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102 Oak Park, Winchester
$269,900
2 Beds ⋅ 1 Baths ⋅ 3623676 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

1101 High St N, Winchester
$245,000
2 Beds ⋅ 1 Baths ⋅ 3620452 MLS ⋅ ACTIVE Status ⋅ 0.17 Acres ⋅ 37398 Zip Code
Just under a mile from the Winchester square, 1101 N High St is 1,292 square feet of character with a lot of updates. The living room is the showpiece, with a tongue-and-groove wood ceiling, warm wood accent walls, recessed lighting and a brick fireplace as its centerpiece. Big windows bring in light throughout, and dark wood-look floors run through the main living areas. The kitchen opens to the dining space and has white cabinetry, light stone-look counters, a wood-front peninsula with seating, a gas range and tile floors. There's a separate laundry room with its own door to the backyard, plus built-in shelving for pantry storage. Both bedrooms have ceiling fans and good closet space, and the bath has a subway-tile tub and shower. For storage, there's walk-up stair access to the attic and a basement below. Outside, the covered front porch has a wood ceiling and a swing. The back has a large privacy-fenced yard, a patio and a long gravel drive. It's a quick drive to shops and restaurants downtown and close to the lake for weekends on the water.

1101 High St N, Winchester

1110 Hunt St, Winchester
$198,000
3 Beds ⋅ 2 Baths ⋅ 3602885 MLS ⋅ ACTIVE Status ⋅ 0.3 Acres ⋅ 37398 Zip Code
Priced to Sell! Welcome home to this spacious 2,040 sq ft double-wide manufactured home on a permanent foundation! This home features large bedrooms throughout, each with a walk in closets, offering plenty of space and storage. The kitchen offers an abundance of countertop space and cabinets, along with a large island - perfect for cooking, gathering, and entertaining. This home offers generous living space and wood burning fireplace. Retreat to to the oversized primary suite, complete with a huge walk in closet and a private bath featuring a soaking tub, an 8' vanity with a dedicated makeup area, and extra storage. Enjoy the outdoors from the large concrete front porch, and take advantage of the fully fenced backyard with a 24' above ground pool- ideal for summer fun! Extra storage provides added convivence.

1110 Hunt St, Winchester

371 Myers Rd, Winchester
$294,900
3 Beds ⋅ 2 Baths ⋅ 3598640 MLS ⋅ ACTIVE Status ⋅ 0.46 Acres ⋅ 37398 Zip Code
Beautiful updates, spacious living, and classic brick charm! Welcome to 371 Myers Rd in Winchester, offering 3 bedrooms, 2 baths, and over 1,800 square feet of comfortable living space. All-new windows and fresh paint throughout give the home a bright, refreshed feel, while beautiful original hardwood floors preserve its character. The generously sized kitchen offers plenty of room for preparing meals and gathering, with a newly added pantry providing outstanding storage. Located near Tims Ford Lake, you can enjoy easy access to boating, fishing, and days on the water, along with the everyday convenience of nearby shopping, dining, and downtown Winchester. Thoughtful renovations blend fresh finishes with timeless details, creating a welcoming space ready for its next chapter. Come see the updates, explore the space, and imagine making it your own. Schedule your private showing today!

371 Myers Rd, Winchester

222 Orchard Ln, Winchester
$225,000
3 Beds ⋅ 2 Baths ⋅ 3597234 MLS ⋅ ACTIVE Status ⋅ 0.52 Acres ⋅ 37398 Zip Code
Welcome to this charming 1,344-square-foot brick ranch offering 3 bedrooms and 2 baths in a convenient Winchester location! This well-located home provides easy access to the activities and amenities that make the area so desirable, including Winchester City Park, beautiful Tims Ford Lake for boating and recreation, and historic Downtown Winchester with local dining, shopping, and the lively Square. Outside, you’ll find a spacious front and back yard with plenty of room for entertaining, relaxing, gardening, or enjoying time with family and friends. A detached metal shop/garage provides abundant space for parking, storage, hobbies, or a workshop, with plenty of room to work and create. The home also has an attached garage. With its classic brick exterior, functional floor plan, generous outdoor spaces, and detached shop/garage, this property offers both comfort and versatility in a great location close to everything Winchester has to offer! Property is Selling As Is.

222 Orchard Ln, 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

203 W Petty Ln, Winchester
$179,900
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

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

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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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