Homes in ZIP Code 40391

/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
Lot 3 Plantations Dr, Winchester, KY 40391

NOW SELLING SFH Buildable Lots of PHASE ONE: 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

Melia Hord

MELIA Realty LLC

(859) 376-1813

Lot 3 Plantations Dr, 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

/34
Est $381,870

Not Listed For Sale

112 Gibson Way, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,496 Sq Ft
- Built 2020
112 Gibson Way, Winchester, KY 40391

Last Sold Summary
- 56 Days On Market

/53
$268,900

Pending
- 4 Beds
- 2.5 Baths
- 1,510 Sq Ft
311 Geronimo Ct, Winchester, KY 40391

Spacious and well - maintained 4 bedroom home featuring 2 full bathrooms, one half bath which is ready to be upgraded with the addition of a shower to function as an additional full bathroom. This home offers a comfortable layout with replacement windows, a cozy wood burning fireplace and updated stainless steel appliances incuding the range, refrigerator, dishwasher and microwave. Enjoy outdoor

Brenda Sipes

WEICHERT REALTORS - ABG Properties

(859) 549-3201

311 Geronimo Ct, 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

/77
Est $488,057

Not Listed For Sale

275 Runnymeade Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,495 Sq Ft
- Built 2017
275 Runnymeade Dr, Winchester, KY 40391

Last Sold Summary
- 21 Days On Market

/89
$939,000
- 3 Beds
- 2 Baths
- 4,019 Sq Ft
200 Old Log Lick Rd, Winchester, KY 40391

Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship — rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried

Brad Smith

RE/MAX Creative, Winchester

(859) 374-7374

200 Old Log Lick Rd, 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

/43
Est $504,185

Not Listed For Sale

430 Fairholme Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,414 Sq Ft
- Built 2017
430 Fairholme Way, Winchester, KY 40391

Last Sold Summary
- 55 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
/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

/16
Est $260,716

Not Listed For Sale

13385 Ironworks Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
- Built 1980
13385 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 4 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
/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

/24
Est $234,877

Not Listed For Sale

13365 Ironworks Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,420 Sq Ft
- Built 1973
13365 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 10 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
/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

/70
Est $323,098

Not Listed For Sale

705 Oil Springs Rd, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,572 Sq Ft
- Built 1979
705 Oil Springs Rd, Winchester, KY 40391

Last Sold Summary
- 35 Days On Market

/92
$1,500,000

$250K PRICE DROP
- 8 Beds
- 9 Baths
- 10,825 Sq Ft
131 Wells Rd, Mount Sterling, KY 40353

Less than 30 minutes from Lexington or 45 minutes from Keeneland, this 35-acre Clark County private sanctuary of Glass, Wood and Water is designed for flexibility, privacy, accessibility, multigenerational living and indoor-outdoor synergy. The home's crown jewel is a 1,200 sq. ft. four-season ***ATRIUM*** encircled by nearly every living space. Featuring a retractable ceiling, a cascading

Terra Long Keller Williams Commonwealth

131 Wells Rd, Mount Sterling, KY 40353
/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

/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

/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
/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

/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

/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
/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

/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

/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
/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

/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

/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
/71
$690,500

Sold Sep 09, 2025

2950 Pretty Run Rd, Ford, KY 40391
- 4 Beds
- 3 Baths
- 2,912 Sq Ft
- Built 2022
Last Sold Summary
- $237/SF
- 3 Days On Market
Current Estimated Value $702,337

Last Listing Agent Angela Newby Calumet Realty

2950 Pretty Run Rd, Ford, 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

/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
/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

/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

/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
/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

/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

/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

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Kentucky Clark County Winchester 40391

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