Winchester, KY Homes for Sale under $100,000

/17
$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

(859) 295-6825

3961 Jackson Ferry Rd, Winchester, KY 40391
Explore Winchester
/29
$70,000

$25K PRICE DROP
- 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

Brenda Sipes

WEICHERT REALTORS - ABG Properties

(859) 328-1402

113 Mimosa Dr, Winchester, KY 40391
/28
$84,900

$5K PRICE DROP
- 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

(859) 903-5711

300 Aspen Ln, Winchester, KY 40391
/17
$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

(859) 600-6640

3991 Jackson Ferry Rd, Winchester, KY 40391
/11
$50,000
- Land
- 17,859 Sq Ft
- $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
/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
/51
$69,900
- Land
- 4.48 Acres
- $15,603 per Acre
1450 Ford Rd, Winchester, KY 40391

Darrell Tackett Dream Maker Realty, LLC

1450 Ford Rd, Winchester, KY 40391
/2
$100,000

$10K PRICE DROP
- Land
- 16,117 Sq Ft
- $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

$10K PRICE INCREASE
- 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
$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
$100,000

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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
/6
$49,500
- Land
- 42,688 Sq Ft
- $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
$100,000

$10K PRICE DROP
- Land
- 13,503 Sq Ft
- $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

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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
$78,500
- Land
- 9,600 Sq Ft
- $356,171 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
/5
$29,000

$4K PRICE DROP
- Land
- 20,037 Sq Ft
- $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
$78,500
- Land
- 9,600 Sq Ft
- $356,171 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
/4
$10,000

$15K PRICE DROP
- Land
- 7,274 Sq Ft
- $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
/2
$100,000
- Land
- 29,620 Sq Ft
- $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
$78,500
- Land
- 9,600 Sq Ft
- $356,171 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
/2
$100,000

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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
/58
$74,950

$15K PRICE DROP
- 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

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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
/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
$100,000

$10K PRICE DROP
- Land
- 13,939 Sq Ft
- $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

Kentucky Clark County Winchester

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 34 days on the market compared to the national average of 58 days. The median sale price for homes in Winchester, KY over the last 12 months is $259,950, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$259,950

Median Single Family Sale Price

$269,000

Median Townhouse Sale Price

$185,000

Average Price Per Sq Ft

$162

Number of Homes for Sale

Last 12 months Home Sales

322

Months of Supply

3.00

Median List Price

$272,450

Median Change From 1st List Price

Median Home Sale Price YoY Change

11%

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

In Winchester, there are currently 27 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.

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