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369 Pickney Rd, Winchester
$599,999
3 Beds ⋅ 3 Baths ⋅ 3527291 MLS ⋅ ACTIVE Status ⋅ 0.92 Acres ⋅ 37398 Zip Code
NEW CONSTRUCTION Construction completion date Mid October 2401 SQ FT Large lot .92 +/- acres. PINCKNEY SUBDIVISION: Welcome home to this brand-new 3-bedroom, 3-bath residence offering an inviting open floor plan designed for modern living. In the desirable Pinckney subdivision, this home delivers space, light, and flexibility from the moment you walk in. The open-concept layout seamlessly connects the living, dining, and kitchen areas—perfect for everyday life and effortless entertaining. Key highlights: Brand-new construction with quality finishes throughout 3 spacious bedrooms and 3 bathrooms Bright, open floor plan that maximizes natural light and flow Taxes TBD. All info needs to be verified by Purchaser. SOME PICTURES ARE AI-enhanced

369 Pickney Rd, Winchester

Davis Ln, Cowan
$475,000
3527085 MLS ⋅ ACTIVE Status ⋅ 37318 Zip Code
Discover a one-of-a-kind mountain retreat featuring three charming tiny homes, ideally located between Nashville and Chattanooga and just 12 miles from the University of the South in Sewanee. More than a peaceful getaway, this property was created for connection, relaxation, and adventure—whether gathering with family and friends, enjoying a couples' retreat, or exploring its income-producing potential. The total square footage reflects all three 1-bedroom, 1-bath homes: Cabin 1 is a 576 sq. ft. site-built home, Cabin 2 is a 448 sq. ft. prefabricated modular cabin, and Cabin 3 is a 240 sq. ft. prefabricated modular cabin. With 3 acres zoned commercial, the property offers exciting investment and short-term rental potential. The partially furnished cabins, hot tub, infrared sauna, pavilion, two fire pits, scenic hiking trails, mountain views, and opportunities for horseback riding and ATV adventures create a distinctive guest experience with multiple ways to enjoy the property. Additional improvements include a large garage, 20' x 26' workshop, abundant parking, and no HOA. Tract 1 consists of 15.69 acres and is offered at $475,000. Tract 2 consists of 16.92 acres and may be purchased for an additional $175,000 in conjunction with Tract 1, for a combined purchase price of $650,000 and a total of 32.61 acres. Seller will consider owner financing on Tract 2 following the purchase of Tract 1. The combined acreage offers excellent potential for a private retreat, recreational property, or investment opportunity.

Davis Ln, Cowan

Davis Ln, Cowan
$475,000
3 Beds ⋅ 3 Baths ⋅ 3527090 MLS ⋅ ACTIVE Status ⋅ 15.69 Acres ⋅ 37318 Zip Code
Discover a one-of-a-kind mountain retreat featuring three charming tiny homes, ideally located between Nashville and Chattanooga and just 12 miles from the University of the South in Sewanee. More than a peaceful getaway, this property was created for connection, relaxation, and adventure—whether gathering with family and friends, enjoying a couples' retreat, or exploring its income-producing potential. The total square footage reflects all three 1-bedroom, 1-bath homes: Cabin 1 is a 576 sq. ft. site-built home, Cabin 2 is a 448 sq. ft. prefabricated modular cabin, and Cabin 3 is a 240 sq. ft. prefabricated modular cabin. With 3 acres zoned commercial, the property offers exciting investment and short-term rental potential. The partially furnished cabins, hot tub, infrared sauna, pavilion, two fire pits, scenic hiking trails, mountain views, and opportunities for horseback riding and ATV adventures create a distinctive guest experience with multiple ways to enjoy the property. Additional improvements include a large garage, 20' x 26' workshop, abundant parking, and no HOA. Tract 1 consists of 15.69 acres and is offered at $475,000. Tract 2 consists of 16.92 acres and may be purchased for an additional $175,000 in conjunction with Tract 1, for a combined purchase price of $650,000 and a total of 32.61 acres. Seller will consider owner financing on Tract 2 following the purchase of Tract 1. The combined acreage offers excellent potential for a private retreat, recreational property, or investment opportunity.

Davis Ln, Cowan

Leatherwood Dr, Winchester
$1,999,000
3 Beds ⋅ 5 Baths ⋅ 3526330 MLS ⋅ ACTIVE Status ⋅ 0.5 Acres ⋅ 37398 Zip Code
Welcome to lake living at its finest! This beautiful, spacious lakefront home offers the perfect combination of comfort, style, and waterfront living. Situated right on the lake with a dock included, the property features an easy, gently sloping walk to the water—perfect for boating, fishing, swimming, and enjoying everything the lake has to offer. The home showcases board-and-batten painted siding, wood porch ceilings, Trex decking, and a stunning stone fireplace. Inside, you’ll find quality finishes throughout, including quartz countertops, LVP flooring, and beautifully finished tile showers. The walkout basement provides additional living and entertaining space while offering convenient access to the backyard and lake. Get it under contract early enough and there may still be an opportunity to negotiate select customizations and finishes, giving the buyer a chance to add their own personal touch before completion. Whether you’re looking for a full-time residence, vacation getaway, or investment property with excellent Airbnb potential, this home checks all the boxes. Enjoy mornings on the porch, evenings by the fireplace, and days on the water—all just steps from your back door. Lakefront living, a dock, beautiful finishes, customization opportunities, and an easy walk to the water make this one you won’t want to miss!

Leatherwood Dr, Winchester

River Watch Way, Winchester
$74,900
3518840 MLS ⋅ ACTIVE Status ⋅ 0.39 Acres ⋅ 37398 Zip Code
Highly Motivated Seller! An extraordinary opportunity awaits at 0 River Watch Way! Nestled in a peaceful, secluded section of the prestigious Twin Creeks community, this prime, level building lot offers the ideal canvas to bring your custom lakeside vision to life. With Tims Ford Lake just steps down the street, you can effortlessly embrace the ultimate resort-style lifestyle every single day. Twin Creeks is renowned as one of Tims Ford Lake’s premier master-planned communities, offering an unparalleled lineup of world-class amenities right at your fingertips: *Resort-Style Amenities: Relax and unwind at the community clubhouse, sparkling pool, cozy fire pit, or the spacious pavilion with seating—perfect for gathering with neighbors and friends. *Lakeside Entertainment: Take advantage of the dedicated special events area featuring sweeping lake views, ideal for hosting unforgettable occasions. *Full-Service Marina & Dining: Enjoy direct access to the full-service marina, boat slip rentals, a boat storage lot, and delicious dining at the waterfront restaurant. *Outdoor Recreation & Guest Accommodations: Explore scenic walking trails, utilize the nearby RV campground, or host visiting family in the six luxury guest rental cottages. Whether you are looking to build a full-time residence or a peaceful weekend retreat, Lot 183 offers privacy, convenience, and vibrant community living all in one package. Don’t miss your chance to secure your piece of paradise on Tims Ford Lake—schedule your visit today!

River Watch Way, Winchester

161 Kentucky Ave, Sewanee
$625,000
3 Beds ⋅ 3 Baths ⋅ 3516600 MLS ⋅ ACTIVE Status ⋅ 0.84 Acres ⋅ 37375 Zip Code
MOTIVATED SELLER! Prime Sewanee Property with Income Potential Nestled directly on the historic campus of the University of the South, this meticulously maintained brick home offers an unbeatable location within easy walking distance to the School of Theology, central campus, and downtown. Combining classic charm with incredible versatility, this property is ideal for an owner-occupant, investor, or campus faculty member. The main residence has 3 Bedrooms, 2 Bathrooms: Features timeless interior finishes with all-hardwood, tile, or brick flooring throughout—no carpet. Kitchen appliances updated within the past year. Includes a large, versatile shop space that can easily be transformed into a spacious second master suite or expanded living area. Outdoor Amenities: A paved circle driveway welcomes you home, complemented by two storage sheds and a small greenhouse for gardening enthusiasts. Income-Producing Apartment is fully equipped with its own separate entrance and private porch. 1 Bedroom, 1 Bathroom: Features an open-concept full kitchen and living area, offering comfortable and private living space for tenants or guests. Complete with a new washer and dryer set installed last year. This lease is located in the Sewanee Village Planning Zone. https://new.sewanee.edu/files/resources/updated-sewanee-village-implementation-plan-packet.pdf

161 Kentucky Ave, Sewanee

27 Shady Cove Ln, Winchester
$768,500
3 Beds ⋅ 2 Baths ⋅ 3516336 MLS ⋅ ACTIVE Status ⋅ 0.51 Acres ⋅ 37398 Zip Code
Enjoy beautiful Tims Ford Lake views from this exceptionally maintained 3-bedroom, 2-bath home in the desirable Hopkins Point community. Built in 2023, this thoughtfully designed home combines high-end finishes with an open, single-level floor plan ideal for everyday living and entertaining. The spacious living area features a vaulted ceiling, fireplace, and large windows that bring in natural light while showcasing the surrounding scenery. The kitchen offers abundant cabinetry, a large island, gas cooking, pantry, and an open connection to the dining and living areas. The primary suite includes a walk-in closet and private bath with double vanities and a tiled walk-in shower. Two additional bedrooms provide plenty of room for family, guests, or a home office. Step outside to the expansive covered deck and take in the lake views while relaxing or entertaining. The architectural design and construction of the home were planned to accommodate the future addition of a walkout basement, offering an opportunity to expand the living space if desired. Additional features include finished wood and tile flooring, a utility room, an attached 2-car garage, concrete driveway, and a beautifully maintained 0.51-acre lot. Hopkins Point residents have access to the community boat ramp and designated parking area, making it easy to enjoy boating, fishing, and everything Tims Ford Lake has to offer. Move-in ready and designed for lake-area living, this home is one you will not want to miss.

27 Shady Cove Ln, Winchester

136 Bay Cove Trl, Winchester
$1,499,000
4 Beds ⋅ 4 Baths ⋅ 3515094 MLS ⋅ ACTIVE Status ⋅ 0.4 Acres ⋅ 37398 Zip Code
Welcome to this beautiful custom-built lake home in Fanning Bend, lovingly maintained by its one and only owner. Thoughtfully designed with a spacious floor plan and an easy, natural flow between the living room, kitchen, and sunroom, this home is perfect for both everyday living and entertaining. The main level features two spacious ensuite bedrooms, offering comfort and privacy for family and guests. It also has a dedicated office/study. Enjoy peaceful lake views from the screened-in porch, the perfect spot to relax and take in the scenery. The finished basement provides even more living and entertaining space with a large recreation room and kitchenette. A spacious heated and cooled garage/utility area offers incredible flexibility for storage, hobbies, or additional workspace. Additional bonus space includes a golf simulator area and storm shelter, making this home truly exceptional and versatile. The sellers have recently added a retaining wall and leveled the backyard, creating an inviting outdoor area to enjoy and take advantage of the lake setting. With its thoughtful design, abundant finished space, lake views, and impressive amenities, this custom-built home offers the perfect combination of comfort, functionality, and relaxed lake living. A rare opportunity to own a truly special home! House has a deeded dock slip with lift as well as a whole house water filtration system, tankless water heater, pet washing station, irrigation system and all basement area is heated and cooled. Fanning Bend also has a beautiful Clubhouse and swimming pool. See attached 3D tour: https://www.zillow.com/view-imx/00795dbd-c812-4ea1-861e-8409087d19db?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard

136 Bay Cove Trl, Winchester

Deep Woods Road, Sewanee
$175,000
3512665 MLS ⋅ ACTIVE Status ⋅ 7.57 Acres ⋅ 37375 Zip Code
Check out this private and tranquil 7.57 acre lot. The road is cut in and bordered by two lots. The property opens up to the buildable areas. There could be many buildable sites. It's very secluded with many deer roaming. Imagine sitting on your porch and taking in the wildlife. You have the feeling of being out and away but yet Hwy 41-A and I- 24 is so close. Chattanooga/Nashville/Huntsville all within an hour, 2 plus. St. Andrews Sewanee School, The University of the South just within 5/10 minutes. There is so much the South Cumberland Plateau has to offer. Please come and enjoy the living dream. There is an option to buy into the HOA at Cooleys Rift to enjoy the beautiful lake and all the amenities.

Deep Woods Road, Sewanee

105 Wilson St, Cowan
$449,900
4 Beds ⋅ 3 Baths ⋅ 3510860 MLS ⋅ ACTIVE Status ⋅ 0.26 Acres ⋅ 37318 Zip Code
Charm, character, and craftsmanship all under one roof! This distinctive 4-bedroom, 2.5-bath home offers over 2,300 sq. ft. of thoughtfully designed living space with details you simply don’t find in every home. Beautiful hardwood floors, abundant natural light, custom woodwork, and built-ins create warmth and character throughout. The spacious kitchen features generous cabinetry, an island, and plenty of room for gathering. Flexible living spaces offer options for a home office, guest space, or everyday living, while the updated primary bath adds both style and function. One of the property’s standout features is the approximately 600 sq. ft. screened pavilion - an incredible extension of the home for morning coffee, outdoor dining, entertaining friends, or game days. Established landscaping and mature trees complete the setting. Conveniently located in Cowan, approximately 10 minutes from Sewanee’s central campus and 15 minutes from Winchester, with easy access to dining, shopping, Tims Ford Lake, and everything the mountain area has to offer. A wonderful option for a full-time residence, second home, or weekend retreat.

105 Wilson St, Cowan

77 Kentucky Ave, Sewanee
$499,900
3 Beds ⋅ 2 Baths ⋅ 3509975 MLS ⋅ ACTIVE Status ⋅ 0.69 Acres ⋅ 37375 Zip Code
Nestled directly within the iconic grounds of the University of the South, 77 Kentucky Ave offers a rare opportunity to own a piece of Sewanee’s storied landscape. This classic brick ranch combines the ease of single-level living with the unmatched prestige of a campus location, making it a standout find for those who value both tradition and versatility. The main residence spans 1,400 square feet, featuring three comfortable bedrooms and two full bathrooms. Windows invite an abundance of natural light into the living spaces, creating an atmosphere that is both bright and grounded. Outside, the expansive yard provides a lush, open canvas for gardening or hosting gatherings. The true jewel of this property is the detached 660-square-foot guesthouse. Complete with its own full kitchenette and a full bathroom, this secondary dwelling is a flexible space that’s hard to find. Whether you envision it as a sophisticated home office, a creative studio, or a private retreat for visitors, it adds incredible value and functionality to the estate. Living on the mountain means being part of a unique, vibrant community where world-class lectures, scenic trails, and collegiate charm are just beyond your doorstep. Properties on the University leasehold are a rarity; 77 Kentucky Ave is your chance to step into the heart of it all.

77 Kentucky Ave, Sewanee

218 Charlotte Dr, Winchester
$488,000
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

1522 Holders Cove Road, Winchester
$350,000
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 new roof installed in 2025 and 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

52 Narrows Dr, Winchester
$999,000
2 Beds ⋅ 2 Baths ⋅ 3500985 MLS ⋅ ACTIVE Status ⋅ 0.57 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

1111 Holders Cove Rd, 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

145 Edgewood Ln, 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

309 Campfire Ct, Winchester
$749,900
4 Beds ⋅ 4 Baths ⋅ 3316017 MLS ⋅ ACTIVE Status ⋅ 0.13 Acres ⋅ 37398 Zip Code
Lake life at its finest -- This beautiful 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 "high end" home with all the bells and whistles at this price. The open floor plan features a spacious living room with a coffered ceiling, built-in cabinetry and a gas fireplace. Luxury vinyl plank floors flow seamlessly throughout this home; no carpet! The kitchen and dining areas offer beautiful wooden beams, granite countertops, stainless steel appliances including a 4-burner gas cooktop w/griddle; creating a perfect mix of elegance and functionality. The kitchen and dining areas are an ideal focal point for family gatherings and entertaining. Just off the kitchen, a screened porch with 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 home that blends luxury, functionality, and a true sense of community. But the true magic is in the lifestyle. Enjoy summer 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 all worlds — comfort, community, and a life that feels like vacation every day. This home has it all! To save you lots of time and money, this home may be purchased FULLY FURNISHED for an additional $25K.

309 Campfire Ct, Winchester

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