Winchester, KY Homes under $200,000

/24
$195,000
- 3 Beds
- 1 Bath
- 1,075 Sq Ft
113 Colonial Park Dr, Winchester, KY 40391

Conveniently located just off Veterans Memorial Bypass, this adorable brick ranch offers easy access to everything Winchester has to offer. Inside, you'll find a freshly painted interior, new flooring, new windows, a new roof and a new HVAC system. The nice-sized kitchen features plenty of cabinet space, perfect for home-cooked meals and gatherings. Nestled in a quiet, well-established

Janet Baldwin Kentucky Land and Home

113 Colonial Park Dr, Winchester, KY 40391
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/5
$105,000
- Land
- 1.00 Acre
- $105,000 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
/3
$135,000
- Land
- 10 Acres
- $13,145 per Acre
4150 Schollsville Rd, Winchester, KY 40391

This land located in the center of hunting paradise, where nature excels her beauty, a place for you to build your perfect home,10.27acres, call todayCity water is East Clark Water and it is across road, as per the seller back of property has a fence that is not true to the property lineThe gate next to this acreage is not on this property, look for the orange markers on the front fence

Mila Ensor Ensor Real Estate LLC

4150 Schollsville Rd, Winchester, KY 40391
/27
$199,900 Open Sat 11AM - 1PM
- 3 Beds
- 1.5 Baths
- 1,348 Sq Ft
139 W Hickman St, Winchester, KY 40391

Welcome Home! Featuring 3 bedrooms and 2 bathrooms, this home is everything you have been looking for. Recent updates include new flooring, appliances, roof, HVAC, and even the water heater. Sit out on your front porch and drink your morning coffee, or enjoy your large back deck for a weekend cookout. This home also has plenty of attic storage. The driveway makes a perfect place to plug in your

Clay David Sutherland ERA Select Real Estate

139 W Hickman St, Winchester, KY 40391
/17
$195,000
- 3 Beds
- 1 Bath
- 1,059 Sq Ft
114 Sunset Heights, Winchester, KY 40391

Conveniently located, well maintained ranch with 3 bedrooms in established neighborhood, awaiting its new owner! With a newer roof, gutters (with guards), furnace and water heater...it helps take some maintenance worries away! Ample storage with storage closet in carport, and detached shed. Three hundred sq.ft. 3-seasons area in rear of home, which could be used year-round with the addition of a

Susan Baldwin Rector Hayden Realtors

114 Sunset Heights, Winchester, KY 40391
/19
$175,000
- 4 Beds
- 1 Bath
- 1,120 Sq Ft
8 1/2 1st St, Winchester, KY 40391

In the heart of downtown Winchester, don't miss out on this adorable home! Newly remodeled and move in ready! New appliances, new HVAC, new windows, and so much more! Kitchen has granite countertops too! Open floor plan that is great for entertaining! Schedule your showing today!

Michelle Ann Tellman Lifstyl Real Estate

8 1/2 1st St, Winchester, KY 40391
/8
$159,000
- 2 Beds
- 3 Baths
- 1,056 Sq Ft
125 Chatham Place, Winchester, KY 40391

Why rent when you can own this Townhome it has 2 bedrooms,3 bathroms (one full bath and 2 half baths) living room,kitchen, locted near schools and shopping,just behind Lowes.Owner/Broker

Garry Milton Milton and Associates Real Estate

125 Chatham Place, Winchester, KY 40391
/15
$135,000
- 3 Beds
- 2 Baths
- 924 Sq Ft
706 Williamsburg Dr, Winchester, KY 40391

This is your opportunity to buy a brand new Clayton tru elation single wide mobile home. 3 bed 2 bath all electric. The .11 acre lot conveys. New front porch and back steps. This house is in the Yorktown trailer park. They currently have an HOA fee of $150 a month and that covers your water, sewer, and trash. The park also offers a play ground for the kids. Please confirm you read over all park

Andrew Fugitt Coldwell Banker McMahan

706 Williamsburg Dr, Winchester, KY 40391
/33
$184,900
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
307 Blair Ave, Winchester, KY 40391

This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new flooring and interior paint. The inviting side porch features a ramp for easy accessibility and leads to a spacious patio—perfect for relaxing or entertaining. A detached two-car garage adds great storage and functionality. Located just minutes from downtown Winchester and I-64, this move-in-ready home

Brooke Otis-Mull RO&CO Real Estate

307 Blair Ave, Winchester, KY 40391
/8
$129,000
- 2 Beds
- 1 Bath
- 637 Sq Ft
109 Spring St, Winchester, KY 40391

Investment opportunity in Winchester! This 2-bedroom, 1-bath home at 109 Spring St is currently tenant-occupied and leased at $900/month. Functional layout with a spacious kitchen and separate living area. Conveniently located near downtown, schools, and local amenities. Whether you're expanding your portfolio or looking for a starter investment, this property offers steady rental income from day

Shari Frasure Keller Williams Commonwealth

109 Spring St, Winchester, KY 40391
/21
$149,000
- 2 Beds
- 1 Bath
- 886 Sq Ft
9 Linden Ave, Winchester, KY 40391

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, no warranties implied or

Emily Hacker-Todd CENTURY 21 Advantage Realty

9 Linden Ave, Winchester, KY 40391
/23
$140,000
- Land
- 5.00 Acres
- $28,000 per Acre
2100 Old Log Lick Rd, Winchester, KY 40391

Dreaming of peaceful country living with a head start on the building process? This beautiful 5-acre tract in the country has everything you need to get started: electric and water already in place, a septic system installed, and a cleared, flat spot just waiting for your dream home. The property features a pond, a gravel driveway, and a small shop with a bathroom and attached carport, perfect

Michelle Blackburn RE/MAX Creative, Winchester

2100 Old Log Lick Rd, Winchester, KY 40391
/16
$175,000
- 3 Beds
- 2 Baths
- 1,072 Sq Ft
117 Buffalo Trace, Winchester, KY 40391

NEW Price Reduction!!! Perfect 3 Bedroom 2 Bathroom Home For A First Time HomeBuyer Or Someone Downsizing. Location Is Convenient To The Interstate, Shopping And Downtown! Nice Size Backyard And Plenty Of Parking In The Front. Shed In The Backyard Is Included. Make This Beautiful And Affordable Home Yours Before The Holidays!

Patrick Arvin Keller Williams Commonwealth

117 Buffalo Trace, 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 Est Serv

3385 Colby Rd, Winchester, KY 40391
/5
$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
/6
$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
/7
$195,000
- Land
- 6 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
/2
$115,000
- Land
- 1.03 Acres
- $111,650 per Acre
210 Hood Ave, Winchester, KY 40391

This is an unique opportunity to own a beautiful acre + building lot in Winchester! Walking distance to downtown, Country Club, College Park & library! The house seat has been graded to accommodate a daylight walk-out basement. City water, sewer, natural gas & electric are available. Currently being resurveyed to include closed alleyway. Minimal restrictions. Owner/agent.

Angie Conley Dixon Dixon Properties

210 Hood Ave, Winchester, KY 40391
/2
$135,000
- 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. Both units are currently used as investment property. Both homes need extensive repair. 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

A. Rebecca Woods Woods Realty Group

175 Magnolia St, Winchester, KY 40391
/15
$187,500
- Land
- 7 Acres
- $25,202 per Acre
7575 Irvine Rd, Winchester, KY 40391

Amazing 7.44 acre country building lot / mini farm / homestead with views! Established driveway leads a nice 38' x 50' pole barn that would serve as a nice shop / garage! Partially fenced with gated entrance. Perfect spot to potentially build a pond. Water meter base and electricity pole already in place.

Jason Townsend Kentucky Residential Real Estate, LLC

7575 Irvine Rd, Winchester, KY 40391
/13
$149,400
- Land
- 2.30 Acres
- $64,957 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

Jarran Thomas The Agency

110 Knox Ct, Winchester, KY 40391
/4
$109,000
- Land
- 4.02 Acres
- $27,114 per Acre
2058 Athens Boonesboro Rd, Winchester, KY 40391

Prime building lot - 4.15 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2058 and 2010 lots approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first

Megan McCoy Keller Williams Legacy Group

2058 Athens Boonesboro Rd, Winchester, KY 40391
/3
$109,000
- Land
- 4.02 Acres
- $27,114 per Acre
2010 Athens Boonesboro Rd, Winchester, KY 40391

Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

Megan McCoy Keller Williams Legacy Group

2010 Athens Boonesboro Rd, Winchester, KY 40391
/4
$139,900
- Land
- 6 Acres
- $24,674 per Acre
1445 Gay Evans Rd, Winchester, KY 40391

Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

Holly Goeing The Agency

1445 Gay Evans Rd, Winchester, KY 40391
/4
$149,900
- Land
- 6 Acres
- $26,768 per Acre
1541 Gay Evans Rd, Winchester, KY 40391

Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

Holly Goeing The Agency

1541 Gay Evans Rd, Winchester, KY 40391
/4
$140,000
- Land
- 3.94 Acres
- $35,533 per Acre
12569 Ironworks Rd, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! These two parcels totaling 3.94 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

Kathryn Cheuvront Coldwell Banker McMahan

12569 Ironworks Rd, Winchester, KY 40391
/2
$195,000
- Land
- 8 Acres
- $23,353 per Acre
6699 Boonesboro Rd, Winchester, KY 40391

READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

Jennifer Ray RE/MAX Elite Lexington

6699 Boonesboro Rd, 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
$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
- 0.27 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
/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
135 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

135 Jacob Ct, 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

Showing Results 1 - 40, Page 1 of 2

Kentucky Winchester

Home Trends in Winchester, KY

On average, homes in Winchester, KY sell after 26 days on the market compared to the national average of 48 days. The median sale price for homes in Winchester, KY over the last 12 months is $240,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$240,000

Median Single Family Sale Price

$265,000

Median Townhouse Sale Price

$193,200

Average Price Per Sq Ft

$162

Number of Homes for Sale

108

Last 12 months Home Sales

348

Months of Supply

3.70

Median List Price

$270,000

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 59 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

More About Living in Winchester

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

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