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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

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

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

76 Chase Cir, Winchester
$369,900
2 Beds ⋅ 2 Baths ⋅ 3528603 MLS ⋅ ACTIVE Status ⋅ 0.15 Acres ⋅ 37398 Zip Code
**New HVAC, water heater, gutters, granite countertops, paint carpet and like new roof** Step into over 1,800 sq. ft. of move-in ready one level condo living. Designed for both comfort and practical living, this 2-bedroom, 2-bathroom residence offers a private front foyer, a dedicated laundry room, and a sun-drenched sunroom enhanced with a newly added air duct and vent for year-round relaxation. The kitchen boasts sleek new granite countertops and a new sink, while the primary suite offers a spacious retreat complete with new primary bath granite and a newly converted walk-in shower. Every major system has been refreshed for peace of mind, featuring a brand-new HVAC system, a 3 year old roof, new 6-inch gutters, a new hot water heater, updated exterior electrical wiring, and newly replaced garage door springs. Outside, enjoy a heated and cooled back porch/sun room built for hosting family and friends, alongside an attached 2-car garage, and an inground storm shelter. Resort-style, low-maintenance living with HOA dues covering all lawn care and common grounds upkeep—including the neighborhood pool, private clubhouse, and Chase Circle road maintenance. All of this is paired with an unbeatable location under a mile from Food City, 2.5 miles from Franklin County Golf & Country Club, and less than two minutes to HWY 64 for an easy commute to Huntsville or Murfreesboro. Schedule your showing today!

76 Chase Cir, Winchester

69 Anderton Dr, Winchester
$479,900
3 Beds ⋅ 3 Baths ⋅ 3527938 MLS ⋅ ACTIVE Status ⋅ 0.05 Acres ⋅ 37398 Zip Code
Enjoy lake living in the gated Twin Creeks Village community on Tims Ford Lake, with up to $10,000 in potential buyer incentives! The seller is offering $5,000 in concessions that can be used toward closing costs and/or an interest rate buy down. This beautifully maintained, move-in-ready condo features fresh exterior paint and an open main-level floor plan with a spacious primary suite, large tile shower, and abundant closet space. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Upstairs offers two additional bedrooms plus a generous bonus area perfect for a home office, game room, media space, or additional lounge area. Relax or entertain on the screened-in back patio after a day on the lake or at one of the community’s resort-style pools. Twin Creeks Village offers multiple pools, clubhouse spaces, walking paths, and convenient access to Twin Creeks Marina and Resort, where boating, lakeside dining, and everything Tims Ford Lake has to offer are just steps away. All kitchen appliances, washer, and dryer remain and convey with the home. Whether you’re looking for a full-time residence, weekend retreat, or investment opportunity, this condo offers comfort, space, and the lake lifestyle all in one. Qualified buyers who use Sterling Smith with First Community Mortgage in Shelbyville may also receive an additional $5,000 lender credit. Contact Sterling at (931) 205-1424 or sterling.smith@fcmhomeloans.com

69 Anderton Dr, 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

416 Colonial Dr, Winchester
$335,000
3 Beds ⋅ 2 Baths ⋅ 3514992 MLS ⋅ ACTIVE Status ⋅ 0.4 Acres ⋅ 37398 Zip Code
Beautiful, well-maintained full brick home on a .40 acre corner lot. The meticulously landscaped front yard welcomes you to this wonderful home! There's attention to detail throughout this 3 bedroom, 2 full bath home. Some of the upgrades include: engineered hardwood flooring in the entry way and living room, crown molding in most of the rooms, tile in the kitchen, utility room and both bathrooms. 9 and 10 foot ceilings, Natural gas fireplace and water heater. The primary bedroom suite has a walk-in closet and easy access to the laundry room. The guest bedrooms are separated from the primary suite for privacy. The fenced backyard is perfect for entertaining, with a deck complete with a pergola, and the patio is the perfect place to grill. Attached 2 car garage. Call and schedule a showing today!

416 Colonial Dr, Winchester

401 E Petty Lane, Winchester
$350,000
3 Beds ⋅ 3 Baths ⋅ 3513357 MLS ⋅ ACTIVE Status ⋅ 0.8 Acres ⋅ 37398 Zip Code
Welcome to 401 East Petty Lane, where classic charm meets central convenience. Nestled in a peaceful neighborhood on an oversized lot, this timeless single-level ranch provides an exceptional location with effortless access to local work commutes, shopping, dining, and entertainment. Outdoor living is a delight on the private stone patio, which overlooks the expansive yard and serves as an ideal retreat for relaxing or taking in the peaceful surroundings. Step inside to discover a spacious, thoughtfully designed layout tailored for everyday living and entertaining guests. At the heart of the home, the elegantly updated chef's kitchen features sleek new appliances and granite countertops. Flowing from the kitchen are multiple living spaces, including a formal living room, a cozy den, and a bright, expansive sunroom perfect for unwinding in the afternoons. The main floor accommodates three bedrooms and two and a half bathrooms, ensuring all your daily essentials remain conveniently accessible on a single level. Adding to the home's impressive value is a full basement. Whether you are needing a works space, a gym, or hobby room this area is perfect. This space has so much potential whether you're a growing family seeking extra room, or you're a savvy buyer looking to generate passive income, this area can adapt to your needs. Complete with a second laundry hookup and an additional bathroom, transforming the lower level into a high-yield rental unit or private guest suite would be simple and straightforward.

401 E Petty Lane, Winchester

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 Road, 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 Road, 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

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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