Refine Search
Sort by
$1,179,000
3 Beds ⋅ 1 Baths ⋅ 3514331 MLS ⋅ ACTIVE Status ⋅ 34 Acres ⋅ 37398 Zip Code
Charming brick home on 34+ acres in peaceful countryside, surrounded by pastureland. Combines classic brick with spacious rural living, ideal for first-time buyers. The home comes partially furnished, with a plumbed garage ready for conversion into a master suite with a full bath. This 34+ acre greenbelt is also perfect for building your dream home and shop. Located a quarter mile from Tims Ford State Park, Bear Trace Golf Course, and within 10 minutes of three marinas. Features a 3-bedroom farmhouse suitable for living or renting. This land is rolling, grass pastures, with a nine-stall pole barn, tack and washrooms, birthing stalls, lean-to, hay loft, and a four-bay gated implement shed, and stock pond. Subdivision into less than 5-acre lots isn't allowed.

5630 Mansford Rd, Winchester

$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

$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

$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

$499,900
3 Beds ⋅ 2 Baths ⋅ 3509975 MLS ⋅ ACTIVE Status ⋅ 0.6900000000000001 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

$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

$385,000
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

$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

$774,900
4 Beds ⋅ 4 Baths ⋅ 3316017 MLS ⋅ ACTIVE Status ⋅ 0.13 Acres ⋅ 37398 Zip Code
Lake life at its finest -- can be purchased FULLY FURNISHED, saving you time and money! 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 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

$1,750,000
3 Beds ⋅ 3 Baths ⋅ 3312749 MLS ⋅ ACTIVE Status ⋅ 2.46 Acres ⋅ 37356 Zip Code
Step into luxury and timeless craftsmanship in this stunning lodge-style retreat. The grand entry opens with eight-foot custom solid wood doors and rich hardwood floors leading into a spacious living space featuring wood gables and a cozy wood-burning fireplace. The chef’s kitchen boasts custom knotty alder cabinetry, a huge island, a coffee and prep station, and a high-end Bertazzoni appliance package complete with a gas cooktop and two electric ovens, perfectly complemented by unique stained glass pantry doors rescued from an Asheville church. Entertain with ease using the Thor bar appliance package featuring a dual-zone wine cooler or relax by one of the three custom wood-burning fireplaces found throughout the home. Exceptional custom details include Black Forest light fixtures, stained solid wood trim, an antique tiger wood vanity with a copper sink in the powder room, and a dedicated dog wash station. Enjoy outdoor living on the covered back porch lounge area with the opportunity to take advantage of a permit for a ten-by-ten boat dock on the 230' of waterfront. Additional highlights include stand-up fully floored attic storage and a massive fully stubbed walk-out basement ready for your personal touch that offers an additional 2,400 square feet when finished, and an underground pet containment system with two collars. Cooley's Rift neighborhood offers a gated entrance, 54-acre private lake, boathouse and waterfalls.

40 Trussell Creek Trl, Monteagle

board logo

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.