity to own a move-in-ready home, private getaway, or established income-producing investment. The home features 2 spacious bedrooms, 3 full bathrooms, and accommodations for up to 8 guests. Every detail has been thoughtfully curated to create a warm, inviting atmosphere where family and friends can relax and reconnect. Step outside to enjoy the expansive outdoor living space featuring a private hot tub, scenic countryside and mountain views, and plenty of room to unwind under the Tennessee sky. The fully equipped kitchen, central HVAC, washer & dryer and ample parking, make this property as practical as it is charming. Located just a short drive from some of Middle Tennessee's favorite destinations, you'll enjoy convenient access to Natchez Hills Vineyard, Amber Falls Winery & Cellars, Keg Springs Winery, and downtown Nashville, making this an ideal location for both personal enjoyment and guest appeal. Property Highlights: Spacious deck and outdoor entertaining area All furnishings included with the sale! Fully equipped kitchen Central heating and air Ample parking Whether you're looking for a peaceful full-time residence, a weekend retreat, or a turnkey investment property with an established reputation, Hampshire Estate offers the perfect blend of comfort, convenience, and Tennessee charm. Simply bring your suitcase—everything else is already here!

3838 Old State Rd, Hampshire

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.

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