26

Winchester, KY Homes for Sale under $800,000

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
  • /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
  • /72

    $775,000

    • 5 Beds
    • 3 Baths
    • 4,437 Sq Ft

    465 Morris Rd, Winchester, KY 40391

    Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

    Agent Photo

    Brenda Leigh Walters

    United Real Estate Bluegrass

    465 Morris Rd, Winchester, KY 40391
  • /46

    $749,900

    • 3 Beds
    • 2.5 Baths
    • 2,735 Sq Ft

    2180 Big Stoner Rd, Winchester, KY 40391

    Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

    Agent Photo

    Ashley Barreto

    Indigo & Co

    2180 Big Stoner Rd, Winchester, KY 40391
  • /92

    $795,000

    • 3 Beds
    • 3 Baths
    • 3,336 Sq Ft

    6356 Van Meter Rd, Winchester, KY 40391

    **Click on the Virtual Tour section to see the video walk through!** Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington,

    Josh Wood Freedom Realty & Property Management

    6356 Van Meter Rd, 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
  • /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
  • /9

    $785,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,476 Sq Ft

    425 Alexis Way, Winchester, KY 40391

    Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

    Shane Underwood Keller Williams Commonwealth

    425 Alexis Way, 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
  • /86

    $789,000

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    6500 Mount Sterling Rd, Winchester, KY 40391

    **Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses,

    Josh Wood Freedom Realty & Property Management

    6500 Mount Sterling Rd, 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
  • /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
  • /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
  • /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
  • /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
  • /73

    $724,950

    Open Sun 1PM - 3PM $100K PRICE DROP
    • 2 Beds
    • 2.5 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
  • /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
  • /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

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