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Winchester, KY Homes for Sale under $400,000

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  • /36

    $319,900 Open Sat 11AM - 1PM

    • 5 Beds
    • 2 Baths
    • 2,082 Sq Ft

    128 Cherokee Dr, Winchester, KY 40391

    **OPEN HOUSE SATURDAY (11/1) From 11AM-1PM Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, and exceptional curb appeal and charm, this home is just

    Agent Photo

    Tyler Hurst

    Thwaites Realtors LLC

    (859) 681-9697

    128 Cherokee Dr, Winchester, KY 40391
  • /14

    $312,975

    • 2 Beds
    • 1 Bath
    • 1,116 Sq Ft

    1363 Clintonville Rd, Winchester, KY 40391

    Here's your chance to own a rare 5-acre property in Clark County, one of Central Kentucky's most desirable areas. Tucked just minutes from downtown Winchester, the Hamburg corridor, and Lexington, this property blends convenience with the peacefulness of country living. Whether you're dreaming of building a brand-new home, expanding into a mini farm, or investing in future growth, this land gives

    Agent Photo

    Rebakah Goodpaster

    Keller Williams Legacy Group

    (859) 659-6863

    1363 Clintonville Rd, Winchester, KY 40391
  • /47

    $372,900

    • 4 Beds
    • 3 Baths
    • 2,105 Sq Ft

    114 Mallard Ln, Winchester, KY 40391

    Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a

    Agent Photo

    Robin Jones

    Keller Williams Legacy Group

    (859) 809-3100

    114 Mallard Ln, Winchester, KY 40391
  • /30

    $349,000

    • 3 Beds
    • 2.5 Baths
    • 2,475 Sq Ft

    212 Woodbine Ct, Winchester, KY 40391

    Step right up - come on in! Its appeal is undeniable, both inside and out! Move-in ready. This well-maintained all-brick ranch on a full basement is full of charm and functionality! — Inside, you'll love having two separate living areas, 1 upstairs and 1 in the basement with a wood burning fireplace in both rooms. Enjoy the cold winter evenings in front of either of the fireplaces with family and

    Kathy Burton Coldwell Banker McMahan

    212 Woodbine Ct, Winchester, KY 40391
  • /104

    $355,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3 Baths
    • 2,520 Sq Ft

    145 Shanahan Ln, Winchester, KY 40391

    This 4-bedroom, 3-bath ranch on a basement offers over 2,500 sq ft of living space with modern updates, a welcoming layout and a safe neighborhood to live in. The large living room with cathedral ceilings flows into a well-appointed kitchen featuring ample counter space and newer appliances. New LVP flooring runs throughout the main level, while new patio doors open to a large deck—perfect for

    Josh Wood Freedom Realty & Property Management

    145 Shanahan Ln, Winchester, KY 40391
  • /36

    $379,000

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft

    121 Fitch Ave, Winchester, KY 40391

    This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful modern updates. Conveniently located just minutes from the interstate close to Lexington, it offers

    Ashley Spencer Keller Williams Commonwealth

    121 Fitch Ave, Winchester, KY 40391
  • /35

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    130 Hibiscus Ln, Winchester, KY 40391

    This beautiful 4 bedroom, 2.5 bath home offers a spacious and thoughtful layout with the primary suite conveniently located on the main level. The open walkway overlooking the great room and vaulted ceilings create an airy, inviting feel, complemented by an electric fireplace for cozy evenings. The kitchen and living areas flow seamlessly for everyday comfort and entertaining. Enjoy the

    Ashley Barreto Indigo & Co

    130 Hibiscus Ln, Winchester, KY 40391
  • /24

    $369,000

    • 4 Beds
    • 2.5 Baths
    • 2,811 Sq Ft

    446 Tremont Ln, Winchester, KY 40391

    Agent is Seller. 2800 square feet with four bedrooms and 2-1/2 baths. A large corner lot with side entry 2 car garage. Walkout patio, remodeled front porch, fully privacy fenced back yard, upgraded hot-water heaters, Upgraded fully insulated garage with steel back insulated door, walk in master closet, two story entry, and gas fireplace are just a few of the features in this home. Call today

    Dylan Langdon The Agency

    446 Tremont Ln, Winchester, KY 40391
  • /9

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 2,868 Sq Ft

    508 Boone Ave, Winchester, KY 40391

    3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. New roof, new freeze resistant water lines, new heat and air, new appliances, and backsplash. Full basement with double space garage. Spacious formal living room and separate formal dining room. Great room includes breakfast area and sitting area, and fireplace. Large master ensuite includes closet with plenty of storage space.

    Donna C. Slone-Crumbie Wright Realty

    508 Boone Ave, Winchester, KY 40391
  • /36

    $355,000

    • 2 Beds
    • 2 Baths
    • 1,568 Sq Ft

    208 Citation Ct, Winchester, KY 40391

    One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under. (see photos) Kitchen appliances include

    Garnett Davis Tom Goebel & Company

    208 Citation Ct, Winchester, KY 40391
  • /4

    $369,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft

    206 Jett Dr, Winchester, KY 40391

    New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

    Mila Ensor Ensor Real Estate, LLC

    206 Jett Dr, Winchester, KY 40391
  • /3

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    270 Evergreen Dr, Winchester, KY 40391

    Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

    Rex Hall United Real Estate Bluegrass

    270 Evergreen Dr, Winchester, KY 40391
  • /3

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    230 Evergreen Dr, Winchester, KY 40391

    Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

    Rex Hall United Real Estate Bluegrass

    230 Evergreen Dr, Winchester, KY 40391
  • /2

    $345,000 New Construction

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

    215 Evergreen Dr, Winchester, KY 40391

    Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

    Rex Hall United Real Estate Bluegrass

    215 Evergreen Dr, Winchester, KY 40391
  • /3

    $345,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    225 Evergreen Dr, Winchester, KY 40391

    Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

    Rex Hall United Real Estate Bluegrass

    225 Evergreen Dr, Winchester, KY 40391
  • /19

    $399,717

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    300 Calmes Blvd, Winchester, KY 40391

    Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 4-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *Four spacious bedrooms with ample closet space *Two and a half

    Darrell Tackett Dream Maker Realty, LLC

    300 Calmes Blvd, Winchester, KY 40391
  • /41

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft

    118 Windridge Dr, Winchester, KY 40391

    Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, this charming brick ranch offers 3 bedrooms, 2 full baths, and character throughout. Inside, you'll find hardwood and tile floors (no carpet!), a spacious kitchen with plenty of cabinet space that opens into the dining area and living room, complete with a cozy ventless gas fireplace. Step out back to your own

    Michelle Blackburn RE/MAX Creative, Winchester

    118 Windridge Dr, Winchester, KY 40391
  • /42

    $319,000

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    410 Corinne Ct, Winchester, KY 40391

    Charming Ranch-Style Home with Lots of Room- Step inside this 8 year old beautiful 1,604 sq. ft. ranch-style home featuring 9-foot ceilings and an open, inviting layout. With 3 comfortable bedrooms and a large, laundry room and back hallway, this home offers both style and functionality. The spacious living areas are enhanced by wood and tile flooring, adding a modern touch and easy maintenance.

    Shelly Sutton Kentucky Realty Group, LLC

    410 Corinne Ct, Winchester, KY 40391
  • /36

    $399,999

    • 4 Beds
    • 4.5 Baths
    • 2,800 Sq Ft

    136 College St, Winchester, KY 40391

    Welcome to this exceptional, fully renovated home located in the heart of downtown Winchester. Meticulously redesigned with a thoughtful rear addition, this 4-bedroom, 4.5-bath residence offers the perfect blend of historic charm and modern luxury. Step inside to discover a bright and open floor plan featuring a spacious first-floor primary suite complete with a private en-suite bathroom,

    Ellie Hatton The Brokerage

    136 College St, Winchester, KY 40391
  • /31

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    407 Corinne Ct, Winchester, KY 40391

    Welcome to 407 Corinne Court a beautifully maintained 3-bedroom, 2-bath all-electric home offering a perfect blend of comfort, style, and functionality. This one-level open-concept ranch sits on a crawl space foundation with a brick and vinyl exterior and features an attached two-car garage. Step inside to find fresh paint throughout, new carpet in the living room and bedrooms, and hardwood

    Shane Underwood Keller Williams Commonwealth

    407 Corinne Ct, Winchester, KY 40391
  • /34

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,531 Sq Ft

    1508 Ford Hampton Rd, Winchester, KY 40391

    Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

    Michelle Blackburn RE/MAX Creative, Winchester

    1508 Ford Hampton Rd, Winchester, KY 40391
  • /31

    $389,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    133 Shala-Mar Rue, Winchester, KY 40391

    Charming 3 Bedroom, 2 Bath Ranch Near Hamburg - Fully Renovated! Don't miss this beautifully updated 3-bedroom, 2-bath ranch-style home located just minutes from Hamburg! This move-in ready gem features brand new windows, siding, gutters, roof, and exterior doors, ensuring both curb appeal and peace of mind. Step inside to a spacious, light-filled living room—perfect for entertaining. The

    Nena Honaker Tom Goebel & Company

    133 Shala-Mar Rue, Winchester, KY 40391
  • /41

    $339,000

    • 2 Beds
    • 1 Bath
    • 1,055 Sq Ft

    1996 White Conkwright Rd, Winchester, KY 40391

    Discover peaceful country living on this charming 4.17-acre farmhouse retreat that has been meticulously maintained by the same loving family for 42 years. From the moment you arrive, the welcoming covered front porch invites you to slow down and take in the serene setting. The home features two bedrooms plus an additional room that could serve as a 3rd bedroom, one full bathroom, and an

    Lucy Martin Jenkins United Real Estate Bluegrass

    1996 White Conkwright Rd, Winchester, KY 40391
  • /70

    $335,000

    • 6 Beds
    • 4 Baths
    • 3,544 Sq Ft

    297 S Main St, Winchester, KY 40391

    Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

    Silvia Torres Tru Life Real Estate

    297 S Main St, Winchester, KY 40391
  • /28

    $319,000

    • 2 Beds
    • 1 Bath
    • 1,170 Sq Ft

    398 Pine Ridge Rd, Winchester, KY 40391

    Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from

    Amie Hieneman ERA Select Real Estate

    398 Pine Ridge Rd, Winchester, KY 40391
  • /14

    $394,999

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    408 Corinne Ct, Winchester, KY 40391

    Come see this immaculate 3 bedroom, 2 bath single-story ranch with an open-concept split bedroom layout and 1,604 square feet of living space. This home has been beautifully maintained and is ready for its next owner. Inside you will find laminate and tile floors and stainless steel appliances that make daily living easy and stylish. The spacious design flows seamlessly, creating a bright and

    Caleb Gonzalez The Brokerage

    408 Corinne Ct, Winchester, KY 40391
  • /47

    $375,000

    • 8 Beds
    • 4 Baths
    • 3,706 Sq Ft

    23 1/2 Wheeler Ave, Winchester, KY 40391

    Prime investment opportunity in Winchester! This 4-plex offers four unique 2-bedroom, 1-bath units, each approximately 900 sqft, with washer/dryer hookups and kitchen appliances included. Tenants enjoy a quiet neighborhood setting just steps from College Park, close to the Public Library and downtown. Alley access for parking makes it feel private and secluded. Units feature wide hallways,

    Michelle Blackburn RE/MAX Creative, Winchester

    23 1/2 Wheeler Ave, Winchester, KY 40391
  • /25

    $309,000

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

    202 Dubuy Dr, Winchester, KY 40391

    Welcome to this move-in ready 3-bedroom, 2.5-bath home built in 2022. With 1,745 sq. ft., a finished walk-out basement, and thoughtful upgrades, it's designed for comfort with a modern touch.The kitchen features upgraded high-gloss cabinetry, custom granite countertops, and stainless steel appliances. Inside, waterproof luxury vinyl plank (LVP) flooring runs throughout the whole home,

    Donna Mink Mink Realty

    202 Dubuy Dr, Winchester, KY 40391
  • /32

    $399,500

    750 Providence Ln, Winchester, KY 40391

    Welcome to your own slice of country paradise tucked away in southern Clark County! This 51+ acre tract offers a mixture of cleared pasture and mature woods, ideal for a variety of uses including cattle, crops, horses, recreation, or even your dream home site. Currently enjoyed as a private recreational family farm, the property already has electricity in place and features a cistern at an old

    Michelle Blackburn RE/MAX Creative, Winchester

    750 Providence Ln, Winchester, KY 40391
  • /6

    $388,000

    • 5 Beds
    • 3 Baths
    • 2,762 Sq Ft

    101 E Lexington Ave, Winchester, KY 40391

    Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

    David Espinosa Bluegrass Realty Pros, Inc

    101 E Lexington Ave, Winchester, KY 40391
  • /13

    $340,000

    • 6 Beds
    • 4 Baths
    • 4,456 Sq Ft

    410 W Lexington Ave, Winchester, KY 40391

    Estate Sale. Selling 'AS IS', in 2024 new roof, walls repaired and freshly painted throughout.Great home for a growing family, covered front porch, 10-foot ceilings upstairs and down, handicap ramp, ample parking in rear. Motivated seller, call for your private showing today

    Melisa McDonald Wrenn Realty

    410 W Lexington Ave, Winchester, KY 40391
  • /13

    $400,000

    • Land
    • 2.19 Acres
    • $182,648 per Acre

    145 Codella Dr, Winchester, KY 40391

    Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

    Greg Leveridge Block + Lot Real Estate

    145 Codella Dr, Winchester, KY 40391
  • /34

    $339,999

    • 4 Beds
    • 3 Baths
    • 1,776 Sq Ft

    213 Orchid Ct, Winchester, KY 40391

    Kasey McCarty 5.23 Real Estate

    213 Orchid Ct, Winchester, KY 40391
  • /3

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    200 Evergreen Dr, Winchester, KY 40391

    Introducing the Run For The Roses - Proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms. The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite bathroom. The kitchen

    Rex Hall United Real Estate Bluegrass

    200 Evergreen Dr, Winchester, KY 40391
  • /27

    $319,900

    • 3 Beds
    • 2.5 Baths
    • 1,730 Sq Ft

    2198 Goshen Rd, Winchester, KY 40391

    Country living at its finest!!!! This gorgeous 3 bed, 2.5 bath home with a basement is ready to be loved. Located just outside Winchester on Goshen Rd, This lovely home has large open concept living and kitchen with deck and large lot. This home won't last long. Come See TODAY!!!

    Jason Szaks EXIT TOWN & COUNTRY REALTORS

    2198 Goshen Rd, Winchester, KY 40391

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$245,000
Median Single Family Sale Price
$260,000
Median Townhouse Sale Price
$195,200
Average Price Per Sq Ft
$161
Number of Homes for Sale
89
Last 12 months Home Sales
316
Months of Supply
3.40
Median List Price
$260,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
4%
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