36

Winchester, KY Homes for Sale under $700,000

Section Image Section Image Section Image
  • /84

    $699,999

    $99K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 7,058 Sq Ft

    186 Chardonnay Ct, Winchester, KY 40391

    Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    186 Chardonnay Ct, Winchester, KY 40391
  • /64

    $420,000

    • 3 Beds
    • 2 Baths
    • 2,027 Sq Ft

    187 Hawthorne Dr, Winchester, KY 40391

    Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    187 Hawthorne Dr, Winchester, KY 40391
  • /18

    $525,000

    $31K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,102 Sq Ft

    110 White Conkwright Rd, Winchester, KY 40391

    Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

    Agent Photo

    Philip 'PJ' Elder

    Omega Real Estate Brokerage LLC

    110 White Conkwright Rd, Winchester, KY 40391
  • /64

    $419,500

    • 4 Beds
    • 2.5 Baths
    • 1,978 Sq Ft

    107 Hibiscus Ln, Winchester, KY 40391

    Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout.

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    107 Hibiscus Ln, Winchester, KY 40391
  • /25

    $425,000

    • Land
    • 25.87 Acres
    • $16,426 per Acre

    2996/3056 Irvine Rd, Winchester, KY 40391

    Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    2996/3056 Irvine Rd, Winchester, KY 40391
  • /45

    $429,900

    New Construction
    • 3 - 5 Beds
    • 2.5 - 4.5 Baths
    • 2,722 Sq Ft

    Eleanor Plan at Boone's Crossing, Winchester, KY 40391

    Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
  • /47

    $427,000

    • 3 Beds
    • 2.5 Baths
    • 2,289 Sq Ft

    20 Edgewood Dr, Winchester, KY 40391

    Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

    Libby VanMeter Marshall Lane Real Estate - Lexington

    20 Edgewood Dr, Winchester, KY 40391
  • /19

    $460,000

    $39K PRICE DROP
    • Land
    • 36.94 Acres
    • $12,453 per Acre

    1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

    Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

    Greg Meade Whitetail Properties Real Estate

    1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
  • /59

    $499,900

    • 4 Beds
    • 3 Baths
    • 5,646 Sq Ft

    16 Manor Dr, Winchester, KY 40391

    One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

    Zella Rosenthal Tom Goebel & Company

    16 Manor Dr, Winchester, KY 40391
  • /10

    $550,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    107 Bella Shae Way, Winchester, KY 40391

    Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

    Shane Underwood Keller Williams Commonwealth

    107 Bella Shae Way, Winchester, KY 40391
  • /55

    $549,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,280 Sq Ft

    108 Bella Shae Way, Winchester, KY 40391

    Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

    Vickie Skeens RE/MAX Elite Lexington

    108 Bella Shae Way, Winchester, KY 40391
  • /63

    $524,900

    • 3 Beds
    • 2.5 Baths
    • 2,514 Sq Ft

    275 Runnymeade Dr, Winchester, KY 40391

    OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new

    Craig Bridgewater Bridgewater Real Estate

    275 Runnymeade Dr, Winchester, KY 40391
  • /7

    $400,000

    • Land
    • 7.31 Acres
    • $54,720 per Acre

    4095 Basin Springs Rd, Winchester, KY 40391

    Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. Location! Location! Location!

    Peggy Baldridge HomeFirst Real Estate

    4095 Basin Springs Rd, Winchester, KY 40391
  • /10

    $575,000

    $75K PRICE DROP
    • Land
    • 2.6 Acres
    • $221,154 per Acre

    529 Bullion Blvd Unit 3B, Winchester, KY 40391

    Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

    Greg Leveridge Block + Lot Homes

    529 Bullion Blvd Unit 3B, Winchester, KY 40391
  • /22

    $665,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    414 Alexis Way, Winchester, KY 40391

    Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

    Shane Underwood Keller Williams Commonwealth

    414 Alexis Way, Winchester, KY 40391
  • /72

    $406,900

    New Construction
    • 3 - 6 Beds
    • 2.5 - 5.5 Baths
    • 2,570 Sq Ft

    Jackie Plan at Boone's Crossing, Winchester, KY 40391

    Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

    James Monroe Homes Builder
    2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
  • /36

    $540,000

    $10K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 4,173 Sq Ft

    600 Boone Ave, Winchester, KY 40391

    Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

    Holly Goeing The Agency

    600 Boone Ave, Winchester, KY 40391
  • /3

    $670,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,261 Sq Ft

    113 Bella Shae Way, Winchester, KY 40391

    Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

    Shane Underwood Keller Williams Commonwealth

    113 Bella Shae Way, Winchester, KY 40391
  • /100

    $429,900

    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    240 Athens Boonesboro Rd, Winchester, KY 40391

    Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

    Darrell Tackett Dream Maker Realty, LLC

    240 Athens Boonesboro Rd, Winchester, KY 40391
  • /9

    $500,000

    $100K PRICE DROP
    • Land
    • 1.52 Acres
    • $328,947 per Acre

    1005 Early Dr, Winchester, KY 40391

    Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

    Whitney Ensor Ensor Real Estate, LLC

    1005 Early Dr, Winchester, KY 40391
  • /14

    $650,000

    • Land
    • 3 Acres
    • $216,667 per Acre

    205 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 Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

    Greg Leveridge Block + Lot Homes

    205 Codella Dr, Winchester, KY 40391
  • /2

    $490,000

    $60K PRICE DROP
    • Land
    • 1.53 Acres
    • $320,261 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
  • /4

    $625,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,405 Sq Ft

    424 Alexis Way, Winchester, KY 40391

    Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

    Shane Underwood Keller Williams Commonwealth

    424 Alexis Way, Winchester, KY 40391
  • /55

    $515,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,563 Sq Ft

    935 Stoner-Ephesus Rd, Winchester, KY 40391

    Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

    Timothy Saylor Threshold Real Estate Services

    935 Stoner-Ephesus Rd, Winchester, KY 40391
  • /39

    $415,000

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft

    215 Delaplain Rd, Winchester, KY 40391

    215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line

    Alyssa Ryan Marshall Lane Real Estate - Lexington

    215 Delaplain Rd, Winchester, KY 40391
  • /5

    $575,000

    • Land
    • 1.71 Acres
    • $336,257 per Acre

    1025 Colby Rd, Winchester, KY 40391

    This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

    Jo Gawthrop Keller Williams Bluegrass Realty

    1025 Colby Rd, Winchester, KY 40391
  • /31

    $479,000

    $26K PRICE DROP
    • 8 Beds
    • 4 Baths
    • 5,058 Sq Ft

    265 S Highland St, Winchester, KY 40391

    Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

    J Corey Griffo RE/MAX Elite Lexington

    265 S Highland St, Winchester, KY 40391
  • /2

    $600,000

    • Land
    • 6.13 Acres
    • $97,879 per Acre

    722 Colby Rd Unit 2, Winchester, KY 40391

    Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

    Cheryl Johnston CMI Properties

    722 Colby Rd Unit 2, Winchester, KY 40391
  • /4

    $635,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,537 Sq Ft

    422 Alexis Way, Winchester, KY 40391

    Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

    Shane Underwood Keller Williams Commonwealth

    422 Alexis Way, Winchester, KY 40391
  • /3

    $700,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    415 Alexis Way, Winchester, KY 40391

    Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

    Shane Underwood Keller Williams Commonwealth

    415 Alexis Way, 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 Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

    Greg Leveridge Block + Lot Homes

    145 Codella Dr, Winchester, KY 40391
  • /3

    $645,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,526 Sq Ft

    106 Bella Shae Way, Winchester, KY 40391

    Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

    Shane Underwood Keller Williams Commonwealth

    106 Bella Shae Way, Winchester, KY 40391
  • /33

    $465,000

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

    287 Logan Lick Rd, Winchester, KY 40391

    This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the

    Dale Hatton Dream Maker Realty, LLC

    287 Logan Lick Rd, Winchester, KY 40391
  • /2

    $550,500

    $31K PRICE INCREASE
    • Land
    • 20.78 Acres
    • $26,492 per Acre

    1395 Two Mile Rd, Winchester, KY 40391

    PLANNED DEVELOPMENT INVESTMENT OPPORTUNITY! Already Zoned Planned Development! There is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. (In addition there is an approximately 24 acre tract suitable for all forms of Residential use. The remaining 103 acres is available for all forms of zoning with frontage on the approved ByPass extension. The two

    Garnett Davis Tom Goebel & Company

    1395 Two Mile Rd, Winchester, KY 40391
  • /10

    $550,000

    $100K PRICE DROP
    • Land
    • 3 Acres
    • $183,333 per Acre

    609 Bullion Blvd Unit 3A, Winchester, KY 40391

    Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

    Greg Leveridge Block + Lot Homes

    609 Bullion Blvd Unit 3A, Winchester, KY 40391
  • /49

    $445,500

    • 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

Home Price Trends

Median Sale Price
$262,500
Median Single Family Sale Price
$269,450
Median Townhouse Sale Price
$195,000
Median 2 Bedroom Sale Price
$167,500
Median 1 Bedroom Sale Price
$164,900
Average Price Per Sq Ft
$162
Number of Homes for Sale
91
Last 12 months Home Sales
303
Months of Supply
3.60
Median List Price
$274,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home