Refine Search
Sort by
$299,999
3 Beds 2 Baths 3244493 MLS ACTIVE Status 0.73 Acres 37398 Zip Code
Lake weekends, peaceful small-town living, and a fully renovated home on an acre — this Winchester property delivers a lifestyle and value that’s hard to find. Just minutes from Tims Ford Lake, you can spend your weekends boating, fishing, hiking, or relaxing by the water, then come home to a quiet cul-de-sac surrounded by mature trees and plenty of space to enjoy the outdoors. The home is completely move-in ready with spacious bedrooms, generous closets, an easy-flowing floor plan, and an oversized side-entry garage. The primary suite features a beautifully renovated shower, while extensive updates throughout the home mean the work has already been done for you. Improvements include a new roof, gutters, HVAC system, interior and exterior paint, doors, baseboards, lighting, fixtures, ceiling fans, electrical outlets, garbage disposal, and wireless smoke and carbon monoxide detectors. Enjoy morning coffee on the covered front porch, evenings around the fire pit, a freshly refinished deck, new landscaping, a large driveway, and a spacious backyard shaded by mature trees. You’re also minutes from Winchester Square, shopping, dining, schools, and medical facilities, only 5 minutes from the Nissan Powertrain Assembly Plant, near Highway 64, and within easy reach of I-24. If you’ve been looking for an updated Middle Tennessee home where you can enjoy more land, less traffic, lake days, and small-town living without sacrificing convenience, this one offers tremendous value. Preferred lender offering up to 1% lender credit toward closing costs for qualified buyers.

88 Meadow Ln, Winchester

$489,900
3 Beds 2 Baths 3243340 MLS ACTIVE Status 0.46 Acres 37398 Zip Code
Welcome to this beautiful brick home offering over 2,000 sq ft of living space in one of the most desirable setting around. This home rests on an amazing lot connecting to Tim's Ford State Park with a short hike to the lake. This property provides direct access to hiking trails and the lake, making it perfect for outdoor enthusiast who enjoy fishing, hiking or nature walks. Inside you will enjoy HW and tile flooring, elegant trim work and spacious bedrooms. A large kitchen makes entertaining and meal prep easy and the separate dining provides the perfect space for family gatherings. Next, step outside to a nice covered deck and relax in the peaceful surroundings. So whether your relaxing at home on the deck, hiking or fishing, this property is a perfect blend. Don't miss your opportunity to own this home in such a perfect setting. No dock or steps permitted. Lake access only.

647 Golf Shores Dr, Winchester

$125,000
3242352 MLS ACTIVE Status 5.05 Acres 37375 Zip Code
Great 5.05 acre Lot with 158' of road frontage making it easy to build on if you want to be nestled in the woods with a Sewanee address and off the domain. This is not a flag lot so less cost up front to build. Just one mile away from St. Andrews school and less than 5 mins from the University of the South entrance. The Deep Woods area is a fantastic location close to Monteagle or Sewanee on a quiet dead end road. Lot has had a rough drive cut in already, a soil test and a survey is available. Take the soil test to get a perc permit. Well will needed to be dug for water, no city water access. Fiber available. Power at the road. Perfect spot to build your mountain cabin, weekend getaway or forever home here on the beautiful South Cumberland Plateau. This lot has the county line running through the front part of the lot.

Deep Woods Road, Sewanee

$299,000
3 Beds 1 Baths 3234068 MLS ACTIVE Status 2.06 Acres 37306 Zip Code
MOTIVATED SELLER!!! COUNTRY LIVING CLOSE TO TOWN! Well-maintained 3-bedroom, 1-bath home situated on 2.06 acres in the beautiful Belvidere community. Enjoy the privacy of a country setting surrounded by farmland and mature shade trees, while being just 10 minutes from The Winchester Square. Features include an eat-in kitchen, large utility room, tile shower, covered porch, metal roof, city water, and central HVAC replaced in 2022. Outside you'll find attractive landscaping, two storage sheds, a barn, and a lean-to shed. Located outside the city limits this property offers the perfect combination of peaceful country living and convenient access to town amenities. This property has plenty of room for kids and pets. Very low traffic on Crawford Lane for you to ride bikes, horses, golf cart, etc safely. Other recent updates include: 2022 - New windows, 2024 - ground up bathroom renovation, 2022 - roof replacement, 2026 - new rear porch deck and covered metal roof, 2026 - fresh interior & exterior paint, 2026 - fresh gravel on driveway, 2022 - new 12x30 mini barn and new 10x20 mini barn. Original concrete block barn has electric and water with storage attic, great for farm animals or chickens.

840 Crawford Ln, Belvidere

$299,000
3232227 MLS ACTIVE Status 10.48 Acres 37375 Zip Code
AMAZING WEST FACING BLUFF VIEW!! Incredible opportunity to get 10 acres of property, with a bluff view, near the domain of The University of the South: Sewanee. Property has been perced, with multiple build sites available. Features an on site well, with electricity and high speed fiber internet at the lot line. Homesite on the bluff has been partially cleared. Property also features a creek that could be dammed up to form a small pond! Access to the interstate, as well as the Sewanee and Monteagle communities, within 15 minutes. 45 minutes from Chattanooga, and an hour and a half to Nashville. This truly is the perfect spot to feel secluded, while still having easy access to the outside world. Let your imagination run wild on this gorgeous piece of mountain land!

Claiborne View Rd, Sewanee

$299,999
3 Beds 2 Baths 3231532 MLS ACTIVE Status 37398 Zip Code
Welcome to Green River—where front porch living, walkable convenience, and small-town charm come together. Located just a half-mile from Winchester’s historic square and only 1.5 miles from Tims Ford Lake, this brand-new home offers the perfect balance of downtown accessibility and outdoor recreation. Enjoy local dining, shopping, festivals, boating, and lake days—all just minutes from your front door. This charming 3-bedroom, 2-bath cottage-style home offers low-maintenance living in one of Winchester’s most desirable walking communities. The open-concept floor plan features a spacious kitchen with a large island, modern finishes, and inviting living and dining areas perfect for everyday living and entertaining. Two bedrooms and a full bath are located on the main level, while the private primary suite occupies the entire second floor, complete with an ensuite bath and generous closet space. Enjoy relaxing on the covered front porch, entertaining on the back deck, and the convenience of a detached one-car garage. Located within walking distance of Downtown Winchester and just minutes from Tims Ford Lake, this home offers easy access to shopping, dining, recreation, and community events. Experience the perfect blend of modern comfort, convenience, and small-town charm.

99 N Shephard St, Winchester

$399,900
4 Beds 4 Baths 3229184 MLS ACTIVE Status 0.47000000000000003 Acres 37398 Zip Code
Renovations complete! Brick ranch style home with so much space! This 4 Bedroom, brick ranch style home in a great location only minutes to the winchester square! Only 15 min to I-24! This renovated 4 bedroom brick home with all of its updates is a gem! The beautiful kitchen has a country french feel with the granite and beautiful backsplash and newly updated cabinets with the finishing touch of bar seating. This well appointed home has a large living room and a florida room for large gatherings. The owner has done many well thought out upgrades and additions to the home. Huge laundry room with 1/2 bath just off of the pool side of the home so wet guests will not need to go through the house. The home has had all of the plumbing updated as well and the seller has added additional gas heating units!. The large 4th bedroom has a full bath and the second bedroom has a 1/2 bath in it as well. This cute as can be home has a salt water pool to relax in that is partially underground and has a deck alongside it for relaxing on under the cabanna. The private back yard is fully fenced with two outbuildings and lots of soft grass and a fountain along with its beautiful landscaping around the property. The ower has also had gutter guards added to keep the gutters leaf free. This home provides extra parking in the back by the carport or would make a great basket ball area for a growing family. This lovely home is just minutes to the popular Twin creeks Marina, Tims ford lake and shopping and local airport. This home is a must see! Schedule your showing today.

44 Houghton Dr, Winchester

$1,849,999
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

$375,000
3 Beds 3 Baths 3225870 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 Tims 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

$1,399,900
6 Beds 6 Baths 3221517 MLS ACTIVE Status 0.45 Acres 37398 Zip Code
A custom built home is located in prestigious Fanning Bend Subdivision. You must see this spectacular fully furnished home on Tim’s Ford Lake. Lake views from breakfast area deck & patio areas Completed in 2022, this luxury lake home features over 6100 SF, 6BR/ 5.5 BA, open floor plan w/seamless flow into Kit, LR & DR areas. LR high ceiling & rock fireplace. Large kitchen custom cabinets ice maker w/Frigidaire Gallery appliances featuring induction cooktop butlers pantry & granite counters.an off kitchen pantry to store all your goodies Primary BR suite w/vaulted ceilings, lavish yourself in the adjoining bath including soak tub, walkin granite shower & double vanity, massive walk-in closet. downstairs w/walk out patio with treated concrete & fabulous lake views. Storm shelter Bedroom 2 baths game area theater room and full kitchen with Electrolux stainless appliances blinds throughout. Home w/true double garage with treated floor. Completely furnished can include boat and golf cart. Very Important This property also features a prominent view corridor selected by the owner with HOA approval. The neighboring home to the left also would like to coordinate theirs with this property to have highest potential create your own canvas

61 Joy Cir, Winchester

$429,900
3 Beds 3 Baths 3221346 MLS ACTIVE Status 2.64 Acres 37398 Zip Code
Located near Tims Ford Lake with deeded lake access, this well-built all brick home offers privacy, space, and plenty of potential on 2.64 wooded acres. With 2,431 sq ft, the home features 3 bedrooms, 2.5 bathrooms, a sunroom, large basement, garage, and attached carport. Mature trees provide a peaceful setting with room to enjoy the outdoors while still being just minutes from Tims Ford State Park and the shopping, dining, and conveniences of Downtown Winchester. The home has been well maintained and is in great overall condition, while offering an opportunity for cosmetic updates to match today’s style and make it your own. A rare combination of space, privacy, and lake-area living in one of Middle Tennessee’s most desirable locations.

90 Owl Hollow Ln, Winchester

$745,000
3 Beds 3 Baths 3221327 MLS ACTIVE Status 0.06 Acres 37398 Zip Code
DON’T MISS THIS AMAZING OPPORTUNITY — Wake up every day to beautiful lake views from your backyard or eat-in kitchen area! This truly turnkey, move-in-ready home is the perfect fit whether you're searching for a primary residence, weekend retreat, or investment opportunity. Thoughtfully designed and meticulously maintained, this stunning home blends timeless finishes with functional upgrades throughout. Step outside and enjoy the beautifully screened-in patio, along with an additional outdoor space ideal for grilling, entertaining, or simply relaxing and taking in the lake lifestyle. The light-filled, open-concept floor plan is enhanced by abundant natural light and scenic lake views. The spacious kitchen serves as the heart of the home, featuring light-colored cabinetry, quartz countertops, a large center island, and an eat-in dining area with plenty of space for gathering with family and friends. The inviting living area showcases a beautiful gas stone fireplace, creating a warm and comfortable atmosphere year-round. The main-level primary suite offers a spacious ensuite bath with double vanities, a dedicated makeup vanity, a large walk-in closet, and abundant storage. An additional main-level bedroom provides flexibility and works perfectly as a home office or guest space. Upstairs, you'll find a third oversized bedroom, and additional extra large storage space, offering multiple options for guests, recreation, or expanded living room Additional upgrades include no carpet throughout and exceptional storage throughout. Enjoy refined, low-maintenance lake living in the highly sought-after gated Twin Creeks community, where the HOA handles lawn care so you can spend more time enjoying the lifestyle. This golf cart-friendly community makes getting around easy and enjoyable. Residents enjoy exceptional amenities including a full-service marina, clubhouse, three pools, and community fire pit plus much more,

25 Dry Fork Dr, Winchester

$285,000
3 Beds 2 Baths 3217206 MLS ACTIVE Status 0.6900000000000001 Acres 37318 Zip Code
Step back in time with this beautiful 1895 historic home in the heart of Cowan, TN, surrounded by mountain scenery and small-town charm. Within walking distance to downtown Cowan shops, restaurants, and local events, and just 10 minutes from Winchester, this home is filled with timeless character and potential. The wraparound porch, mature shade trees, spacious park-like yard, and period wrought iron fencing create incredible curb appeal. Inside, you'll find soaring ceilings, tall windows and doors, original trim and molding, stained glass accents, antique doorknobs, a charming clawfoot tub, six fireplaces, and an impressive staircase showcasing the craftsmanship of another era. Original hardwood floors are believed to be preserved beneath the carpet, ready to be restored. The home features 3 spacious upstairs bedrooms, plus an additional main-level room that could serve as a primary bedroom, guest room, or office. Two upstairs bedrooms share access to a balcony overlooking the beautiful yard and mature trees. A newer roof, HVAC system, and water heater provide peace of mind while still leaving room for your own updates and personal touch. If you love historic homes, mountain town living, and classic Southern charm, this property is one you’ll want to see in person.

103 W Cowan St, Cowan

$574,900
3217180 MLS ACTIVE Status 1.13 Acres 37398 Zip Code
Rare Lakefront Opportunity: Just Over an Acre of Private Paradise! Septic approved. TVA Section 26a dock permit application is currently in the environmental review phase. Site visit has been completed, and TVA has indicated they do not anticipate any issues. Documentation is available in MLS. Final approval remains subject to TVA review. Discover the perfect canvas for your dream lake home on this exceptional 1.13-acre lot, beautifully situated in the desirable Dripping Springs area within Dry Creek Estates. Offering the ultimate combination of convenience and serenity, this unique property places you just minutes from town, yet feels world's away nestled among majestic, old-growth hardwood trees that provide ultimate privacy. This lot stands out with highly sought-after features that are becoming increasingly rare to find together: gentle terrain: forget steep cliffs; allowing for a comfortable path directly down to the water's edge. Built-in Value: Neighborhood standards are well-established. Both neighboring properties have successfully perked for 3+ bedroom homes, and both feature private docks. Buyers have an excellent precedent to apply for their own custom TVA dock approval. Investment Potential: Located in a neighborhood that explicitly permits short-term rentals, making it a lucrative option for a luxury vacation property or a premium investment build. Opportunities with this blend of privacy, gentle lake access, rental flexibility, and proximity to town are nearly gone. Don't let this rare piece of Dry Creek Estates pass you by. Plat maps and appraisal are available upon request.

Dry Creek Lane, Winchester

$1,150,000
3 Beds 3 Baths 3216704 MLS ACTIVE Status 5.1 Acres 37356 Zip Code
Welcome to your mountain retreat in the highly sought-after Clifftops community on Monteagle Mountain. This beautifully appointed home seamlessly blends rustic charm with modern luxury and is being sold fully furnished, making it truly turnkey. The main level features a spacious primary suite, an inviting great room with stunning fireplace, dedicated office/sunroom, additional bedroom, and a full bath. Upstairs offers a cozy bunk room with five full-size mattresses, a third bedroom, and another full bath — ideal for hosting family and guests. Enjoy abundant natural light from large windows, a gorgeous rock gas fireplace, and inviting front and rear flagstone porches perfect for relaxing in the mountain air. Outdoors, you’ll find a wood burning fireplace, fire pit, and a pad ready for a future hot tub. Short-term rentals are permitted, offering investment potential. Located in Clifftops, a private 2,000-acre gated community on the South Cumberland Plateau between Nashville and Chattanooga, residents enjoy wooded landscapes, bluff views, streams, and waterfalls. Community amenities include a private lake with beach area (fish, swim, kayak, canoe), clubhouse, pool, tennis courts, brand new pickle-ball courts, scenic walking trails throughout, playground, and community garden. Conveniently situated just 1.5 hours from Nashville, 1 hour from Murfreesboro, and 1 hour from Chattanooga, and only minutes from Sewanee and The University of the South. Under contract - with a first right of refusal (Sale of home contingency)

2425 Westlake Ave, 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.