Winchester, KY Homes

/70
$335,000 Pending
- 6 Beds
- 4 Baths
- 3,544 Sq Ft
297 S Main St, Winchester, KY 40391

Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

Silvia Torres Tru Life Real Estate

297 S Main St, Winchester, KY 40391
/58
$345,000 Sold Nov 14, 2025

205 Chardonnay Ct, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,179 Sq Ft
- Built 1991
Last Sold Summary
- 8% Below List Price
- $158/SF
- 59 Days On Market
Current Estimated Value $357,768

Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

205 Chardonnay Ct, Winchester, KY 40391

/39
Est $375,715 Not Listed For Sale

3232 Old Ruckerville Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,424 Sq Ft
- Built 1994
3232 Old Ruckerville Rd, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $225/SF
- 2 Days On Market
Last Sold Price $320,000

Last Listing Agent Megan McCoy Keller Williams Legacy Group

/38
$359,900 Pending
- 4 Beds
- 4.5 Baths
3600 Crowe Ridge Rd, Winchester, KY 40391

Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 20' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

Maggie Napier Napier Realtors

3600 Crowe Ridge Rd, Winchester, KY 40391
/27
$210,000 Sold Sep 04, 2025

305 Geronimo Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,150 Sq Ft
- Built 1999
Last Sold Summary
- 5% Below List Price
- $183/SF
- 1 Day On Market
Current Estimated Value $216,633

Last Listing Agent Aaron Kendall Lifstyl Real Estate

305 Geronimo Ct, Winchester, KY 40391

/36
Est $452,904 Not Listed For Sale

5487 Irvine Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,892 Sq Ft
- Built 1978
5487 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $134/SF
- 47 Days On Market
Last Sold Price $388,000

Last Listing Agent Wayne Elkins RE/MAX

/12
$296,000
- 5 Beds
- 2 Baths
- 2,214 Sq Ft
55 Hillcrest Dr, Winchester, KY 40391

All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving.

Nina Vanetten RE/MAX Elite Lexington

55 Hillcrest Dr, Winchester, KY 40391
/44
$320,000 Sold Nov 21, 2025

104 Teakwood Ct, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,970 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $162/SF
- 24 Days On Market
Current Estimated Value $322,889

Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

104 Teakwood Ct, Winchester, KY 40391

/34
Est $368,891 Not Listed For Sale

4759 Ironworks Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,633 Sq Ft
- Built 1985
4759 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 6% Above List Price
- $214/SF
- 2 Days On Market
Last Sold Price $349,500

Last Listing Agent Hannah Simpkins National Real Estate

/12
$299,900
- 4 Beds
- 4 Baths
- 2,072 Sq Ft
1128 Dale Dr, Winchester, KY 40391

Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

Brian Hatfield Coldwell Banker McMahan

1128 Dale Dr, Winchester, KY 40391
/2
$195,000 Sold May 15, 2025

Unlisted Address
- 4 Beds
- 2 Baths
- 1,822 Sq Ft
- Built 1980
Last Sold Summary
- $107/SF
Current Estimated Value $215,950

Last Listing Agent Null Non-Member Non-Member Office

Unlisted Address

/41
Est $333,895 Not Listed For Sale

2100 Miller Hunt Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,550 Sq Ft
- Built 1988
2100 Miller Hunt Rd, Winchester, KY 40391

Last Sold Summary
- 2% Below List Price
- $219/SF
- 44 Days On Market
Last Sold Price $340,000

Last Listing Agent Patrick Doyle Lifstyl Real Estate

/55
$334,900
- 3 Beds
- 2 Baths
- 1,222 Sq Ft
1291 Muddy Creek Rd, Winchester, KY 40391

Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

Terri McGraw FC Tucker Bluegrass

1291 Muddy Creek Rd, Winchester, KY 40391
/27
$274,900 Sold May 23, 2025

707 Terry Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,770 Sq Ft
- Built 1978
Last Sold Summary
- 5% Below List Price
- $155/SF
- 40 Days On Market
Current Estimated Value $290,759

Last Listing Agent Kymberly McCreary Kentucky Land and Home

707 Terry Dr, Winchester, KY 40391

/38
Est $353,423 Not Listed For Sale

875 Miller Hunt Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,904 Sq Ft
- Built 1976
875 Miller Hunt Rd, Winchester, KY 40391

Last Sold Summary
- 14% Above List Price
- $163/SF
- 150 Days On Market
Last Sold Price $310,000

Last Listing Agent Amy J Lopez CENTURY 21 Advantage Realty

/36
$289,900 Pending
- 3 Beds
- 2 Baths
- 1,995 Sq Ft
2225 Old Boonesboro Rd, Winchester, KY 40391

You might have found it! A brick ranch home of considerable size on a generous lot. The large family room and nice size sunroom are hard to beat. With plenty of space and a spacious backyard, this property has a lot to offer. Located close to the new high school, shopping centers, and medical facilities makes it even more attractive.

Teresa Richmond Freedom Realty & Property Management

2225 Old Boonesboro Rd, Winchester, KY 40391
/39
$549,000 Sold Jul 30, 2025

154 Hawthorne Dr, Winchester, KY 40391
- 5 Beds
- 3.5 Baths
- 3,478 Sq Ft
- Built 2020
Last Sold Summary
- 2% Below List Price
- $158/SF
- 100 Days On Market
Current Estimated Value $562,711

Last Listing Agent Jarran Thomas The Agency

154 Hawthorne Dr, Winchester, KY 40391

/42
Est $333,804 Not Listed For Sale

1570 Little Stoner Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,488 Sq Ft
- Built 1990
1570 Little Stoner Rd, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $202/SF
- 1 Day On Market
Last Sold Price $300,000

Last Listing Agent Joyce Ratliff Tom Goebel & Company

/97
$335,000
- 3 Beds
- 2.5 Baths
- 1,794 Sq Ft
322 S Burns Ave, Winchester, KY 40391

This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining

Nancy Hibbitts CENTURY 21 Advantage Realty

322 S Burns Ave, Winchester, KY 40391
/47
$374,900 Sold Sep 19, 2025

714 Concord Ave, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,750 Sq Ft
- Built 2017
Last Sold Summary
- $214/SF
- 23 Days On Market
Current Estimated Value $377,293

Last Listing Agent Josh Wood Freedom Realty & Property Management

714 Concord Ave, Winchester, KY 40391

/41
Est $357,542 Not Listed For Sale

5751 Mount Sterling Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,988 Sq Ft
- Built 1976
5751 Mount Sterling Rd, Winchester, KY 40391

Last Sold Summary
- 45% Above List Price
- $124/SF
- 54 Days On Market
Last Sold Price $245,900

Last Listing Agent Chandler Williams Keller Williams Legacy Group

/67
$325,000
- 3 Beds
- 3 Baths
- 2,821 Sq Ft
3622 Stamper Dr, Winchester, KY 40391

This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

Josh Wood Freedom Realty & Property Management

3622 Stamper Dr, Winchester, KY 40391
/92
$1,075,000 Sold Mar 18, 2026

6237 Bybee Rd, Winchester, KY 40391
- 5 Beds
- 7 Baths
- 8,236 Sq Ft
- Built 2000
Last Sold Summary
- 10% Below List Price
- $131/SF
- 212 Days On Market
Current Estimated Value $1,072,420

Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

6237 Bybee Rd, Winchester, KY 40391

/36
Est $367,890 Not Listed For Sale

610 Old Ruckerville Rd, Winchester, KY 40391
- 2 Beds
- 2.5 Baths
- 1,800 Sq Ft
- Built 1997
610 Old Ruckerville Rd, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $190/SF
- 37 Days On Market
Last Sold Price $342,000

Last Listing Agent Garnett Davis Tom Goebel & Company

/34
$300,000 Pending
- 2 Beds
- 1 Bath
- 1,531 Sq Ft
1508 Ford Hampton Rd, Winchester, KY 40391

Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

Michelle Blackburn RE/MAX Creative, Winchester

1508 Ford Hampton Rd, Winchester, KY 40391
/36
$309,000 Sold May 21, 2025

172 Buckingham Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,958 Sq Ft
- Built 1999
Last Sold Summary
- 6% Below List Price
- $158/SF
- 29 Days On Market
Current Estimated Value $320,482

Last Listing Agent Mila Ensor Ensor Real Estate, LLC

172 Buckingham Ln, Winchester, KY 40391

/35
Est $273,111 Not Listed For Sale

3230 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,510 Sq Ft
- Built 1978
3230 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 16% Above List Price
- $156/SF
- 47 Days On Market
Last Sold Price $235,000

Last Listing Agent Cindy Hellinger Diamond Real Estate Group, Inc

/51
$775,000
- 5 Beds
- 3.5 Baths
- 2,904 Sq Ft
1783 Gay Evans Rd, Winchester, KY 40391

Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

Lucy Martin Jenkins United Real Estate Bluegrass

1783 Gay Evans Rd, Winchester, KY 40391
/42
$390,000 Sold Oct 21, 2025

19 Snowfall Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,625 Sq Ft
- Built 1950
Last Sold Summary
- 11% Above List Price
- $240/SF
- 2 Days On Market
Current Estimated Value $359,983

Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

19 Snowfall Dr, Winchester, KY 40391

/16
Est $165,295 Not Listed For Sale

2584 Irvine Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 990 Sq Ft
- Built 1950
2584 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 35% Above List Price
- $123/SF
- 29 Days On Market
Last Sold Price $122,000

Last Listing Agent Veronica Norwood All Star Real Estate, Inc.

/100
$1,789,000
- 3 Beds
- 2.5 Baths
- 4,518 Sq Ft
3166 Colby Rd, Winchester, KY 40391

PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

Alyssa M Boley Coldwell Banker McMahan

3166 Colby Rd, Winchester, KY 40391
/34
$369,500 Sold Aug 22, 2025

148 Gibson Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,456 Sq Ft
- Built 2022
Last Sold Summary
- 4% Below List Price
- $150/SF
- 11 Days On Market
Current Estimated Value $364,901

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

148 Gibson Way, Winchester, KY 40391

/17
Est $201,631 Not Listed For Sale

2504 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,221 Sq Ft
- Built 1955
2504 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 44% Above List Price
- $115/SF
- 4 Days On Market
Last Sold Price $140,000

Last Listing Agent Brian Weir DIY Listing

/52
$275,000
- 4 Beds
- 2 Baths
- 2,417 Sq Ft
104 Jackson Ferry Rd, Winchester, KY 40391

Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

Bob Sophiea eXp Realty, LLC

104 Jackson Ferry Rd, Winchester, KY 40391
/26
$200,000 Sold Oct 02, 2025

34 N Burns Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- Built 1945
Last Sold Summary
- 11% Below List Price
- $133/SF
- 8 Days On Market
Current Estimated Value $209,622

Last Listing Agent Ashley Barreto Indigo & Co

34 N Burns Ave, Winchester, KY 40391

/32
Est $306,555 Not Listed For Sale

2615 Ironworks Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,694 Sq Ft
- Built 1965
2615 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 4% Above List Price
- $174/SF
- 1 Day On Market
Last Sold Price $295,000

Last Listing Agent Jim Woodrum RE/MAX

/2
$1,200,000
- Land
- 24.15 Acres
- $49,689 per Acre
1395 Two Mile Rd, Winchester, KY 40391

PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

Garnett Davis Tom Goebel & Company

1395 Two Mile Rd, Winchester, KY 40391
/16
$214,900 Sold Dec 05, 2025

15 Holly Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $179/SF
- 52 Days On Market
Current Estimated Value $213,472

Last Listing Agent Nena Honaker Tom Goebel & Company

15 Holly Ave, Winchester, KY 40391

/45
Est $500,058 Not Listed For Sale

1159 Cabin Creek Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,244 Sq Ft
- Built 2007
1159 Cabin Creek Rd, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $203/SF
- 14 Days On Market
Last Sold Price $455,000

Last Listing Agent Kimberly Fields Coldwell Banker McMahan

/6
$171,000
- 2 Beds
- 1 Bath
- 870 Sq Ft
102 W Hickman St, Winchester, KY 40391

102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

David Espinosa Bluegrass Realty Pros, Inc

102 W Hickman St, Winchester, KY 40391

Showing Results 121 - 160, Page 4 of 18

Kentucky Clark County Winchester

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Winchester, KY Homes

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