Refine Search
Sort by
539 Strawberry Dr, Winchester
$379,000
3 Beds ⋅ 2 Baths ⋅ 3546456 MLS ⋅ ACTIVE Status ⋅ 0.29 Acres ⋅ 37398 Zip Code
Welcome home to this impeccably maintained home! This home offers so much...Thoughtfully designed open-concept living and kitchen area with a desirable split-bedroom floor plan, beautiful kitchen with Custom cabinets, built in pantry with pull out drawers, large seamless island, stainless steel appliances and more! Attached garage is heated and cooled. Detached garage measures 16x16 with concrete drive. Screened in back deck with gorgeous mountain views, large outside patio area perfect for entertaining complete with a hot tub which conveys! Fenced in back yard and underneath the deck has been closed in offering even more storage! And this gorgeous yard is STUNNING! Beautifully landscaped and planed with Zoysia grass complete with irrigation system. YOU DO NOT WANT TO MISS THIS ONE!! Items to convey with buyer: Hot tub, patio furniture, back porch cabinet with TV and Bose home theater system, washer and dryer, all kitchen appliances.

539 Strawberry Dr, Winchester

72 Driftwood Ct, Winchester
$744,900
4 Beds ⋅ 4 Baths ⋅ 3546298 MLS ⋅ ACTIVE Status ⋅ 0.18 Acres ⋅ 37398 Zip Code
Lake living meets a layout you’ll love in Twin Creeks Village! This 4-bedroom, 4-full-bath home offers space to gather and room to retreat, with two bedrooms and two full baths on each level. The main-level primary bedroom provides everyday convenience, while the open living room, dining area, and large, open kitchen with abundant cabinets and an island create a welcoming space for entertaining or simply enjoying time together. Off one of the upstairs bedrooms is another heated/cooled space measuring approximately 14'x9'; ideal for conditioned storage, music or hobby room, or whatever you may need! The huge screened porch is a standout, featuring a gas fireplace and plenty of room for dining, playing games, or relaxing by the fire! Inside, a huge bonus room opens up even more possibilities—movie nights, game days, or that extra hangout space everyone will appreciate. But wait -- there’s a surprise tucked away—a secret room hidden behind a shelf adds a playful touch of mystery and character! Whether you’re welcoming weekend guests or settling into full-time living, this flexible floor plan makes it easy to feel at home. Twin Creeks residents enjoy three community pools, a clubhouse, and an on-site waterfront restaurant and marina, bringing recreation and relaxation close to home. From afternoons by the pool to dinner by the water, there’s plenty to love about life here. Come for the home, stay for the lifestyle! Short-term rentals require a permit; contact the HOA representative for current information and requirements.

72 Driftwood Ct, Winchester

319 Chase Cir, Winchester
$389,000
2 Beds ⋅ 2 Baths ⋅ 3545836 MLS ⋅ ACTIVE Status ⋅ 0.15 Acres ⋅ 37398 Zip Code
Welcome to this beautiful all-brick patio home located in the popular Fox Run community! This thoughtfully designed home offers an easy, comfortable floor plan with spacious living areas and plenty of room to relax and entertain. The open-concept living room and kitchen create a welcoming gathering space and the kitchen features stainless steel appliances, granite countertops, and a beautiful tile backsplash. The two oversized bedrooms and two full baths provide comfort and privacy. A small office, craft room, or hobby room offers the perfect flex space to suit your needs. Step outside to enjoy the screened-in back porch—a wonderful spot to sip your morning coffee, unwind in the evening, or enjoy the peaceful surroundings. As a resident of Fox Run, you’ll also enjoy wonderful community amenities including a swimming pool, clubhouse, and lawn care included. This home offers low-maintenance living in a desirable community, making it the perfect place to call home! Convenient to downtown Winchester, shopping, dining, grocery stores and Tim's Ford Lake!

319 Chase Cir, Winchester

605 River Watch Way, Winchester
$524,900
3 Beds ⋅ 3 Baths ⋅ 3545612 MLS ⋅ ACTIVE Status ⋅ 0.14 Acres ⋅ 37398 Zip Code
Weekends away...or here to stay...this adorable home may be exactly what you're looking for. Here's where you find your affordable, every day escape in Twin Creeks Village! This inviting 3-bedroom, 2.5-bath home with 3/4" sand and finish flooring combines an open floor plan with wonderful spaces to relax, gather, and enjoy the outdoors. The covered front porch (with arched stone entry!) offers a welcoming first impression, while the large screened porch steals the show—perfect for morning coffee or simply settling in with a good book. Inside, this home makes everyday living and entertaining feel effortless. A main level primary bedroom adds convenience while two additional bedrooms upstairs offer room for guests, a home office, or whatever suits your lifestyle. The large laundry room is complete with cabinets and a sink. Whether you’re searching for a full-time home or lake get-away, this home is ready for your next chapter. Furniture and furnishings are available for negotiation, offering the opportunity to spend less time furnishing and more time enjoying your new home!

605 River Watch Way, Winchester

338 Royal Oak Dr, Winchester
$339,900
3 Beds ⋅ 2 Baths ⋅ 3545572 MLS ⋅ ACTIVE Status ⋅ 0.92 Acres ⋅ 37398 Zip Code
Privacy, space, and comfortable one-level living come together beautifully. Situated on nearly an acre surrounded by mature trees, this 3-bedroom, 2-bath home offers a peaceful setting with plenty of room to relax both inside and out. A large front porch with new Trex decking creates an inviting first impression and the perfect spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home offers a warm and functional layout featuring a separate dining room, keeping room, and a welcoming living space centered around a gas fireplace. The kitchen features maple cabinetry and tile countertops with plenty of space for everyday meal preparation and gathering. Just beyond the main living areas, the heated and cooled sunroom extends the home's usable living space year-round—ideal for relaxing, entertaining, or creating a bright home office or hobby space. The primary suite provides a comfortable retreat with separate his-and-hers walk-in closets and a private bath with a walk-in shower. Partial new carpeting adds a fresh touch throughout the home, while the included washer and natural gas dryer provide added convenience. Outside, mature trees create a wonderful sense of privacy and a peaceful backdrop for enjoying the spacious property. With nearly an acre, inviting indoor and outdoor living spaces, and a floor plan designed for comfortable everyday living,

338 Royal Oak Dr, Winchester

107 Brandi Way, Winchester
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 3544332 MLS ⋅ ACTIVE Status ⋅ 0.5 Acres ⋅ 37398 Zip Code
Welcome to your Tims Ford Lake retreat! A beautifully maintained 3-bedroom, 2-bath lake house offering the perfect blend of privacy, space, and waterfront living. Set on half an acre with a private dock and boat lift on year-round water, this home puts lake life right outside your back door. Step inside to find a newly renovated kitchen, ready for everything from quiet mornings to entertaining guests. Skylights throughout the home flood the living spaces with natural light, creating a bright, airy feel from room to room. Upstairs, the sprawling primary suite offers a true owner's retreat, while the walkout unfinished basement adds abundant storage or future expansion potential. The two-car garage provides everyday convenience, and the two-story layout gives everyone room to spread out. The true showstopper is the sunroom, where floor-to-ceiling views of Tims Ford Lake and your private dock make it easy to imagine morning coffee or evening sunsets right at home. Beyond the water, the location delivers everyday peace of mind and convenience - city fire and police are close by, the hospital is just 2.2 miles away, and you're within easy walking distance of the city square for shopping and dining. This lovingly maintained home is lakefront living at its finest. Don't miss your chance to own a slice of Tims Ford Lake.

107 Brandi Way, Winchester

810 Cumberland Dr, Winchester
$399,900
3 Beds ⋅ 2 Baths ⋅ 3544234 MLS ⋅ ACTIVE Status ⋅ 0.56 Acres ⋅ 37398 Zip Code
Welcome to 810 Cumberland Dr.! This charming 3-bedroom, 2-bath home offers 2,260 square feet of living space in a beautiful, established Winchester setting. Thoughtfully updated throughout, the home features all-new windows, a new HVAC system with gas heat, new dishwasher, sink, disposal and microwave, professionally cleaned ductwork, fresh interior and exterior paint, new LED recessed lighting throughout, and new ceiling fans in the primary bedroom and sunroom—all completed in 2025. The water heater was also replaced in 2023. Outside, mature trees and fresh landscaping create a welcoming setting, while the spacious driveway offers plenty of parking. Conveniently located near the Franklin County Country Club and just minutes from downtown Winchester, you'll enjoy easy access to shopping, dining, recreation and local amenities. With extensive updates already completed and plenty of space to enjoy, this home is ready to welcome its next owners!

810 Cumberland Dr, Winchester

71 Windjammer Ct, Winchester
$740,000
4 Beds ⋅ 4 Baths ⋅ 3543235 MLS ⋅ ACTIVE Status ⋅ 0.29 Acres ⋅ 37398 Zip Code
Welcome to your dream home in Twin Creeks Village, where comfort meets style and convenience. This beautiful 4-bedroom, 3.5-bath home offers spacious living with a thoughtful layout and high-end touches throughout. Downstairs you will find a seamless flow between the living room and kitchen, perfect for entertaining or relaxing. The Primary Suite is also on the main level providing a private retreat with generous space and en-suite bath. Upstairs you will find three additional bedrooms, each with large closets, plus a bonus room ideal for a home office, gym, or media room. Enjoy the covered back porch complete with a hot tub—perfect for year-round relaxation. Located in amenity-rich Twin Creeks Village, offering access to 3 pools, golf cart trails to the marina and floating restaurant and more! Don't miss this opportunity to live in one of the area's most desirable communities

71 Windjammer Ct, Winchester

602 Style St, Winchester
$239,000
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

1790 Old Estill Springs Rd, Winchester
$299,000
3 Beds ⋅ 2 Baths ⋅ 3542865 MLS ⋅ ACTIVE Status ⋅ 0.96 Acres ⋅ 37398 Zip Code
Lots of space, a beautiful nearly one acre flat lot, and a convenient Winchester location! This updated 3 bedroom, 1.5 bath brick home offers a great combination of indoor and outdoor living with plenty of room to spread out. Inside, you’ll find two large living areas, including a huge family room at the front of the home and an additional spacious family room with a fireplace. The home has been nicely updated with a new kitchen featuring new cabinets and brand new stainless steel appliances, new laminate flooring, fresh interior paint, updated fixtures, and convenient inside laundry. Outside, the nearly acre flat property provides a large, usable yard with plenty of room to enjoy. A huge covered back patio creates a great space for relaxing, entertaining, and outdoor living. The home also features a classic brick exterior, metal roof, large asphalt driveway, and plenty of parking. Conveniently located in Winchester close to shopping, dining, schools, and everyday amenities. With its spacious floor plan, large flat lot, extensive updates, covered outdoor living area, and great location, this move in ready property has a lot to offer!

1790 Old Estill Springs Rd, Winchester

366 Oak Leaf Cir, Winchester
$?
3 Beds ⋅ 2 Baths ⋅ 3542217 MLS ⋅ ACTIVE Status ⋅ 0.61 Acres ⋅ 37398 Zip Code
AUCTION ON SAT., SEPT., 26TH AT 2 PM! This move in ready all brick home offers 3 bedrooms and 2 bathrooms on a secluded .61 +/- acre corner lot. The property features mature shade trees, a mini barn, a 2-car garage, and is just minutes from Tims Ford Lake & State Park, and local marinas. Whether you are looking for your next home, an investment opportunity, or a property with potential to flip/rent, this one is sure to check your boxes! This property will be selling at auction on September 26th at 2 PM. Bid in person or online from wherever you are, and don’t miss your chance to own this great home in Winchester! Call the auctioneer with any questions or for additional information.

366 Oak Leaf Cir, Winchester

108 Lookout Drive, Winchester
$443,900
3 Beds ⋅ 2 Baths ⋅ 3541127 MLS ⋅ ACTIVE Status ⋅ 0.28 Acres ⋅ 37398 Zip Code
Welcome to this beautiful 1.5-level home designed for comfort, convenience, and style! This 3-bedroom home features a zoned primary suite on the main floor, offering privacy and functionality for modern living. The open-concept layout creates an inviting space perfect for entertaining family and friends, while the spacious covered back porch provides the ideal spot to relax and unwind outdoors. Enjoy premium finishes throughout, including Moen black matte plumbing fixtures and elegant Dallas White granite countertops that add a touch of sophistication to the kitchen and baths. The huge finished bonus room offers endless possibilities—whether it’s a media room, playroom, or home office. Located in a gated, family-friendly community, this home is just minutes from shopping, restaurants, doctors’ offices, and the stunning Tims Ford Lake. Love the outdoors? You’ll be only 3 minutes from Sharp Springs Boat Ramp, where you can launch your boat, kayak, or canoe and spend your days fishing or exploring the water.

108 Lookout Drive, Winchester

160 Wakeboard Way, Winchester
$1,199,900
4 Beds ⋅ 4 Baths ⋅ 3529994 MLS ⋅ ACTIVE Status ⋅ 0.33 Acres ⋅ 37398 Zip Code
Incredible opportunity to own a well appointed custom designed home that comes with 5 Wall Mounted TV's and a specific list of furnishings included in the purchase price. In this home you will find attention to finest details speaks for themselves. Starting with the porcelain pavers at the front entry, hardwood throughout the main floor and common area, Natural gas fireplace with Custom Steel Logs, Calcutta Supremo Quartz countertops, custom designed cabinets with wine tower, and Thermador appliances. Solid Core 3 Panel interior doors, Hunter Douglas Blinds, and Andersen wood sliding glass doors leading you out onto the porcelain paved covered back porch with 4-Flush Mounted Ceiling electric heaters, and another steel log fireplace. The outdoor entertainment area is finished with brick pavers that lead you into the vaulted summer kitchen that is completed with NatureKast weatherproof cabinets, Stainless Steel Alfresco Natural Gas appliances -30” Gas Grill with Rotisserie, refrigerator, under counter ice maker, pizza oven, versa burner, double side burners, warming drawer and built-in Big Green Egg XL smoker . The entire yard is irrigated and has whole yard landscape lighting of which illuminates steel gas log firepit. This home has wifi system that controls everything- including the camaras, alarm system, hvac, lighting, appliances, surround sound system and more all from the convenience of your phone. The 3 car garage has Epoxy Floors, insulated garage doors, overhead garage storage and more. This home has a Briggs and Stratton 26KW Natural Gas Whole House Generator, tankless instant hot water tank, whole house two stage Water Filter System, and a Vacu-flow Central Vacuum System throughout house, garage and back porch. This is truly a one-of-a-kind opportunity. Call about additional seller concessions that are be offered .

160 Wakeboard Way, Winchester

no property photo
$580,458
3 Beds ⋅ 2 Baths ⋅ 3529310 MLS ⋅ ACTIVE Status ⋅ 37398 Zip Code
Winchesters newest 55 plus community ideal for low maintenance living. This new neighborhood features amenities such as Clubhouse, fitness center , pool, dog park and lawn maintenance. Located less than 1/2 mile to Food City and is a short drive to downtown. Tims Ford Lake Homes will be constructing a variety of floor plans in Deer Valley along with other quality custom home builders. This floor plans features over 2174 sq ft of heated and cooled living space . There are 3 spacious bedrooms on the main floor and a bonus room over the 22x26 ft garage. The kitchen will be completed with upgraded stainless steel appliance package. The entire home will highlight LVP wood plank flooring, tile showers , granite or quartz countertops, custom closet shelving and more. For a limited time you can make all interior selections. This home is located on one of the larger lots in the neighborhood and has a private back yard. See Photos for more details -- Owner/ Agent/ Builder

Deer Valley, Winchester

203 W Petty Ln, Winchester
$199,900
3 Beds ⋅ 1 Baths ⋅ 3527849 MLS ⋅ ACTIVE Status ⋅ 0.2 Acres ⋅ 37398 Zip Code
Charming Winchester Starter Home or Turnkey Rental Opportunity! Make this home just the way you want it! Welcome to 203 W Petty Ln in Winchester, TN! This efficient 1,271 sq. ft., 3-bedroom, 1-bathroom home features a practical single-level layout and a convenient attached one-car carport. Whether you are looking for an affordable path to homeownership or adding a strong performer to your real estate portfolio, this versatile property delivers exceptional value. Key Highlights *Move-In Ready or Rental Ready: Proven track record as a successful investment property—ideal for immediate cash flow or a turnkey starter home. *Functional Layout: 3 comfortable bedrooms and a shared full bath optimized to maximize every square foot of living space. *Convenient Features: Covered one-car carport offering sheltered parking and additional outdoor storage potential. *Prime Winchester Location: Situated in a peaceful neighborhood close to local schools, downtown Winchester shopping, and just minutes from beautiful Tim's Ford Lake.

203 W Petty Ln, Winchester

205 Billy Goat Hill Rd, Winchester
$585,000
2 Beds ⋅ 3 Baths ⋅ 3527505 MLS ⋅ ACTIVE Status ⋅ 1.11 Acres ⋅ 37398 Zip Code
This is a unique opportunity to own a Tims Ford Lake lakefront home offering privacy, character, and lake access at a reasonable price! This spacious home features 3 bedrooms and 2 baths, a living room with a soaring stone fireplace, a new HVAC system, and an updated kitchen with all new appliances. The full basement offers incredible flexibility, with a sauna, office, kitchen, dining area, sunroom, bathroom, two additional rooms, and two fireplaces—creating plenty of space for entertaining, guests, hobbies, or a potential short-term rental setup. Outside, you'll find multiple decks, patio areas, and a beautiful waterfall, providing wonderful spaces to relax and enjoy the peaceful surroundings. A private area with lake access is just an easy two-minute walk from the home, offering a great spot to unwind by the water and enjoy your favorite beverage. The property is being offered furnished, making it even more appealing as a vacation home, second home, or potential investment property. You also have the option to remove trees up to 3 inches in diameter and limb up larger trees between the home and the lake on TVA property, potentially opening up an even better lake view. With its privacy, lake access, unique features, and convenient location on Tims Ford Lake, this property offers a wonderful opportunity to enjoy lake living and all it has to offer!

205 Billy Goat Hill Rd, Winchester

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

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

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

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.