36

Winchester, KY Homes for Sale under $100,000

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  • /27

    $72,500

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    725 Berry Ct, Winchester, KY 40391

    Looking for affordable homeownership in Winchester, KY? This move-in ready 3-bedroom, 2-bath manufactured home offers modern living at an incredible value. Built just 3 years ago and meticulously maintained, this home feels like new from the moment you step inside. Located in the heart of Winchester, you'll enjoy easy access to local restaurants, shopping, grocery stores, parks, and everyday

    Christa Joynt Keller Williams Commonwealth

    725 Berry Ct, 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
  • /3

    $70,000

    • Land
    • 2.04 Acres
    • $34,314 per Acre

    150 Spencer Ln, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and let the land grow in value. This lot totaling 2.041 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

    Kathryn Cheuvront Coldwell Banker McMahan

    150 Spencer Ln, Winchester, KY 40391
  • /4

    $67,500

    • Land
    • 1.92 Acres
    • $35,156 per Acre

    12569 Ironworks Rd, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

    Kathryn Cheuvront Coldwell Banker McMahan

    12569 Ironworks Rd, 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
  • /8

    $25,000

    • Land
    • 0.1 Acre
    • $250,000 per Acre

    61 Melbourne St, Winchester, KY 40391

    Opportunity is knocking to build your dream home or investment property on this 0.1035 -acre residential lot at 61 Melbourne St, located in the North Park neighborhood right cross the street from the park and easy access to local amenities, schools, and roadways. With public utilities available, this lot offers endless possibilities for new construction or future development, providing a great

    Brian Lewis Guide Realty, Inc.

    61 Melbourne St, Winchester, KY 40391
  • /4

    $64,900

    • Land
    • 0.64 Acre
    • $101,406 per Acre

    102 Royal Oak Dr, Winchester, KY 40391

    A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..64 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

    Melia Hord Keller Williams Legacy Group

    102 Royal Oak Dr, Winchester, KY 40391
  • /4

    $64,900

    • Land
    • 0.52 Acre
    • $124,808 per Acre

    101 Royal Oak Dr, Winchester, KY 40391

    A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..52 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

    Melia Hord Keller Williams Legacy Group

    101 Royal Oak Dr, Winchester, KY 40391
  • /7

    $45,000

    1559 Amster Grove Rd, Winchester, KY 40391

    Looking for your next investment or weekend escape? This unique property offers two dwellings on one lot, right along the KY River. While it needs a full restoration, the possibilities are endless—whether you're dreaming of a private vacation retreat, a charming getaway spot, or a high-income short-term rental, this is a diamond in the rough ready to shine. Key Highlights: Two dwellings on one

    Erin Lewis Christies International Real Estate Bluegrass

    1559 Amster Grove Rd, Winchester, KY 40391
  • /4

    $10,000

    • Land
    • 0.17 Acre
    • $58,824 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
  • /10

    $100,000

    • Land
    • 3.91 Acres
    • $25,575 per Acre

    6345 Muddy Creek Rd, Winchester, KY 40391

    Beautiful lot in Clark County with just under four acres. Owner/ Agent property. Deed restrictions apply

    Chase Parrish Taylor Real Estate, LLC

    6345 Muddy Creek Rd, Winchester, KY 40391
  • /11

    $100,000

    • Land
    • 3.91 Acres
    • $25,575 per Acre

    6413 Muddy Creek Rd, Winchester, KY 40391

    Beautiful lot in Clark County with just under four acres. Septic tank and utilities already on site. Buyer to confirm condition. Owner/ Agent property. Deed restrictions apply. Link to 3D model of lot:

    Chase Parrish Taylor Real Estate, LLC

    6413 Muddy Creek 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 Commonwealth

    308 Duclair Dr, Winchester, KY 40391
  • /4

    $100,000

    • Land
    • 2.62 Acres
    • $38,168 per Acre

    100 Spencer Ln, Winchester, KY 40391

    Eskippakithiki overlooks development. Has a 2.615 acre lot (parcel #8) available for sale waiting for you to build your dream home with beautiful views of serene countryside.

    Priscila Hale FC Tucker Bluegrass

    100 Spencer Ln, 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
    • 0.68 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
  • /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
  • /2

    $80,000

    • Land
    • 5.75 Acres
    • $13,913 per Acre

    1341 Sewell Shop Rd, Winchester, KY 40391

    Parcel 4 -5.753 acreas 1341 Sewell Shop Rd

    Zella Rosenthal Tom Goebel & Company

    1341 Sewell Shop Rd, Winchester, KY 40391
  • /2

    $75,000

    • Land
    • 6.43 Acres
    • $11,664 per Acre

    1431 Sewell Shop Rd, Winchester, KY 40391

    parcel 6 -1431 Sewell Shop Rd. 6.428 acres

    Zella Rosenthal Tom Goebel & Company

    1431 Sewell Shop Rd, Winchester, KY 40391
  • /2

    $80,000

    • Land
    • 5.85 Acres
    • $13,675 per Acre

    7244 Ecton Rd, Winchester, KY 40391

    Parcel 11 - 5.848 acres has a 50 foot easement, pipeline (Ashland Pipeline Co) in rear area of the parcel

    Zella Rosenthal Tom Goebel & Company

    7244 Ecton Rd, 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

    $15,000

    • Land
    • 0.48 Acre
    • $31,250 per Acre

    0 Lot 80 Ivy Ln, Wellington, KY 40387

    Looking for the perfect summer getaway or a smart investment? These beautifully situated lots just minutes from Cave Run Lake offer endless potential for developers, investors, and outdoor enthusiasts alike! Build your dream vacation rentals or Airbnb cabins Create a charming campground or glamping retreat Develop a private getaway or family compound Or simply invest in land that grows in value

    Dustin Williams RE/MAX Elite Lexington

    0 Lot 80 Ivy Ln, Wellington, KY 40387
  • /2

    $89,100

    • Land
    • 7.86 Acres
    • $11,336 per Acre

    13067 Irvine Rd, Winchester, KY 40391

    Mendel Tipton Natural Bridge Realty

    13067 Irvine Rd, Winchester, KY 40391
  • /2

    $99,900

    • Land
    • 8.82 Acres
    • $11,327 per Acre

    13015 Irvine Rd Unit Parcel 5, Winchester, KY 40391

    Mendel Tipton Natural Bridge Realty

    13015 Irvine Rd Unit Parcel 5, Winchester, KY 40391

Home Trends in Winchester, KY

Housing Trends

Median Sale Price
$246,000
Median Single Family Sale Price
$260,000
Median Townhouse Sale Price
$195,000
Average Price Per Sq Ft
$161
Number of Homes for Sale
88
Last 12 months Home Sales
327
Months of Supply
3.20
Median List Price
$260,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
5%
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