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Winchester, KY Homes for Sale under $300,000

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  • /32

    $259,900

    • 3 Beds
    • 2 Baths
    • 1,251 Sq Ft

    414 Wellington Way, Winchester, KY 40391

    Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance

    Amy Diamond ERA Select Real Estate

    414 Wellington Way, Winchester, KY 40391
  • /30

    $254,900

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

    217 S Highland St, Winchester, KY 40391

    This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

    Michael Hilario The Agency

    217 S Highland St, Winchester, KY 40391
  • /17

    $299,000

    • Land
    • 14.51 Acres
    • $20,606 per Acre

    3056 Irvine Rd, Winchester, KY 40391

    Own a genuine piece of Kentucky splendor! Beautiful 14.5 acres of gently rolling land is ideal for building your custom home! The property offers creek access and a barn with electric and water. Don't miss this opportunity to own a farm only 20 miles to Hamburg and 5 miles to Winchester Bypass. No city sewage. Deed restrictions apply. Additional parcel with 11.36 acres is also available. Perfect

    Lura Justice Rector Hayden Realtors

    3056 Irvine Rd, Winchester, KY 40391
  • /32

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    528 Estes Dr, Winchester, KY 40391

    Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

    Josh Wood Freedom Realty & Property Management

    528 Estes Dr, Winchester, KY 40391
  • /31

    $215,000

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    5434 Pine Ridge Rd, Winchester, KY 40391

    Jim Woodrum RE/MAX Creative, Winchester

    5434 Pine Ridge Rd, Winchester, KY 40391
  • /22

    $260,000

    • 4 Beds
    • 2 Baths
    • 2,332 Sq Ft

    35 Cherokee Ct, Winchester, KY 40391

    Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

    Brenda Rue Keller Williams Bluegrass Realty

    35 Cherokee Ct, Winchester, KY 40391
  • /48

    $287,000

    • 4 Beds
    • 1.5 Baths
    • 2,116 Sq Ft

    214 S Burns Ave, Winchester, KY 40391

    Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless

    Christa Joynt Keller Williams Commonwealth

    214 S Burns Ave, Winchester, KY 40391
  • /21

    $249,900

    • 3 Beds
    • 1.5 Baths
    • 1,494 Sq Ft

    720 Estes Dr, Winchester, KY 40391

    This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

    Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

    720 Estes Dr, Winchester, KY 40391
  • /27

    $269,000

    • 3 Beds
    • 2.5 Baths
    • 1,456 Sq Ft

    222 Bracken Ct, Winchester, KY 40391

    Great flloor plan -- great location -- GREAT price! Nice open space on the first level with fully-equipped kitchen and dining area and a very generously-sized family room. Backs up to Ecton Road so you are not looking at the back of another house. Primary bedroom and laundry upstairs with two other bedrooms. All three bedrooms have walk-in closets! The storage building conveys. This home is less

    Jim Woodrum RE/MAX Creative, Winchester

    222 Bracken Ct, Winchester, KY 40391
  • /47

    $235,000

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    23 Kittison Dr, Winchester, KY 40391

    ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

    Teresa Richmond Freedom Realty & Property Management

    23 Kittison Dr, Winchester, KY 40391
  • /33

    $215,000

    • 4 Beds
    • 1 Bath
    • 1,743 Sq Ft

    218 E Washington St, Winchester, KY 40391

    Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking

    Fernando Andrade Rector Hayden Realtors

    218 E Washington St, Winchester, KY 40391
  • /7

    $270,000

    • Land
    • 0.84 Acre
    • $321,429 per Acre

    800 Interstate Dr, Winchester, KY 40391

    Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

    Whitney Ensor Ensor Real Estate, LLC

    800 Interstate Dr, Winchester, KY 40391
  • /22

    $221,500

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    443 Jameson Way, Winchester, KY 40391

    This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

    Tyler I Back The Brokerage

    443 Jameson Way, Winchester, KY 40391
  • /28

    $298,900

    • 3 Beds
    • 3.5 Baths
    • 2,526 Sq Ft

    24 N Burns Ave, Winchester, KY 40391

    Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

    Sarah Hess Keller Williams Commonwealth

    24 N Burns Ave, Winchester, KY 40391
  • /29

    $234,900

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    11 Shelley Dr, Winchester, KY 40391

    SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in

    Nichole Bingham CENTURY 21 Advantage Realty

    11 Shelley Dr, Winchester, KY 40391
  • /23

    $270,000

    • 4 Beds
    • 2 Baths
    • 1,984 Sq Ft

    108 Ashley Dr, Winchester, KY 40391

    Be among the first to discover this exceptional property! This is a brand new listing, presenting a unique opportunity to own a home in a highly sought-after location. Imagine living in a neighborhood where everything you need is just a stone's throw away. This fabulous property boasts not only a full basement, offering endless possibilities for recreation, storage, or a home office, but also an

    A. Rebecca Woods Woods Realty Group

    108 Ashley Dr, Winchester, KY 40391
  • /12

    $269,900

    • 4 Beds
    • 1 Bath
    • 1,610 Sq Ft

    120 Windsor Dr, Winchester, KY 40391

    Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

    Team Farthing - Mitch Farthing Southern Legacy Realty

    120 Windsor Dr, Winchester, KY 40391
  • /34

    $260,000

    • Land
    • 6.08 Acres
    • $42,763 per Acre

    190 Privacy Ln, Winchester, KY 40391

    6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

    Jason Joseph Keller Williams Commonwealth

    190 Privacy Ln, Winchester, KY 40391
  • /24

    $286,000

    • 12 Beds
    • 4 Baths
    • 4,010 Sq Ft

    149 Winn Ave, Winchester, KY 40391

    Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units

    Libby VanMeter Marshall Lane Real Estate - Lexington

    149 Winn Ave, Winchester, KY 40391
  • /34

    $275,700

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft

    404 Wellington Way, Winchester, KY 40391

    This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family and friends. The sellers added fiber optics

    Craig Bridgewater Bridgewater Real Estate

    404 Wellington Way, Winchester, KY 40391
  • /62

    $259,500

    • 3 Beds
    • 2 Baths
    • 1,247 Sq Ft

    3614 Stamper Dr, Winchester, KY 40391

    Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

    Darrell Tackett Dream Maker Realty, LLC

    3614 Stamper Dr, Winchester, KY 40391
  • /10

    $215,000

    211 Ashton Oak Way, Winchester, KY 40391

    Here is the Blank Canvas to build your Dream Home in the Plantation Subdivision. This two story brick building, formerly the Sales Office for the Subdivision, has been gutted to offer the unique opportunity to build a 3118 Sq Ft Home consisting of Four Bedrooms, Two and Half Baths, an open concept on the main level with the addition of a two car garage. Contact listing agent to discuss current

    Melia Hord Keller Williams Legacy Group

    211 Ashton Oak Way, Winchester, KY 40391
  • /53

    $265,000

    • 2 Beds
    • 2 Baths
    • 1,521 Sq Ft

    174 Hidden Grove Ln, Winchester, KY 40391

    Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

    Kathryn Cheuvront Coldwell Banker McMahan

    174 Hidden Grove Ln, Winchester, KY 40391
  • /34

    $235,000

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft

    12 Linden Ave, Winchester, KY 40391

    Cute ranch with easy access to I-64 and downtown Winchester. Walk to the breweries, shopping and restaurants. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard. This property has a interesting feature of a building that's 14 x 40 that has been a rental but can be used as storage or a mother in-law suite.

    Roni Porter RE/MAX Creative Realty

    12 Linden Ave, Winchester, KY 40391
  • /59

    $279,950

    • 4 Beds
    • 3 Baths
    • 2,112 Sq Ft

    115 Watercrest Cir, Winchester, KY 40391

    Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

    Darrell Tackett Dream Maker Realty, LLC

    115 Watercrest Cir, Winchester, KY 40391
  • /14

    $240,000

    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    10 Upper St, Winchester, KY 40391

    Modern Ranch residence full un-finished basement, large lot.

    E. Clark Toleman Real Estate Appraisal Services

    10 Upper St, Winchester, KY 40391
  • /9

    $206,000

    • Land
    • 7.77 Acres
    • $26,512 per Acre

    368 Flanagan Station Rd, Winchester, KY 40391

    Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

    Shari Frasure Keller Williams Commonwealth

    368 Flanagan Station Rd, Winchester, KY 40391
  • /11

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,534 Sq Ft

    646 Laura Dr, Winchester, KY 40391

    Three bedrooms ranch, that has been updated with a new kitchen, with granite tops ,new appliances, new flooring ,new interior paintiing ,plus much more, located in Verna Hills S/D located between Winchester and Lexington . Owner/Agent

    Garry Milton Milton and Associates Real Estate

    646 Laura Dr, Winchester, KY 40391
  • /12

    $230,000

    • 2 Beds
    • 1 Bath
    • 1,484 Sq Ft

    605 College St, Winchester, KY 40391

    Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

    Steve Adams Steven D Adams Real Estate Services, LLC

    605 College St, Winchester, KY 40391
  • /32

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft

    17 Euclid Ave, Winchester, KY 40391

    Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bedroom two full bath home may be the one you are looking for. Beautiful Hardwood floors throughout most of the home. Two additional bedrooms are upstairs with a full bath. Fenced in back yard and a large deck for you summertime entertaining. Don't wait, let's take a look.

    Donna Thwaites Thwaites Realtors LLC

    17 Euclid Ave, Winchester, KY 40391
  • /23

    $230,000

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

    313 S Burns Ave, Winchester, KY 40391

    This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detached garage behind the home. Plus, it's walkable to downtown Winchester, the public library, and College Park. Inside, you'll find tall ceilings, a traditional living and dining room, and a unique layout that gives you options for how you use the space. The kitchen opens to the back deck, and a ramp at the

    Michelle Blackburn RE/MAX Creative, Winchester

    313 S Burns Ave, Winchester, KY 40391
  • /26

    $246,400

    • 5 Beds
    • 3 Baths
    • 3,007 Sq Ft

    221 S Highland St, Winchester, KY 40391

    INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

    Joshua Lynch The Brokerage

    221 S Highland St, Winchester, KY 40391
  • /37

    $219,000

    • 3 Beds
    • 1 Bath
    • 1,188 Sq Ft

    314 E Broadway St, Winchester, KY 40391

    Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of classic charm on a spacious 0.26-acre lot! This home blends timeless character with thoughtful updates, featuring an inviting single-level layout, bright living areas, well-sized bedrooms, and an updated kitchen with an added pantry for extra storage. Out back, enjoy an attached and enclosed sunroom perfect for

    Ashley Spencer Keller Williams Commonwealth

    314 E Broadway St, Winchester, KY 40391
  • /34

    $300,000

    • 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

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$255,000
Median Single Family Sale Price
$260,500
Median Townhouse Sale Price
$191,750
Average Price Per Sq Ft
$162
Number of Homes for Sale
78
Last 12 months Home Sales
328
Months of Supply
2.90
Median List Price
$265,500
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
9%
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