Winchester, KY Homes for Sale under $100,000

/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 Bluegrass Realty

102 Royal Oak Dr, Winchester, KY 40391
Explore Winchester
/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 Bluegrass Realty

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
$25,000
- Land
- 0.17 Acre
- $147,059 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
/28
$44,999
- 3 Beds
- 2 Baths
- 924 Sq Ft
706 Pear Ct, Winchester, KY 40391

Cozy and full of charm! This 3-bedroom, 2-bath manufactured home offers an inviting space with plenty of natural light, a roomy kitchen, and comfortable bedrooms. Located on leased land in a peaceful community, this home is a hidden gem for those looking to own without the high price tag. Current lot rent is $475/ month. Includes a shed for extra storage. Call your agent to schedule an

Deangela Robinson Keller Williams Commonwealth

706 Pear Ct, Winchester, KY 40391
/5
$95,000
- Land
- 1 Acre
- $95,000 per Acre
1730 Mcclure Rd, Winchester, KY 40391

Awesome property, just waiting for you to build your perfect home, ready to fulfill your dreams, great area close to everything.Seller will run the water line to the propertyLots One and Two have entrances beside each other, shown on plat

Mila Ensor Ensor Real Estate, LLC

1730 Mcclure Rd, Winchester, KY 40391
/4
$85,000
- Land
- 1.09 Acres
- $77,982 per Acre
1700 Mcclure Rd, Winchester, KY 40391

Awesome property, just waiting for you to build your perfect home, ready to fulfill your dreams, great area close to everything.Seller will run the water line to the propertyLots One and Two have entrances beside each other, shown on plat

Mila Ensor Ensor Real Estate, LLC

1700 Mcclure Rd, 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
/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
- 0.32 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
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
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
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
$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
- 0.31 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
- 0.37 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
- 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
- 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
- 0.68 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
$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
/5
$95,000
- Land
- 1 Acre
- $95,000 per Acre
1750 Mcclure Rd, Winchester, KY 40391

Mila Ensor Ensor Real Estate, LLC

1750 Mcclure Rd, Winchester, KY 40391

Kentucky Clark County Winchester

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 30 days on the market compared to the national average of 52 days. The median sale price for homes in Winchester, KY over the last 12 months is $240,500, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$240,500

Median Single Family Sale Price

$259,900

Median Townhouse Sale Price

$194,000

Average Price Per Sq Ft

$161

Number of Homes for Sale

Last 12 months Home Sales

320

Months of Supply

3.30

Median List Price

$260,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 28 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Winchester, KY. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

Winchester Types of Homes for Sale

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