168

Newest Homes for Sale in Winchester, KY

Section Image Section Image
  • /5

    $95,000

    • 3 Beds
    • 2 Baths
    • 750 Sq Ft

    113 Mimosa Dr, Winchester, KY 40391

    Discover the perfect balance between home ownership, affordability, and rural tranquility in this charming 3-bedroom two bath home. Conveniently located near shopping areas and interstates providing easy access to Lexington, Winchester and many central Kentucky cities. The interior features freshly updated flooring, offering a cohesive feel to living spaces. The true highlight of this property is

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 328-1402

    113 Mimosa Dr, Winchester, KY 40391
  • /7

    $440,000

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

    870 Pilot View Rd, Winchester, KY 40391

    Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings

    Chelsea Morguson McCallie Real Estate

    870 Pilot View Rd, Winchester, KY 40391
  • /26

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    4305 Old Boonesboro Rd, Winchester, KY 40391

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    (859) 549-3072

    4305 Old Boonesboro Rd, Winchester, KY 40391
  • /17

    $129,900

    • 2 Beds
    • 1 Bath
    • 876 Sq Ft

    122 Calloway St, Winchester, KY 40391

    Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. Recently vacated, the home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and

    Darrell Tackett Dream Maker Realty, LLC

    122 Calloway St, Winchester, KY 40391
  • /24

    $290,000

    • 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
  • /2

    $110,000

    • Land
    • 0.47 Acre
    • $234,043 per Acre

    139 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    139 Jacob Ct, Winchester, KY 40391
  • /2

    $150,000

    • Land
    • 2.11 Acres
    • $71,090 per Acre

    125 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Knox Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    250 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    250 Duclair Dr, Winchester, KY 40391
  • /13

    $1,250,000

    345 Providence Ln, Winchester, KY 40391

    120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream home. Conveniently located just

    Megan McCoy Keller Williams Legacy Group

    345 Providence Ln, Winchester, KY 40391
  • /2

    $150,000

    • Land
    • 2.16 Acres
    • $69,444 per Acre

    120 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    120 Knox Ct, Winchester, KY 40391
  • /47

    $452,500

    • 3 Beds
    • 2.5 Baths
    • 2,961 Sq Ft

    42 Mockingbird Valley Rd, Winchester, KY 40391

    This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

    Markus Cross McCallie Real Estate

    42 Mockingbird Valley Rd, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.27 Acre
    • $407,407 per Acre

    125 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    125 Jacob Ct, Winchester, KY 40391
  • /24

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    120 Sunset Heights, Winchester, KY 40391

    Your search is over with this hard to find 3 bedroom 2 bathroom ranch located close to town, College Park and featured a nice fenced level yard. Your will love the cathedral ceiling in the Great Room and Kitchen as well as the above ground pool with a new liner ready to be installed. You will love the oversized rear deck which will be great for entertaining. A covered front porch as well as

    Keith Wilson Coldwell Banker McMahan

    120 Sunset Heights, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.32 Acre
    • $343,750 per Acre

    115 Jacob Ct, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    115 Jacob Ct, Winchester, KY 40391
  • /2

    $110,000

    • Land
    • 0.5 Acre
    • $220,000 per Acre

    260 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    260 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.68 Acre
    • $147,059 per Acre

    100 Duclair Dr, Winchester, KY 40391

    Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

    John Wilson Bluegrass Properties Group

    100 Duclair Dr, Winchester, KY 40391
  • /7

    $190,000

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft

    41 7th St, Winchester, KY 40391

    Welcome to 41 7th Street! This all-brick ranch features 3 bedrooms, 2 full baths, and beautiful hardwood floors throughout the living room, hallway, and bedrooms. Tucked at the end of the street, the property offers added privacy and peaceful farm views behind the home. Enjoy newer windows, a new HVAC system, and a new water heater for added comfort and efficiency. The attached garage provides

    Austina Bruton Re/Max Elite Realty - Hamburg

    41 7th St, Winchester, KY 40391
  • /34

    $325,000

    • 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
  • /33

    $367,000

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

    446 Tremont Ln, Winchester, KY 40391

    Are your ready for a lifestyle change? Do you need more space? How about approximately 2800 square feet with four bedrooms and 2-1/2 baths. A nice size corner lot with side entry 2 car garage. Walkout patio, walk in closet, two story entry and gas fireplace are just a few of the features in this home. Recent upgrades include TWO new hot water heaters, UV filtration installed in HVAC, Full privacy

    Dylan Langdon The Agency

    446 Tremont Ln, 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
  • /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
  • /34

    $275,000

    • 4 Beds
    • 3 Baths
    • 1,850 Sq Ft

    20 Bon-Haven Ave, Winchester, KY 40391

    Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

    Jacqueline Marchildon Lifstyl Real Estate

    20 Bon-Haven Ave, Winchester, KY 40391
  • /21

    $139,000

    • 2 Beds
    • 1 Bath
    • 886 Sq Ft

    9 Linden Ave, Winchester, KY 40391

    Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

    Emily Hacker-Todd CENTURY 21 Advantage Realty

    9 Linden Ave, Winchester, KY 40391
  • /43

    $269,900

    • 7 Beds
    • 3 Baths
    • 3,393 Sq Ft

    146 W Lexington Ave, Winchester, KY 40391

    This investment property has strong rent potential to add to your portfolio. Property is conveniently located in the heart of Downtown Winchester and is zoned R-4. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Downstairs unit has 4 bedrooms and 2 full bathrooms, and its currently leased for $1,495 a

    Kevin Bradley KB Realty Group

    146 W Lexington Ave, Winchester, KY 40391
  • /86

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 3,848 Sq Ft

    125 Casa Landa Way, Winchester, KY 40391

    Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on .40 of an acre lot with side

    Maggie Napier Napier Realtors

    125 Casa Landa Way, Winchester, KY 40391
  • /2

    $550,000

    • Land
    • 1.53 Acres
    • $359,477 per Acre

    33-41 Winn Ave, Winchester, KY 40391

    Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

    Bob Sophiea eXp Realty, LLC

    33-41 Winn Ave, Winchester, KY 40391
  • /23

    $250,000

    • 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
  • /31

    $295,000

    • 3 Beds
    • 3 Baths
    • 1,738 Sq Ft

    420 Willowbrook Rd, Winchester, KY 40391

    Tucked near the cul-de-sac on a dead-end street in the Windridge neighborhood, this 3 bedroom, 3 bath ranch offers easy access to the Bypass and Boone Ave along with a functional, spacious layout. A foyer entry opens to a formal living room featuring a wood-burning fireplace, built-in shelving, and a charming cased opening that provides sightlines into the kitchen and dining area, while a den

    Michelle Blackburn RE/MAX Creative, Winchester

    420 Willowbrook Rd, Winchester, KY 40391
  • /22

    $270,000

    • 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
  • /59

    $825,000

    • 2 Beds
    • 1.5 Baths
    • 2,361 Sq Ft

    455 Davis Ln, Winchester, KY 40391

    Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

    Dale Hatton Dream Maker Realty, LLC

    455 Davis Ln, Winchester, KY 40391
  • /65

    $609,900

    • 5 Beds
    • 4 Baths
    • 4,515 Sq Ft

    6595 Mount Sterling Rd, Winchester, KY 40391

    INCREDIBLE! This custom-built home sits on 2.59 acres in a prime location just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms

    Brooke Otis Mullins RO&CO Real Estate

    6595 Mount Sterling Rd, Winchester, KY 40391
  • /2

    $369,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,558 Sq Ft

    204 Jett Dr, Winchester, KY 40391

    New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

    Mila Ensor Ensor Real Estate, LLC

    204 Jett Dr, Winchester, KY 40391
  • /30

    $259,900

    • 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
  • /49

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    233 Cunningham Ln, Winchester, KY 40391

    Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Parkway making it easily accessible. One level, ranch home that features 3 bedrooms, a luxurious primary ensuite... corner jetter tub, seperate walk in shower with glass door, double bowl raised height vanity and a linen closet complete the bathroom and the bedroom has vaulted ceilings, walk in closet and

    Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

    233 Cunningham Ln, Winchester, KY 40391
  • /28

    $309,900

    • 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
  • /39

    $384,900 New Construction

    • 4 Beds
    • 4.5 Baths

    3600 Crowe Ridge Rd, Winchester, KY 40391

    Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 21' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

    Maggie Napier Napier Realtors

    3600 Crowe Ridge Rd, Winchester, KY 40391
  • /36

    $379,000

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

    133 Shala-Mar Rue, Winchester, KY 40391

    Welcome to your next home in one of Clark County's most desirable neighborhoods—Shala Mar Estates! This beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and modern convenience. Step into the expansive primary bedroom, a true retreat, complete with a stunning ensuite bathroom featuring a brand-new soaking tub and a separate tiled shower. The additional

    Nena Honaker Tom Goebel & Company

    133 Shala-Mar Rue, Winchester, KY 40391
  • /26

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    21 Virginia Ave, Winchester, KY 40391

    Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets,

    Emily Crump EXP Realty, LLC

    21 Virginia Ave, Winchester, KY 40391
  • /19

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,072 Sq Ft

    117 Buffalo Trace, Winchester, KY 40391

    Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! Conveniently located in a great neighborhood. Owner/Agent

    Nena Honaker Tom Goebel & Company

    117 Buffalo Trace, Winchester, KY 40391
  • /42

    $349,900

    • 3 Beds
    • 3 Baths
    • 2,821 Sq Ft

    3622 Stamper Dr, Winchester, KY 40391

    This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to

    Josh Wood Freedom Realty & Property Management

    3622 Stamper Dr, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 5

Frequently Asked Questions

What is the average home price in Winchester, KY?
Homes for sale in Winchester, KY have an average home price of $326,315.
How many homes have sold over the last 12 months in Winchester, KY?
332 homes have sold in Winchester, KY over the last 12 months.
Is Winchester, KY a safe city?
In general, the safest neighborhoods in Winchester, KY with lower crime scores are Old Pine Grove, Becknerville and Wyandotte.
What are the most popular zip codes in Winchester, KY?
The most popular zip codes in Winchester, KY include 40391, 40361, 40353, 40516 and 40475.
What are the most popular neighborhoods in Winchester, KY?
The most popular neighborhoods in Winchester, KY with the most homes for sale are Old Pine Grove, Becknerville and Wyandotte.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $269,000. If you put a 20% down payment of $53,800 and had a 30-year fixed mortgage with an interest rate of 6.15%, your estimated principal and interest payment would be $1,310 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $56K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winchester, KY?
Winchester, KY has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Strode Station Elementary School, George Rogers Clark High School and Baker Intermediate School. The neighborhoods in Winchester with the highest rated schools are Old Pine Grove, Becknerville and Wyandotte. Browse all the schools in Winchester, KY to learn more.

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$249,950
Median Single Family Sale Price
$265,000
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$161
Number of Homes for Sale
84
Last 12 months Home Sales
332
Months of Supply
3.00
Median List Price
$269,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
6%
How to Buy a Home How to Finance a Home How to Sell a Home