Refine Search
Map
Sort by
$559,500
4 Beds ⋅ 3 Baths ⋅ 3250482 MLS ⋅ ACTIVE Status ⋅ 0.85 Acres ⋅ 37398 Zip Code
Welcome to 92 Freeman Court in Winchester, Tennessee, where comfort, convenience, and exceptional amenities come together just minutes from Historic Downtown Winchester and beautiful Tims Ford Lake. Enjoy easy access to multiple nearby boat launches, marinas, and waterfront recreation, making this property ideal for lake lovers and outdoor enthusiasts. This well-maintained home features beautiful hardwood floors, a spacious living room with an electric fireplace, and an attached sunroom perfect for relaxing year-round. The primary suite offers a heated whirlpool tub for a true spa-like retreat, while electric shades add both convenience and style. A installed surround sound speaker system enhances the living and entertainment spaces. The kitchen and home are equipped with numerous upgrades, including a water softener and water filtration system, gas water heater, full home alarm system, and security cameras (all equipment to remain). Many appliances will remain with the home, and some furniture is negotiable, creating a move-in-ready opportunity for the next owner. Outside, enjoy summer days by the above-ground pool and appreciate the incredible garage and workshop space. In addition to the attached 2-car garage, the property features a detached 2-car garage complete with its own 3/4 bathroom, ideal for a pool bathroom, storage, a workshop, or future guest space. The detached garage is powered by solar panels, and the solar-generated power can be converted to supply the home as well if desired. Whether you're looking for a primary residence, a lake-area retreat, or a property with exceptional storage and workspace options, this home offers a rare combination of functionality, comfort, and location near everything Winchester and Tims Ford Lake have to offer.

92 Freeman Ct, Winchester
$479,000
5 Beds ⋅ 4 Baths ⋅ 3248768 MLS ⋅ ACTIVE Status ⋅ 2.21 Acres ⋅ 37398 Zip Code
Welcome home to the perfect blend of space, comfort, and convenience!! Nestled on 2.21 beautiful acres at the end of a cul-de-sac just minutes from Tims Ford Lake, shopping/dining, this impressive 4,244 sq ft home offers room for everyone inside and out. Boasting 5 spacious bedrooms, 2 full bathrooms, and 2 half baths, this home is designed for both everyday living and entertaining. The fully finished basement provides endless possibilities for a recreation room, home office, gym, media room, or guest space. You'll appreciate the many recent updates, including a new roof and new windows. Situated outside the city limits, you'll enjoy added privacy and fewer restrictions while being conveniently close to all amenities you need. Natural gas is available at the road. Whether you're looking for space to grow, entertain, or simply enjoy peaceful country living near the lake, this exceptional property checks all the boxes.

466 Willow Oak Dr, Winchester
$775,000
4 Beds ⋅ 3 Baths ⋅ 3248748 MLS ⋅ ACTIVE Status ⋅ 0.17 Acres ⋅ 37398 Zip Code
Welcome to lake living at it's finest in the private gated community of Twin Creeks located on Tims Ford Lake! This beautifully maintained 4-bedroom home offers the perfect blend of comfort, convenience, and outdoor enjoyment. Nestled in a peaceful setting, you'll love relaxing on the spacious screened-in back porch that is ideal for morning coffee, entertaining guest, or unwinding after a day on the lake. Enjoy the security and exclusivity of gated community living while being moments from swimming in one of the 3 pool on the property. OR rent a boat from the marina for the day of fishing or water skiing!! Weather your looking for a full-time residence or a weekend retreat, this home is ready to welcome you home!!Golf Cart included with the property.

22 Hammock Dr, Winchester
$455,000
3 Beds ⋅ 3 Baths ⋅ 3248387 MLS ⋅ ACTIVE Status ⋅ 0.33 Acres ⋅ 37398 Zip Code
Welcome to this meticulously designed new home! The residence features three spacious bedrooms and two bathrooms, along with a supplemental room with a half bath. It includes upscale features like top-of-the-line stainless steel appliances, custom-built expansive wardrobes, and an exquisite coffered ceiling in the main living area. Through precise craftsmanship and the use of premium materials, this home is ready to provide a blend of opulence and sophistication to its first occupant. Don't miss out on this move-in-ready gem.

201 Lookout Dr, Winchester
$774,900
4 Beds ⋅ 5 Baths ⋅ 3248070 MLS ⋅ ACTIVE Status ⋅ 0.6900000000000001 Acres ⋅ 37398 Zip Code
The perfect blend of comfort, space, and functionality in this stunning walkout basement home. The main level features a beautifully designed covered porch with vaulted ceilings —ideal for relaxing or entertaining—alongside a striking floor-to-ceiling stone fireplace that anchors the living space. You’ll also find two thoughtfully zoned bedrooms on the first floor, providing privacy and convenience, along with a versatile dining room or home office and a half bath for guests. Upstairs offers approximately 500 square feet of unfinished space, giving you the flexibility to expand and customize to fit your needs. The fully finished walkout basement is a true extension of the home, featuring two additional bedrooms, two full bathrooms, a kitchenette, and an abundance of storage space—perfect for multi-generational living, guests, or entertaining. This home delivers both everyday comfort and long-term versatility, all in one thoughtfully designed layout.

210 Cascade Dr, Winchester
$430,000
3 Beds ⋅ 2 Baths ⋅ 3247907 MLS ⋅ ACTIVE Status ⋅ 1.38 Acres ⋅ 37398 Zip Code
Welcome to 84 Meadowood Ln, a beautiful new construction home completed in June 2026 that offers the perfect blend of modern style, thoughtful design, and an exceptional location. Situated on a spacious 1.38-acre lot, this property provides plenty of room to enjoy now while offering endless possibilities for the future, including space to add a shop or pool. Inside, you'll find a well-designed floor plan featuring modern finishes and a layout created for both everyday living and entertaining. The home also features a spacious two-car garage, providing ample room for vehicles, storage, and hobbies. Large windows throughout the living room and dining area fill the home with natural light and provide beautiful views of the expansive backyard. Step outside to the spacious covered back deck, the perfect place to relax, entertain guests, or enjoy the peaceful setting. Conveniently located just outside of town, this home offers the tranquility of country living while remaining only minutes from both Tims Ford Lake and Winchester, giving you easy access to recreation, dining, shopping, and everyday conveniences. This is a rare opportunity to own a brand-new home on acreage in one of the area's most desirable locations.

84 Meadowood Ln, Winchester
$449,000
3 Beds ⋅ 2 Baths ⋅ 3247095 MLS ⋅ ACTIVE Status ⋅ 0.44 Acres ⋅ 37398 Zip Code
Step into this beautifully renovated 1950s ranch where timeless charm meets modern comfort. This move-in ready home features 3 bedrooms and 2 full bathrooms, thoughtfully updated throughout. The spacious great room is the heart of the home, highlighted by the original stone fireplace that creates a warm and inviting atmosphere for gathering with family and friends. The updated interior offers stylish finishes, custom closet shelving for added organization, and a functional layout designed for everyday living. Step outside to enjoy the covered tile patio, perfect for relaxing, entertaining, or enjoying your morning coffee. Situated on a desirable corner lot, this property provides additional outdoor space and curb appeal. Conveniently located and beautifully renovated, this home is ready for its next owner to enjoy. Owner/Agent. ** Preferred lender is offering lender paid 1-0 rate buydown and free appraisal to qualified buyers**

109 Oak Park, Winchester
$1,049,994
4 Beds ⋅ 5 Baths ⋅ 3245715 MLS ⋅ ACTIVE Status ⋅ 0.18 Acres ⋅ 37398 Zip Code
Built in 2024, this stunning home is practically new and is immaculate! Don't miss this -- the 6-seater, Advanced EV Golf Cart conveys with property with accepted offer! Living Room, Dining Set, and Barstools are negotiable. Enjoy gorgeous lake views on both levels of this beautifully designed home. The open floor plan features soaring ceilings and walls of expansive windows for a great first impression!. Chef's kitchen with Cafe' appliances, plaster hood vent, oversized island, pantry and coffee bar/wet bar. Another downstairs flex space is ideal for your home office or a formal dining room. The main level Primary Bedroom has an ensuite bath with soaking tub and large tiled shower. Upstairs you'll find another Primary Suite/Bath with balcony. BR 3 (with balcony) and BR4. A Jack-n-Jill bath connects BRs 3 and 4. HUGE Bonus Room over the garage. Designer fixtures and finishes throughout!

155 Hammock Dr, Winchester
$329,900
3 Beds ⋅ 2 Baths ⋅ 3244505 MLS ⋅ ACTIVE Status ⋅ 1.06 Acres ⋅ 37398 Zip Code
Nice 3BR, 2BA home on a double corner lot in Pine Bluff Subdivision! Features include a stone fireplace, large utility room, primary bedroom with walk-in closet, screened back patio, mature shade trees, and carport with workshop. Enjoy access to Pine Bluff's private boat launch and boat storage with convenient access to Tims Ford Lake. Great location between Winchester and Tullahoma!

30 W Paradise Dr, Winchester
$159,000
3243837 MLS ⋅ ACTIVE Status ⋅ 2.19 Acres ⋅ 37398 Zip Code
Discover the possibilities on this beautiful 2.19-acre property, ready for your next project. Whether you're envisioning a mini farm, a custom dream home, or an investment opportunity, this versatile tract offers exceptional potential. A preliminary soil test supports a 4-bedroom home site, making it easier to start planning your build. Zoned R-2, the property may also accommodate duplex development, offering flexibility for homeowners, investors, or builders seeking income-producing opportunities. Enjoy the space and freedom of country-style living while maintaining convenient access to nearby amenities. With ample room for gardens, animals, workshops, recreational space, or multiple residential units, this property is a rare find with endless possibilities! Soil sample attached

Metcalf Road, Winchester
$499,900
4 Beds ⋅ 4 Baths ⋅ 3242752 MLS ⋅ ACTIVE Status ⋅ 0.33 Acres ⋅ 37398 Zip Code
With T ims Ford Lake just across the street, be prepared to love the LAKE VIEWS year round from the front porch! GREAT location with all the conveniences nearby -- Twin Creeks Marina, restaurants, shopping on the town Square and numerous boat ramps nearby. Wonderfully open floor plan! Primary downstairs; three bedrooms and open flex space at top of stairs. Bedroom 2 upstairs with its own private bath suite could be a 2nd Primary bedroom for you! Bedrooms 3 and 4 share a Jack-n-Jill bath. Downstairs Office w/glass french doors. Kitchen with island, stainless steel appliances and pantry. Waterproof LVP flooring throughout; NO carpet! Primary bath features tile flooring, large, tiled shower w/frameless glass door and two vanities. Quartz counters throughout. Solid wood custom cabinets w/soft close. Natural gas fireplace, tankless water heater. Closets galore! Upgraded trim throughout. Covered front porch and covered rear porch. The space in this home will amaze you. Don't miss the floored attic space accessible through one of the bedroom closets! This home is like new and can be purchased fully furnished/turn key (and ready to rent immediately) or not. Endless AirBnb/rental possibilities make this a great investment or 2nd home opportunity! Turn key ready to rent; includes kitchen items, sheets towels, etc. Barely lived in; come see!

805 N Jefferson St, Winchester
$455,000
3 Beds ⋅ 3 Baths ⋅ 3242345 MLS ⋅ ACTIVE Status ⋅ 0.59 Acres ⋅ 37398 Zip Code
Welcome home to this beautifully remodeled all-brick ranch offering the convenience of one-level living in one of Winchester’s most sought-after lake communities. Located just a block from a boat ramp, you’ll enjoy easy access to the lake & all the recreation it has to offer. Step inside to an inviting open floor plan designed for comfortable living & entertaining. The stunning newly remodeled kitchen features granite countertops, stainless steel appliances & an abundance of beautiful white cabinetry, providing both style and functionality. The spacious great room offers a cozy fireplace, recessed lighting & plenty of room to gather w guests. Big ticket items have already been replaced making this newly remodeled home basically new for you! Newly installed heating & air, roof, insulated garage door, split hvac unit for garage & so much more! This home features 3 spacious bedrooms & 3 full bathrooms, including a beautifully updated primary suite with a renovated bathroom, walk-in shower & upscale finishes. A huge laundry room includes a full wall of built-in cabinets for exceptional storage & an attached full bathroom for added convenience. The attached deep one-car garage offers ample space for a vehicle, boat, golf cart, or recreational equipment. Outside, you’ll find even more room for storage, hobbies, and outdoor enjoyment with a detached garage/workshop, detached carport, and fully fenced backyard. Whether you need space for projects, extra parking, pets, or entertaining, this property delivers. Let’s not forget relaxing. Have a sweet tea or morning coffee on your large covered patio located right off the kitchen & great room. With modern updates throughout, abundant storage, multiple outbuildings, and a prime location near the lake, this move-in-ready home offers the perfect blend of comfort, convenience, and lifestyle. Don’t miss this opportunity to own a beautifully updated home in one of Winchester’s most desirable lake neighborhoods.

106 Chattin St, Winchester
$359,000
3 Beds ⋅ 2 Baths ⋅ 3242003 MLS ⋅ ACTIVE Status ⋅ 1 Acres ⋅ 37398 Zip Code
Charming Farmhouse on 1 Acre – Move-In Ready! Welcome to your peaceful country retreat! This adorable farmhouse sits on 1 acre and offers the perfect blend of charm and modern updates. The home features 3 bedrooms and 2 full baths, with thoughtful renovations completed in 2015, including updated plumbing and electrical systems. Home was just completely repainted with a neutral paint throughout. Step into the lovely kitchen, where you’ll find custom cabinetry with abundant storage—perfect for keeping everything organized while enjoying a warm, inviting space to cook and gather. The upstairs bedroom provides a cozy and private area, ideal for a teen, guest room, or home office. Outside, the property continues to impress with a large detached 4 CAR GARAGE offering plenty of space for vehicles, hobbies, or extra storage. You’ll also find a carport, an additional storage building, and even a storm shelter for added safety and convenience. With plenty of room to roam and all the right updates already in place, this charming farmhouse is ready to welcome you home!

6606 Old Tullahoma Rd, Winchester
$319,900
2 Beds ⋅ 2 Baths ⋅ 3234828 MLS ⋅ ACTIVE Status ⋅ 2.5 Acres ⋅ 37398 Zip Code
Charming 2 bed, 2 bath home situated on 2.4 acres, offering the perfect blend of modern comfort and peaceful country living. This 1,080 sqft home features high ceilings, updated finishes, and a beautifully renovated primary bathroom. Enjoy year-round relaxation in the Florida room, or step outside to take in the scenic surroundings. The newly built shop provides excellent space for storage, hobbies, or projects. Conveniently located just 10 minutes from town, this property delivers both privacy and accessibility in a truly storybook setting.

1687 Georgia Crossing Rd, Winchester
$369,500
3 Beds ⋅ 2 Baths ⋅ 3230993 MLS ⋅ ACTIVE Status ⋅ 0.33 Acres ⋅ 37398 Zip Code
Welcome to this beautiful 3 br 2 ba brick home located in the areas most desirable subdivision. This home features an inviting open floor plan perfect for entertaining or everyday living. You'll love the gorgeous HW floors, custom cabinetry, and abundant counterspace. The oversize laundry room provides additional convenience while the huge closets ensure plenty of organization. The huge primary suite offers a relaxing retreat with plenty of closet space and quality craftsmanship. Don't miss this opportunity!

145 Murray Lake Dr, Winchester
$2,119,040
4 Beds ⋅ 6 Baths ⋅ 3230557 MLS ⋅ ACTIVE Status ⋅ 0.36 Acres ⋅ 37398 Zip Code
Elevated Lake Living. Lakeside Luxury at the Finest! 3 Level Home that Has It All and More. In Gated Boutique Community Close to Downtown Winchester. HOA incl Lawn Mowing, Gate Maintenance, Common Area and Dock Maintenance/Insurance. This Home is 3 Level of Luxury with 3 Private Primary Suites - 1 on the Main Level, and 2 Upstairs- all with Double Vanities, Large Showers, Water Closets, and Soaking Tubs. Your Guests Can Stay in Suites like a Hotel! 4th Bedroom has 2 Queen Beds and Bonus Room with 4 Full Beds share Hallway Bath. Bunk Room (4 Twin XL) in the Basement Level has Access to a Full Bathroom on the Basement Level. 2 Laundry Rooms. 2 Kitchens with 3 Dishwashers Total. Main Level Kitchen has Dacor Appliances- 48" Range, Double Oven, 48" Panel Fridge, Microwave Drawer. Basement Kitchen has an Icemaker with Cafe Dishwasher and Full Size Fridge. Basement Living Room has RH Navy Velvet Sofa. Movie Room with Surround Sound on Lower Basement Level. Whole Home has Pella Windows, Sliders, and Doors. Custom Cabinetry in Whole Home- Custom Paint/Stain and Handmade in all Bathrooms and Kitchens. Custom Millwork throughout. Built-ins. Televator for Living Room TV. Upscale Designer Finishes and Cutting Edge Lighting. Lower Level has Pool Table/ Fooseball/Game Area, Closet for a Christmas Tree, Mechanical Storage Closet (can store boating tube, etc). Tankless Hot Water Heater AND Tank Water Heater. Entertainer's Dream Lake House. Luxury Awaits. Shared Community Dock and Exclusive Boat Slip #5. Income Potential if you Choose- sleeps 22. FULLY FURNISHED (Valued at over $100k in Furnishings)- Hot Tub, Pool Table, Tv's, Fooseball, and Dock Box, AND BOAT LIFT INCLUDED IN SALE! TURN KEY LAKE LIFE LIVING.

318 N Porter St, Winchester
$349,000
3230499 MLS ⋅ ACTIVE Status ⋅ 0.62 Acres ⋅ 37398 Zip Code
Ready to build your dream lake home? This pristine 0.60-acre lot on Tims Ford Lake offers incredible, unobstructed views and is just minutes from downtown Winchester. Combining peaceful waterfront living with quick access to local dining and shopping, this property is the perfect canvas for your custom retreat. Bring your builder and start living the lake life today! THIS LOT DOES NOT HAVE A DOCK PERMIT. There is a dock on the property that has been there for years but it is not permitted.

Agate St, Winchester
$475,000
3 Beds ⋅ 3 Baths ⋅ 3228371 MLS ⋅ ACTIVE Status ⋅ 1 Acres ⋅ 37398 Zip Code
Seller says to bring an offer!! They are ready to sell!! This distinguished residence at 615 Lakeview Way offers a rare blend of timeless elegance and everyday comfort within the desirable lakefront subdivision of Winchester. Set on a serene, park-like 1 acre corner lot, the 3,067-square-foot home welcomes you with stained glass windows that bathe the entry in soft, colorful light. Inside, the spacious formal living room invites conversation beneath its impressive coffered ceilings, while the adjacent formal dining room, adorned with rich hardwood floors, creates the perfect setting for memorable gatherings. The beautifully appointed kitchen features stunning cabinetry and two full-sized pantry cabinets, providing both style and abundant storage for the home cook. Natural light pours into the expansive Florida room, where walls of windows frame peaceful views of the surrounding grounds. A separate gathering room offers a more intimate space for relaxation, while the private master suite provides a true retreat, complete with direct access to a charming gazebo just beyond the doors. Two generously sized guest bedrooms with ample closet space ensure comfort for family and visitors, complemented by two and a half baths throughout. Additional practical features include a three-car attached garage, a dedicated tornado shelter for peace of mind, and an outdoor storage building for seasonal items. With its thoughtful layout and graceful details, this home feels like the place where life slows down just enough to truly enjoy it. Whether you're savoring morning coffee in the sun-filled Florida room or hosting friends in the formal living spaces, 615 Lakeview Way offers the warmth and substance you've been seeking. This special property is ready for you today!! Come see before someone else does!!

615 Lakeview Way, Winchester
$144,900
3223526 MLS ⋅ ACTIVE Status ⋅ 0.49 Acres ⋅ 37398 Zip Code
Come build your dream home on this large lot in the Twin Creeks Community. Whether you live here year round or get away here on weekends, you can build to suit what you are looking for. Amenities include Marina with Boat Slips Rental, Restaurant with Water Front Dining, Guest Rental Cottages, Club house, Three Swimming Pools, Tennis, RV Campground, Sandy Beach with Boat Launch, Event Pavillion, Putting Green, Fire Pit. Make this one your own today!

Cannonball Ct, Winchester
$649,000
5 Beds ⋅ 4 Baths ⋅ 3223240 MLS ⋅ ACTIVE Status ⋅ 0.8 Acres ⋅ 37398 Zip Code
Spacious and beautifully maintained 5 bedroom, 4 bath home loaded with upgrades and thoughtful features throughout. From the stunning tiger wood hardwoods floors to the large primary en suite, this home offers both comfort and functionality. Enjoy year-round relaxation in the sun room overlooking the fully fenced backyard. The fully encapsulated crawlspace comes with a lifetime warranty for added peace of mind, while the fully installed whole-home Generac standby generator powered by natural gas keeps you prepared in any season as it's efficiency covers the whole home. With a 3-car garage, two washer and dryer hookups, and plenty of space for everyday living and entertaining, this home truly checks all of the boxes.

292 Ridgecrest Dr, Winchester
$99,999
3221516 MLS ⋅ ACTIVE Status ⋅ 37398 Zip Code

Campfire Ct, Winchester
$997,500
3 Beds ⋅ 2 Baths ⋅ 3218367 MLS ⋅ ACTIVE Status ⋅ 0.37 Acres ⋅ 37398 Zip Code
Nestled in the exclusive community of Lee Ford Estates, this exceptional lakefront retreat offers breathtaking waterfront living just minutes from downtown Winchester. Designed to maximize the beauty of the lake from every angle, the home features French doors throughout, creating stunning panoramic water views and seamless indoor-outdoor living. This beautiful home offers 3 bedrooms and 2 baths, highlighted by a warm gas fireplace and a spacious eat-in kitchen perfect for gathering with family and friends. Step outside to enjoy resort-style amenities including an in-ground pool, expansive deck space, and private waterfront access ideal for entertaining or relaxing lakeside. A coveted TVA permit accommodates two boats and includes a sun deck, making this property a rare opportunity for boating and lake enthusiasts. Complete with a 2-car garage and located in one of the area’s most desirable lake communities, this home combines privacy, convenience, and luxury waterfront living.

423 Shasteen Bend Dr, Winchester
$69,900
3217771 MLS ⋅ ACTIVE Status ⋅ 0.5680000000000001 Acres ⋅ 37398 Zip Code
Construction will start once we have an agreement for land purchase. Builder offering financing!! Build your dream home right here on this beautiful lot. Buyers have the opportunity to choose finishes and adjust the floor plan to fit their lifestyle. Standard features include luxury vinyl plank flooring throughout, beautiful granite countertops, soft-close cabinetry, a durable hardboard exterior and a concrete driveway. Experience the benefits of new construction in a desirable location near Tim’s Ford Lake. Let's make this one yours!

Mansford Rd, Winchester
$209,900
3 Beds ⋅ 1 Baths ⋅ 3217503 MLS ⋅ ACTIVE Status ⋅ 0.48 Acres ⋅ 37398 Zip Code
LARGE PRICE REDUCTION! Welcome home to this charming rambler in the City of Winchester. This home is bursting with character and sits on a large +/- 0.48-acre lot on a quiet street. Walking distance to the historic Winchester Square and Tim’s Ford Lake. Hardwood floors, new kitchen counters, and a fully fenced back yard for your four-legged friends. Mature trees line the back and side yard. Detached, single car garage with concrete floor. Single car attached carport. Roof replaced +/- 2 years ago. Great starter home or investment property. Close to it all, but with the benefits of country life.

208 Lillian St, Winchester
$99,900
3217392 MLS ⋅ ACTIVE Status ⋅ 2.44 Acres ⋅ 37398 Zip Code
Build your dream home on this 2.44-acre lot! There’s plenty of space and room for privacy, with a minimum house size of 1,800 sq. ft. Public utilities at street-water, sewer, electricity, cable, telephone. There is a small inactive sinkhole on the back of the property that poses no threats according to the geological report that is listed under documents

Sugar Leaf Cir, Winchester
$338,000
4 Beds ⋅ 3 Baths ⋅ 3213616 MLS ⋅ ACTIVE Status ⋅ 0.9 Acres ⋅ 37398 Zip Code
Welcome to peaceful country living in beautiful Winchester, Tennessee. Priced below appraised value, this is the perfect option to have instant equity in your next home. This charming property at 240 Myers Road offers the perfect blend of privacy and convenience, nestled on a serene setting just minutes from Tims Ford Lake, city parks, and the historic Winchester town square. Enjoy the quiet surroundings, open space, and natural beauty that make this home ideal for relaxing or entertaining. Conveniently located near local amenities, shopping, dining, and outdoor recreation, you'll love the balance of rural charm and accessibility. This one level ranch home home has an open, airy floor plan that is perfect for entertaining and families. There are 4 bed rooms and 3 full bathrooms, 2 of which are on suite bathrooms. Don't miss this opportunity to own your slice of Tennessee countryside!

240 Myers Road, Winchester
$695,000
5 Beds ⋅ 4 Baths ⋅ 3208025 MLS ⋅ ACTIVE Status ⋅ 0.62 Acres ⋅ 37398 Zip Code
This captivating property, beautifully blending residential charm with commercial potential, is now on the market and ready to redefine your living or working experience. Whether you're looking for a family home or an investiment property, this mixed-use gem offers unparalleled flexibility. Nestled in a vibrant historic district, this property offers superb visibility and accessibility. With a mix of residential and commercial spaces surrounding it, just steps away from local shops, restaurants, and cultural attractions. The formal living room welcomes you with its elegant built-in bookshelves framing a stunning gas log fireplace, perfect for cozy evenings. The beautifully finished wood floors enhance the home's warmth and character, making it an inviting space for both family gatherings or professional meetings. The separate study/office, featuring a private entrance and a second gas log fireplace is ideal for those who work from home or need a quiet space for client meetings. Built-in shelves enhance this versatile room's functionality. The downstairs layout features large bedrooms that share a well appointed jack-and-jill style full bath, offering convenience and privacy. Upstairs, Bedroom 3 includes its own full bath, while Bedroom 4 boasts a separate heat and air unit for personalized climate control. The private suite above the garage is perfect for guests, comlete with its own shower-only full bathroom. This property includes a basement that offers possibilities for storage, or a creative studio. Enjoy extra yard space that fronts S Porter St, presenting unique opportunities for outdoor seating framed by the unique stone bench at the edge of the property. The flexible outdoor area is perfect for a potential cafe outdoor dining, garden or additional parking for a retail business. You have the flexibility to continue using it as a home or convert it into a commercial space to host your business endeavors. (copy video link) https://youtu.be/HU5RftclNE8

110 S Porter St, Winchester
$689,900
4 Beds ⋅ 4 Baths ⋅ 3207054 MLS ⋅ ACTIVE Status ⋅ 0.92 Acres ⋅ 37398 Zip Code
Step into this magnificent 3,705 square foot home, an absolute gem in the highly sought-after Franklin Hills Subdivision. Designed for both grand entertaining and comfortable family living, this residence offers 4 bedrooms and 3.5 baths across two levels. You will immediately notice the architectural elegance, highlighted by premier trim work and stunning tray ceilings. The entryway is graced by a stunning staircase, one of the home's beautiful architectural features, complemented by a gas fireplace that serves as a warm, artistic centerpiece. The main floor features an array of gathering spaces: a gracious Formal Dining Room, a dedicated Sitting Room, and a cozy Living Room warmed by a gas fireplace. The heart of the home is the Kitchen, featuring premium granite countertops and a suite of stainless steel appliances, highlighted by a new oven installed in 2025 , perfect for the home chef, along with a sunny Breakfast Nook. Retreat to the private master bedroom on the main floor, complete with a luxurious full bath. Flooring is a mix of high-quality hardwood, tile, and carpeting. Upstairs, you'll find the additional bedrooms and a spacious Loft. Enjoy outdoor living on the large, covered front porch or relax on the back patio by the warmth of the brick fireplace. Storage and parking are plentiful with the oversized 3-car garage. The washer and dryer, all bedroom furniture, and potentially select living room items convey with acceptable offer.

356 Ridgecrest Dr, Winchester
$475,000
3206894 MLS ⋅ ACTIVE Status ⋅ 1.27 Acres ⋅ 37398 Zip Code
Rare opportunity to acquire development-ready waterfront land for sale in Winchester, TN with flexible R3A zoning, dual road access, and strong residential development potential on Boiling Fork Creek with access to Tims Ford Lake. This 1.27-acre tract in Franklin County offers level topography, scenic water views, and a highly desirable location just minutes from downtown Winchester and the Winchester square. The property’s zoning supports multiple residential possibilities, including single-family homes, duplexes, and multifamily configurations, providing flexibility for developers seeking a future residential project. The level buildable area and access on two roads create added site-planning options and convenient access points. Located near Hwy 41A, shopping, dining, schools, healthcare, parks, and lake recreation, the property combines accessibility with waterfront appeal. Tims Ford Lake remains one of Middle Tennessee’s most sought-after destinations for residential and recreational development, adding long-term desirability to the location. Buyer to verify all information.

SE 2nd Ave, Winchester
$475,000
5 Beds ⋅ 2 Baths ⋅ 3205990 MLS ⋅ ACTIVE Status ⋅ 0.34 Acres ⋅ 37398 Zip Code
SELLER OFFERING OWNER FINANCING AT 5.75% — This income-producing property just over a block from downtown Winchester, provides a rare opportunity for buyers seeking investment property in Tennessee with immediate rental income and future flexibility. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence generates approximately $2,000/month in rental income and includes approximately 3,922 sq ft on a .34-acre lot in the heart of Winchester. The property features original hardwood floors, spacious living areas, and a covered front porch that adds character and tenant appeal. A detached 1-car garage and driveway parking provide additional functionality. Located seconds from the Winchester square and Hwy 41A, the property is conveniently positioned within the community. Currently office space with a long-term tenant of 7 years, the layout and location support multiple potential uses, including long-term rental hold, mixed-use potential, or future repositioning within a growing downtown area. Convenient access to local amenities and a strong occupancy history contribute to the property's appeal for investors seeking a centrally located asset in a developing corridor. Buyer to verify all information.

309 NW 2nd Ave, 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.