Winchester, KY Homes

/43
$269,000
- 3 Beds
- 2 Baths
- 1,960 Sq Ft
564 Trapp-Goffs Corner Rd, Winchester, KY 40391

Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

Felicia Mayes The Real Estate Co.

564 Trapp-Goffs Corner Rd, Winchester, KY 40391
/48
$330,000 Sold May 23, 2025

113 Holiday Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,090 Sq Ft
- Built 1970
Last Sold Summary
- 3% Below List Price
- $158/SF
- 35 Days On Market
Current Estimated Value $313,960

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

113 Holiday Rd, Winchester, KY 40391

/47
Est $341,080 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,380 Sq Ft
106 Old Ironworks Rd, Winchester, KY 40391

106 Old Ironworks Rd, Winchester, KY 40391

/103
$3,500,000
- 6 Beds
- 5.5 Baths
- 7,274 Sq Ft
5045 Van Meter Rd, Winchester, KY 40391

Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

The Prather Team - Michael Prather Keller Williams Bluegrass Realty

5045 Van Meter Rd, Winchester, KY 40391
/48
$300,000 Sold Feb 07, 2025

509 Lasalle Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,484 Sq Ft
- Built 1987
Last Sold Summary
- 5% Below List Price
- $121/SF
- 155 Days On Market
Current Estimated Value $348,438

Last Listing Agent Kasey McCarty 5.23 Real Estate

509 Lasalle Ct, Winchester, KY 40391

/25
Est $258,826 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,428 Sq Ft
325 Vanover Way, Winchester, KY 40391

325 Vanover Way, Winchester, KY 40391

/2
$369,900 New Construction
- 3 Beds
- 2 Baths
- 1,558 Sq Ft
204 Jett Dr, Winchester, KY 40391

New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

Mila Ensor Ensor Real Estate, LLC

204 Jett Dr, Winchester, KY 40391
/38
$173,000 Sold Sep 22, 2025

44 5th St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,270 Sq Ft
- Built 1952
Last Sold Summary
- 2% Above List Price
- $136/SF
- 2 Days On Market
Current Estimated Value $173,905

Last Listing Agent Tirza Cooper The Howard Realty Co

44 5th St, Winchester, KY 40391

/17
Est $250,738 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,737 Sq Ft
206 Buffalo Trace, Winchester, KY 40391

206 Buffalo Trace, Winchester, KY 40391

/25
$310,000
- 2 Beds
- 1 Bath
- 1,170 Sq Ft
398 Pine Ridge Rd, Winchester, KY 40391

Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

Amie Hieneman ERA Select Real Estate

398 Pine Ridge Rd, Winchester, KY 40391
/18
$200,000 Sold Jan 14, 2026

245 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,074 Sq Ft
- Built 1940
Last Sold Summary
- 9% Below List Price
- $186/SF
- 2 Days On Market
Last Listing Agent Anthony Gigilo ListWithFreedom.com

245 Ecton Rd, Winchester, KY 40391

/32
Est $213,251 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,088 Sq Ft
303 Geronimo Ct, Winchester, KY 40391

303 Geronimo Ct, Winchester, KY 40391

/2
$195,000
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
/52
$500,000 Sold Aug 25, 2025

1778 Elkin Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,020 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $248/SF
- 103 Days On Market
Last Listing Agent Vicki VanWinkle ERA Select Real Estate

1778 Elkin Rd, Winchester, KY 40391

/28
Est $225,871 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
306 Geronimo Ct, Winchester, KY 40391

306 Geronimo Ct, Winchester, KY 40391

/3
$670,000 New Construction
- 3 Beds
- 2 Baths
- 2,261 Sq Ft
113 Bella Shae Way, Winchester, KY 40391

Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

Shane Underwood Keller Williams Commonwealth

113 Bella Shae Way, Winchester, KY 40391
/21
$233,000 Sold Jan 31, 2025

4190 Trapp-Goffs Corner Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 992 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $235/SF
- 49 Days On Market
Current Estimated Value $242,287

Last Listing Agent Christina Bucher Keller Williams Legacy Group

4190 Trapp-Goffs Corner Rd, Winchester, KY 40391

/22
Est $208,277 Not Listed For Sale
- 3 Beds
- 2 Baths
- 960 Sq Ft
113 Buffalo Trace, Winchester, KY 40391

113 Buffalo Trace, Winchester, KY 40391

/26
$255,000 Pending
- 3 Beds
- 2 Baths
- 1,749 Sq Ft
21 Virginia Ave, Winchester, KY 40391

Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets,

Emily Crump EXP Realty, LLC

21 Virginia Ave, Winchester, KY 40391
/80
$524,000 Sold Dec 16, 2025

160 Agawam Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 4,933 Sq Ft
- Built 1978
Last Sold Summary
- 9% Below List Price
- $106/SF
- 51 Days On Market
Last Listing Agent Megan McCoy Keller Williams Legacy Group

160 Agawam Rd, Winchester, KY 40391

/47
Est $559,867 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,020 Sq Ft
1305 Irvine Rd, Winchester, KY 40391

1305 Irvine Rd, 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
/28
$203,900 Sold Dec 10, 2025

25 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 925 Sq Ft
- Built 1968
Last Sold Summary
- 3% Below List Price
- $220/SF
- 35 Days On Market
Last Listing Agent Sarah Hess Keller Williams Commonwealth

25 Hiawatha Trail, Winchester, KY 40391

/99
Est $300,610 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,394 Sq Ft
514 E Broadway St, Winchester, KY 40391

514 E Broadway St, Winchester, KY 40391

/13
$1,250,000
345 Providence Ln, Winchester, KY 40391

120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream home. Conveniently located just

Megan McCoy Keller Williams Legacy Group

345 Providence Ln, Winchester, KY 40391
/3
$220,000 Sold Jul 30, 2025

412 Paisley Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,300 Sq Ft
- Built 2005
Last Sold Summary
- 4% Below List Price
- $169/SF
- 38 Days On Market
Current Estimated Value $224,516

Last Listing Agent John Wilson Bluegrass Properties Group

412 Paisley Ct, Winchester, KY 40391

/30
Est $203,195 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,584 Sq Ft
1 Apache Trail, Winchester, KY 40391

1 Apache Trail, Winchester, KY 40391

/31
$379,717
- 3 Beds
- 2.5 Baths
- 2,636 Sq Ft
300 Calmes Blvd, Winchester, KY 40391

Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half

Darrell Tackett Dream Maker Realty, LLC

300 Calmes Blvd, Winchester, KY 40391
/37
$228,000 Sold May 02, 2025

102 E Clark Dr, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,247 Sq Ft
- Built 1962
Last Sold Summary
- 1% Below List Price
- $183/SF
- 6 Days On Market
Current Estimated Value $227,170

Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

102 E Clark Dr, Winchester, KY 40391

/22
Est $179,307 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 918 Sq Ft
10 Pocahontas Trail, Winchester, KY 40391

10 Pocahontas Trail, Winchester, KY 40391

/64
$420,000
- 5 Beds
- 2.5 Baths
- 2,924 Sq Ft
1857 Ironworks Rd, Winchester, KY 40391

Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room

Meredith Walker Bluegrass Sotheby's International Realty

1857 Ironworks Rd, Winchester, KY 40391
/35
$185,000 Sold Apr 02, 2025

125 Magnolia St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,251 Sq Ft
- Built 1945
Last Sold Summary
- 2% Below List Price
- $148/SF
- 31 Days On Market
Current Estimated Value $204,620

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

125 Magnolia St, Winchester, KY 40391

/57
Est $182,318 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,000 Sq Ft
17 Hiawatha Trail, Winchester, KY 40391

17 Hiawatha Trail, Winchester, KY 40391

/9
$500,000
- Land
- 1.52 Acres
- $328,947 per Acre
1005 Early Dr, Winchester, KY 40391

Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

Whitney Ensor Ensor Real Estate, LLC

1005 Early Dr, Winchester, KY 40391
/61
$372,500 Sold Mar 28, 2025

521 Lasalle Ct, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,101 Sq Ft
- Built 1979
Last Sold Summary
- 2% Below List Price
- $177/SF
- 15 Days On Market
Current Estimated Value $375,011

Last Listing Agent Keith Wilson Coldwell Banker McMahan

521 Lasalle Ct, Winchester, KY 40391

/15
Est $221,553 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,006 Sq Ft
13 Hiawatha Trail, Winchester, KY 40391

13 Hiawatha Trail, Winchester, KY 40391

/14
$650,000
- Land
- 3 Acres
- $216,667 per Acre
205 Codella Dr, Winchester, KY 40391

Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

Greg Leveridge Block + Lot Real Estate

205 Codella Dr, Winchester, KY 40391
/41
$300,300 Sold Nov 07, 2025

37 Lynnway Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 3,220 Sq Ft
- Built 1976
Last Sold Summary
- $93/SF
- 58 Days On Market
Last Listing Agent Donna Thwaites Thwaites Realtors LLC

37 Lynnway Dr, Winchester, KY 40391

/33
Est $265,386 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,831 Sq Ft
16 Apache Trail, Winchester, KY 40391

16 Apache Trail, Winchester, KY 40391

/2
$590,000 Pending
- 4 Beds
- 3.5 Baths
- 3,585 Sq Ft
184 Casa Landa Way, Winchester, KY 40391

A unique floor plan for today's unique lifestyles! 4 bedrooms, 3.5 baths with 2 Primary Suites (one on main level, one on second floor), 3 car attached garage and a newly-renovated sunroom. Amenities include hardwood flooring, granite countertops with an abundance of crown molding throughout. Great curb appeal! Less than 5 minutes from the Winchester Bypass, 20 minutes to Hamburg/Lexington or 20

Jim Woodrum RE/MAX Creative, Winchester

184 Casa Landa Way, Winchester, KY 40391

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Kentucky Clark County Winchester

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