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

3961 Jackson Ferry Rd, Winchester, KY 40391
Explore Winchester
/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

MELIA Realty LLC

Lot 4 Plantations Dr, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
241 Plantations Dr Unit LOT 7, Winchester, KY 40391

Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #7 is now available and ready for you to bring your own builder and create the home you've

Melia Hord

MELIA Realty LLC

241 Plantations Dr Unit LOT 7, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
229 Plantations Dr Unit LOT 1, Winchester, KY 40391

**Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #1** is now available and ready for you to bring your own builder and create

Melia Hord

MELIA Realty LLC

229 Plantations Dr Unit LOT 1, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
237 Plantations Dr Unit LOT 5, Winchester, KY 40391

**Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #5** is now available and ready for you to bring your own builder and create

Melia Hord

MELIA Realty LLC

237 Plantations Dr Unit LOT 5, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
233 Plantations Dr Unit LOT 3, Winchester, KY 40391

Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #3 is now available and ready for you to bring your own builder and create the home you've

Melia Hord

MELIA Realty LLC

233 Plantations Dr Unit LOT 3, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
239 Plantations Dr Unit LOT 6, Winchester, KY 40391

**Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #6** is now available and ready for you to bring your own builder and create

Melia Hord

MELIA Realty LLC

239 Plantations Dr Unit LOT 6, 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

MELIA Realty LLC

Lot 3 Plantations Dr, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
235 Plantations Dr Unit LOT 4, Winchester, KY 40391

Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #4 is now available and ready for you to bring your own builder and create the home you've

Melia Hord

MELIA Realty LLC

235 Plantations Dr Unit LOT 4, Winchester, KY 40391
/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
231 Plantations Dr Unit LOT 2, Winchester, KY 40391

Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #2 is now available and ready for you to bring your own builder and create the home you've

Melia Hord

MELIA Realty LLC

231 Plantations Dr Unit LOT 2, 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

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
/23
$99,900
- 3 Beds
- 2 Baths
- 675 Sq Ft
2799 Pine Ridge Rd, Winchester, KY 40391

If your looking for a fixer upper, this is it. House on 2 acres in the country with lots of potential. Laundry is off the kitchen, but floor is soft from a water leak. From the kitchen you will see a guest bath, dining and living area. To the left is a hallway that leads to 2 bedrooms, drywalled just needs to be finished. To the right of the living area is your master bedroom and bath. With some

Robin Horn Keller Williams Commonwealth

2799 Pine Ridge 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
/31
$89,900
- 2 Beds
- 2 Baths
- 828 Sq Ft
308 Market St, Winchester, KY 40391

Newly built and ready for its first owner, this 2-bedroom, 2-bathroom home in Quick Shop delivers the layout and finishes most buyers want without the price tag of new site-built construction. The main living area opens directly into the kitchen, giving the space a connected, airy feel that suits quiet evenings and gatherings alike. Down the hall, 2 bedrooms are sized for real furniture and real

Hailey Blaylock Quick Shop MHC

308 Market St, Winchester, KY 40391
/4
$35,000
- Land
- 1 Acre
- $35,000 per Acre
2828 Athens Boonesboro Rd, Winchester, KY 40391

Property has electric, water, and a septic tank located on site. The septic tank is underground and may need work as it is small and was constructed in the 90's for a two bedroom home capacity.

Kristian Kiskaden Keller Williams Commonwealth

2828 Athens Boonesboro Rd, 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
/21
$99,500

$5K PRICE DROP
- 2 Beds
- 2 Baths
- 924 Sq Ft
563 Constitution Dr, Winchester, KY 40391

Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per

Jason Townsend Kentucky Residential Real Estate, LLC

563 Constitution Dr, 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
/37
$69,900
- 2 Beds
- 2 Baths
- 960 Sq Ft
617 Banana Dr, Winchester, KY 40391

Well-maintained 2024 manufactured home with 960 sq ft, 2 bedrooms and 2 bathrooms. Located in Quick Shop MHC in Winchester, KY. Land lease $475/month.

Hailey Blaylock Quick Shop MHC

617 Banana 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
$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
$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
/40
$40,000
- 3 Beds
- 1 Bath
- 1,842 Sq Ft
16 Virginia Ave, Winchester, KY 40391

Auction Live or Online August 1 at 10 AM. 1800 square foot home. We will be selling by the deed. Sale terms: If you bid online you must submit a letter of good standing from your bank at least 24 hours prior to auction. Selling by the deed. Call Auctioneer Ken DeGrant license # 281879 www.highpointky.com

Kenneth DeGrant High Point Realty & Auction

16 Virginia Ave, 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

Home Prices in Winchester, KY

The median home sale price in Winchester, KY is $262,500, up 9% year-over-year. Homes in Winchester sell in 31 days on average, compared to the national average of 57 days.

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 92	Last 12 months Home Sales 305
Months of Supply 3.60	Median List Price $274,900
Median Change From 1st List Price 2%	Median Home Sale Price YoY Change 9%

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

In Winchester, there are currently 34 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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