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102 Oak Park, Winchester
$269,900
2 Beds ⋅ 1 Baths ⋅ 3282483 MLS ⋅ ACTIVE Status ⋅ 0.74 Acres ⋅ 37398 Zip Code
Make plans now to see this extensively renovated home with a FULL basement in the heart of Winchester! Sitting on a huge corner lot and surrounded by mature shade trees, there is still room to expand. Beautifully renovated inside and out, some of the major updates include a new roof, new Hardie Board siding, new heat/air system, new plumbing, new electric, new water heater, new windows, new gutters and downspouts. The newly renovated kitchen includes new cabinets, new quartz counters, new stainless steel appliance package, new faucets and light fixtures. Beautiful new LVP flooring throughout the main level. The renovated bathroom features a custom tiled shower. Updates also include new recessed lighting plus updated drywall, trim and paint. Original pine bedroom walls add character while the rest of the home offers modern finishes and an open, functional layout. Best of all, the FULL basement and oversized lot offer opportunities for additional living space, workshop, storage, garage, recreation area, or future expansion. This home is a great option for owner/occupants (especially if you operate a home-based business!), investors, long or short-term rentals (think AirBnb/VRBO opportunities)! Great location--roughly 1.5 miles to Downtown Winchester and so convenient to Tims Ford Lake, Nissan Decherd, AEDC, Tullahoma, Manchester, and Huntsville.

102 Oak Park, Winchester
1200 Little St, Winchester
$289,000
5 Beds ⋅ 2 Baths ⋅ 3278665 MLS ⋅ ACTIVE Status ⋅ 0.54 Acres ⋅ 37398 Zip Code
--- MOVE IN READY --- 1 Level - FLEX space galore - Fully rehabbed from top to bottom and 100% move-in ready, this solid, single-level ranch offers modern comfort just minutes from Tims Ford Lake and Boiling Fork Creek. Designed with zero stairs and two separate living areas, this highly versatile layout is the perfect setup for a large family, multi-generational living or a high-yield rental investment. Enjoy absolute peace of mind with premium upgrades throughout, including a brand-new metal roof, siding, windows, and a stunning designer kitchen. Outside, the brand-new back deck overlooks a spacious, level half-acre lot—providing an ideal space for entertaining and plenty of room to park your boat, trailer and lake toys. A rock-solid, fully renovated home in a fantastic location. PRICED TO SELL!

1200 Little St, Winchester
358 Bookout Ln, Cowan
$279,000
3 Beds ⋅ 2 Baths ⋅ 3262550 MLS ⋅ ACTIVE Status ⋅ 0.79 Acres ⋅ 37318 Zip Code
Welcome to this beautiful home in the heart of Cowan! Enjoy easy single-level living with an open layout, a 2-car garage, and a fantastic back deck to enjoy the spacious yard. Located on a quiet cul-de-sac just minutes from Downtown Winchester.

358 Bookout Ln, Cowan
23 Woods Edge Rd, Winchester
$275,000
3 Beds ⋅ 2 Baths ⋅ 3259669 MLS ⋅ ACTIVE Status ⋅ 1.23 Acres ⋅ 37398 Zip Code
A welcoming living space boasts a stunning double-opening fireplace, perfect for cozy evenings spent with family and friends. The abundant natural light streaming through replacement windows creates an airy ambiance that will make you feel right at home. The dining room conveniently opens to an outdoor patio through sliding doors, making it an entertainer's dream. Imagine hosting gatherings with seamless indoor-outdoor flow, where laughter and good food abound beneath the stars. Enjoy the convenience of instant hot water with a state-of-the-art gas system. This property features not only a spacious 2-car attached garage for daily convenience but also a detached 2-car garage/shop that offers additional storage and versatility. Whether you need space for vehicles, hobbies, or tools, you will never be short on space. With over an acre to explore, you have the perfect canvas for gardening, outdoor activities, or simply basking in the beauty of nature. The expansive yard provides endless possibilities for relaxation or recreation, making it an ideal space for families, pets, and outdoor enthusiasts alike. Situated in a tranquil setting, yet conveniently located near schools, shopping, Winchester City Park and Tims Ford Lake, you can enjoy the best of both worlds – peace and accessibility. Selling ‘As Is’.

23 Woods Edge Rd, Winchester
992 Shelly Rd, Decherd
$269,000
3 Beds ⋅ 3 Baths ⋅ 3254845 MLS ⋅ COMING SOON / HOLD Status ⋅ 0.75 Acres ⋅ 37324 Zip Code
Solid Brick house with BONUS Sunroom Added on for maximum relaxation no matter the season! On large .75 acre lot located convenient to Tim's Ford Lake just 15 miles. Close to Town just outside the city limits(lower taxes)! 3 Miles to Walmart 3 miles to Nissan 1.5 Mile to Elementary school unbeatable location! Call today for your personal showing!

992 Shelly Rd, Decherd
114 Bel Aire Dr, Winchester
$249,900
3 Beds ⋅ 2 Baths ⋅ 3248233 MLS ⋅ ACTIVE Status ⋅ 0.35000000000000003 Acres ⋅ 37398 Zip Code
Completely remodeled brick house with new roof, windows, central unit, water heater, countertops, vanities, light fixtures, plumbing fixtures, paint, luxury vinyl flooring thruout and pex water and sewer pipes. Large covered patio and carport and yard has nice shade trees. Paved driveway. Only about 1/4 mile to Sharp Springs boat ramp on Tims Ford Lake and very convenient to Winchester town square.

114 Bel Aire Dr, Winchester
108 Lemont Ln, Tullahoma
$274,000
3 Beds ⋅ 3 Baths ⋅ 3246572 MLS ⋅ ACTIVE Status ⋅ 0.66 Acres ⋅ 37388 Zip Code
Beautiful move-in-ready home situated on an oversized lot! This inviting property features a desirable primary suite on the main level and a spacious kitchen complete with a full appliance package, abundant counter space, and beautiful cabinetry. Gorgeous hardwood floors add warmth and character throughout the home. Step outside to the large rear deck, perfect for relaxing or entertaining while overlooking the expansive backyard. A storage shed provides additional space for tools, equipment, or outdoor essentials. Don't miss this wonderful opportunity to own a home that combines comfort, functionality, and outdoor living.

108 Lemont Ln, Tullahoma
1717 Georgia Crossing Rd, Winchester
$99,900
3 Beds ⋅ 2 Baths ⋅ 3234838 MLS ⋅ ACTIVE Status ⋅ 0.5 Acres ⋅ 37398 Zip Code
Unlock the potential of this versatile 1,500± sq. ft. property! Offering a unique opportunity for investors, renovators, or buyers looking to create a space tailored to their vision, this property provides a blank slate with flexible layout possibilities. Whether you envision an open-concept design, additional living areas, or a completely customized floor plan, there is plenty of room to bring your ideas to life. Outside, a detached block building with a durable metal roof offers additional space for a workshop, storage, hobbies, or future improvements. An attached one-car garage adds even more functionality. A new water meter will need to be installed for the property. This property was recently created through a minor division separating it from the neighboring property, now offered as MLS #3234828.

1717 Georgia Crossing Rd, Winchester
99 N Shephard St, Winchester
$295,999
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
8988 Old Tullahoma Rd, Estill Springs
$289,900
3 Beds ⋅ 2 Baths ⋅ 3229150 MLS ⋅ ACTIVE Status ⋅ 4.28 Acres ⋅ 37330 Zip Code
Country living without sacrificing convenience! Nestled on 4.28 acres in Estill Springs, this charming 3-bedroom, 2-bath home offers 1,962 sq ft of inviting living space and a peaceful setting that feels miles away from it all—yet remains just a short drive from town. Built in 1945, the home blends timeless character with everyday comfort, creating a warm and welcoming atmosphere throughout. Enjoy the freedom of wide-open space, mature surroundings, and room to make the property your own. Whether you're looking for a private homestead, hobby farm potential, or simply a place to unwind, this property delivers the privacy you want and the convenience you need.

8988 Old Tullahoma Rd, Estill Springs
100 Waggoner St, Decherd
$247,000
3 Beds ⋅ 2 Baths ⋅ 3221815 MLS ⋅ ACTIVE Status ⋅ 0.29 Acres ⋅ 37324 Zip Code
IMPROVED PRICE!! Beautifully maintained home in the heart of Decherd offering exceptional convenience to shopping, restaurants, Nissan, and Tims Ford Lake. This property features an open‑concept living and kitchen area with attractive LVP flooring, a 4‑seat counter bar, and pantry. A step‑down multipurpose room provides flexible space for a family room, den, or game room. The large primary suite includes a sitting area and a spacious walk‑in closet. Outdoors, enjoy a privately fenced backyard and a partially covered deck perfect for entertaining. Storage shed conveys with the property for all of your lawn tools and toys. This home is truly move‑in ready and offers the comfort, space, and location buyers are looking for.

100 Waggoner St, Decherd
214 Myers St, Cowan
$229,000
3 Beds ⋅ 2 Baths ⋅ 3221022 MLS ⋅ ACTIVE Status ⋅ 0.24 Acres ⋅ 37318 Zip Code
Welcome home to this beautifully renovated 3-bedroom, 2 bath home located in the heart of town! From the moment you step inside, you'll love the fresh updates and modern touches throughout. Featuring a nice layout, this move-in ready home offers comfortable living with style and convenience. Outside, enjoy a large yard with plenty of room for entertaining, kids, pets, or gardening, plus a storage building for all your extra tools and equipment. Check this one out before it's gone!!

214 Myers St, Cowan
201 N Hodges St, Cowan
$170,000
3 Beds ⋅ 3 Baths ⋅ 3205567 MLS ⋅ ACTIVE Status ⋅ 0.34 Acres ⋅ 37318 Zip Code
Older home, Covered Front Porch 40 X 8** Kitchen has been updated with Granite Counter Tops * Main floor features High Ceilings, Nice size Living Room, Formal Dining Rm, Eat-in Kitchen * Master bedroom on main floor * Utility Rm * Extra room downstairs 15 X 12 could be used as a 4th Bedroom, game room, office, Etc... 2nd Floor has 2 Bedrooms and a Full Bath * Crawl Space was encapsulated in 2023 and has a dehumidifier. Some windows have been replaced in 2017 * HVAC 2015 * Circuit Breaker Box installed in 2023, Please see updated Property Disc.#1 & 2 Cash or Conventional, FHA Renovation Loan or VA Renovation Loan

201 N Hodges St, Cowan
173 Country Club Ter, Winchester
$299,000
3 Beds ⋅ 3 Baths ⋅ 3198195 MLS ⋅ ACTIVE Status ⋅ 0.42 Acres ⋅ 37398 Zip Code
Lovely neighborhood! Landscaping in the flower beds to be tidied up and shrubs to be pruned. 'Selling As Is".

173 Country Club Ter, Winchester
201 W England St, Cowan
$165,900
3 Beds ⋅ 2 Baths ⋅ 3191614 MLS ⋅ ACTIVE Status ⋅ 0.25 Acres ⋅ 37318 Zip Code
**Seller will pay $4,000 in buyers closing expenses** Charming 3 bedroom, 2 bathroom home for sale in Cowan featuring a spacious layout & open living area. Situated on a desirable corner lot, this home offers a large yard and easy access to town, schools, and local amenities. Perfect for first-time homebuyers, downsizers, or investment property seekers looking for affordable living in Middle Tennessee. Enjoy small-town living with room to relax both inside and out! Freshly painted, new carpet, & new metal roof!

201 W England St, Cowan
110 Allen Dr, Winchester
$224,900
3190517 MLS ⋅ ACTIVE Status ⋅ 37398 Zip Code
Great investment property, located in cul de sac. All brick! Two units with central heating and cooling, one with a brand new unit. Large, private back yard. Located close to grocery store, shopping, restaurants, etc. Great return on your money. Both units are rented at 875.00 and 950.00.

110 Allen Dr, Winchester
810 N High St, Winchester
$245,000
3190516 MLS ⋅ ACTIVE Status ⋅ 37398 Zip Code
Great duplex in perfect location...convenient to Tims Ford lake, Twin Creeks marina and downtown Winchester! One side had an extensive overhaul in 2025. Both sides are currently rented at 975.00 each. Great return on your money! Allow 24hr showing notice to alert tenants.

810 N High St, Winchester
102 N Hodges St, Cowan
$199,000
2 Beds ⋅ 1 Baths ⋅ 3186083 MLS ⋅ ACTIVE Status ⋅ 0.17 Acres ⋅ 37318 Zip Code
Charming in-town starter home featuring a 2-car detached garage, new windows, fresh paint, and a metal roof. Efficient layout with comfortable living space and great natural light. Level lot with usable outdoor space. Centrally located near shops and dining.

102 N Hodges St, Cowan
106 N Willow St, Cowan
$255,000
3 Beds ⋅ 2 Baths ⋅ 3180787 MLS ⋅ ACTIVE Status ⋅ 0.34 Acres ⋅ 37318 Zip Code
Looking for the perfect blend of comfort and utility? This move-in-ready 3 bedroom 1.5 bathroom home offers 1215 sq. ft. of well maintained living space, ideal for first-time buyers or those looking to downsize. A ranch style with a welcoming front porch and an attached carport, Relax on your large covered back porch with the privacy of a 6 ft. wooden fence. Also incdludes, 20x20 Det Shop with electricty, fire pit, Garden shed, washer and drier, Refridgerator, Dishwasher, Stove/Oven, Concrete driveway.

106 N Willow St, Cowan
71 Oakwood Ln, Tullahoma
$150,000
4 Beds ⋅ 2 Baths ⋅ 3145574 MLS ⋅ ACTIVE Status ⋅ 1.54 Acres ⋅ 37388 Zip Code
**home sale contingency fell through** 4-bedroom, 2-bath brick home on a 1.54 acre wooded lot offering approximately 2,231 square feet. Built in 1960, the property presents a clear opportunity for investors or contractors looking for a full renovation project. The level, wooded lot provides space and privacy that is increasingly difficult to find. Recent cleanup has removed debris and cleared trees around the home, opening up the property and making it easier to evaluate. Cash or renovation financing likely required. Property is being sold as-is and the seller will make no repairs. Utilities may not be active. Enter at your own risk; some parts of the floor may not be safe to walk on. The home has recently been cleaned out and trees surrounding the house have been cleared. Updated photos reflecting these improvements will be added soon.

71 Oakwood Ln, Tullahoma
10367 Sewanee Hwy, Sewanee
$85,000
3131482 MLS ⋅ ACTIVE Status ⋅ 5 Acres ⋅ 37383 Zip Code
Public Remarks: This unique property is ready for your personal touch. Originally built by local townsmen for card games with a bluff front view of the valley below. Water and septic were never installed, but could be by new buyers. This is the perfect location for Air BNB or VRBO. The cabin sits between Cowan and Sewanee and is 5 minutes to either town. The Seller has removed all walls, ceilings, insulation, and sheetrock;(the hard part) and it is ready for your new cabin design. Paths have been cleared for walking or 4 wheelers to the back of the 5 acres. There is power run to the cabin with no breaker box, and Seller never had it turned on. AS IS Agent is related to Seller.

10367 Sewanee Hwy, Sewanee
Pleasant Grove Road, Estill Springs
$264,900
2 Beds ⋅ 1 Baths ⋅ 3049262 MLS ⋅ ACTIVE Status ⋅ 1.7000000000000002 Acres ⋅ 37330 Zip Code
The foundation is complete and the home is ready to be framed, with full construction to continue once an agreement is accepted, allowing buyers to select finishes and even modify floor plans to suit their needs. On almost two acres you could have a brand new, customizable open floor plan home. Located in the desirable area near Tims Ford Lake. Imagine this being your primary home, second home or even an investment property to store your boat and toys. There is space for a detached building, large fire pit and even a pool. Standard features include luxury vinyl plank flooring throughout, granite countertops, soft-close drawers, custom tile shower and fans in all the bedrooms. Enjoy the advantages of an energy efficient new construction. Financing available. Note: Completed photos are for reference only and do not depict the actual home. Final details subject to change based on buyer selections.

Pleasant Grove Road, Estill Springs
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