Winchester, KY Homes

/2
$100,000
- Land
- 0.68 Acre
- $147,059 per Acre
100 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

100 Duclair Dr, Winchester, KY 40391
/25
$287,000 Sold Aug 20, 2025

220 Mcdowell Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,402 Sq Ft
- Built 1987
Last Sold Summary
- 12% Below List Price
- $205/SF
- 36 Days On Market
Current Estimated Value $291,635

Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

220 Mcdowell Dr, Winchester, KY 40391

/27
Est $388,962 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,428 Sq Ft
200 Moundale Ave, Winchester, KY 40391

200 Moundale Ave, Winchester, KY 40391

/59
$825,000
- 2 Beds
- 1.5 Baths
- 2,361 Sq Ft
455 Davis Ln, Winchester, KY 40391

Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

Dale Hatton Dream Maker Realty, LLC

455 Davis Ln, Winchester, KY 40391
/33
$240,000 Sold Sep 10, 2025

752 Wayland Dr, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,472 Sq Ft
- Built 1969
Last Sold Summary
- 11% Below List Price
- $97/SF
- 18 Days On Market
Current Estimated Value $253,485

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

752 Wayland Dr, Winchester, KY 40391

/48
Est $362,082 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,175 Sq Ft
220 Moundale Ave, Winchester, KY 40391

220 Moundale Ave, Winchester, KY 40391

/14
$240,000
- 3 Beds
- 2.5 Baths
- 2,380 Sq Ft
10 Upper St, Winchester, KY 40391

Modern Ranch residence full un-finished basement, large lot.

E. Clark Toleman Real Estate Appraisal Services

10 Upper St, Winchester, KY 40391
/2
$110,750 Sold Feb 07, 2025

Unlisted Address
- 2 Beds
- 2 Baths
- 906 Sq Ft
- Built 1995
Last Sold Summary
- $122/SF
Current Estimated Value $151,392

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

Unlisted Address

/28
Est $244,376 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,764 Sq Ft
358 Crescent Ave, Winchester, KY 40391

358 Crescent Ave, Winchester, KY 40391

/29
$329,500 Pending
- 3 Beds
- 2 Baths
- 1,719 Sq Ft
374 N Middletown Rd, Winchester, KY 40391

Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

Danielle Haggard Keller Williams Commonwealth

374 N Middletown Rd, Winchester, KY 40391
/27
$245,000 Sold Jun 13, 2025

8 Seneca Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
- Built 1968
Last Sold Summary
- 2% Above List Price
- $142/SF
- 8 Days On Market
Current Estimated Value $243,888

Last Listing Agent Michael Hilario The Agency

8 Seneca Dr, Winchester, KY 40391

/77
Est $317,412 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,709 Sq Ft
328 S Main St, Winchester, KY 40391

328 S Main St, Winchester, KY 40391

/3
$645,000 New Construction
- 4 Beds
- 2.5 Baths
- 2,526 Sq Ft
106 Bella Shae Way, Winchester, KY 40391

Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

Shane Underwood Keller Williams Commonwealth

106 Bella Shae Way, Winchester, KY 40391
/47
$375,000 Sold Mar 07, 2025

372 Arrowhead Ln, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,744 Sq Ft
- Built 2001
Last Sold Summary
- $137/SF
- 2 Days On Market
Current Estimated Value $388,545

Last Listing Agent Lori Tolson Lifstyl Real Estate

372 Arrowhead Ln, Winchester, KY 40391

/57
Est $382,292 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,689 Sq Ft
286 S Main St, Winchester, KY 40391

286 S Main St, Winchester, KY 40391

/9
$206,000
- Land
- 7.77 Acres
- $26,512 per Acre
368 Flanagan Station Rd, Winchester, KY 40391

Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

Shari Frasure Keller Williams Commonwealth

368 Flanagan Station Rd, Winchester, KY 40391
/26
$239,900 Sold Jun 23, 2025

134 Boone Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,878 Sq Ft
- Built 1920
Last Sold Summary
- 3% Below List Price
- $128/SF
- 74 Days On Market
Current Estimated Value $249,030

Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

134 Boone Ave, Winchester, KY 40391

/34
Est $289,973 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,355 Sq Ft
312 S Main St, Winchester, KY 40391

312 S Main St, Winchester, KY 40391

/6
$388,000
- 5 Beds
- 3 Baths
- 2,762 Sq Ft
101 E Lexington Ave, Winchester, KY 40391

Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

101 E Lexington Ave, Winchester, KY 40391
/40
$206,000 Sold Apr 29, 2025

194 Spruce Ct, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,053 Sq Ft
- Built 1970
Last Sold Summary
- 2% Below List Price
- $196/SF
- 25 Days On Market
Current Estimated Value $210,159

Last Listing Agent Peggy Baldridge HomeFirst Real Estate

194 Spruce Ct, Winchester, KY 40391

/52
Est $291,962 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,673 Sq Ft
14 Lisle Ln, Winchester, KY 40391

14 Lisle Ln, Winchester, KY 40391

/21
$189,500
- 2 Beds
- 2.5 Baths
- 1,197 Sq Ft
109 Quail Ridge Rd, Winchester, KY 40391

Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

Kim Dice EXP Realty, LLC

109 Quail Ridge Rd, Winchester, KY 40391
/31
$240,200 Sold Oct 28, 2025

203 Inverness Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,935 Sq Ft
- Built 2004
Last Sold Summary
- 2% Below List Price
- $124/SF
- 16 Days On Market
Last Listing Agent Kymberly McCreary EXP Realty, LLC

203 Inverness Ln, Winchester, KY 40391

/20
Est $254,482 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,082 Sq Ft
18 Lisle Ln, Winchester, KY 40391

18 Lisle Ln, Winchester, KY 40391

/24
$329,500 Pending
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
360 N Middletown Rd, Winchester, KY 40391

Investment Opportunity! This is the Child Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

Danielle Haggard Keller Williams Commonwealth

360 N Middletown Rd, Winchester, KY 40391
/13
$38,700 Sold May 20, 2025

11 Spring St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- Built 1945
Last Sold Summary
- 3% Below List Price
- $35/SF
- 33 Days On Market
Current Estimated Value $45,024

Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

11 Spring St, Winchester, KY 40391

/51
Est $339,914 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,421 Sq Ft
20 Lisle Ln, Winchester, KY 40391

20 Lisle Ln, Winchester, KY 40391

/84
$849,900
- 4 Beds
- 3.5 Baths
- 4,922 Sq Ft
2509 Mount Sterling Rd, Winchester, KY 40391

Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

Josh Wood Freedom Realty & Property Management

2509 Mount Sterling Rd, Winchester, KY 40391
/36
$345,000 Sold Jun 02, 2025

1173 Lafayette Blvd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,910 Sq Ft
- Built 1996
Last Sold Summary
- 3% Below List Price
- $181/SF
- 36 Days On Market
Current Estimated Value $355,290

Last Listing Agent Janna Smith United Real Estate Bluegrass

1173 Lafayette Blvd, Winchester, KY 40391

/54
Est $345,879 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,816 Sq Ft
35 Lisle Ln, Winchester, KY 40391

35 Lisle Ln, Winchester, KY 40391

/23
$255,000 Pending
- 3 Beds
- 2.5 Baths
- 1,416 Sq Ft
208 Watercrest Way, Winchester, KY 40391

Welcome home! This charming 3 bedroom, 2.5 bath property offers comfort and style with thoughtful updates, a 1-car garage, and a spacious fenced yard with covered deck. Enjoy a view of the large backyard from your eat-in kitchen that features a tiled backsplash and new appliances. Primary bedroom includes a new tiled shower and multiple closets. Second and third bedrooms conveniently share a full

Chad Bowman The Brokerage

208 Watercrest Way, Winchester, KY 40391
/28
$195,000 Sold Feb 11, 2025

916 Muddy Creek Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,000 Sq Ft
- Built 1943
Last Sold Summary
- 13% Below List Price
- $195/SF
- 39 Days On Market
Current Estimated Value $218,068

Last Listing Agent Janet Jones RE/MAX Elite Lexington

916 Muddy Creek Rd, Winchester, KY 40391

/32
Est $241,549 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,740 Sq Ft
540 S Maple St, Winchester, KY 40391

540 S Maple St, Winchester, KY 40391

/11
$249,000
- 3 Beds
- 2 Baths
- 1,534 Sq Ft
646 Laura Dr, Winchester, KY 40391

Three bedrooms ranch, that has been updated with a new kitchen, with granite tops ,new appliances, new flooring ,new interior paintiing ,plus much more, located in Verna Hills S/D located between Winchester and Lexington . Owner/Agent

Garry Milton Milton and Associates Real Estate

646 Laura Dr, Winchester, KY 40391
/18
$240,000 Sold Mar 14, 2025

110 Buckingham Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,240 Sq Ft
- Built 2001
Last Sold Summary
- $194/SF
- 8 Days On Market
Current Estimated Value $277,053

Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

110 Buckingham Ln, Winchester, KY 40391

/37
Est $308,269 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,783 Sq Ft
17 Short St, Winchester, KY 40391

17 Short St, Winchester, KY 40391

/34
$325,000 Pending
- 4 Beds
- 3 Baths
- 1,776 Sq Ft
213 Orchid Ct, Winchester, KY 40391

Kasey McCarty 5.23 Real Estate

213 Orchid Ct, Winchester, KY 40391
/36
$472,500 Sold Sep 09, 2025

208 Royal Oak Dr, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,593 Sq Ft
- Built 2007
Last Sold Summary
- 1% Above List Price
- $182/SF
- 1 Day On Market
Current Estimated Value $475,682

Last Listing Agent Megan McCoy Keller Williams Legacy Group

208 Royal Oak Dr, Winchester, KY 40391

/34
Est $380,750 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,928 Sq Ft
214 Boone Ave, Winchester, KY 40391

214 Boone Ave, Winchester, KY 40391

/12
$189,900
- 3 Beds
- 2 Baths
- 1,116 Sq Ft
41 7th St, Winchester, KY 40391

Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a solid foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views

Austina Bruton Re/Max Elite Realty - Hamburg

41 7th St, Winchester, KY 40391

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Kentucky Clark County Winchester

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