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416 Colonial Dr, Winchester
$335,000
3 Beds ⋅ 2 Baths ⋅ 3514992 MLS
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
338 Royal Oak Dr, Winchester
$334,900
3 Beds ⋅ 2 Baths ⋅ 3545572 MLS
Privacy, space, and comfortable one-level living come together beautifully. Situated on nearly an acre surrounded by mature trees, this 3-bedroom, 2-bath home offers a peaceful setting with plenty of room to relax both inside and out. A large front porch with new Trex decking creates an inviting first impression and the perfect spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home offers a warm and functional layout featuring a separate dining room, keeping room, and a welcoming living space centered around a gas fireplace. The kitchen features maple cabinetry and tile countertops with plenty of space for everyday meal preparation and gathering. Just beyond the main living areas, the heated and cooled sunroom extends the home's usable living space year-round—ideal for relaxing, entertaining, or creating a bright home office or hobby space. The primary suite provides a comfortable retreat with separate his-and-hers walk-in closets and a private bath with a walk-in shower. Partial new carpeting adds a fresh touch throughout the home, while the included washer and natural gas dryer provide added convenience. Outside, mature trees create a wonderful sense of privacy and a peaceful backdrop for enjoying the spacious property. With nearly an acre, inviting indoor and outdoor living spaces, and a floor plan designed for comfortable everyday living,

338 Royal Oak Dr, Winchester
117 Carol Cir, Winchester
$330,000
3 Beds ⋅ 2 Baths ⋅ 3544164 MLS
3 BR, 2 bath home, all on a 1/2 acre in desirable neighborhood! Hardwood floors in main area and main bedroom. With beautiful cabinetry in the kitchen, stainless appliances and a 6-burner stove. Large jack/jill bath w/double vanities and walk-in closets throughout each bedroom of the house. Large master bedroom, with a huge closet, double vanity sink, tile shower, and large whirlpool tub. Backyard fenced for privacy; Storage building does convey. Come check out this must see home, and make an offer! Home is vacant and can be easily shown!

117 Carol Cir, Winchester
667 Maple Bend Rd, Winchester
$320,000
2 Beds ⋅ 2 Baths ⋅ 3168548 MLS
Close to the Fairview Boat Ramp.Fantastic 3.5 acres with mature trees, abundant wildlife, and privacy. Property extends 75 feet into woods. Room for a Garden or a Mini Farm Home is a 2 bedroom 1.5 half baths. Original Septic Permit is for a 3 Bedroom home. Room to Expand. New Roof and HVAC. 30x30 Detached Garage/shop with Wood Burning Stove or use the Propane Heater. 2 Metal Sheds for Storage. Seller willing to give a Carpet Allowance or Negotiate Price. Close to Town and Lake. Easy to Show, Just Don't let Cat Out. Motivated Sellers.

667 Maple Bend Rd, Winchester
1543 Paynes Church Rd, Winchester
$315,000
3 Beds ⋅ 2 Baths ⋅ 3256592 MLS
BRAND NEW! ONE LEVEL, 3BD | 2BTH home LVP flooring throughout, NO CARPET OR STAIRS! ideal for easy maintenance! The kitchen features custom cabinetry, and SS kitchen appliances with brush nickel finishes. Open Concept layout & split bedroom floorplan- providing added privacy to the primary suite. This large yard offers plenty of space to host BBQ's, Garden or let the pups run & play! Take in the idyllic country setting & enjoy the fresh air from your covered front porch! Schedule your showing today! No HOA or Restrictions!

1543 Paynes Church Rd, Winchester
1605 Paynes Church Rd, Winchester
$315,000
3 Beds ⋅ 2 Baths ⋅ 3256595 MLS
BRAND NEW! ONE LEVEL, 3BD | 2BTH home LVP flooring throughout, NO CARPET OR STAIRS! ideal for easy maintenance! The kitchen features custom cabinetry, and SS kitchen appliances with brush nickel finishes. Open Concept layout & split bedroom floorplan- providing added privacy to the primary suite. This large yard offers plenty of space to host BBQ's, Garden or let the pups run & play! Take in the idyllic country setting & enjoy the fresh air from your covered front porch! Schedule your showing today! No HOA or Restrictions!

1605 Paynes Church Rd, Winchester
1585 Paynes Church Rd, Winchester
$315,000
3 Beds ⋅ 2 Baths ⋅ 3256588 MLS
BRAND NEW! ONE LEVEL, 3BD | 2BTH home LVP flooring throughout, NO CARPET OR STAIRS! ideal for easy maintenance! The kitchen features custom cabinetry, and SS kitchen appliances with brush nickel finishes. Open Concept layout & split bedroom floorplan- providing added privacy to the primary suite. This large yard offers plenty of space to host BBQ's, Garden or let the pups run & play! Take in the idyllic country setting & enjoy the fresh air from your covered front porch! Schedule your showing today! No HOA or Restrictions!

1585 Paynes Church Rd, Winchester
1563 Paynes Church Rd, Winchester
$315,000
3 Beds ⋅ 2 Baths ⋅ 3256590 MLS
BRAND NEW! ONE LEVEL, 3BD | 2BTH home LVP flooring throughout, NO CARPET OR STAIRS! ideal for easy maintenance! The kitchen features custom cabinetry, and SS kitchen appliances with brush nickel finishes. Open Concept layout & split bedroom floorplan- providing added privacy to the primary suite. This large yard offers plenty of space to host BBQ's, Garden or let the pups run & play! Take in the idyllic country setting & enjoy the fresh air from your covered front porch! Schedule your showing today! No HOA or Restrictions!

1563 Paynes Church Rd, Winchester
2121 Bible Crossing Rd, Winchester
$309,000
3 Beds ⋅ 2 Baths ⋅ 3630032 MLS
This 3 bed 2 bath home has so many great features. It starts with an open concept for your living room and completely remodeled kitchen, that also connects to your large covered back porch. If you go upstairs, you have a full bathroom in the hallway that has also been remodeled. Further down the hall, you have 2 good sized bedrooms, and then your primary bedroom with it's own full bathroom and shower. Downstairs you have a laundry room, a nice flex room, and your connected garage. Outside the home, you have a paved driveway with plenty or parking that also connects to the 20x30 shop with electricity and a garage door opener. You have a privacy fence that faces the main road, with a gate large enough for a truck, boat, or trailer, and then a chain link fence for the rest of the back yard. In the back yard you have an above-ground pool that will remain with the home, decking for that pool, a metal storage shed, a nice carport, and access to the connected Florida room. Schedule your showing today!

2121 Bible Crossing Rd, Winchester
115 7th Ave Ne, Winchester
$309,000
3 Beds ⋅ 2 Baths ⋅ 3529508 MLS
Incredible renovation in prime location! So close to Clark Elementary and situated in a wonderful part of town surrounded by beautiful homes with a partial views of the water. This home really has it all - 3 bedrooms, 2 full bathrooms, plus a newly remodeled flex room that can be a home office, den, or playroom. Newer roof with a BRAND NEW kitchen with new cabinets, countertops, and appliances, beautiful real hardwood floors just refinished professionally by Hanger's Hardwood, new bathrooms, fresh paint, new light fixtures, too much to list! Attached 2 car carport with a shed in the back.New bathroom has modern vanity with tile shower.

115 7th Ave Ne, Winchester
400 Cessna Cir, Winchester
$309,000
5 Beds ⋅ 3 Baths ⋅ 3241949 MLS
5 Bedroom 3 Bath home with 2218 sqft. Great Sunroom overlooking the pool and fully fenced backyard. The largest downstairs bedroom already has connections for a kitchenette, and could easily be converted to a full apartment with a separate entrance. Utility building with electricity. Sold with all appliances. Single basement garage and double carport. Storm/safe room 6x8 concrete with steel door. Pool is functional just winterized.

400 Cessna Cir, Winchester
260 Union Rd, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 3593690 MLS
Seller will pay up to $15,000 in closing costs, prepaids, buy downs, etc. Great location close to Tim's Ford Marina and golf course. New construction!!! House features open floor plan with great room, kitchen, dining area, 3 bedrooms, 2 baths, utility, covered porch and rear patio.

260 Union Rd, Winchester
220 Union Rd, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 3593692 MLS
Seller will pay up to $15,000 in closing costs, prepaids, buy downs, etc. Great location close to Tim's Ford Marina and golf course. New construction!!! House features open floor plan with 3 bedrooms, 2 baths, covered porch and rear patio on large lot.

220 Union Rd, Winchester
206 Homeward Ave, Winchester
$299,900
4 Beds ⋅ 2 Baths ⋅ 3543108 MLS
Space, style, and valuable extras—this beautifully maintained home has it all! Enjoy hardwood floors, fresh paint, updated lighting, multiple living areas, and flex space. The fourth bedroom can easily serve as a media room, guest suite, or additional living area. All kitchen appliances remain, along with the washer, dryer, and storage shed. Outside, relax on the screened-in patio, enjoy sunrise coffee or sunset evenings, and make the spacious yard your own. Conveniently located near historic downtown Winchester, the hospital, and Tims Ford Lake! Buyers and buyer's agents verify all pertinent information.

206 Homeward Ave, Winchester
266 Woods Edge Rd, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 3305852 MLS
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
99 N Shephard St, Winchester
$295,999
3 Beds ⋅ 2 Baths ⋅ 3231532 MLS
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
371 Myers Rd, Winchester
$294,900
3 Beds ⋅ 2 Baths ⋅ 3598640 MLS
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
1200 Little St, Winchester
$289,000
5 Beds ⋅ 2 Baths ⋅ 3278665 MLS
--- 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! Appliance credit could be considered with acceptable offer.

1200 Little St, Winchester
801 S High St, Winchester
$279,900
3 Beds ⋅ 2 Baths ⋅ 3305185 MLS
Move-in ready with charm, space, and versatility. This beautifully refreshed home has been updated with fresh paint throughout, new light fixtures, and fresh landscaping. The spacious primary bedroom features vaulted ceilings and natural lighting. A brand new water heater and included washer and dryer add convenience for the new owner. Step outside to enjoy the large, beautiful backyard, perfect for entertaining, gardening, or simply relaxing. The detached mother-in-law suite with its own screened in porch offers endless possibilities-- ideal for guests, extended family, or home office. This home is conveniently located minutes from town and a short distance to the Winchester Square.

801 S High St, Winchester
173 Country Club Ter, Winchester
$279,000
3 Beds ⋅ 3 Baths ⋅ 3198195 MLS
Lovely neighborhood! Landscaping in the flower beds to be tidied up and shrubs to be pruned. 'Selling As Is".

173 Country Club Ter, Winchester
23 Woods Edge Rd, Winchester
$275,000
3 Beds ⋅ 2 Baths ⋅ 3259669 MLS
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
102 Oak Park, Winchester
$269,900
2 Beds ⋅ 1 Baths ⋅ 3623676 MLS
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
114 Hillcrest Dr, Winchester
$264,900
3 Beds ⋅ 2 Baths ⋅ 3599190 MLS
Welcome home to this beautiful 3br 2ba home located in a nice, established neighborhood! This home features beautiful HW flooring, a new roof, and a welcoming covered front porch for that morning coffee. Inside you will find a spacious layout with a huge kitchen offering plenty of room for entertainment, cooking, and gatherings of family and friends. The sunroom provides a wonderful added space to relax and enjoy natural light year round. This home is a must see!!

114 Hillcrest Dr, Winchester
300 Edgewater Dr, Winchester
$250,000
3 Beds ⋅ 2 Baths ⋅ 3615203 MLS
Tims Ford Lake opportunity in Winchester! This 3-bedroom, 2-bath ranch offers approximately 1,552 sq. ft. on approximately 0.54 acres with plenty of potential for the buyer ready to make it their own. Features include hardwood flooring, spacious living areas, an attached garage/carport area, and a generous yard in the Rogers Haven community. Selling AS-IS. Buyer to independently verify any TVA dock/shoreline permit eligibility. Some listing photos have been digitally enhanced to remove personal belongings; the home’s permanent features and current condition should be verified in person.

300 Edgewater Dr, 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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