Winchester, KY Homes

/20
Est $259,271 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,498 Sq Ft
1121 Muddy Creek Rd, Winchester, KY 40391

1121 Muddy Creek Rd, Winchester, KY 40391

/4
$139,900
- Land
- 5.67 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
/23
$244,895 Sold Jun 10, 2025
- 2,536 Sq Ft
- $97/SF
- 10 Days On Market
- 3 Beds
- 3 Baths
- Built 2006
244 Bay Hill Ct, Winchester, KY 40391

A super rare opportunity to own a townhome with all the luxuries and space of a single family home! From the open floor plan to the gleaming hardwood floors, this home has so much to offer! With three bedrooms on the main floor and a potential fourth on the lower level, this home has room for everyone. Whether you like to play inside or out there's room for both. The basement has a huge bonus

Destiny Darby Keller Williams Commonwealth

244 Bay Hill Ct, Winchester, KY 40391

/79
Est $226,417 Not Listed For Sale
- 3 Beds
- 1 Bath
- 946 Sq Ft
205 French Ave, Winchester, KY 40391

205 French Ave, Winchester, KY 40391

/4
$149,900
- Land
- 5.6 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
/51
$560,000 Sold Jun 10, 2025
- 3,160 Sq Ft
- $177/SF
- 11 Days On Market
- 3 Beds
- 4 Baths
- Built 2012
520 Gay Evans Rd, Winchester, KY 40391

Custom-built, 1-owner home nestled on 4.29 private acres minutes from Winchester & I-64. Located on a peaceful lane, this handsome ranch w/partially finished basement offers a bright & welcoming space that you will want to call home. The home boasts Hardie board-type siding/brick, Anderson windows, UPDATED 2025 shingles & a spacious front porch for relaxing. Inside, 9' & vaulted ceilings create

Robin Jones Keller Williams Legacy Group

520 Gay Evans Rd, Winchester, KY 40391

/24
Est $209,057 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,634 Sq Ft
5 Kentucky St, Winchester, KY 40391

5 Kentucky St, Winchester, KY 40391

/10
$374,900
- Land
- 1.29 Acres
- $290,620 per Acre
395 Croxton Way, Winchester, KY 40391

1.29 acre Commercial Lot zoned B-3 that's slightly elevated with maximum visibility for your business. Ideal location for a gas station, fast food restaurant or retail shop. Lot near Clark Medical Center Hospital. To the south is Lexington Road (US 60), to the west is Floyd Clay Drive, and to the North is Croxton Way. Making three (3) different entrances to enhance accessibility to any business.

Rich Decker Rector Hayden Realtors

395 Croxton Way, Winchester, KY 40391
/55
$448,000 Sold Jun 09, 2025
- 4,260 Sq Ft
- $105/SF
- 12 Days On Market
- 3 Beds
- 3 Baths
- Built 1998
207 Bentbrook Ct, Winchester, KY 40391

Spacious Ranch with Pool & Finished BasementOver 4,200 sq ft of versatile living space on a quiet cul-de-sac—perfect for large or multigenerational families!Main Features:• 3 bedrooms on the main floor, including a large primary suite• Ensuite with soaking tub, separate shower, double vanity & walk-in closet• Open living room with wood-burning fireplace & stone surround•

Melodie Lincavage RE/MAX Elite Realty

207 Bentbrook Ct, Winchester, KY 40391

/23
Est $161,636 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,708 Sq Ft
11 Kentucky St, Winchester, KY 40391

11 Kentucky St, Winchester, KY 40391

/15
$925,000
- Land
- 3.77 Acres
- $245,358 per Acre
300 Rolling Hills Ln, Winchester, KY 40391

Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

Josh Wood Freedom Realty & Property Management

300 Rolling Hills Ln, Winchester, KY 40391
/15
$249,900 Sold Jun 09, 2025
- 1,463 Sq Ft
- $171/SF
- 17 Days On Market
- 3 Beds
- 2 Baths
- Built 2005
234 Prescott Ln, Winchester, KY 40391

Welcome Home! This stunning 1.5-story home is ready for its next owner! The primary suite is conveniently located on the ground floor, featuring a large walk-in closet for all your storage needs. The cozy living room boasts vaulted ceilings, creating an open, airy feel, while the brand-new tile shower in the full downstairs bathroom adds a touch of modern elegance. Upstairs, you'll find two

Darrell Tackett Dream Maker Realty, LLC

234 Prescott Ln, Winchester, KY 40391

/24
Est $205,438 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
21 Kentucky St, Winchester, KY 40391

21 Kentucky St, Winchester, KY 40391

/8
$209,900
- 3 Beds
- 1 Bath
- 1,100 Sq Ft
222 Holiday Rd, Winchester, KY 40391

Great location close t o down town Winchester, shopping, school, recreation areas, I 64 ,in beautiful Winchester,nice 3 bedroom ,1 bath , all brick home, with all appliances, including washer and dryer roof 1 year old, fenced yard, storage building private drive. nice back yard and more.

Sophia Herald Herald Real Estate

222 Holiday Rd, Winchester, KY 40391
/77
$464,900 Sold Jun 09, 2025
- 2,495 Sq Ft
- $186/SF
- 21 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2017
275 Runnymeade Dr, Winchester, KY 40391

This stunning property is ideally located and is an absolute must see! Featuring a beautiful kitchen that boasts a large island, gas range, tiled backsplash, and granite countertops.The primary suite offers an incredible en-suite full bath with a tiled walk in shower, oversized soaking tub, granite countertops on a large double vanity, and a walk-in closet.This lovely

Tyson Walters Kassie & Associates

275 Runnymeade Dr, Winchester, KY 40391

/18
Est $121,747 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,080 Sq Ft
129 Kentucky St, Winchester, KY 40391

129 Kentucky St, 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
/33
$250,000 Sold Jun 09, 2025
- 1,500 Sq Ft
- $167/SF
- 75 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1940
14 Calloway St, Winchester, KY 40391

Beautiful and completely remodeled! Welcome to this stunning home. As you pull up, you will notice a brand new driveway and the inviting front entry.Upon entering, you will love the open floor plan and the brand new luxury vinyl plank flooring. The bright inviting kitchen is just waiting for you to cook and entertain. With brand new cabinets, quartz countertops, stainless steel appliances and

Libby VanMeter Marshall Lane Real Estate - Lexington

14 Calloway St, Winchester, KY 40391

/17
Est $222,871 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,734 Sq Ft
102 Kentucky St, Winchester, KY 40391

102 Kentucky St, 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
/36
$184,742 Sold Jun 06, 2025
- 1,140 Sq Ft
- $162/SF
- 3 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1990
120 Heather Ln, Winchester, KY 40391

This Townhome is Adorable and move in ready. It offers vaulted tongue and groove ceilings and a wood burning fireplace in the living room. There are beautiful hardwood floors in the kitchen and dining room. In the kitchen you will find custom oak cabinets and granite counter tops. The full bathroom also has a custom oak cabinet with a granite sink and numerous closets made of cedar throughout the

Julie Wiggington RE/MAX Creative, Winchester

120 Heather Ln, Winchester, KY 40391

/16
Est $165,331 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,122 Sq Ft
141 Alabama St, Winchester, KY 40391

141 Alabama St, 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
/33
$450,000 Sold Jun 06, 2025
- 3,046 Sq Ft
- $148/SF
- 49 Days On Market
- 4 Beds
- 3 Baths
- Built 2006
210 Candlewood Dr, Winchester, KY 40391

Gorgeous brick home in the Royal Oaks neighborhood in Clark County! Quiet and peaceful location on a cul-de-sac on over a half acre lot. Surrounded by farmland with fabulous views, but only 2 minutes to the I-64 ramp and close to schools, shopping and restaurants. Over 3,000 square feet of finished space, walkout basement, 4 bedrooms (5 BR's with one non-conforming), 3 full baths, and a HUGE

Jim Woodrum RE/MAX Creative, Winchester

210 Candlewood Dr, Winchester, KY 40391

/16
Est $357,829 Not Listed For Sale
- 4 Beds
- 2 Baths
- 4,176 Sq Ft
122 French Ave, Winchester, KY 40391

122 French Ave, 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
/40
$278,500 Sold Jun 06, 2025
- 2,400 Sq Ft
- $116/SF
- 130 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1970
8 Chickadee Ln, Winchester, KY 40391

Classic Brick Ranch Home with all the charm! 4 bedrooms, 2.5 bathrooms, Living Room, and Large Family Room offers space for entertaining, Adorable Sunroom to enjoy all seasons, Carport with beautiful brick pavers, storage building, a very well maintained spacious beautifully manicured and landscaped yard, an indoor room with hot tub, all in a great location on a cul de sac street!!!

Whitney Ensor Ensor Real Estate, LLC

8 Chickadee Ln, Winchester, KY 40391

/31
Est $163,345 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,946 Sq Ft
134 Central Ave, Winchester, KY 40391

134 Central Ave, 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
/27
$229,000 Sold Jun 05, 2025
- 1,200 Sq Ft
- $191/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 2025
13 Fairview Ave, Winchester, KY 40391

New Construction - 3 Bed, 2 Bath Home on Spacious Lot!Located in a well-established neighborhood just minutes from downtown Winchester, this brand-new 3-bedroom, 2-bath home offers modern comfort and convenience. The kitchen features granite countertops, stainless steel appliances, and stylish finishes throughout. Enjoy the benefits of a large lot—perfect for outdoor entertaining. Don't miss

Nena Honaker Tom Goebel & Company

13 Fairview Ave, Winchester, KY 40391

/19
Est $198,126 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,322 Sq Ft
130 Central Ave, Winchester, KY 40391

130 Central Ave, 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
/34
$366,500 Sold Jun 05, 2025
- 2,496 Sq Ft
- $147/SF
- 56 Days On Market
- 4 Beds
- 3 Baths
- Built 2020
112 Gibson Way, Winchester, KY 40391

Amazing space in this 4 bedroom 3 bath home located in a great neighborhood, almost brand new well maintained, call today, close to shopping, churches, schools, I-64 and I-75, Richmond and Lexington,

Mila Ensor Ensor Real Estate, LLC

112 Gibson Way, Winchester, KY 40391

/8
Est $264,332 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,359 Sq Ft
109 Alabama St, Winchester, KY 40391

109 Alabama St, 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
/33
$299,900 Sold Jun 04, 2025
- 1,876 Sq Ft
- $160/SF
- 22 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2002
107 Morning Glory Ct, Winchester, KY 40391

Move-in ready and waiting for you! This stunning split-foyer home in McClure Manor offers everything you need for comfortable living. Featuring 4 bedrooms and 2.5 baths, this home provides ample space for everyone. The inviting living room flows seamlessly into a well-appointed kitchen with stainless steel appliances, while the downstairs family room offers additional space to relax and

Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

107 Morning Glory Ct, Winchester, KY 40391

/23
Est $196,031 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,738 Sq Ft
112 Georgia St, Winchester, KY 40391

112 Georgia St, 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
/70
$424,900 Sold Jun 02, 2025
- 2,952 Sq Ft
- $144/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 1990
4353 Boonesboro Rd, Winchester, KY 40391

WELCOME HOME - Discover your private retreat on almost 1.3 acres! This spacious brick home offers modern comfort with granite kitchen countertops, an open layout, and Whirlpool appliances on the main level. A fully equipped second kitchen downstairs, alongside a versatile'man cave' room, provides ample space for entertaining or mullti-generational living. With 4 bedrooms, there is a bonus

M Gail Cleaver United Real Estate Bluegrass

4353 Boonesboro Rd, Winchester, KY 40391

/44
Est $171,166 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
118 Alabama St, Winchester, KY 40391

118 Alabama St, Winchester, KY 40391

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