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105 Wilson St, Cowan
$449,900
4 Beds ⋅ 3 Baths ⋅ 3510860 MLS ⋅ ACTIVE Status ⋅ 0.26 Acres ⋅ 37318 Zip Code
Charm, character, and craftsmanship all under one roof! This distinctive 4-bedroom, 2.5-bath home offers over 2,300 sq. ft. of thoughtfully designed living space with details you simply don’t find in every home. Beautiful hardwood floors, abundant natural light, custom woodwork, and built-ins create warmth and character throughout. The spacious kitchen features generous cabinetry, an island, and plenty of room for gathering. Flexible living spaces offer options for a home office, guest space, or everyday living, while the updated primary bath adds both style and function. One of the property’s standout features is the approximately 600 sq. ft. screened pavilion - an incredible extension of the home for morning coffee, outdoor dining, entertaining friends, or game days. Established landscaping and mature trees complete the setting. Conveniently located in Cowan, approximately 10 minutes from Sewanee’s central campus and 15 minutes from Winchester, with easy access to dining, shopping, Tims Ford Lake, and everything the mountain area has to offer. A wonderful option for a full-time residence, second home, or weekend retreat.

105 Wilson St, Cowan

312 Harris Chapel Rd, Estill Springs
$350,000
4 Beds ⋅ 3 Baths ⋅ 3510726 MLS ⋅ ACTIVE Status ⋅ 1.3 Acres ⋅ 37330 Zip Code
Discover this inviting home on 1.28+/- acres just outside city limits, only minutes from Tims Ford Lake. Bask in natural light from the Florida Sunroom, sip coffee on the spacious front porch, and enjoy plenty of room to play in the large yard. Pecan trees, roses, Yucca plants, muscadine vine (golden and blue varieties) is mature for making wine, jams & jellies to name a few of the beautiful landscaping touches. From the tall crepe myrtles to the shady driveway this home has potential. The attached 2-car garage, plus a detached shop and carport, offers abundant space for vehicles, hobbies, storage, or a workshop. With endless potential and a peaceful, convenient location, this property is ready for your personal touch. Don’t miss this rare opportunity - schedule your showing today!

312 Harris Chapel Rd, Estill Springs

77 Kentucky Ave, Sewanee
$499,900
3 Beds ⋅ 2 Baths ⋅ 3509975 MLS ⋅ ACTIVE Status ⋅ 0.69 Acres ⋅ 37375 Zip Code
Nestled directly within the iconic grounds of the University of the South, 77 Kentucky Ave offers a rare opportunity to own a piece of Sewanee’s storied landscape. This classic brick ranch combines the ease of single-level living with the unmatched prestige of a campus location, making it a standout find for those who value both tradition and versatility. The main residence spans 1,400 square feet, featuring three comfortable bedrooms and two full bathrooms. Windows invite an abundance of natural light into the living spaces, creating an atmosphere that is both bright and grounded. Outside, the expansive yard provides a lush, open canvas for gardening or hosting gatherings. The true jewel of this property is the detached 660-square-foot guesthouse. Complete with its own full kitchenette and a full bathroom, this secondary dwelling is a flexible space that’s hard to find. Whether you envision it as a sophisticated home office, a creative studio, or a private retreat for visitors, it adds incredible value and functionality to the estate. Living on the mountain means being part of a unique, vibrant community where world-class lectures, scenic trails, and collegiate charm are just beyond your doorstep. Properties on the University leasehold are a rarity; 77 Kentucky Ave is your chance to step into the heart of it all.

77 Kentucky Ave, Sewanee

1012 Hunt St, Winchester
$325,000
3509952 MLS ⋅ ACTIVE UNDER CONTRACT Status ⋅ 37398 Zip Code
Investors, take notice! 1012/1014 Hunt St, Winchester, TN! This new-construction duplex offers an excellent opportunity to add a modern, low-maintenance property to your portfolio in a convenient Winchester location. Each unit features 2 bedrooms and 2 full bathrooms, an attractive floor plan for renters seeking comfortable, functional living space. Both units offer desirable modern finishes, including LVP flooring, custom cabinets, and private patios. New construction means today's finishes and fewer immediate maintenance concerns, making this property an appealing option for both seasoned investors and those looking to expand their rental portfolio. Conveniently located just minutes from downtown Winchester, Nissan, shopping, dining, and other everyday amenities, the property offers easy access to Nissan and other lifestyle destinations—an important advantage for attracting and retaining tenants. With two separate units, modern construction, desirable 2BR/2BA layouts, and a convenient location, this duplex presents a strong opportunity for investors seeking a turnkey-style rental property in the Winchester market. Some photos have been virtually enhanced to completion for illustrative purposes only. Actual photos are also included. Final finishes and details may vary. Buyer/buyer’s agent to verify all pertinent information.

1012 Hunt St, Winchester

112 Short St, Winchester
$310,500
3509953 MLS ⋅ ACTIVE UNDER CONTRACT Status ⋅ 37398 Zip Code
Investors, take notice! 112/114 Short St Winchester, TN! This new-construction duplex offers an excellent opportunity to add a modern, low-maintenance property to your portfolio in a convenient Winchester location. Each unit features 2 bedrooms and 2 full bathrooms, an attractive floor plan for renters seeking comfortable, functional living space. Both units offer desirable modern finishes, including LVP flooring, custom cabinets, and private patios. New construction means today's finishes and fewer immediate maintenance concerns, making this property an appealing option for both seasoned investors and those looking to expand their rental portfolio. Conveniently located just minutes from downtown Winchester, Nissan, shopping, dining, and other everyday amenities, the property offers easy access to Nissan and other lifestyle destinations—an important advantage for attracting and retaining tenants. With two separate units, modern construction, desirable 2BR/2BA layouts, and a convenient location, this duplex presents a strong opportunity for investors seeking a turnkey-style rental property in the Winchester market. Some photos have been virtually enhanced to completion for illustrative purposes only. Actual photos are also included. Final finishes and details may vary. Buyer/buyer’s agent to verify all pertinent information.

112 Short St, Winchester

12571 Old Tullahoma Rd, Tullahoma
$275,000
3 Beds ⋅ 2 Baths ⋅ 3509894 MLS ⋅ ACTIVE Status ⋅ 0.75 Acres ⋅ 37388 Zip Code
If you've been searching for a home where all the hard work has already been done, this one deserves a spot at the top of your list! Sitting on approximately .75 acres just outside the Tullahoma city limits, you'll enjoy the convenience of being only minutes from both Tullahoma and Winchester while still having room to spread out and enjoy your own space. This home has been completely renovated from top to bottom, making it an easy choice for a first-time home buyer, someone looking to downsize without giving up space, or anyone wanting a move-in-ready home. Step inside and you'll immediately notice the spacious layout and split bedroom design, giving everyone a little extra privacy. The heart of the home is the beautifully updated kitchen with plenty of cabinet space, modern finishes, and room for family dinners, holiday gatherings, or simply enjoying your morning coffee. The updated bathroom continues the fresh, clean feel found throughout the home. Big-ticket items? Already taken care of! Enjoy peace of mind with a new roof, new windows, and a new water heater. The HVAC is approximately six years old, has been recently serviced, and is working great. Outside, you'll find a large yard with endless possibilities. Whether you want a garden, a place for kids or pets to play, or room for your next backyard cookout, you'll have the space to make it your own. The storage shed stays, giving you even more storage space. Finding a home with this much square footage, this many updates, and this great of a location isn't easy. It's comfortable, functional, and ready for its next chapter. All that's missing is you. Come take a look and see why this one feels like home.

12571 Old Tullahoma Rd, Tullahoma

218 Charlotte Dr, Winchester
$488,000
4 Beds ⋅ 3 Baths ⋅ 3501421 MLS ⋅ ACTIVE Status ⋅ 0.46 Acres ⋅ 37398 Zip Code
Beautifully Maintained Home With Space, Comfort, and Incredible Extras! Pride of ownership shines throughout this very-well maintain 4-bedroom, 3-bath home located in a wonderful, established neighborhood. Offering a thoughtfully designed layout with plenty of space and flexibility, this home features a main level primary suite, plus an additional upstairs primary suite/bonus room. Perfect for guests, extended family, or multi-generational living. The spacious kitchen is made for those who love to cook and entertain featuring double ovens, a large gas range, a walk-in pantry, and an abundance of cabinetry. Charming details such as a clawfoot tub add character and personality. Step outside and enjoy the screened-back patio, an ideal spot for morning coffee or relaxing evenings. Car enthusiasts, hobbyists, and RV owners will appreciate both an attached and detached garage, along with 30 and 50 amp hookups and a dedicated septic connection for a motorhome. Major improvements and thoughtful upgrades add even more value, including a new roof in 2020, Leafguard gutter system, a new hot water heater, and automatic crawl space vents. With generous living space, excellent storage, multiple garage options, RV accommodations, and so many well-planned features, this home offers the perfect combination of comfort, convenience, and versatility.

218 Charlotte Dr, Winchester

1522 Holders Cove Rd, Winchester
$350,000
3 Beds ⋅ 2 Baths ⋅ 3501390 MLS ⋅ ACTIVE Status ⋅ 1.45 Acres ⋅ 37398 Zip Code
Welcome to 1522 Holders Cove Road, a truly unique, fully updated, single-level ranch offering a new roof installed in 2025 and backyard paradise that embodies the American dream. Situated on nearly 1.5 private acres, this move-in-ready home offers the ideal blend of peaceful privacy and everyday convenience, located just minutes from downtown Winchester's shopping, dining, and local attractions. Inside, you will discover a thoughtful and efficient layout designed for modern living. The bright, open living area welcomes you with abundant natural light and flows seamlessly into a tastefully updated kitchen with new appliances. A dedicated home office and a separate laundry room provide a rare level of everyday functionality. The primary suite serves as a true retreat, complete with a spa-like ensuite bathroom, while two additional bedrooms and a stylish full guest bath ensure everyone has plenty of room to spread out. Step through the back door into your personal outdoor paradise. The current owners spared no expense curating a beautifully landscaped backyard experience. You can entertain guests effortlessly on the expansive patio featuring a cozy fire pit, or follow the stone footpath to the custom raised garden beds. The back yard finale is the custom water feature and pristine koi pond, complete with its own private sun deck for relaxing afternoons. Don't miss your chance to own this extraordinary property in Winchester, TN. Call today to schedule your private tour.

1522 Holders Cove Rd, Winchester

262 Crimson Dr, Winchester
$449,000
3 Beds ⋅ 2 Baths ⋅ 3322405 MLS ⋅ ACTIVE Status ⋅ 0.69 Acres ⋅ 37398 Zip Code
ATTN: Sellers are offering $10,500 to buyers for a 2-1 buydown on interest rates with an accepted offer!! (Ex. If interest rates are currently 7.5%, then your first year rate would be 5.5% and 2nd year interest would be 6.5%) That is a game changer for buyers! Or buyers can use the money toward their closing costs or whatever they choose. Welcome home to this beautiful brick ranch 3-bedroom, 2-full-bath brick home situated on a spacious 0.7-acre lot in a quiet, established subdivision in a great location. Featuring a desirable split-bedroom floor plan, this property offers the perfect blend of privacy, comfort, and convenience. The primary bedroom is a true sanctuary, featuring 252' sq ft of space with a large walk-in closet plus a convenient second closet for ample storage. For mealtime or entertaining guests the house features a separate dining room, bar space in the kitchen and an eat-in breakfast area right in the kitchen. Sunlit Florida Room: The large Florida room offers seamless indoor-outdoor transition with direct access from both the main living room and the primary bedroom. The expansive 0.7-acre yard provides a beautiful, serene backdrop perfect for outdoor gatherings, gardening, or weekend relaxation. Enjoy peace of mind knowing the roof is only 4 years old, and the HVAC system was replaced just 6 years ago. Winchester is positioned in a highly sought-after area of Southern Middle Tennessee, and you are just minutes away from everything Winchester has to offer: Historic downtown Winchester shopping and dining; Winchester City Park; local medical facilities; pristine waters and recreation at Tims Ford Lake. This move-in-ready gem truly is a must-see to fully appreciate all of its fine details. Schedule your private tour today before it's gone! (HVAC 2020; Roof 2022)

262 Crimson Dr, Winchester

1111 Holders Cove Rd, Winchester
$354,900
3 Beds ⋅ 2 Baths ⋅ 3320086 MLS ⋅ ACTIVE Status ⋅ 0.928 Acres ⋅ 37398 Zip Code
**Double lot with large shop** This beautiful, well-maintained brick home is convenient to everywhere - less than 1.5 miles from downtown Winchester - a mile from the Country Club -1.2 miles from the Hospital and 2 miles from Food City! It's perfectly positioned on a desirable corner lot and includes a second lot as well! Offering 3 bedrooms and 1.5 baths, this home combines timeless charm with clear pride of ownership throughout. A sizeable living room with an eat-in kitchen or separate dining area and wonderful florida room ready for entertaining. The property includes a single car attached garage and carport and a 30 x 40 detached double door garage with it's own small carport..perfect for a woodworking shop or lake toys or whatever your heart desires. Both the shop and home have metal roofs and a circular drive enters both. This well cared for home is ready for the updates you desire or could be move-ready for the young buyer!

1111 Holders Cove Rd, Winchester

145 Edgewood Ln, Winchester
$209,900
3 Beds ⋅ 2 Baths ⋅ 3319920 MLS ⋅ ACTIVE Status ⋅ 3.11 Acres ⋅ 37398 Zip Code
Opportunity Awaits! Situated on 3.12± acres spanning two lots, this 3-bedroom, 2-bath home offers a peaceful setting with plenty of room to enjoy country living or create your dream property. The home is nicely positioned on the land and features a spacious yard surrounded by mature trees. A standout feature is the large detached shop, complete with electricity and water, making it ideal for storage, hobbies, a workshop, or small business use. The property is being sold As-Is, presenting an excellent opportunity for investors, renovators, or buyers looking to add their personal touch. Please use caution when viewing the front deck, as it is in need of repair. With acreage, a functional shop, and endless possibilities, this property is ready for its next owner to unlock its full potential.

145 Edgewood Ln, Winchester

525 Sharp Springs Rd, Winchester
$220,000
2 Beds ⋅ 2 Baths ⋅ 3318900 MLS ⋅ ACTIVE Status ⋅ 0.43 Acres ⋅ 37398 Zip Code
Whether you're buying your very first home, looking to simplify life with less maintenance, or searching for the perfect vacation retreat, this charming 2-bedroom, 2-bath home checks every box. Thoughtfully designed with comfortable living spaces and a functional layout, this home offers the perfect balance of convenience and comfort. Its unbeatable location near Tims Ford Lake and Twin Creeks Marina makes it easy to spend your weekends boating, fishing, dining, or simply enjoying everything lake life has to offer. For first-time homebuyers, it's an affordable opportunity to begin building equity in a desirable location. For those ready to downsize, it provides the ease of low-maintenance living without sacrificing comfort. And for investors, its proximity to one of Middle Tennessee's most sought-after lake destinations makes it an excellent opportunity as a short-term rental or weekend getaway. Whether you're looking for a place to call home or a smart investment with year-round appeal, this property offers endless possibilities in a location you'll love.

525 Sharp Springs Rd, Winchester

Aedc Lakeview Rd, Estill Springs
$405,000
3 Beds ⋅ 2 Baths ⋅ 3318452 MLS ⋅ ACTIVE Status ⋅ 0.81 Acres ⋅ 37330 Zip Code
Build your dream home from the ground up on AEDC Lakeview Lot 2! Priced at $405,000, this to-be-built home gives you the opportunity to personalize many of the finishes to match your style. Buyers can choose from 7 siding colors, 7 interior paint colors, 7 flooring options, 5 cabinet colors, 5 countertop selections, and 5 brick colors, making it easy to create a home that feels uniquely yours. Looking for extra space? A 30x30 detached shop can be added for an additional $40,000, providing plenty of room for hobbies, storage, or a workshop. Don’t miss your chance to build a brand-new home in the desirable AEDC Lakeview community. Secure your lot today and start customizing your future home!

Aedc Lakeview Rd, Estill Springs

60 Lightning Bug Ln, Sewanee
$449,000
3 Beds ⋅ 2 Baths ⋅ 3315997 MLS ⋅ ACTIVE UNDER CONTRACT Status ⋅ 1.09 Acres ⋅ 37375 Zip Code
Serene Mountain Retreat | Minutes from the University of the South Tucked away in a tranquil wooded setting, this beautifully designed home offers over 1,500 sq ft of bright, airy, open-concept living. An abundance of oversized windows floods the main living space with natural light, bringing the peaceful beauty of the surrounding forest inside. The light-filled interior features an intuitive open floor plan, highlighted by stylish concrete countertops in the kitchen—perfect for cooking and entertaining. Step outside to relax on the classic stained concrete front porch, or retreat to the spacious screened-in back porch to enjoy quiet mountain evenings without the bugs. Additional amenities include an attached garage and a fenced-in backyard, offering a safe, secure space for pets to roam freely. Located just a 10-minute drive from the heart of Sewanee and the University of the South, this versatile home is ideal as a primary residence, a seasonal getaway, or an income-producing opportunity as a short- or long-term rental. Schedule your tour today to experience this private retreat!

60 Lightning Bug Ln, Sewanee

1601 Old Estill Springs Rd, Tullahoma
$450,000
3 Beds ⋅ 3 Baths ⋅ 3311983 MLS ⋅ ACTIVE Status ⋅ 0.43 Acres ⋅ 37388 Zip Code
Stunning Modern Farmhouse with High-End Finishes and NO HOA! Step into this gorgeous new construction home that blends timeless charm with luxury design. You’ll find quartz countertops throughout, a stylish marble backsplash, elegant gold fixtures, and designer lighting. The kitchen features soft-close cabinetry, a farmhouse sink, and sleek black stainless steel appliances. Every bedroom showcases trey ceilings, while the primary suite includes an oversized closet, a spa-inspired tile shower, and a standalone soaking tub. The secondary bedrooms are connected by a convenient Jack-and-Jill style bath. A spacious laundry room includes built-in storage, folding space, and a half bath for added functionality. Outside, enjoy the warmth of wood-accented trim and ceilings on both the inviting front and expansive back porches. Upscale exterior lighting and full landscaping add to the home’s curb appeal. Located near Tullahoma’s shopping and dining hubs and zoned for Tullahoma High School, this home offers the perfect combination of comfort and convenience. Don’t miss your opportunity to see this exceptional property—schedule your showing today!

1601 Old Estill Springs Rd, Tullahoma

404 S Jefferson St, Winchester
$228,000
2 Beds ⋅ 2 Baths ⋅ 3306656 MLS ⋅ ACTIVE UNDER CONTRACT Status ⋅ 0.39 Acres ⋅ 37398 Zip Code
This property has so much to offer... Updated kitchen with stainless range. Tankless water heater recently installed. Primary bathroom added with walk-.in shower and large walk-in closet. Walk-in tub in hall bath, expandable attic space with framing already completed. Huge rocking chair front porch. Private covered back deck, and a fantastic 28x44 detached 3 car garage with (2) 220 outlets, 3 garage doors and a heated and cooled workshop area with bathroom and shower. Additional storage over garage. The beautiful backyard is partially fenced with assorted ornamental trees. All measurements approx. & are not guaranteed. Buyer to verify all pertinent information to include school zones, utilities, etc. Property selling As/Is

404 S Jefferson St, Winchester

266 Woods Edge Rd, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 3305852 MLS ⋅ ACTIVE Status ⋅ 0.27 Acres ⋅ 37398 Zip Code
Welcome to your forever haven - where comfort meets timeless charm. Step inside to vaulted ceilings with exposed beam, a ceiling fan, and rich finished wood floors that flow seamlessly into the living area. Cozy up by the natural gas fireplace or open the dining room's double doors to a sun-drenched three-season room - your retreat for morning coffee or evening breezes. The kitchen is sure to please: granite countertops, stainless steel appliances, and a clever movable bar that expands your entertaining space at a moment's notice. The master suite offers a peaceful escape with wood floors, walk-in closet, ceiling fan, and a full bath. The second bedroom - currently a den/study - opens to the patio, perfect for a home office or guest hideaway. Bedroom three also features wood floors, a ceiling fan, and its own full bath with vinyl flooring and linen closet. But it's what you can't see that sets this home apart: French drains for peace of mind, a tankless gas water heater (2021), a new central unit motor (2023), reinforced walls and floors, and an AFS-encapsulated crawl space with a dehumidifier. Blinds and kitchen appliances stay. Must See!

266 Woods Edge Rd, Winchester

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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.

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