Winchester, KY Homes

/25
$425,000
- Land
- 25.87 Acres
- $16,426 per Acre
2996/3056 Irvine Rd, Winchester, KY 40391

Rare opportunity to own over 25 acres of beautiful Kentucky countryside on Irvine Road, combining two adjoining tracts into one exceptional offering. With gently rolling hills and multiple ideal building sites, this property provides the perfect setting to create your dream home, private estate, or mini-farm. The land offers a wonderful balance of usability and natural beauty, featuring a scenic

Christa Joynt

Keller Williams Commonwealth

2996/3056 Irvine 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 $230,681

Last Listing Agent Tisha Monte Bluegrass Properties Group

204 Crawford Ct, Winchester, KY 40391

/61
Est $452,071

Not Listed For Sale

2601 Crowe Ridge Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,435 Sq Ft
- Built 2002
2601 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 32 Days On Market
Last Listing Agent Morton Trimble HomeFirst Real Estate

/49
$247,500

$7K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,533 Sq Ft
377 Crescent Ave, Winchester, KY 40391

"Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is

Bill VanWinkle

Joyce Marcum Realty

377 Crescent Ave, 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 $233,979

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

301 Cabin Creek Heights, Winchester, KY 40391

/45
Est $382,318

Not Listed For Sale

1600 Crowe Ridge Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,846 Sq Ft
- Built 2012
1600 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 147 Days On Market
Last Listing Agent Joyce Ratliff Tom Goebel & Company

/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

Lot 3 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 $167,928

Last Listing Agent Michael Hilario The Agency

47 Buckner St, Winchester, KY 40391

/56
Est $694,426

Not Listed For Sale

9953 Ironworks Rd, Winchester, KY 40391
- 6 Beds
- 2.5 Baths
- 3,800 Sq Ft
- Built 2003
9953 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 7 Days On Market
Last Listing Agent Tara Smith Keller Williams Commonwealth

/2
$78,500
- Land
- 9,600 Sq Ft
- $356,171 per Acre
235 Plantations Dr Unit LOT 4, Winchester, KY 40391

Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #4 is now available and ready for you to bring your own builder and create the home you've

Melia Hord

MELIA Realty LLC

235 Plantations Dr Unit LOT 4, 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 $319,318

Last Listing Agent Kerry Ball Local First Realty, LLC

215 Old Log Lick Rd, Winchester, KY 40391

/17
Est $501,638

Not Listed For Sale

1026 Crowe Ridge Rd, Winchester, KY 40391
- 1 Bath
- Built 1945
1026 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 56 Days On Market
Last Listing Agent Sophia Herald Herald Real Estate

/46
$749,900
- 3 Beds
- 2.5 Baths
- 2,735 Sq Ft
2180 Big Stoner Rd, Winchester, KY 40391

Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

Ashley Barreto

Indigo & Co

2180 Big Stoner Rd, 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 $283,019

Last Listing Agent Teresa Richmond Freedom Realty & Property Management

225 Prescott Ln, Winchester, KY 40391

/26
Est $336,788

Not Listed For Sale

11705 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 2,668 Sq Ft
- Built 1988
11705 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 81 Days On Market
Last Listing Agent Matthew J. Reffett Re/Max Legacy Group - Paintsville

/4
$64,900
- Land
- 27,878 Sq Ft
- $101,406 per Acre
102 Royal Oak Dr, Winchester, KY 40391

One of the Few Remaining Estate Homesites in Royal Oaks Estates! An exceptional opportunity awaits to build your custom dream home in the Estate Section of Royal Oaks, one of Clark County's most established and desirable communities. Situated on 0.64 acres, 102 Royal Oak Drive offers the space, setting, and flexibility to create a home tailored to your lifestyle while enjoying the beauty and

Melia Hord

MELIA Realty LLC

102 Royal Oak 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 $751,142

Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

4040 Muddy Creek Rd, Winchester, KY 40391

/33
Est $252,126

Not Listed For Sale

7344 Ironworks Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
- Built 1925
7344 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 2 Days On Market
Last Listing Agent Jason Rainey Executive Real Estate, LLC

/2
$14,100,000
- Land
- 274.52 Acres
- $51,362 per Acre
2395 Paris Rd, Winchester, KY 40391

NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development--an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods. Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family homes, and

Melia Hord

MELIA Realty LLC

2395 Paris Rd, 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 $215,704

Last Listing Agent Serena Cassidy Coldwell Banker McMahan

7 Hiawatha Trail, Winchester, KY 40391

/51
Est $608,353

Not Listed For Sale

5600 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,841 Sq Ft
- Built 1992
5600 Ecton Rd, Winchester, KY 40391

Last Sold Summary
- 62 Days On Market
Last Listing Agent Kymberly McCreary Keller Williams Commonwealth

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

Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #2 is now available and ready for you to bring your own builder and create the home you've

Melia Hord

MELIA Realty LLC

231 Plantations Dr Unit LOT 2, 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 $344,425

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

219 Hampton Ave, Winchester, KY 40391

/38
Est $381,349

Not Listed For Sale

3070 Goshen Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,866 Sq Ft
- Built 1998
3070 Goshen Rd, Winchester, KY 40391

Last Sold Summary
- 2 Days On Market
Last Listing Agent Kevin Bradley Keller Williams Legacy Group

/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

465 Morris Rd, 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 $96,246

Last Listing Agent Christa Joynt Keller Williams Commonwealth

32 Hays St, Winchester, KY 40391

/88
Est $784,464

Not Listed For Sale

865 Sugar Ridge Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,146 Sq Ft
- Built 1997
865 Sugar Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 88 Days On Market
Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

/51
$413,000

$14K PRICE DROP
- 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
/30
$180,000

Sold Jul 02, 2026

217 S Highland St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,683 Sq Ft
- Built 1930
Last Sold Summary
- 31% Below List Price
- $67/SF
- 151 Days On Market
Current Estimated Value $206,616

Last Listing Agent Michael Hilario The Agency

217 S Highland St, Winchester, KY 40391

/76
Est $568,213

Not Listed For Sale

775 Sugar Ridge Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,860 Sq Ft
- Built 1996
775 Sugar Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 2 Days On Market
Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty

/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
/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 $283,985

Last Listing Agent Josh Wood Freedom Realty & Property Management

227 Cross Brook Ln, Winchester, KY 40391

/53
Est $290,623

Not Listed For Sale

1489 White Conkwright Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,126 Sq Ft
- Built 1995
1489 White Conkwright Rd, Winchester, KY 40391

Last Sold Summary
- 45 Days On Market
Last Listing Agent Sabina Chambers Semonin Realtors

/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
/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 $290,760

Last Listing Agent Jennifer Guyton White Realty, LLC

126 Ashley Dr, Winchester, KY 40391

/78
Est $518,530

Not Listed For Sale

7625 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,689 Sq Ft
- Built 2006
7625 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 42 Days On Market
Last Listing Agent Elizabeth Torchia Caswell Prewitt Realty, Inc

/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
/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 $363,491

Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

205 Chardonnay Ct, Winchester, KY 40391

/18
Est $250,631

Not Listed For Sale

6278 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,176 Sq Ft
- Built 1978
6278 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 35 Days On Market
Last Listing Agent Angela Yonts eXp Realty, LLC

/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

Showing Results 81 - 120, Page 3 of 18

Kentucky Clark County

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