Winchester, KY Homes

/91
Est $371,110 Not Listed For Sale

2184 Cole Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,514 Sq Ft
- Built 1970
2184 Cole Rd, Winchester, KY 40391

Last Sold Summary
- $147/SF
- 11 Days On Market
Last Sold Price $370,000

Last Listing Agent Greg Wood Freedom Realty & Property Management

/22
$665,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,643 Sq Ft
414 Alexis Way, Winchester, KY 40391

Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

Shane Underwood Keller Williams Commonwealth

414 Alexis Way, 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
Current Estimated Value $204,011

Last Listing Agent Anthony Gigilo ListWithFreedom.com

245 Ecton Rd, Winchester, KY 40391

/23
Est $246,866 Not Listed For Sale

421 Jameson Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,487 Sq Ft
- Built 2003
421 Jameson Way, Winchester, KY 40391

Last Sold Summary
- 1% Below List Price
- $168/SF
- 9 Days On Market
Last Sold Price $250,000

Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

/9
$785,000 New Construction
- 4 Beds
- 2.5 Baths
- 2,476 Sq Ft
425 Alexis Way, Winchester, KY 40391

Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

Shane Underwood Keller Williams Commonwealth

425 Alexis Way, 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

/54
Est $248,436 Not Listed For Sale

427 Jameson Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,776 Sq Ft
- Built 2002
427 Jameson Way, Winchester, KY 40391

Last Sold Summary
- 4% Below List Price
- $146/SF
- 121 Days On Market
Last Sold Price $260,000

Last Listing Agent Christa Joynt Keller Williams Commonwealth

/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
/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
Current Estimated Value $201,587

Last Listing Agent Sarah Hess Keller Williams Commonwealth

25 Hiawatha Trail, Winchester, KY 40391

/47
Est $345,504 Not Listed For Sale

106 Old Ironworks Rd, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 3,380 Sq Ft
- Built 1900
106 Old Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 19% Above List Price
- $86/SF
- 115 Days On Market
Last Sold Price $291,000

Last Listing Agent John Groft RE/MAX

/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
/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
Current Estimated Value $523,772

Last Listing Agent Megan McCoy Keller Williams Legacy Group

160 Agawam Rd, Winchester, KY 40391

/25
Est $234,318 Not Listed For Sale

325 Vanover Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,428 Sq Ft
- Built 2002
325 Vanover Way, Winchester, KY 40391

Last Sold Summary
- 3% Below List Price
- $169/SF
- 1 Day On Market
Last Sold Price $240,880

Last Listing Agent Brad Harmon LexHomes Real Estate

/17
$432,000
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
104 Colby Hills Dr, Winchester, KY 40391

(Reducted 50,000) for fast sell. Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

Garry Milton Milton and Associates Real Estate

104 Colby Hills Dr, 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 $224,217

Last Listing Agent John Wilson Bluegrass Properties Group

412 Paisley Ct, Winchester, KY 40391

/17
Est $234,359 Not Listed For Sale

206 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 1,737 Sq Ft
- Built 1998
206 Buffalo Trace, Winchester, KY 40391

Last Sold Summary
- 2% Below List Price
- $138/SF
- 30 Days On Market
Last Sold Price $239,000

Last Listing Agent Kymberly McCreary EXP Realty, LLC

/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
/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 $230,120

Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

102 E Clark Dr, Winchester, KY 40391

/32
Est $198,034 Not Listed For Sale

303 Geronimo Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,088 Sq Ft
- Built 1998
303 Geronimo Ct, Winchester, KY 40391

Last Sold Summary
- $182/SF
- 6 Days On Market
Last Sold Price $198,000

Last Listing Agent Marie Waddell-Pearson RE/MAX

/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
/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 $206,674

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

125 Magnolia St, Winchester, KY 40391

/19
Est $178,940 Not Listed For Sale

125 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 932 Sq Ft
- Built 1997
125 Buffalo Trace, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $178/SF
- 43 Days On Market
Last Sold Price $166,000

Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

/10
$591,650 Pending
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
104 Bella Shae Way, Winchester, KY 40391

Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

Shane Underwood Keller Williams Commonwealth

104 Bella Shae Way, 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 $371,744

Last Listing Agent Keith Wilson Coldwell Banker McMahan

521 Lasalle Ct, Winchester, KY 40391

/22
Est $192,247 Not Listed For Sale

113 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 960 Sq Ft
- Built 1998
113 Buffalo Trace, Winchester, KY 40391

Last Sold Summary
- 13% Above List Price
- $177/SF
- 2 Days On Market
Last Sold Price $170,000

Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

/48
$287,000
- 4 Beds
- 1.5 Baths
- 2,116 Sq Ft
214 S Burns Ave, Winchester, KY 40391

Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless

Christa Joynt Keller Williams Commonwealth

214 S Burns Ave, 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
Current Estimated Value $309,811

Last Listing Agent Donna Thwaites Thwaites Realtors LLC

37 Lynnway Dr, Winchester, KY 40391

/47
Est $559,163 Not Listed For Sale

1305 Irvine Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 3,020 Sq Ft
- Built 1918
1305 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 3% Above List Price
- $179/SF
- 406 Days On Market
Last Sold Price $542,000

Last Listing Agent Bonnie Mays United Real Estate Bluegrass

/28
$135,000 Pending
- 2 Beds
- 1.5 Baths
- 960 Sq Ft
46 Judy Ann Ct, Winchester, KY 40391

Welcome to 46 Judy Ann Court, a well-maintained and conveniently located townhome tucked away on a quiet street in Winchester, KY. This inviting 2-bedroom, 1.5-bath residence offers a functional layout with durable LVP flooring throughout, creating a clean, cohesive look. The kitchen features stainless steel appliances and ample cabinet space. Both bedrooms are generously sized. Outside you can

Lukas Owens The Brokerage

46 Judy Ann Ct, Winchester, KY 40391
/41
$247,000 Sold Sep 19, 2025

3588 Stamper Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,530 Sq Ft
- Built 1987
Last Sold Summary
- 1% Below List Price
- $161/SF
- 4 Days On Market
Current Estimated Value $245,895

Last Listing Agent Zach Johnson The Brokerage

3588 Stamper Dr, Winchester, KY 40391

/99
Est $261,702 Not Listed For Sale

514 E Broadway St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,394 Sq Ft
- Built 1960
514 E Broadway St, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $172/SF
- 1 Day On Market
Last Sold Price $239,900

Last Listing Agent Josh Wood Freedom Realty & Property Management

/38
$389,900
- 4 Beds
- 2 Baths
- 2,659 Sq Ft
6239 Old Boonesboro Rd, Winchester, KY 40391

Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

Kenya Woods United Real Estate Bluegrass

6239 Old Boonesboro Rd, Winchester, KY 40391
/20
$205,000 Sold Aug 19, 2025

202 Custer Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,113 Sq Ft
- Built 1999
Last Sold Summary
- 8% Above List Price
- $184/SF
- 2 Days On Market
Current Estimated Value $200,469

Last Listing Agent Brittany Beer EXP Realty, LLC

202 Custer Ct, Winchester, KY 40391

/30
Est $197,865 Not Listed For Sale

1 Apache Trail, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,584 Sq Ft
- Built 1969
1 Apache Trail, Winchester, KY 40391

Last Sold Summary
- 28% Above List Price
- $98/SF
- 10 Days On Market
Last Sold Price $155,000

Last Listing Agent Peter doCouto Plum Tree Realty

/26
$184,000
- 2 Beds
- 1.5 Baths
- 1,102 Sq Ft
356 Colby Ridge Blvd, Winchester, KY 40391

This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone looking to expand their investment portfolio. The inviting living room features a propane-operated fireplace that provides a reliable backup heat source. The spacious primary bedroom includes his-and-her closets, and both bedrooms are equipped with additional split units for personalized comfort. A full

Nena Honaker Tom Goebel & Company

356 Colby Ridge Blvd, Winchester, KY 40391
/15
$176,000 Sold Oct 17, 2025

7575 Irvine Rd, Winchester, KY 40391
Last Sold Summary
- 6% Below List Price
- 2 Days On Market
Current Estimated Value $199,641

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

7575 Irvine Rd, Winchester, KY 40391

/57
Est $182,894 Not Listed For Sale

17 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,000 Sq Ft
- Built 1968
17 Hiawatha Trail, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $170/SF
- 32 Days On Market
Last Sold Price $170,000

Last Listing Agent Josh Wood Freedom Realty & Property Management

/43
$269,000 Pending
- 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
/40
$400,000 Sold May 23, 2025

109 Monet Blvd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,432 Sq Ft
- Built 1995
Last Sold Summary
- 5% Below List Price
- $164/SF
- 26 Days On Market
Current Estimated Value $417,408

Last Listing Agent Melissa Brown Keller Williams Legacy Group

109 Monet Blvd, Winchester, KY 40391

/15
Est $205,590 Not Listed For Sale

13 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,006 Sq Ft
- Built 1968
13 Hiawatha Trail, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $184/SF
- 50 Days On Market
Last Sold Price $185,000

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

Showing Results 201 - 240, Page 6 of 18

Kentucky Clark County Winchester

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage