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Winchester, TN Homes for Sale under $400,000

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  • /49

    $354,900

    • 2 Beds
    • 2 Baths
    • 1,701 Sq Ft

    362 Chase Cir, Winchester, TN 37398

    Occupied Home. Must have a 24 hour notice. Beautifully Updated 2-Bedroom Condo in Fox Run Estates! Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the desirable Fox Run Estates—offering 1,700 square feet of thoughtfully designed living space. From the moment you arrive, you’ll appreciate the fresh landscaping and brand-new flooring that elevate this move-in ready home. Step

    Agent Photo

    John Peck

    Peck Realty Group, LLC

    (931) 277-6487

    362 Chase Cir, Winchester, TN 37398
  • /44

    $349,900

    • 4 Beds
    • 2 Baths
    • 3,888 Sq Ft

    311 N Jefferson St, Winchester, TN 37398

    Step into timeless charm with this stunning 1923 historic brick home located just off the Downtown Winchester square. Offering 3,888 square feet of space, this well-kept beauty blends vintage character with everyday comfort. You’ll fall in love with the large covered porch, perfect for relaxing, and the grand staircase that makes a statement in the heart of the home. Inside, original hardwood

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 458-1256

    311 N Jefferson St, Winchester, TN 37398
  • /20

    $305,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    383 Strawberry Dr, Winchester, TN 37398

    Welcome to this well-maintained, move in ready, 3 bedroom, 2 full bath home situated on a full one-acre lot, offering space, privacy, and outdoor enjoyment. The fully fenced backyard is perfect for entertaining and everyday living, featuring a swimming pool, fire pit, and play set. Enjoy relaxing or hosting gatherings on the covered concrete patio, ideal for year-round use. There is a 50 amp

    Aubrey Layne Century 21 Coffee County Realty & Auction

    383 Strawberry Dr, Winchester, TN 37398
  • /32

    $363,899

    • 3 Beds
    • 1.5 Baths
    • 1,812 Sq Ft

    1445 Georgia Crossing Rd, Winchester, TN 37398

    This stunning Franklin County, Tennessee, country home, originally built in 1912, has undergone a complete modernization while retaining its rustic 1900s charm! The exterior boasts new windows, updated trim, and a new front door, while the interior has been virtually gutted and completely redone with a new HVAC system, flooring, updated ceiling heights, and beautiful wooden staircase accents.

    Brian Whitt Arrowhead Land Company

    1445 Georgia Crossing Rd, Winchester, TN 37398
  • /24

    $314,000

    • 5 Beds
    • 3 Baths
    • 2,218 Sq Ft

    400 Cessna Cir, Winchester, TN 37398

    5 Bedroom home on largest lot in Airport Acres. The largest downstairs bedroom already has connections for a kitchenette, and could easily be converted to a full apartment. Fully fenced rear yard. Utility building with electricity. Sold with all appliances. Single basement garage and double carport. Storm/safe room 6x8 concrete with steel door.

    Mark Ryder Benchmark Realty, LLC

    400 Cessna Cir, Winchester, TN 37398
  • /23

    $327,900

    • 3 Beds
    • 2.5 Baths
    • 1,358 Sq Ft

    105 N Shephard St, Winchester, TN 37398

    “Behind Blue Eyes" is the tranquil retreat you have been looking for... Located within walking distance of Downtown Winchester, and just 1.5 miles from Tims Ford Lake, this 3 bedroom 2.5 bathroom bungalow in Terrapin Station truly has all of the details and finishes. The spacious living room leads into the open kitchen/dining area. The kitchen includes new stainless appliances and quartz

    Ashley Nelson Franklin County Realty

    105 N Shephard St, Winchester, TN 37398
  • /40

    $325,000

    • 3 Beds
    • 2 Baths
    • 2,053 Sq Ft

    209 Franklin Park, Winchester, TN 37398

    COMPLETELY UPDATED AND PRICED TO SELLl! This beautifully renovated, all-brick home offers timeless charm paired with sophisticated modern upgrades throughout. Thoughtfully redesigned from top to bottom, the home features a new roof, new windows, doors, and custom trim work, refinished hardwood floors, and new LVP/LVT flooring that blend durability with refined style. Major mechanical updates

    Hannah Monilaw Better Homes & Gardens Real Estate Heritage Group

    209 Franklin Park, Winchester, TN 37398
  • /55

    $388,000

    • 4 Beds
    • 2.5 Baths
    • 2,472 Sq Ft

    500 Golf Shores Dr, Winchester, TN 37398

    Premier Location!! Golf Shores Dr is a very quite street that ends in a cul-de-sac. approximately one mile from Tim's Ford State Park, only minutes from Bear Trace Golf Course, 3 marina's and multiple boat ramps. Concrete drive and a two car/boat carport! Spend those hot summer days enjoying the above ground pool! The large deck area is great place for entertaining offering a view of the forest

    Elsie (Marie) Ferguson Sewanee Realty

    500 Golf Shores Dr, Winchester, TN 37398
  • /39

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft

    247 Golf Shores Dr, Winchester, TN 37398

    Motivated Seller says bring an offer! Charming Craftsman-style home just minutes from Tims Ford Lake and Tims Ford State Park/Bear Trace Golf Course. This 3-bedroom, 2-bath home features an inviting open floor plan with cathedral ceilings, a modern kitchen with quartz countertops and SS Appliances, and a spacious living area perfect for entertaining. Enjoy the outdoors with a fenced yard, deck

    Teresa Young WEICHERT, REALTORS Joe Orr & Associates

    247 Golf Shores Dr, Winchester, TN 37398
  • /61

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft

    103 Lisa Cir, Winchester, TN 37398

    Popular Tims Ford Lake neighborhood with access to a community lot with a dock. $25.00 Yearly fee for access to the community lake lot and boat dock for day use. Minutes from Down town Winchester and shopping areas.

    Sharon Swafford Swaffords Property Shop

    103 Lisa Cir, Winchester, TN 37398
  • /26

    $394,000

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    295 Metcalf Rd, Winchester, TN 37398

    Price Reduced to $394,000,,,,,, Tucked within the peaceful Winchester Springs Community, this refreshed brick home feels like a modern retreat in the countryside. Surrounded by open fields in front and back, it offers privacy, calm and endless views. The secluded primary suite provides a quiet escape with its spa-like walk-in shower and spacious closet. Cathedral ceilings soar above the open

    Jerry Shelton Shelton Auction and Realty

    295 Metcalf Rd, Winchester, TN 37398
  • /49

    $389,900

    • 3 Beds
    • 2 Baths
    • 2,101 Sq Ft

    657 Country Club Ln, Winchester, TN 37398

    Charming, well-maintained 3-bedroom, 2-bath home on Country Club Lane offering a comfortable open layout with bright living spaces, a functional kitchen, and easy flow into dining and gathering areas. Bonus room provides added flexibility for a home office, playroom, or hobby space. The primary suite features a private bath, while two additional bedrooms and a second full bath accommodate family

    Sabrina Kimball Simple Real Estate - Keller Williams

    657 Country Club Ln, Winchester, TN 37398
  • /52

    $369,550 New Construction

    • 3 Beds
    • 2 Baths
    • 1,726 Sq Ft

    1718 Galloway Ln, Winchester, TN 37398

    New Construction Home just STEPS away from Tims Ford Lake. Public Boat Ramp and Public Access to lake is only ONE MINUTE away. Tims Ford State Park property is walking distance. Boat ramp and public access is at Anderton Branch Road right next to this property. 3 bedrooms, 2 bathrooms. This home could be your very own lake home OR it could be a investment property to lease out. Large covered rear

    isaac zimmerle Benchmark Realty, LLC

    1718 Galloway Ln, Winchester, TN 37398
  • /33

    $320,000

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    667 Maple Bend Rd, Winchester, TN 37398

    Beautiful 3.5 acres. Blocks from Fairview boat ramp launch. Property extends 75 feet into woods. Lots of wildlife.Room for Garden space or animals. Home is a 2 bedroom 1.5 half baths, but the original septic is for a 3 bedroom home. New Roof and HVAC. 30x30 detached garage/shop with lift, commercial compressor and jack. Also has wood stove and/or propane heater. 2 smaller metal sheds for storage.

    Pam Ford Benchmark Realty, LLC

    667 Maple Bend Rd, Winchester, TN 37398
  • /27

    $399,999

    • 2 Beds
    • 2 Baths
    • 2,244 Sq Ft

    74 Freedom Ln, Winchester, TN 37398

    Escape to peaceful country living in this charming 2bdr/2bath brick home set on nearly an acre of scenic land. Inside, you'll find beautifully updated LVP flooring flowing throughout a warm inviting layout, designed for both comfort and easy upkeep. Outside the property continues to impress with a spacious detached shop perfect for hobbies, equipment, or extra parking-as well as a generous

    Angela Miller John Smith Jr Realty and Auction LLC

    74 Freedom Ln, Winchester, TN 37398
  • /22

    $309,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,213 Sq Ft

    99 N Shephard St, Winchester, TN 37398

    Terrapin Station recently completed new construction on lot 6. This 3 bedroom 2 bath home is within walking distance from downtown Winchester and only 1.5 miles from the highly desired Tims Ford Lake. Large open floor plan. All new appliances. Quartz countertops. Entire second level consists of a master suite. Extremely energy efficient home with spray foam insulation in rafters. 12x22 Detached

    Tom Banks Monteagle Sewanee REALTORS

    99 N Shephard St, Winchester, TN 37398
  • /40

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft

    605 Strawberry Dr, Winchester, TN 37398

    Charming, stylish, and move-in ready — this 3 bedroom, 2 bath home feels like new and offers the perfect mix of comfort and convenience! Step inside to an inviting open-concept layout with stainless steel appliances, plenty of natural light, and a smart split-bedroom design for added privacy.Love outdoor living? You’ll swoon over the large front porch for morning coffee and the expansive

    Kate Bryant RE/MAX 1st Realty

    605 Strawberry Dr, Winchester, TN 37398
  • /35

    $365,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,487 Sq Ft

    26 Maple Bend Rd, Winchester, TN 37398

    This stunning 1487 sqft. brick home features 3 bedrooms and 2 full bathrooms. The master bedroom features an elegant double tray ceiling and a walk in closet perfect for utilizing the most of your space. The master bath has dual sinks, offering ideal space for morning routines. The property was fully remodeled in the summer of 2018. It has an 18 ft. ceiling in the open great room. The open floor

    Sierra Owens Century 21 Coffee County Realty & Auction

    26 Maple Bend Rd, Winchester, TN 37398
  • /63

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,213 Sq Ft

    103 N Shephard St, Winchester, TN 37398

    Welcome home to “A Whiter Shade of Pale,” a home that beautifully blends classic character with modern comfort. Perfectly situated within walking distance of downtown Winchester and just 1.5 miles from stunning Tims Ford Lake, this home offers the best of small-town living and outdoor adventure. Step inside to discover an inviting open-concept main level designed for both everyday living and

    Eberley Holloway Southern Middle Realty

    103 N Shephard St, Winchester, TN 37398
  • /64

    $375,000

    • 4 Beds
    • 3 Baths
    • 2,528 Sq Ft

    144 Wood Bluff Rd, Winchester, TN 37398

    LOCATION and a serene inviting neighborhood! This 2528 sq ft home offers a perfect blend of comfort, style, and functionality. The home boasts 2 bedroom and 1 full bath on the first level. The spacious living room is adorned with oversized windows that allows in natural light, offering picturesque views of your own private inground pool. An added bonus is the inground pool is surrounded with

    Melissa Stewart Swaffords Property Shop

    144 Wood Bluff Rd, Winchester, TN 37398
  • /43

    $399,000

    • 3 Beds
    • 2 Baths
    • 3,050 Sq Ft

    219 Old Mill Rd, Winchester, TN 37398

    Second chance opportunity! This property is back on the market after a temporary tenant situation and is now ready for new ownership. Reintroduced at a new price, 219 Old Mill Rd offers excellent value for today’s buyer. Ideal for owner-occupants or investors looking for a well-located property with strong potential. Zoned commercial. Can be rezoned to residential. Buyer and/or Buyers agent to

    Leanne Bonning EXIT Noble Realty Group

    219 Old Mill Rd, Winchester, TN 37398
  • /32

    $327,900

    • 3 Beds
    • 2.5 Baths
    • 1,358 Sq Ft

    101 N Shephard St, Winchester, TN 37398

    Welcome home to “Tangerine,” a vibrant and inviting residence inspired by the warmth and soul of the classic Tangerine. Nestled within the colorful Terrapin Station subdivision, this thoughtfully designed home offers both personality and modern comfort. Step onto the large covered front porch with striking wood accents and into an open-concept living space filled with natural light. Luxury vinyl

    Eberley Holloway Southern Middle Realty

    101 N Shephard St, Winchester, TN 37398
  • /36

    $364,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3 Baths
    • 1,864 Sq Ft

    305 Oak Leaf Cir, Winchester, TN 37398

    This spacious four-bedroom home with a bonus room and three full baths offers a wonderful blend of comfort, character, and opportunity. A detached garage with a versatile room above provides ideal space for a storage or a studio. The backyard is an entertainer’s retreat, featuring an in-ground pool surrounded by a generous deck and framed by a serene wooded backdrop that offers both privacy and

    Hannah Monilaw Better Homes & Gardens Real Estate Heritage Group

    305 Oak Leaf Cir, Winchester, TN 37398
  • /34

    $349,900

    • 3 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    305 Duncan Ln, Winchester, TN 37398

    Charming 3-Bedroom Home on a Corner Lot – Family-Friendly Neighborhood!Welcome to this inviting 3-bedroom, 2-bath single-family home offering 1,692 sq. ft. of comfortable living space. Built in 2007, this well-maintained property sits on a spacious corner lot in a family-friendly neighborhood close to town, schools, and local amenities. The home is just down the street from the Twin Creeks

    Dawn Parrish Leading Edge Real Estate Group

    305 Duncan Ln, Winchester, TN 37398
  • /24

    $389,500

    • 4 Beds
    • 3 Baths
    • 2,640 Sq Ft

    205 Houghton Dr, Winchester, TN 37398

    A must see well kept home in a great location and in a market that has this beauty priced to sell. LOCATION, LOCATION,LOCATION! Walking distance to the Golf Course and a few minutes from the town square that has a great coffee shop. restaurants, a bakery, shops, and movie theater. Do not miss getting your offer in to a motivated seller. Awesome floor plan with 4 bedrooms and three baths. Hardwood

    Flora (Cat) Myers Dalton Wade, Inc

    205 Houghton Dr, Winchester, TN 37398
  • /41

    $388,204

    • 3 Beds
    • 3 Baths
    • 2,476 Sq Ft

    204 8th Ave SE, Winchester, TN 37398

    Bonus Room above the garage is not included in the square feet. Lots of living space with 3 bedrooms & 3 full bathrooms (2 are Master suites with bathrooms). There are separate living room and formal dining room, separate office/den, screened patio, open patio, and 2 outbuildings for extra storage. Whole house generator goes with the home.

    Sharon Swafford Swaffords Property Shop

    204 8th Ave SE, Winchester, TN 37398
  • /51

    $358,400

    • 2 Beds
    • 2 Baths
    • 1,782 Sq Ft

    114 Chase Cir, Winchester, TN 37398

    Experience zero-step living in this immaculate 1,782 sq. ft. single-level condo. This 2-bedroom, 2-bathroom home combines upgrades with total peace of mind. The open-concept interior features high ceilings, recessed lighting, and beautiful wood flooring leading to a stunning focal-point fireplace.New 2025 Upgrades Include:New HVAC and a new garage door opener/keypad.New roof and

    Sean Crabtree Blue Door Realty Group

    114 Chase Cir, Winchester, TN 37398
  • /33

    $395,000

    • 3 Beds
    • 1.5 Baths
    • 1,508 Sq Ft

    1111 Holders Cove Rd, Winchester, TN 37398

    Brick home in amazing location with sunroom, carport, and double lot with detached garage. A must see.

    Bj Rigsby Lynch Rigsby Realty & Auction, LLC

    1111 Holders Cove Rd, Winchester, TN 37398
  • /38

    $338,000

    • 4 Beds
    • 3 Baths
    • 1,960 Sq Ft

    240 Myers Rd, Winchester, TN 37398

    Welcome to this charming one level home! The home offers the perfect blend of comfort and convenience. Inside, you’ll find a cozy fireplace and spacious living areas, while outside boasts a carport, shop, and a huge yard sitting on just under an acre. The shop is perfect for storage and projects. Located only minutes from beautiful Tims Ford Lake, this property offers both space and lifestyle.

    Chloe Thomas Southern Middle Realty

    240 Myers Rd, Winchester, TN 37398
  • /12

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    204 Orchard Ln, Winchester, TN 37398

    Charming 1,680 sq. ft. single-story home in a well-established neighborhood. Features 3 spacious bedrooms, 2 full baths, hardwood floors, ample storage, and kitchen with refrigerator, stove, and dishwasher. Enjoy HVAC, a fenced yard, detached 1-car garage, and a workshop. Brand new roof in 2024! Don't miss this great opportunity!

    Daniel Demers Sell Your Home Services, LLC

    204 Orchard Ln, Winchester, TN 37398
  • /34

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,668 Sq Ft

    442 Golf Shores Dr, Winchester, TN 37398

    Location!! This property combines a beautiful and peaceful setting on a dead end street to Tim’s Ford Lake! Just minutes from Tim’s Ford Lake, Marina and State Park, Bear Trace Golf Course and historic Lynchburg! Well maintained home and move in ready.

    Lydia Billington Benchmark Realty, LLC

    442 Golf Shores Dr, Winchester, TN 37398
  • /35

    $300,000

    • 3 Beds
    • 1 Bath
    • 1,822 Sq Ft

    111 Dogwood Ln, Winchester, TN 37398

    Updated brick ranch single story, in the Scenic Heights subdivision, featuring 1822 square feet with three bedrooms, 1 bath, hardwood floors, central air and heat. This large corner lot has a BIG backyard with fully fenced backyard, separate storage building, five parking spaces, close to downtown, minutes from Tims Ford Lake. Updates include HVAC and hot water heater less 5 years old, roof is

    Susan Holmes University Realty

    111 Dogwood Ln, Winchester, TN 37398

Home Trends in Winchester, TN

Housing Trends

Median Sale Price
$357,900
Median Single Family Sale Price
$364,950
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$354,150
Average Price Per Sq Ft
$204
Number of Homes for Sale
102
Last 12 months Home Sales
155
Months of Supply
7.90
Median List Price
$399,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
0%
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