30

Winchester, KY Homes for Sale under $100,000

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  • /29

    $70,000

    • 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
  • /8

    $97,500

    • Land
    • 7.99 Acres
    • $12,201 per Acre

    3991 Jackson Ferry Rd, Winchester, KY 40391

    Offering the same peaceful setting and rare river access, this tract provides a fantastic opportunity for recreational land ownership at an affordable price. Backing directly to the Kentucky River, it's an ideal spot for camping, weekend retreats, arrowhead hunting or enjoying the outdoors with kayaking, fishing, and more right at your fingertips. This property's fertile soil opens the door for

    Christa Joynt Keller Williams Commonwealth

    3991 Jackson Ferry Rd, Winchester, KY 40391
  • /6

    $97,500

    • Land
    • 8.46 Acres
    • $11,522 per Acre

    3961 Jackson Ferry Rd, Winchester, KY 40391

    Escape to your own slice of Kentucky countryside with this 8.462-acre tract nestled along a scenic stretch of Jackson Ferry Road. Backing up to the Kentucky River, this property is perfect for recreational use, whether you're looking to camp, garden, or create a weekend getaway. This land provides plenty of space for campers and outdoor enjoyment throughout much of the year. The soil is rich and

    Christa Joynt Keller Williams Commonwealth

    3961 Jackson Ferry Rd, Winchester, KY 40391
  • /11

    $50,000

    • Land
    • 0.41 Acre
    • $121,951 per Acre

    308 Duclair Dr, Winchester, KY 40391

    Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

    Joseph Miller Keller Williams Legacy Group

    308 Duclair Dr, Winchester, KY 40391
  • /4

    $10,000

    • Land
    • 0.17 Acre
    • $59,880 per Acre

    117 4th St, Winchester, KY 40391

    Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

    Anita McDermott Keller Williams Bluegrass Realty

    117 4th St, Winchester, KY 40391
  • /3

    $84,900

    • Land
    • 3.39 Acres
    • $25,044 per Acre

    160 Rector Ln, Winchester, KY 40391

    UNIQUE Opportunity - 3.39 acres with a small pond - tucked away on a private lane, flat land and totally surrounded by trees. What a unique setting!! Convenience is the key to this property. Water is available at the main road. Internet has been extended down Rector Lane, electricity is accessible for connection. Deed Restrictions apply. Do Not Miss Your Chance to own this SPECIAL piece of land.

    M Gail Cleaver United Real Estate Bluegrass

    160 Rector Ln, Winchester, KY 40391
  • /4

    $42,500

    • Land
    • 0.19 Acre
    • $223,684 per Acre

    113 Mayfair Ct, Winchester, KY 40391

    Wowser! Looking for a lot that backs up to greenspace and will NOT have another home on one side? Here it IS! This may be just what you're looking for. Originally, the street was supposed to connect, but due to the changes in grade, this won't be happening! Plus, with the way the lot sits, you can enjoy many beautiful sunsets. It's a hidden gem just waiting for you to find it! The home to be

    Jo Gawthrop Keller Williams Bluegrass Realty

    113 Mayfair Ct, Winchester, KY 40391
  • /3

    $42,500

    • Land
    • 0.2 Acre
    • $212,500 per Acre

    108 Dorset Ln, Winchester, KY 40391

    The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

    Jo Gawthrop Keller Williams Bluegrass Realty

    108 Dorset Ln, Winchester, KY 40391
  • /58

    $89,900

    • 2 Beds
    • 1 Bath
    • 825 Sq Ft

    1860 Ford Rd, Winchester, KY 40391

    Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space

    Darrell Tackett Dream Maker Realty, LLC

    1860 Ford Rd, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.37 Acre
    • $270,270 per Acre

    225 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

    225 Jacob Ct, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 1.1 Acres
    • $90,909 per Acre

    270 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

    270 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    111 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

    111 Jacob Ct, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    169 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

    169 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    115 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

    115 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.31 Acre
    • $322,581 per Acre

    215 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

    215 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    155 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

    155 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    141 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

    141 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    129 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

    129 Duclair Dr, Winchester, KY 40391
  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    165 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

    165 Duclair Dr, Winchester, KY 40391
  • /28

    $84,900

    • 3 Beds
    • 2 Baths
    • 1,946 Sq Ft

    300 Aspen Ln, Winchester, KY 40391

    Welcome home to this well-maintained 3 bedroom, 2 bathroom double wide manufactured home in Treehaven, offering close to 2,000 square feet of comfortable living space...a rare find for buyers looking for room, functionality, and flexibility. Inside, you'll love the open-concept layout that connects the large living room, kitchen, and dining area, making it ideal for both everyday living and

    Christa Joynt Keller Williams Commonwealth

    300 Aspen Ln, 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
  • /5

    $29,000

    • Land
    • 0.46 Acre
    • $63,043 per Acre

    102 Augusta Dr, Winchester, KY 40391

    This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

    Dale Hatton Dream Maker Realty, LLC

    102 Augusta Dr, Winchester, KY 40391
  • /5

    $70,000

    • Land
    • 1.72 Acres
    • $40,698 per Acre

    12541 Ironworks Rd, Winchester, KY 40391

    Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

    Daniela Virguez National Real Estate

    12541 Ironworks Rd, Winchester, KY 40391
  • /2

    $78,500

    • Land
    • 0.22 Acre
    • $356,818 per Acre

    Lot 5 Plantations Dr, Winchester, KY 40391

    NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

    Melia Hord Keller Williams Legacy Group

    Lot 5 Plantations Dr, Winchester, KY 40391
  • /2

    $78,500

    • Land
    • 0.22 Acre
    • $356,818 per Acre

    Lot 3 Plantations Dr, Winchester, KY 40391

    NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

    Melia Hord Keller Williams Legacy Group

    Lot 3 Plantations Dr, Winchester, KY 40391
  • /2

    $78,500

    • Land
    • 0.22 Acre
    • $356,818 per Acre

    Lot 4 Plantations Dr, Winchester, KY 40391

    NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

    Melia Hord Keller Williams Legacy Group

    Lot 4 Plantations Dr, Winchester, KY 40391
  • /6

    $49,500

    • Land
    • 0.98 Acre
    • $50,510 per Acre

    204 Wigeon Ct, Winchester, KY 40391

    Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

    Jim Woodrum RE/MAX Creative, Winchester

    204 Wigeon Ct, Winchester, KY 40391
  • /2

    $67,500

    • Land
    • 1.89 Acres
    • $35,695 per Acre

    250 Spencer Ln, Winchester, KY 40391

    Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

    Craig Bridgewater Bridgewater Real Estate

    250 Spencer Ln, Winchester, KY 40391
  • /2

    $10,000

    • Land
    • 0.06 Acre
    • $166,667 per Acre

    75 4th St, Winchester, KY 40391

    Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

    Bob Sophiea eXp Realty, LLC

    75 4th St, Winchester, KY 40391
  • /2

    $42,500

    • Land
    • 0.26 Acre
    • $163,462 per Acre

    105 Bella Ct, Winchester, KY 40391

    Jo Gawthrop Keller Williams Bluegrass Realty

    105 Bella Ct, Winchester, KY 40391

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$256,700
Median Single Family Sale Price
$260,500
Median Townhouse Sale Price
$194,000
Average Price Per Sq Ft
$163
Number of Homes for Sale
74
Last 12 months Home Sales
322
Months of Supply
2.80
Median List Price
$265,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
8%
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