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Winchester, TN Homes for Sale under $400,000

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  • /26

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    1587 By Pass Rd, Winchester, TN 37398

    Beautiful 3 Bedroom, 2 bath, brick home located minutes from beautiful downtown Winchester, featuring quaint shops and a wide variety of restaurants to choose from. Also minutes Tims Ford Lake, Wood Reservoir & Nissan.Attached garage and detached garage/workshop.

    Agent Photo

    Patricia Boswell

    Hanson Realty & Auction Company

    (931) 369-3291

    1587 By Pass Rd, Winchester, TN 37398
  • /36

    $334,500

    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft

    387 Fairview Cir, Winchester, TN 37398

    Welcome to this beautifully maintained all-brick home situated on a spacious corner lot of over half an acre! This charming one-level residence offers a desirable split-bedroom floor plan, providing both privacy and functionality for everyday living. Inside, you'll find a well-cared-for interior featuring comfortable living spaces, a practical layout, and plenty of natural light throughout. The

    Agent Photo

    Ashley Lynch

    Lynch Rigsby Realty & Auction, LLC

    (931) 321-6797

    387 Fairview Cir, Winchester, TN 37398
  • /39

    $369,900

    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft

    120 Dogwood Ln, Winchester, TN 37398

    One level living at it's finest! Don't miss out on this gorgeous ranch home in the middle of charming Winchester Tennessee! This home features 3 spacious bedrooms with original hardwood floors. The huge living room is flooded with natural light and connects to the formal dining area with plenty of room for those you love to gather around your table! The kitchen has been updated with granite

    Agent Photo

    Katie Schmeltzer

    Southern Homes Real Estate LLC

    (931) 377-2077

    120 Dogwood Ln, Winchester, TN 37398
  • /32

    $352,000

    • 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
  • /49

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft

    367 Carol Cir, Winchester, TN 37398

    Welcome home to this move-in ready 3-bedroom, 2-bath home perfectly situated on a corner lot in a quiet Winchester neighborhood—located outside the city limits and just minutes from Tims Ford Lake and Twin Creeks Marina. Built in 2003, this 1,420 sq. ft. home offers a comfortable, functional layout with an attached two-car garage and thoughtful updates throughout. Inside, you’ll find welcoming

    Paige Morris Southern Middle Realty

    367 Carol Cir, Winchester, TN 37398
  • /23

    $355,000

    • 2 Beds
    • 2 Baths
    • 1,683 Sq Ft

    38 Murray Lake Dr, Winchester, TN 37398

    Welcome home to this 1 owner and well took care of home that is Move In Ready. It boasts of split bedroom floor plan of 2 bedrooms with a 3rd that is a bedroom by definition and 2 nice bathrooms. The master suite has dual vanities and a spacious walk-in closet and shower too. The roof was replaced in 2023. The home has a spacious living room, kitchen, and dining area. Also comes with a gas

    Landon Keller Peck Realty Group, LLC

    38 Murray Lake Dr, Winchester, TN 37398
  • /40

    $320,000

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

    667 Maple Bend Rd, Winchester, TN 37398

    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.

    Pam Ford Benchmark Realty, LLC

    667 Maple Bend Rd, Winchester, TN 37398
  • /52

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft

    614 Fairview Cir, Winchester, TN 37398

    Beautiful and well-maintained 3-bedroom, 2-bath home located in a quiet area. This home offers a comfortable layout with spacious living areas, a nice kitchen, and well-sized bedrooms. The flooring has been updated within the last two years and the home has been very well taken care of. The home features a propane gas fireplace, and the propane tank is owned and will remain with the property. The

    Andrea Cruz John Smith Jr Realty and Auction LLC

    614 Fairview Cir, Winchester, TN 37398
  • /25

    $395,000

    • Land
    • 0.33 Acre
    • $1,196,970 per Acre

    0 Hickory Point Dr Unit 2, Winchester, TN 37398

    Discover the perfect setting for your dream home in the sought‐after Cline Ridge subdivision on Tims Ford Lake. This gorgeous lake lot offers the ideal blend of privacy, convenience, and year‐round recreation. You’ll enjoy easy ACCESS YOUR OWN PRIVATE DOCK on Out Lot A, just a short drive from your homesite—perfect for fishing, boating, or simply relaxing by the water. Located only minutes from

    Daryl Welch Freedom Realty Group

    0 Hickory Point Dr Unit 2, Winchester, TN 37398
  • /17

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    101 Lisa Cir, Winchester, TN 37398

    Welcome Home, Lots of Updates already completed- Roof 2018, Water Heater-2025, HVAC-2022, Bathrooms-2025, Windows-2026,Water Softener System within the last 5 years,All ceiling fans within last 5 years too, Move In Ready 3 bed 2 bath with 1 car attached garage, a 16x20 insulated Detached Garage with electricity too, the subdivision has a communal dock for lake access, minutes from Tim's Ford Lake

    Landon Keller Peck Realty Group, LLC

    101 Lisa Cir, Winchester, TN 37398
  • /51

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,618 Sq Ft

    1114 N High St, Winchester, TN 37398

    Great opportunity for Lake Life without the Lake front headache! Property is Lake View situated 0.5 mile or less to the Winchester City Park and Boat Ramp. Enjoy Family time at the City Park or Lake. This is a beautifully maintained home with upgrades such as hardwood and tile flooring - new in much of the house. Electrical panel and wiring upgrades - New HVAC installed Jul. 2025; Roof installed

    Donald Golden WEICHERT, REALTORS Joe Orr & Associates

    1114 N High St, Winchester, TN 37398
  • /37

    $364,900

    • 2 Beds
    • 2 Baths
    • 1,339 Sq Ft

    52 Island Way, Winchester, TN 37398

    Welcome to lake living at its best in the highly sought-after Twin Creeks Village on Tims Ford Lake! This beautifully maintained townhome offers the perfect combination of comfort, style, and low-maintenance living in one of Winchester’s most desirable waterfront communities. Inside, you’ll find a bright open-concept layout with hardwood floors, a spacious living area anchored by a stunning stone

    Shelia Lunsford Benchmark Realty, LLC

    52 Island Way, Winchester, TN 37398
  • /37

    $359,000

    • 5 Beds
    • 3 Baths
    • 3,343 Sq Ft

    121 N Cedar St, Winchester, TN 37398

    Fresh! Beautifully renovated home that features vintage charm with modern updates such as a spacious walk-in tile shower and new light fixtures. Storage building. This home is within walking distance to the Winchester Courthouse Square's restaurants, shops, and the Oldham Theater.

    Sharon Swafford Swaffords Property Shop

    121 N Cedar St, Winchester, TN 37398
  • /47

    $385,000

    • 4 Beds
    • 3 Baths
    • 2,202 Sq Ft

    190 Chase Cir, Winchester, TN 37398

    A STUNNING all-brick HOME nestled in the city limits of Winchester, Tennessee where its convenience to town will make very day life a BREEZE!!! Because of its prime location you are also just a stones throw away from BEAUTIFUL TIMS FORD LAKE & TWIN CREEKS MARINA. Boasting an expansive 2200 sqft of living space this beautiful home features 4 bedrooms & 3 full bathrooms across two spacious levels,

    Fallon Massey Van Massey Realty & Auction

    190 Chase Cir, Winchester, TN 37398
  • /79

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,653 Sq Ft

    401 E Petty Ln, Winchester, TN 37398

    Step into this beautifully updated 3BR/2.5BA home offering comfort, style, and room to grow. The open kitchen shines with stainless appliances and a modern hood, flowing easily into the den where a welcoming fireplace sets the tone for cozy evenings. A bright Florida room and a partially finished basement with new flooring add versatile living areas. Separate Living room offers added space and it

    Daryl Welch Freedom Realty Group

    401 E Petty Ln, Winchester, TN 37398
  • /41

    $379,900

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

    204 8th Ave SE, Winchester, TN 37398

    Motivated sellers. 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
  • /24

    $380,500

    • 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
  • /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
  • /34

    $339,900

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

    442 Golf Shores Dr, Winchester, TN 37398

    NEW PRICE, AMAZING Location!! This property combines a beautiful and peaceful setting on a dead-end street to Tim’s Ford State Park! 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
  • /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. UNDER CONTRACT- 48 HOUR ROR

    Mark Ryder Benchmark Realty, LLC

    400 Cessna Cir, 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
  • /76

    $358,900

    • 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
  • /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
  • /28

    $358,200

    0 Rowe Gap Rd, Winchester, TN 37398

    17 + acres in the Greenbelt. Looking for a family compound; A Blank Slate to to Build Your Dream Estate or Potential for Multiple Estates. Stocked Pond at the front of the Property and a Meandering Creek in the back. 5 Minutes to Tims Ford Lake. Come explore this beautiful tract. The most beautiful Mountain Sunrises await. Property is currently leased and possession would be contingent on the

    Christy Brown Compass

    0 Rowe Gap Rd, Winchester, TN 37398
  • /63

    $309,900 Open Sun 2PM - 4PM

    • 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
  • /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
  • /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
  • /66

    $325,000

    • 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
  • /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
  • /33

    $325,000 New Construction

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

    1605 Paynes Church Rd, Winchester, TN 37398

    **Move in for only $99 AND a fixed rate as low as 5.5%** 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

    Kasidy Lowe Compass Tennessee, LLC

    1605 Paynes Church Rd, Winchester, TN 37398
  • /36

    $325,000 New Construction

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

    1563 Paynes Church Rd, Winchester, TN 37398

    **Move in for only $99 AND a fixed rate as low as 5.5%**** 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

    Kasidy Lowe Compass Tennessee, LLC

    1563 Paynes Church Rd, Winchester, TN 37398
  • /36

    $325,000 New Construction

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

    1585 Paynes Church Rd, Winchester, TN 37398

    **Move in for only $99 AND a fixed rate as low as 5.5%**** 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

    Kasidy Lowe Compass Tennessee, LLC

    1585 Paynes Church Rd, Winchester, TN 37398
  • /36

    $325,000 New Construction

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

    1517 Paynes Church Rd, Winchester, TN 37398

    ****Move in for only $99 AND a fixed rate as low as 5.5%**** 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

    Kasidy Lowe Compass Tennessee, LLC

    1517 Paynes Church Rd, Winchester, TN 37398
  • /36

    $325,000 New Construction

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

    1543 Paynes Church Rd, Winchester, TN 37398

    **Move in for only $99 AND a fixed rate as low as 5.5%** 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

    Kasidy Lowe Compass Tennessee, LLC

    1543 Paynes Church Rd, Winchester, TN 37398
  • /52

    $359,000 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

Home Trends in Winchester, TN

Housing Trends

Median Sale Price
$357,450
Median Single Family Sale Price
$364,900
Median Townhouse Sale Price
$442,450
Median 2 Bedroom Sale Price
$357,450
Average Price Per Sq Ft
$206
Number of Homes for Sale
107
Last 12 months Home Sales
162
Months of Supply
7.90
Median List Price
$399,900
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
0%
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