Winchester, KY Homes

/27
Est $147,892 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,632 Sq Ft
47 Buckner St, Winchester, KY 40391

47 Buckner St, Winchester, KY 40391

/2
$149,900
- Land
- 6.32 Acres
- $23,718 per Acre
1397 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 6 acres of unrestricted land. Schedule your showing today!

Holly Goeing The Agency

1397 Gay Evans Rd, Winchester, KY 40391
/55
$520,000 Sold May 15, 2025
- 4,659 Sq Ft
- $112/SF
- 61 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1995
427 Calmes Blvd, Winchester, KY 40391

Welcome to 427 Calmes Blvd, a spacious and beautifully updated home in the desirable Oak Hill subdivision. This 4-bedroom, 3.5-bath home sits on a corner lot with a fenced yard, offering plenty of space both inside and out. The main level features a first-floor primary suite, along with two additional bedrooms, while a second master suite upstairs provides extra privacy—perfect for guests or

Kymberly McCreary EXP Realty, LLC

427 Calmes Blvd, Winchester, KY 40391

/47
Est $278,056 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,818 Sq Ft
221 S Highland St, Winchester, KY 40391

221 S Highland St, Winchester, KY 40391

/2
$139,900
- Land
- 5.02 Acres
- $27,869 per Acre
1495 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

1495 Gay Evans Rd, Winchester, KY 40391
/63
$1,325,000 Sold May 15, 2025
- 5,736 Sq Ft
- $231/SF
- 72 Days On Market
- 5 Beds
- 8 Baths
- Built 2021
6755 Boonesboro Rd, Winchester, KY 40391

Stunning and private! This bluegrass property spans 13.9 acres and is ideally located 15 minutes from Lexington, and minutes to Richmond, and Winchester. It boasts a custom, designer chef's kitchen with a gas range, double oven, double refrigerator, and a massive granite island that seats 10+ people. The open concept features a gorgeous great room with shiplap ceilings, exposed wood beams and a

Jennifer Ray RE/MAX Elite Lexington

6755 Boonesboro Rd, Winchester, KY 40391

/11
Est $211,214 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,902 Sq Ft
110 E Hickman St, Winchester, KY 40391

110 E Hickman St, Winchester, KY 40391

/2
$189,900
- Land
- 10.73 Acres
- $17,698 per Acre
1045 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 10 acres of unrestricted land with many building sites. Schedule your showing today!

Holly Goeing The Agency

1045 Gay Evans Rd, Winchester, KY 40391
/24
$186,000 Sold May 14, 2025
- 1,188 Sq Ft
- $157/SF
- 77 Days On Market
- 3 Beds
- 2 Baths
- Built 1994
205 Arbor Ct, Winchester, KY 40391

Charming 3 bedroom, 2 bath cottage with a fenced side yard, perfect for the furbabies or just for outdoor relaxation. Property includes a shed for extra storage. Your cozy new home awaits!

Kathryn Cheuvront Coldwell Banker McMahan

205 Arbor Ct, Winchester, KY 40391

/26
Est $165,473 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,696 Sq Ft
150 W Broadway St, Winchester, KY 40391

150 W Broadway St, Winchester, KY 40391

/2
$199,900
- Land
- 11.33 Acres
- $17,643 per Acre
995 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 11 acres of unrestricted land. Schedule your showing today!

Holly Goeing The Agency

995 Gay Evans Rd, Winchester, KY 40391
/6
$51,000 Sold May 14, 2025
- Land
- 0.25 Acre
- $204,000 per Acre
- 325 Days On Market
214 Ashton Oak Way, Winchester, KY 40391

A Unique Opportunity to Build your Dream Home in the Plantation Section of Royal Oaks in Clark County. Situated on..25. acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

Melia Hord Keller Williams Bluegrass Realty

214 Ashton Oak Way, Winchester, KY 40391

/19
Est $166,254 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,394 Sq Ft
29 Oliver St, Winchester, KY 40391

29 Oliver St, Winchester, KY 40391

/2
$2,000,000
- Land
- 17.87 Acres
- $111,919 per Acre
1509 Boonesboro Rd, Winchester, KY 40391

17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. &

Cheryl Johnston CMI Properties

1509 Boonesboro Rd, Winchester, KY 40391
/36
$177,500 Sold May 13, 2025
- 1,259 Sq Ft
- $141/SF
- 3 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1998
406 Pepperwood Ct, Winchester, KY 40391

Looking for stress free living with a beautiful view in a great location? This townhouse overlooks the rolling hills of KY, located just off I-64 with easy access to Lexington and the Mountain Parkway. Features hardwood floors, ceramic tile and LVT flooring. Separate utility room and spacious 2 car garage with a large unfinished room in the basement. 2 bedrooms upstairs, each with their own

Peggy Baldridge HomeFirst Real Estate

406 Pepperwood Ct, Winchester, KY 40391

/12
Est $147,091 Not Listed For Sale
- 3 Beds
- 1 Bath
- 900 Sq Ft
25 Oliver St, Winchester, KY 40391

25 Oliver St, Winchester, KY 40391

/2
$89,100
- Land
- 7.86 Acres
- $11,336 per Acre
13067 Irvine Rd, Winchester, KY 40391

Mendel Tipton Natural Bridge Realty

13067 Irvine Rd, Winchester, KY 40391
/20
$135,000 Sold May 13, 2025
- 1,194 Sq Ft
- $113/SF
- 13 Days On Market
- 3 Beds
- 1 Bath
- Built 1920
100 Dallas Alley, Winchester, KY 40391

Check out this beautifully refreshed home featuring a brand-new metal roof and a unique floorplan designed for flexibility. Enjoy easy access to downtown and ample parking space for 4 to 6 vehicles. The versatile layout allows for additional bedrooms, making it perfect for growing families or guests. Don't miss this opportunity for modern comfort with convenient urban access!

Emidio Figueroa Rector Hayden Realtors

100 Dallas Alley, Winchester, KY 40391

/11
Est $136,303 Not Listed For Sale
- 2 Beds
- 1 Bath
- 768 Sq Ft
30 Madison Ave, Winchester, KY 40391

30 Madison Ave, Winchester, KY 40391

/2
$99,900
- Land
- 8.82 Acres
- $11,327 per Acre
13015 Irvine Rd Unit Parcel 5, Winchester, KY 40391

Mendel Tipton Natural Bridge Realty

13015 Irvine Rd Unit Parcel 5, Winchester, KY 40391
/2
$110,000 Sold May 13, 2025
- Land
- 0.42 Acre
- $261,905 per Acre
- 900 Days On Market
140 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

140 Duclair Dr, Winchester, KY 40391

/25
Est $175,766 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 960 Sq Ft
15 Madison Ave, Winchester, KY 40391

15 Madison Ave, Winchester, KY 40391

/20
$219,000
13015 Irvine Rd, Winchester, KY 40391

Mendel Tipton Natural Bridge Realty

13015 Irvine Rd, Winchester, KY 40391
/23
$210,000 Sold May 12, 2025
- 1,200 Sq Ft
- $175/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 1998
202 Washington Square, Winchester, KY 40391

Step into this beautifully updated home featuring 3 spacious bedrooms and 2 full bathrooms. The modern kitchen boasts sleek granite countertops, stainless steel appliances, and plenty of cabinet space perfect for cooking or entertaining.

Aaron Kendall Lifstyl Real Estate

202 Washington Square, Winchester, KY 40391

/20
Est $146,524 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,776 Sq Ft
2 1st St, Winchester, KY 40391

2 1st St, Winchester, KY 40391

/5
$95,000
- Land
- 1 Acre
- $95,000 per Acre
1750 Mcclure Rd, Winchester, KY 40391

Mila Ensor Ensor Real Estate, LLC

1750 Mcclure Rd, Winchester, KY 40391
/24
$207,000 Sold May 12, 2025
- 1,040 Sq Ft
- $199/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 2023
411 Pueblo Ct, Winchester, KY 40391

Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the desirable Ft. Estill neighborhood in Winchester. Only 2 years old, this home offers peace of mind with all major systems—including HVAC, roof, and water heater—just 2 years young. Enjoy an open, functional layout perfect for modern living, with spacious bedrooms and a comfortable primary suite.Situated in a

Zach Johnson The Brokerage

411 Pueblo Ct, Winchester, KY 40391

/16
Est $188,252 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,298 Sq Ft
123 2nd St, Winchester, KY 40391

123 2nd St, Winchester, KY 40391

/16
$219,900 New Construction
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
15 Holly Ave, Winchester, KY 40391

New Construction! Modern 3 Bedroom, 2 Bath Home Near Downtown Winchester!Step into this beautiful new construction 3 bedroom, 2 full bath home featuring an open concept layout, granite countertops, stainless steel appliances, and stylish finishes throughout.The large backyard boasts a generous deck perfect for entertaining, gardening, or relaxing. Whether you're hosting a summer

Nena Honaker Tom Goebel & Company

15 Holly Ave, Winchester, KY 40391
/22
$90,000 Sold May 12, 2025
- 50 Days On Market
9776 Ironworks Rd, Winchester, KY 40391

Beautiful piece of land to build your dream Barndominium, house, tiny house, manufactured home, workshop, whatever meets county regulations. No deed restrictions! 40' x 60' x 16' pole barn style garage / home already started for you! An older barn with stalls for the animals! Barn needs a little love. Approximately 515 feet of road frontage. Current access to property is a small easement from the

Jason Townsend Kentucky Residential Real Estate, LLC

9776 Ironworks Rd, Winchester, KY 40391

/25
Est $188,241 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,124 Sq Ft
200 Madison Ave, Winchester, KY 40391

200 Madison Ave, Winchester, KY 40391

/3
$430,000 New Construction
- 3 Beds
- 2 Baths
- 1,855 Sq Ft
265 Evergreen Dr, Winchester, KY 40391

Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

Rex Hall United Real Estate Bluegrass

265 Evergreen Dr, Winchester, KY 40391
/21
$207,000 Sold May 12, 2025
- 1,344 Sq Ft
- $154/SF
- 35 Days On Market
- 4 Beds
- 2 Baths
- Built 2001
513 Acadia Way, Winchester, KY 40391

This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of AMI for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

Tyler I Back The Brokerage

513 Acadia Way, Winchester, KY 40391

/51
Est $253,863 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,134 Sq Ft
840 Two Mile Rd, Winchester, KY 40391

840 Two Mile Rd, Winchester, KY 40391

/3
$430,000 New Construction
- 3 Beds
- 2 Baths
- 1,855 Sq Ft
250 Evergreen Dr, Winchester, KY 40391

Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

Rex Hall United Real Estate Bluegrass

250 Evergreen Dr, Winchester, KY 40391
/22
$173,000 Sold May 09, 2025
- 1,287 Sq Ft
- $134/SF
- 1 Day On Market
- 2 Beds
- 1 Bath
- Built 1960
160 Autumn Ct, Winchester, KY 40391

Attention Investors, Flippers & First-Time Buyers! This 2-bedroom, 1-bath home is bursting with potential! Whether you're looking to renovate and resell, add to your rental portfolio, or put your personal touch on your first home, this is the opportunity you've been waiting for. With solid bones and a great layout, a little modernizing will go a long way in maximizing its value.Outside,

Phillip Neeley-Morrison Bluegrass Home Group

160 Autumn Ct, Winchester, KY 40391

/67
Est $415,419 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,314 Sq Ft
2 Moundale Ave, Winchester, KY 40391

2 Moundale Ave, Winchester, KY 40391

/3
$430,000 New Construction
- 3 Beds
- 2 Baths
- 1,855 Sq Ft
220 Evergreen Dr, Winchester, KY 40391

Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private

Rex Hall United Real Estate Bluegrass

220 Evergreen Dr, Winchester, KY 40391
/21
$199,500 Sold May 09, 2025
- 1,539 Sq Ft
- $130/SF
- 3 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1998
445 Colby Ridge Blvd, Winchester, KY 40391

Spacious 3 bedroom duplex townhome in the Heart of Winchester! This beautifully maintained 3 bedroom, 2.5 bath townhome offers the perfect blend of space, convenience and comfort right in the heart of Winchester. The main level features a large living room, ideal for relaxing or entertaining, along with a spacious kitchen & dining area that offers plenty of room for cooking & gathering, along

Mary Layton FC Tucker Bluegrass

445 Colby Ridge Blvd, Winchester, KY 40391

/74
Est $571,312 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,941 Sq Ft
4 Moundale Ave, Winchester, KY 40391

4 Moundale Ave, Winchester, KY 40391

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Kentucky Clark County Winchester

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