Winchester, KY Homes

/23
$150,000
- Land
- 9.39 Acres
- $15,971 per Acre
3821 Jackson Ferry Rd, Winchester, KY 40391

If you've been dreaming of building a home with river access, this is it. Located along a breathtaking stretch of Jackson Ferry Road, this 9.392-acre tract offers a rare combination of a viable build site and direct access to the scenic Kentucky River. Whether it's morning coffee overlooking the countryside or afternoons spent kayaking and fishing, this property delivers a lifestyle that's hard

Christa Joynt

Keller Williams Commonwealth

(859) 696-7578

3821 Jackson Ferry Rd, Winchester, KY 40391
/25
$223,000

Sold Nov 04, 2025

204 Crawford Ct, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,636 Sq Ft
- Built 1960
Last Sold Summary
- 3% Below List Price
- $136/SF
- 1 Day On Market
Current Estimated Value $227,856

Last Listing Agent Tisha Monte Bluegrass Properties Group

204 Crawford Ct, Winchester, KY 40391

/51
Est $508,924

Not Listed For Sale

2051 Kiddville Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,654 Sq Ft
- Built 2001
2051 Kiddville Rd, Winchester, KY 40391

Last Sold Summary
- 39 Days On Market

/72
$775,000
- 5 Beds
- 3 Baths
- 4,437 Sq Ft
465 Morris Rd, Winchester, KY 40391

Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

Brenda Leigh Walters

United Real Estate Bluegrass

(859) 459-0504

465 Morris Rd, Winchester, KY 40391
/29
$227,500

Sold Sep 11, 2025

301 Cabin Creek Heights, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,220 Sq Ft
- Built 1970
Last Sold Summary
- 1% Above List Price
- $186/SF
- 0 Days On Market
Current Estimated Value $233,397

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

301 Cabin Creek Heights, Winchester, KY 40391

/44
Est $452,678

Not Listed For Sale

1927 Kiddville Rd, Winchester, KY 40391
- 5 Beds
- 4 Baths
- 2,056 Sq Ft
- Built 2001
1927 Kiddville Rd, Winchester, KY 40391

Last Sold Summary
- 22 Days On Market

/2
$882,000
- Land
- 3.93 Acres
- $224,427 per Acre
Lot 1 - 7 Plantations Dr, Winchester, KY 40391

NOW SELLING PHASE ONE: 7 of the 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build

Melia Hord

MELIA Realty LLC

(859) 587-3785

Lot 1 - 7 Plantations Dr, Winchester, KY 40391
/16
$165,000

Sold Apr 30, 2026

47 Buckner St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,635 Sq Ft
- Built 1930
Last Sold Summary
- 8% Below List Price
- $101/SF
- 24 Days On Market
Current Estimated Value $177,975

Last Listing Agent Michael Hilario The Agency

47 Buckner St, Winchester, KY 40391

/47
Est $441,960

Not Listed For Sale

372 Arrowhead Ln, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,744 Sq Ft
- Built 2001
372 Arrowhead Ln, Winchester, KY 40391

Last Sold Summary
- 2 Days On Market

/45
$429,900

New Construction
- 3 - 5 Beds
- 2.5 - 4.5 Baths
- 2,722 Sq Ft
Eleanor Plan at Boone's Crossing, Winchester, KY 40391

Experience elevated living with the Eleanor floor plan, a thoughtfully designed new construction home available through one of the most trusted home builders in Central Kentucky. Created for today’s buyers seeking flexibility, luxury, and energy efficiency, the Eleanor blends timeless design with modern functionality for families looking for new construction homes in Lexington KY and surrounding

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824255, Winchester, KY 40391
/56
$320,000

Sold Jun 03, 2026

215 Old Log Lick Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,450 Sq Ft
- Built 2002
Last Sold Summary
- 9% Below List Price
- $221/SF
- 53 Days On Market
Current Estimated Value $330,695

Last Listing Agent Kerry Ball Local First Realty, LLC

215 Old Log Lick Rd, Winchester, KY 40391

/112
Est $765,104

Not Listed For Sale

703 Kiddville Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,311 Sq Ft
- Built 1980
703 Kiddville Rd, Winchester, KY 40391

Last Sold Summary
- 276 Days On Market

/35
$360,900

New Construction
- 3 - 4 Beds
- 2.5 - 3.5 Baths
- 1,828 Sq Ft
Grace Plan at Boone's Crossing, Winchester, KY 40391

Discover the Grace floor plan, a thoughtfully designed new construction home that blends open-concept living with private, comfortable bedroom spaces. Built by one of the leading home builders in Central Kentucky, the Grace is a perfect fit for buyers searching for new construction homes in Lexington KY and nearby communities who want flexibility, style, and energy efficiency.From the moment you

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391
/41
$279,900

Sold Aug 12, 2025

225 Prescott Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,808 Sq Ft
- Built 2006
Last Sold Summary
- $155/SF
- 8 Days On Market
Current Estimated Value $286,532

Last Listing Agent Teresa Richmond Freedom Realty & Property Management

225 Prescott Ln, Winchester, KY 40391

/43
Est $408,156

Not Listed For Sale

700 Vienna Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,826 Sq Ft
- Built 2004
700 Vienna Rd, Winchester, KY 40391

Last Sold Summary
- 18 Days On Market

/31
$310,000

$20K PRICE DROP Pending
- 5 Beds
- 3 Baths
- 2,624 Sq Ft
28 Churchill Dr, Winchester, KY 40391

***Motivated Sellers*** Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being primary suites, one on the main level and one in the basement. This house is perfect for multigenerational living. New paint, floors, back splash, kitchen cabinets and granite counter tops. The fully finished basement has a newly added primary bedroom and bath. The updated bathroom

Libby VanMeter Marshall Lane Real Estate - Lexington

28 Churchill Dr, Winchester, KY 40391
/94
$759,000

Sold Jun 17, 2026

4040 Muddy Creek Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 4,584 Sq Ft
- Built 2007
Last Sold Summary
- 15% Below List Price
- $166/SF
- 262 Days On Market
Current Estimated Value $750,513

Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

4040 Muddy Creek Rd, Winchester, KY 40391

/96
Est $461,928

Not Listed For Sale

2430 Log Lick Rd, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 2,700 Sq Ft
- Built 1938
2430 Log Lick Rd, Winchester, KY 40391

Last Sold Summary
- 184 Days On Market

/46
$347,900

New Construction
- 3 - 6 Beds
- 2 - 4 Baths
- 1,580 Sq Ft
Martha Plan at Boone's Crossing, Winchester, KY 40391

The Martha floor plan is your canvas for creating a home that perfectly fits your lifestyle, offering unmatched flexibility, thoughtful design, and timeless appeal. Built by one of the leading home builders in Central Kentucky, the Martha is an excellent choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space that adapts to how they

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824258, Winchester, KY 40391
/20
$217,500

Sold May 22, 2026

7 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,190 Sq Ft
- Built 1968
Last Sold Summary
- 3% Below List Price
- $183/SF
- 10 Days On Market
Current Estimated Value $218,710

Last Listing Agent Serena Cassidy Coldwell Banker McMahan

7 Hiawatha Trail, Winchester, KY 40391

/30
Est $253,051

Not Listed For Sale

3604 Pine Ridge Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
- Built 1998
3604 Pine Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 3 Days On Market

/28
$363,900

New Construction
- 4 - 5 Beds
- 2.5 - 3.5 Baths
- 2,100 Sq Ft
Elizabeth Plan at Boone's Crossing, Winchester, KY 40391

Experience the Elizabeth floor plan, a beautifully crafted new construction home designed for families who value open-concept living, thoughtful organization, and flexible bedroom space. Offered by one of the most trusted home builders in Central Kentucky, the Elizabeth is a standout option for buyers searching for new construction homes in Lexington KY and surrounding communities.From the moment

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824250, Winchester, KY 40391
/24
$185,000

Sold Jun 23, 2025

605 Dixiana Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,044 Sq Ft
- Built 1990
Last Sold Summary
- 3% Below List Price
- $177/SF
- 23 Days On Market
Current Estimated Value $198,347

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

605 Dixiana Dr, Winchester, KY 40391

/101
Est $385,697

Not Listed For Sale

3642 Crowe Ridge Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,928 Sq Ft
- Built 1953
3642 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 121 Days On Market

/73
$1,349,000

New Construction
- 4 Beds
- 4.5 Baths
- 3,350 Sq Ft
1200 Craig Crossing, Winchester, KY 40391

Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom.

Michael Hilario The Agency

1200 Craig Crossing, Winchester, KY 40391
/58
$850,000

Sold Jun 27, 2025

2158 Venable Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,980 Sq Ft
- Built 1988
Last Sold Summary
- $285/SF
- 1 Day On Market
Current Estimated Value $866,775

Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

2158 Venable Rd, Winchester, KY 40391

/16
Est $207,000

Not Listed For Sale

4523 Trapp Goffs Corner Rd, Winchester, KY 40391
- Studio
- 1,271 Sq Ft
- Built 1974
4523 Trapp Goffs Corner Rd, Winchester, KY 40391

Last Sold Summary
- 178 Days On Market

/85
$397,900

New Construction
- 3 - 5 Beds
- 2.5 - 4.5 Baths
- 2,263 Sq Ft
Abigail Plan at Boone's Crossing, Winchester, KY 40391

Step into the award-winning Abigail floor plan, a standout choice for buyers searching for new construction homes in Lexington, KY and Central Kentucky. Designed with today’s lifestyle in mind, this home offers the perfect blend of flexible floor plans, energy efficiency, and modern comfort—everything you expect from a trusted home builder in Lexington, KY.From the moment you arrive, the Abigail

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824251, Winchester, KY 40391
/39
$340,000

Sold Oct 10, 2025

219 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,929 Sq Ft
- Built 1972
Last Sold Summary
- 7% Below List Price
- $116/SF
- 48 Days On Market
Current Estimated Value $356,139

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

219 Hampton Ave, Winchester, KY 40391

/40
Est $377,758

Not Listed For Sale

409 Kiddville Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,840 Sq Ft
- Built 1971
409 Kiddville Rd, Winchester, KY 40391

Last Sold Summary
- 1 Day On Market

/52
$369,900

New Construction
- 3 - 6 Beds
- 2 Baths
- 1,770 Sq Ft
Barbara Plan at Boone's Crossing, Winchester, KY 40391

Experience the true essence of homecoming with the Barbara floor plan, a beautifully designed new construction home available through one of the most trusted home builders in Central Kentucky. Thoughtfully crafted for modern living, this plan blends timeless exterior charm with a warm, open interior designed for comfort, flexibility, and everyday functionality.Step onto the inviting covered front

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824253, Winchester, KY 40391
/28
$83,000

Sold May 08, 2026

32 Hays St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,540 Sq Ft
- Built 1950
Last Sold Summary
- 8% Below List Price
- $54/SF
- 5 Days On Market
Current Estimated Value $95,129

Last Listing Agent Christa Joynt Keller Williams Commonwealth

32 Hays St, Winchester, KY 40391

/39
Est $434,600

Not Listed For Sale

900 Vienna Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,314 Sq Ft
- Built 2005
900 Vienna Rd, Winchester, KY 40391

Last Sold Summary
- 0 Days On Market

/47
$427,000
- 3 Beds
- 2.5 Baths
- 2,289 Sq Ft
20 Edgewood Dr, Winchester, KY 40391

Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a

Libby VanMeter Marshall Lane Real Estate - Lexington

20 Edgewood Dr, Winchester, KY 40391
/69
$282,500

Sold Sep 30, 2025

227 Cross Brook Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,508 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $187/SF
- 9 Days On Market
Current Estimated Value $282,813

Last Listing Agent Josh Wood Freedom Realty & Property Management

227 Cross Brook Ln, Winchester, KY 40391

/23
Est $798,663

Not Listed For Sale

1275 Old Log Lick Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
- Built 1982
1275 Old Log Lick Rd, Winchester, KY 40391

Last Sold Summary
- 474 Days On Market

/41
$343,900

New Construction
- 3 - 5 Beds
- 2 - 4 Baths
- 1,424 Sq Ft
Lucy Plan at Boone's Crossing, Winchester, KY 40391

Experience the Lucy floor plan, a versatile and thoughtfully designed new construction home that gives every member of the family the space they need to live, work, and thrive. Built by one of the most trusted home builders in Central Kentucky, the Lucy is a top choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want flexibility, comfort, and

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824256, Winchester, KY 40391
/75
$289,900

Sold Aug 11, 2025

126 Ashley Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,429 Sq Ft
- Built 1992
Last Sold Summary
- $203/SF
- 0 Days On Market
Current Estimated Value $293,814

Last Listing Agent Jennifer Guyton White Realty, LLC

126 Ashley Dr, Winchester, KY 40391

/43
Est $283,034

Not Listed For Sale

2270 Mina Station Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,358 Sq Ft
- Built 1971
2270 Mina Station Rd, Winchester, KY 40391

Last Sold Summary
- 72 Days On Market

/37
$378,900

New Construction
- 3 - 5 Beds
- 2.5 - 3.5 Baths
- 2,098 Sq Ft
Nancy Plan at Boone's Crossing, Winchester, KY 40391

Experience the Nancy floor plan, a masterfully designed two-story new construction home that blends smart functionality with open-concept living. Built by one of the most trusted home builders in Central Kentucky, the Nancy is an ideal choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want style, flexibility, and efficient use of space.From the

James Monroe Homes Builder

2070 Boonesboro Rd Unit 39824252, Winchester, KY 40391

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Kentucky Clark County Winchester

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