Winchester, KY Homes for Sale under $100,000

/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
Explore Winchester
/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
/4
$64,900
- Land
- 27,878 Sq Ft
- $101,406 per Acre
102 Royal Oak Dr, Winchester, KY 40391

One of the Few Remaining Estate Homesites in Royal Oaks Estates! An exceptional opportunity awaits to build your custom dream home in the Estate Section of Royal Oaks, one of Clark County's most established and desirable communities. Situated on 0.64 acres, 102 Royal Oak Drive offers the space, setting, and flexibility to create a home tailored to your lifestyle while enjoying the beauty and

Melia Hord

MELIA Realty LLC

102 Royal Oak Dr, 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
/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
/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
/2
$42,500
- Land
- 11,369 Sq Ft
- $162,835 per Acre
105 Bella Ct, Winchester, KY 40391

Jo Gawthrop Keller Williams Bluegrass Realty

105 Bella Ct, 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
/29
$50,000
- 1 Bed
- 1 Bath
- 870 Sq Ft
141 Coffee Springs Ln, Winchester, KY 40391

This is a public auction. You are buying as/is. Please come and preview the property. 10% Buyers premium added to the final bid. 10% down night of the sell. This property can be made into a dream home. Where else can you find a property for 50,000.00 dollars? Rony Jo Ballou Auctioneer 859-595-6808 bid at www.goochsells.com. Realtors you are welcome to bring your clients to preview this property.

Rony Jo Ballou Power House Realty

141 Coffee Springs 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
/3
$42,500
- Land
- 8,712 Sq Ft
- $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
/17
$66,000

$3K PRICE DROP
- 2 Beds
- 2 Baths
- 924 Sq Ft
546 Constitution Dr, Winchester, KY 40391

This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.

Dale Hatton Dream Maker Realty, LLC

546 Constitution Dr, 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
/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
/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
/4
$42,500
- Land
- 8,276 Sq Ft
- $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
/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

Home Prices in Winchester, KY

The median home sale price in Winchester, KY is $263,250, up 10% year-over-year. Homes in Winchester sell in 33 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $263,250	Median Single Family Sale Price $269,900
Median Townhouse Sale Price $189,000	Median 2 Bedroom Sale Price $165,000
Median 1 Bedroom Sale Price $102,950	Average Price Per Sq Ft $161
Number of Homes for Sale 83	Last 12 months Home Sales 302
Months of Supply 3.30	Median List Price $272,450
Median Change From 1st List Price 2%	Median Home Sale Price YoY Change 10%

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

In Winchester, there are currently 33 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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