Winchester, KY Homes

/14
$129,300
- Land
- 2.3 Acres
- $56,217 per Acre
110 Knox Ct, Winchester, KY 40391

The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

Amanda Thomas The Agency

110 Knox Ct, Winchester, KY 40391
/34
$380,000 Sold Nov 21, 2025

110 Hampton Avenue Exd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,516 Sq Ft
Last Sold Summary
- 1% Above List Price
- $151/SF
- 5 Days On Market
Current Estimated Value $373,324

Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

110 Hampton Avenue Exd, Winchester, KY 40391

/20
Est $252,645 Not Listed For Sale

208 Bracken Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,351 Sq Ft
- Built 2002
208 Bracken Ct, Winchester, KY 40391

Last Sold Summary
- 15% Above List Price
- $163/SF
- 0 Days On Market
Last Sold Price $220,000

Last Listing Agent Nicholas Ratliff The LEXpert

/2
$110,000
- Land
- 0.34 Acre
- $323,529 per Acre
230 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

230 Duclair Dr, Winchester, KY 40391
/30
$289,100 Sold Nov 03, 2025

223 Bartram Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,606 Sq Ft
- Built 2004
Last Sold Summary
- $180/SF
- 46 Days On Market
Current Estimated Value $287,174

Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

223 Bartram Ct, Winchester, KY 40391

/37
Est $285,916 Not Listed For Sale

311 Fern Ct, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,326 Sq Ft
- Built 1999
311 Fern Ct, Winchester, KY 40391

Last Sold Summary
- 4% Below List Price
- $128/SF
- 8 Days On Market
Last Sold Price $298,000

Last Listing Agent Robyn Bradley Woods Realty Group

/37
$1,595,000
- 37 Beds
- 19.5 Baths
- 26,124 Sq Ft
2 N Main St, Winchester, KY 40391

Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

Blanca Cheung Tsubaki Group, LLC

2 N Main St, Winchester, KY 40391
/42
$400,000 Sold Dec 05, 2025

210 College St, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 2,718 Sq Ft
- Built 1895
Last Sold Summary
- 5% Below List Price
- $147/SF
- 59 Days On Market
Current Estimated Value $392,732

Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

210 College St, Winchester, KY 40391

/49
Est $306,387 Not Listed For Sale

317 Fern Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,588 Sq Ft
- Built 1999
317 Fern Ct, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $173/SF
- 0 Days On Market
Last Sold Price $275,500

Last Listing Agent Sherry Stephens Murphy Realty Group

/16
$169,900
- 3 Beds
- 1 Bath
- 1,097 Sq Ft
220 E Washington St, Winchester, KY 40391

Investors take note, tenant occupied home, 3 bedrooms, 1 bathroom, one level living! Flippers, downsizing, or First-time buyers get ready! Wood style floors, covered front porch, back yard with patio...Do not miss an opportunity to add to your rental portfolio investment, start your real estate adventure, or make this home your own! Home is occupied 24-hour notice is required to show.

Whitney Ensor Ensor Real Estate, LLC

220 E Washington St, Winchester, KY 40391
/64
$360,000 Sold Oct 17, 2025

309 Gallahadion Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,920 Sq Ft
- Built 2024
Last Sold Summary
- 3% Below List Price
- $188/SF
- 60 Days On Market
Current Estimated Value $366,587

Last Listing Agent Josh Wood Freedom Realty & Property Management

309 Gallahadion Ct, Winchester, KY 40391

/75
Est $268,825 Not Listed For Sale

314 Fern Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,844 Sq Ft
- Built 1999
314 Fern Ct, Winchester, KY 40391

Last Sold Summary
- 3% Below List Price
- $150/SF
- 23 Days On Market
Last Sold Price $276,000

Last Listing Agent Sherry Stephens Murphy Realty Group

/4
$625,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,405 Sq Ft
424 Alexis Way, Winchester, KY 40391

Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

Shane Underwood Keller Williams Commonwealth

424 Alexis Way, Winchester, KY 40391
/23
$130,000 Sold Apr 24, 2025

103 Gary Ct, Winchester, KY 40391
- 2 Beds
- 1.5 Baths
- 1,008 Sq Ft
Last Sold Summary
- 7% Below List Price
- $129/SF
- 13 Days On Market
Current Estimated Value $145,967

Last Listing Agent Dawn Wheeler United Real Estate Bluegrass

103 Gary Ct, Winchester, KY 40391

/23
Est $181,007 Not Listed For Sale

464 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,330 Sq Ft
- Built 1910
464 Ecton Rd, Winchester, KY 40391

Last Sold Summary
- 132% Above List Price
- $59/SF
- 3 Days On Market
Last Sold Price $78,000

Last Listing Agent Darrell Lewis DIY Flat Fee.com

/18
$243,000
- 3 Beds
- 2 Baths
- 1,502 Sq Ft
357 Silverton Way, Winchester, KY 40391

This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in every room, upstairs bonus room, modern lighting in the kitchen and bath, and new appliances, countertops, and backsplash. Enjoy a peaceful, quiet neighborhood and a relaxing rural view from the backyard. A clean, comfortable, move-in-ready home with thoughtful upgrades throughout.

Frank Mulder Tru Life Real Estate

357 Silverton Way, Winchester, KY 40391
/64
$415,000 Sold Feb 25, 2026

1857 Ironworks Rd, Winchester, KY 40391
- 5 Beds
- 2.5 Baths
- 2,924 Sq Ft
- Built 1865
Last Sold Summary
- 3% Below List Price
- $142/SF
- 70 Days On Market
Current Estimated Value $413,670

Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

1857 Ironworks Rd, Winchester, KY 40391

/35
Est $247,989 Not Listed For Sale

1896 Mount Sterling Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,942 Sq Ft
- Built 1960
1896 Mount Sterling Rd, Winchester, KY 40391

Last Sold Summary
- 15% Above List Price
- $111/SF
- 10 Days On Market
Last Sold Price $215,000

Last Listing Agent Keith Wilson Coldwell Banker McMahan

/44
$850,000
- Land
- 83.71 Acres
- $10,154 per Acre
7075 Ecton Rd, Winchester, KY 40391

ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding, this exceptional 83.714± acre Clark County farm will sell on Saturday, March 7, 2026 at 10:30 AM (EST) at 7075 Ecton Rd, Winchester, KY 40391. Tract One: 36.825Acres, Tract Two: 5.196 Acres, Tract Three: 5.022 Acres Tract Four: 36.671 Acres The property

Jonathan Noel Noel Auctioneers and Real Estate Advisors

7075 Ecton Rd, Winchester, KY 40391
/23
$225,000 Sold Aug 21, 2025

26 Stefanie Ct, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,080 Sq Ft
- Built 1972
Last Sold Summary
- $208/SF
- 12 Days On Market
Current Estimated Value $225,138

Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

26 Stefanie Ct, Winchester, KY 40391

/35
Est $365,245 Not Listed For Sale

2195 Pretty Run Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,062 Sq Ft
- Built 2000
2195 Pretty Run Rd, Winchester, KY 40391

Last Sold Summary
- 1% Above List Price
- $175/SF
- 46 Days On Market
Last Sold Price $360,000

Last Listing Agent Josh Wood Freedom Realty & Property Management

/15
$925,000
- Land
- 3.77 Acres
- $245,358 per Acre
300 Rolling Hills Ln, Winchester, KY 40391

Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

Josh Wood Freedom Realty & Property Management

300 Rolling Hills Ln, Winchester, KY 40391
/50
$465,000 Sold Aug 11, 2025

701 Lisletown Ln, Winchester, KY 40391
- 2 Beds
- 2.5 Baths
- 2,784 Sq Ft
- Built 2008
Last Sold Summary
- $167/SF
- 2 Days On Market
Current Estimated Value $469,386

Last Listing Agent Robin Jones Keller Williams Legacy Group

701 Lisletown Ln, Winchester, KY 40391

/38
Est $316,294 Not Listed For Sale

3635 Jackson Ferry Rd, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,201 Sq Ft
- Built 1920
3635 Jackson Ferry Rd, Winchester, KY 40391

Last Sold Summary
- 13% Above List Price
- $127/SF
- 17 Days On Market
Last Sold Price $279,900

Last Listing Agent Betsy Brown United Real Estate Bluegrass

/21
$199,000 Pending
- 3 Beds
- 2.5 Baths
- 1,224 Sq Ft
319 Essex Ct, Winchester, KY 40391

This Colby Ridge neighborhood townhome location is hard to beat as it is just minutes from Kroger, Walmart, the Bypass, interstate access, and a wide variety of restaurants and everyday conveniences. The main floor offers a convenient half bath, a welcoming living room that opens naturally into the dining area and kitchen, and a laundry room tucked just inside the one-car garage entry. Off the

Michelle Blackburn RE/MAX Creative, Winchester

319 Essex Ct, Winchester, KY 40391
/2
$75,000 Sold Jan 05, 2026

1341 Sewell Shop Rd, Winchester, KY 40391
- Land
- 5.75 Acres
- $13,043 per Acre
Last Sold Summary
- 6% Below List Price
- 10 Days On Market
Last Listing Agent Zella Rosenthal Tom Goebel & Company

1341 Sewell Shop Rd, Winchester, KY 40391

/105
Est $709,957 Not Listed For Sale

1039 Cole Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
- Built 1977
1039 Cole Rd, Winchester, KY 40391

Last Sold Summary
- 1% Below List Price
- $281/SF
- 11 Days On Market
Last Sold Price $719,000

Last Listing Agent Josh Wood Freedom Realty & Property Management

/2
$168,500 Pending
- 3 Beds
- 2 Baths
- 1,026 Sq Ft
12 Apache Trail, Winchester, KY 40391

Welcome to this charming 3-bedroom, 2-full bath ranch located in the desirable Indian Hills Subdivision! This home features a large covered front porch, perfect for relaxing and enjoying your morning coffee or evening sunsets. Inside, you'll find a spacious layout with plenty of potential to make it your own. The full unfinished basement offers endless possibilities for storage, a home gym, or

Stephen Brashear Keller Williams Commonwealth

12 Apache Trail, Winchester, KY 40391
/2
$555,000 Sold Jan 16, 2026

184 Casa Landa Way, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,585 Sq Ft
- Built 1998
Last Sold Summary
- 6% Below List Price
- $155/SF
Current Estimated Value $587,030

Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

184 Casa Landa Way, Winchester, KY 40391

/17
Est $438,276 Not Listed For Sale

420 Fairholme Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 3,183 Sq Ft
- Built 2022
420 Fairholme Way, Winchester, KY 40391

Last Sold Summary
- 19% Below List Price
- $171/SF
- 237 Days On Market
Last Sold Price $544,000

Last Listing Agent Vickie Skeens RE/MAX

/58
$525,000
- 2 Beds
- 1.5 Baths
- 5,054 Sq Ft
808 Bypass Rd, Winchester, KY 40391

Unique Mixed-Use Opportunity! This versatile property offers prime potential for a restaurant, café, or retail space in a high-visibility location. The commercial space is turn key for a culinary venture or boutique business. Attached is a separate rental unit with private entrance, offering additional income or an ideal live/work setup. Additional space available for potential 2nd Apartment.

Diana C Brooker Lifstyl Real Estate

808 Bypass Rd, Winchester, KY 40391
/29
$408,000 Sold Sep 12, 2025

4732 Old Boonesboro Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,361 Sq Ft
- Built 1945
Last Sold Summary
- 18% Below List Price
- $173/SF
- 285 Days On Market
Current Estimated Value $412,771

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

4732 Old Boonesboro Rd, Winchester, KY 40391

/44
Est $396,468 Not Listed For Sale

207 Citation Ct, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,304 Sq Ft
- Built 2005
207 Citation Ct, Winchester, KY 40391

Last Sold Summary
- 26% Above List Price
- $95/SF
- 6 Days On Market
Last Sold Price $315,000

Last Listing Agent Megan McCoy Keller Williams Legacy Group

/2
$110,000
- Land
- 0.27 Acre
- $407,407 per Acre
125 Jacob Ct, 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

125 Jacob Ct, Winchester, KY 40391
/43
$165,000 Sold May 20, 2025

12005 Irvine Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,130 Sq Ft
- Built 1980
Last Sold Summary
- 13% Below List Price
- $146/SF
- 96 Days On Market
Current Estimated Value $174,694

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

12005 Irvine Rd, Winchester, KY 40391

/8
Est $484,076 Not Listed For Sale

419 Fairholme Way, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 4,447 Sq Ft
- Built 2022
419 Fairholme Way, Winchester, KY 40391

Last Sold Summary
- 21% Below List Price
- $137/SF
- 231 Days On Market
Last Sold Price $610,986

Last Listing Agent Vickie Skeens RE/MAX

/7
$800,000 Pending
- Land
- 4.87 Acres
- $164,271 per Acre
1108 W Lexington Ave, Winchester, KY 40391

Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park! All building and engineering plans included to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87

Jason Townsend Kentucky Residential Real Estate, LLC

1108 W Lexington Ave, Winchester, KY 40391
/22
$88,000 Sold May 08, 2025

423 E Broadway St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 2,363 Sq Ft
- Built 1878
Last Sold Summary
- 76% Above List Price
- $37/SF
- 23 Days On Market
Current Estimated Value $171,012

Last Listing Agent Tanya McKee Bluegrass Auction, Appraisal & Realty, LLC

423 E Broadway St, Winchester, KY 40391

/20
Est $369,879 Not Listed For Sale

307 Gallahadion Ct, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,487 Sq Ft
- Built 2004
307 Gallahadion Ct, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $135/SF
- 18 Days On Market
Last Sold Price $335,000

Last Listing Agent Lindsay Rhodus Keller Williams Legacy Group

/21
$430,000 Pending
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
870 Pilot View Rd, Winchester, KY 40391

Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings

Chelsea Morguson McCallie Real Estate

870 Pilot View Rd, Winchester, KY 40391

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Kentucky Clark County Winchester

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