Winchester, KY Homes for Sale under $200,000

/22
$147,000
- 2 Beds
- 1 Bath
- 807 Sq Ft
3208 Ford Hampton Rd, Winchester, KY 40391

Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

Brenda Sipes

WEICHERT REALTORS - ABG Properties

(859) 765-6889

3208 Ford Hampton Rd, Winchester, KY 40391
Explore Winchester
/6
$171,000
- 2 Beds
- 1 Bath
- 870 Sq Ft
102 W Hickman St, Winchester, KY 40391

102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

David Espinosa Bluegrass Realty Pros, Inc

102 W Hickman St, Winchester, KY 40391
/2
$150,000
- Land
- 2.77 Acres
- $54,152 per Acre
3385 Colby Rd, Winchester, KY 40391

Small acreage lot on Colby Road! Accessed by easement from neighbors driveway.

Steve Adams Steven D Adams Real Estate Services, LLC

3385 Colby Rd, Winchester, KY 40391
/2
$110,000
- Land
- 0.47 Acre
- $234,043 per Acre
139 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

139 Jacob Ct, Winchester, KY 40391
/2
$150,000
- Land
- 2.11 Acres
- $71,090 per Acre
125 Knox 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

125 Knox Ct, Winchester, KY 40391
/17
$129,900
- 2 Beds
- 1 Bath
- 876 Sq Ft
122 Calloway St, Winchester, KY 40391

Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. Recently vacated, the home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and

Darrell Tackett Dream Maker Realty, LLC

122 Calloway St, Winchester, KY 40391
/4
$137,500
- Land
- 3.94 Acres
- $34,898 per Acre
12569 Ironworks Rd, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it gows in value. Offering 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

Kathryn Cheuvront Coldwell Banker McMahan

12569 Ironworks Rd, Winchester, KY 40391
/19
$125,000
- Land
- 4.01 Acres
- $31,172 per Acre
1940 Athens Boonesboro Rd, Winchester, KY 40391

Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land. This lot sits directly across from the

Laura Sizemore Kentucky Land and Home

1940 Athens Boonesboro Rd, Winchester, KY 40391
/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
250 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

250 Duclair Dr, Winchester, KY 40391
/21
$139,000
- 2 Beds
- 1 Bath
- 886 Sq Ft
9 Linden Ave, Winchester, KY 40391

Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

Emily Hacker-Todd CENTURY 21 Advantage Realty

9 Linden Ave, Winchester, KY 40391
/19
$199,900
- 3 Beds
- 2 Baths
- 1,072 Sq Ft
117 Buffalo Trace, Winchester, KY 40391

Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! Conveniently located in a great neighborhood. Owner/Agent

Nena Honaker Tom Goebel & Company

117 Buffalo Trace, Winchester, KY 40391
/6
$110,000
- Land
- 2.06 Acres
- $53,398 per Acre
1185 Craig Crossing Rd, Winchester, KY 40391

Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

1185 Craig Crossing Rd, Winchester, KY 40391
/30
$199,900
- 3 Beds
- 1 Bath
- 1,354 Sq Ft
40 Garner St, Winchester, KY 40391

Check out this lovely all brick, beautifully renovated 3-bedroom,1bath home located in Winchester perfectly blending timeless charm with modern updates. This move-in ready home features a new roof, updated electrical and plumbing, an upgraded kitchen, new flooring, a fully renovated bathroom, fresh paint throughout, and all new appliances. Situated on a spacious corner lot, the property offers

Nicole Seals Guide Realty, Inc.

40 Garner St, Winchester, KY 40391
/2
$150,000
- Land
- 2.16 Acres
- $69,444 per Acre
120 Knox Ct, Winchester, KY 40391

Looking for a place to build a Upscale home in 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

120 Knox Ct, Winchester, KY 40391
/14
$129,800
- Land
- 2.3 Acres
- $56,435 per Acre
110 Knox Ct, Winchester, KY 40391

The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

Amanda Thomas The Agency

110 Knox Ct, Winchester, KY 40391
/2
$110,000
- Land
- 0.27 Acre
- $407,407 per Acre
125 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

125 Jacob Ct, Winchester, KY 40391
/8
$195,000
- Land
- 6.15 Acres
- $31,707 per Acre
990 Craig Crossing Rd, Winchester, KY 40391

Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

990 Craig Crossing Rd, Winchester, KY 40391
/3
$146,000
- 3 Beds
- 1 Bath
- 1,020 Sq Ft
228 Jackson St, Winchester, KY 40391

Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

228 Jackson St, Winchester, KY 40391
/4
$115,000
- 4 Beds
- 2.5 Baths
- 2,131 Sq Ft
205 E Washington St, Winchester, KY 40391

PRICE DROP!!! FLIP This House! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/2 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Finish This Home It Will Be A Showstopper Better Than New Construction With Large Sq Ft What Many Buyers Are Looking For. Great Opportunity To Make Money Or Live In This

Patrick Arvin Keller Williams Commonwealth

205 E Washington St, Winchester, KY 40391
/18
$115,000
- 2 Beds
- 1 Bath
- 910 Sq Ft
114 Magnolia St, Winchester, KY 40391

Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

Michelle Blackburn RE/MAX Creative, Winchester

114 Magnolia St, Winchester, KY 40391
/4
$199,900
- Land
- 11.36 Acres
- $17,597 per Acre
2996 Irvine Rd, Winchester, KY 40391

Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

Lura Justice Rector Hayden Realtors

2996 Irvine Rd, Winchester, KY 40391
/6
$200,000
- Land
- 0.81 Acre
- $246,914 per Acre
550 Bullion Blvd, Winchester, KY 40391

Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer. Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers. Winchester, Kentucky is the county

Greg Leveridge Block + Lot Real Estate

550 Bullion Blvd, Winchester, KY 40391
/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
115 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

115 Jacob Ct, Winchester, KY 40391
/2
$110,000
- Land
- 0.5 Acre
- $220,000 per Acre
260 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

260 Duclair Dr, Winchester, KY 40391
/27
$182,000
- 3 Beds
- 2 Baths
- 1,305 Sq Ft
6 Monroe Ave, Winchester, KY 40391

Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifully maintained 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional.

Lindsey Bivens Berkshire Hathaway de Movellan Properties

6 Monroe Ave, Winchester, KY 40391
/7
$180,000
- Land
- 4.45 Acres
- $40,449 per Acre
1030 Craig Crossing Rd, Winchester, KY 40391

Lot # 14 contains 4.450 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

1030 Craig Crossing Rd, Winchester, KY 40391
/14
$159,900
- Land
- 2.66 Acres
- $60,113 per Acre
590 Craig Crossing, Winchester, KY 40391

Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

Keith Wilson Coldwell Banker McMahan

590 Craig Crossing, 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
/7
$190,000
- 3 Beds
- 2 Baths
- 1,116 Sq Ft
41 7th St, Winchester, KY 40391

Welcome to 41 7th Street! This all-brick ranch features 3 bedrooms, 2 full baths, and beautiful hardwood floors throughout the living room, hallway, and bedrooms. Tucked at the end of the street, the property offers added privacy and peaceful farm views behind the home. Enjoy newer windows, a new HVAC system, and a new water heater for added comfort and efficiency. The attached garage provides

Austina Bruton Re/Max Elite Realty - Hamburg

41 7th St, Winchester, KY 40391
/9
$102,000
- 2 Beds
- 1 Bath
- 552 Sq Ft
39 S Highland St, Winchester, KY 40391

Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

39 S Highland St, Winchester, KY 40391
/12
$144,000
- 3 Beds
- 1 Bath
- 805 Sq Ft
150 Cook Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

150 Cook Ave, Winchester, KY 40391
/12
$194,900
- 3 Beds
- 1 Bath
- 1,046 Sq Ft
175 Magnolia St, Winchester, KY 40391

Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

A. Rebecca Woods Woods Realty Group

175 Magnolia St, Winchester, KY 40391
/20
$139,900
- 3 Beds
- 1 Bath
- 1,150 Sq Ft
103 Yorktowne Ct, Winchester, KY 40391

Affordable and move-in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping,

Susy Esquivel Allied Realty

103 Yorktowne Ct, Winchester, KY 40391
/13
$140,000
- 2 Beds
- 1 Bath
- 1,254 Sq Ft
208 4th St, Winchester, KY 40391

Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

Anita McDermott Keller Williams Bluegrass Realty

208 4th St, Winchester, KY 40391

Kentucky Clark County Winchester

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 31 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, KY over the last 12 months is $249,900, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$249,900

Median Single Family Sale Price

$265,000

Median Townhouse Sale Price

$194,000

Average Price Per Sq Ft

$161

Number of Homes for Sale

Last 12 months Home Sales

331

Months of Supply

3.00

Median List Price

$269,000

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, you'll find a diverse selection of properties with 34 homes for sale under $200,000, catering to budget-conscious buyers seeking affordable housing solutions. Whether you're a first-time homebuyer in search of a cozy starter home or an investor eyeing a promising opportunity, these affordable homes provide a gateway into the real estate market in Winchester, KY.

Winchester Types of Homes for Sale

Winchester Homes by Price

Winchester Real Estate Listings

Winchester New Construction Homes

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