Winchester, KY Homes

/21
$139,000
- 2 Beds
- 1 Bath
- 886 Sq Ft
9 Linden Ave, Winchester, KY 40391

Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

Emily Hacker-Todd CENTURY 21 Advantage Realty

9 Linden Ave, Winchester, KY 40391
/79
$849,900 Sold May 23, 2025

3714 Wades Mill Rd, Winchester, KY 40391
- 5 Beds
- 3.5 Baths
- 3,818 Sq Ft
- Built 2001
Last Sold Summary
- $223/SF
- 55 Days On Market
Current Estimated Value $898,831

Last Listing Agent Nora Williams Keller Williams Commonwealth

3714 Wades Mill Rd, Winchester, KY 40391

/87
Est $263,527 Not Listed For Sale

418 Jameson Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
- Built 1996
418 Jameson Way, Winchester, KY 40391

Last Sold Summary
- 5% Above List Price
- $149/SF
- 3 Days On Market
- Last Sold Price $250,000
- Apr 18, 2025
Last Listing Agent Josh Wood Freedom Realty & Property Management

/2
$188,500
- Land
- 12.1 Acres
- $15,579 per Acre
155 Spring Ridge Way, Winchester, KY 40391

Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to call the listing

Jo Gawthrop Keller Williams Bluegrass Realty

155 Spring Ridge Way, Winchester, KY 40391
/51
$560,000 Sold Jun 10, 2025

520 Gay Evans Rd, Winchester, KY 40391
- 3 Beds
- 4 Baths
- 3,160 Sq Ft
- Built 2012
Last Sold Summary
- 3% Below List Price
- $177/SF
- 11 Days On Market
Current Estimated Value $568,335

Last Listing Agent Robin Jones Keller Williams Legacy Group

520 Gay Evans Rd, Winchester, KY 40391

/38
Est $204,098 Not Listed For Sale

412 Jameson Way, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,073 Sq Ft
- Built 1990
412 Jameson Way, Winchester, KY 40391

Last Sold Summary
- 25% Above List Price
- $153/SF
- 0 Days On Market
- Last Sold Price $163,900
- Aug 23, 2024
Last Listing Agent Josh Wood Freedom Realty & Property Management

/10
$591,650 Pending
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
104 Bella Shae Way, Winchester, KY 40391

Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

Shane Underwood Keller Williams Commonwealth

104 Bella Shae Way, Winchester, KY 40391
/17
$30,000 Sold Jun 30, 2025

12591 Ironworks Rd, Winchester, KY 40391
- Land
- 1.72 Acres
- $17,442 per Acre
Last Sold Summary
- 14% Below List Price
- 51 Days On Market
Current Estimated Value $125,073

Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

12591 Ironworks Rd, Winchester, KY 40391

/14
Est $196,220 Not Listed For Sale

411 Jameson Way, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Built 1990
411 Jameson Way, Winchester, KY 40391

Last Sold Summary
- 27% Above List Price
- $155/SF
- 19 Days On Market
- Last Sold Price $155,000
- Feb 06, 2025
Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

/64
$259,900 Pending
- 3 Beds
- 1.5 Baths
- 1,161 Sq Ft
17 Holiday Rd, Winchester, KY 40391

This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a

Josh Wood Freedom Realty & Property Management

17 Holiday Rd, Winchester, KY 40391
/46
$282,900 Sold Jan 02, 2026

165 Hilltop Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,454 Sq Ft
- Built 2020
Last Sold Summary
- 1% Below List Price
- $195/SF
- 6 Days On Market
Current Estimated Value $277,277

Last Listing Agent Tyson Walters Kassie & Associates

165 Hilltop Dr, Winchester, KY 40391

/33
Est $290,818 Not Listed For Sale

137 Summerhill Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
- Built 2003
137 Summerhill Way, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $210/SF
- 6 Days On Market
- Last Sold Price $270,000
- Mar 07, 2025
Last Listing Agent Keith Wilson Coldwell Banker McMahan

/2
$1,800,000
- Land
- 4.36 Acres
- $412,844 per Acre
722 Colby Rd Unit 1, Winchester, KY 40391

Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

Cheryl Johnston CMI Properties

722 Colby Rd Unit 1, Winchester, KY 40391
/41
$650,000 Sold Jun 23, 2025

357 Wades Mill Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,007 Sq Ft
- Built 2002
Last Sold Summary
- 6% Below List Price
- $216/SF
- 15 Days On Market
Current Estimated Value $677,737

Last Listing Agent Emily Belcher Rector Hayden Realtors

357 Wades Mill Rd, Winchester, KY 40391

/31
Est $229,606 Not Listed For Sale

121 Summerhill Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,302 Sq Ft
- Built 2002
121 Summerhill Way, Winchester, KY 40391

Last Sold Summary
- 18% Above List Price
- $150/SF
- 70 Days On Market
- Last Sold Price $195,000
- May 23, 2024
Last Listing Agent Peter doCouto Plum Tree Realty

/43
$259,000
- 3 Beds
- 2 Baths
- 1,960 Sq Ft
564 Trapp-Goffs Corner Rd, Winchester, KY 40391

Private unrestricted 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers

Felicia Mayes The Real Estate Co.

564 Trapp-Goffs Corner Rd, Winchester, KY 40391
/23
$210,000 Sold May 12, 2025

202 Washington Square, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1998
Last Sold Summary
- 11% Above List Price
- $175/SF
- 1 Day On Market
Current Estimated Value $213,246

Last Listing Agent Aaron Kendall Lifstyl Real Estate

202 Washington Square, Winchester, KY 40391

/23
Est $270,815 Not Listed For Sale

302 Salem Ave, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,490 Sq Ft
- Built 2001
302 Salem Ave, Winchester, KY 40391

Last Sold Summary
- 6% Above List Price
- $171/SF
- 34 Days On Market
- Last Sold Price $255,000
- Oct 01, 2024
Last Listing Agent Emily Donaldson Keller Williams Commonwealth

/103
$3,500,000
- 6 Beds
- 5.5 Baths
- 7,274 Sq Ft
5045 Van Meter Rd, Winchester, KY 40391

Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

The Prather Team - Michael Prather Keller Williams Bluegrass Realty

5045 Van Meter Rd, Winchester, KY 40391
/26
$250,000 Sold Feb 20, 2026

21 Virginia Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,749 Sq Ft
- Built 1962
Last Sold Summary
- 4% Below List Price
- $143/SF
- 40 Days On Market
Current Estimated Value $251,872

Last Listing Agent Emily Crump EXP Realty, LLC

21 Virginia Ave, Winchester, KY 40391

/17
Est $292,111 Not Listed For Sale

218 Bracken Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,292 Sq Ft
- Built 2005
218 Bracken Ct, Winchester, KY 40391

Last Sold Summary
- 5% Above List Price
- $215/SF
- 7 Days On Market
- Last Sold Price $278,000
- Apr 15, 2025
Last Listing Agent Vickie Skeens RE/MAX

/2
$100,000
- Land
- 16,117 Sq Ft
- $270,270 per Acre
225 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

225 Jacob Ct, Winchester, KY 40391
/44
$206,500 Sold May 21, 2025

206 W Clark Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,107 Sq Ft
- Built 1962
Last Sold Summary
- 6% Below List Price
- $187/SF
- 23 Days On Market
Current Estimated Value $211,956

Last Listing Agent Peggy Baldridge HomeFirst Real Estate

206 W Clark Dr, Winchester, KY 40391

/20
Est $254,727 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
- 16% Above List Price
- $163/SF
- 0 Days On Market
- Last Sold Price $220,000
- Jul 05, 2023
Last Listing Agent Nicholas Ratliff The LEXpert

/5
$369,900 New Construction
- 3 Beds
- 2 Baths
- 1,558 Sq Ft
204 Jett Dr, Winchester, KY 40391

New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

Mila Ensor Ensor Real Estate, LLC

204 Jett Dr, Winchester, KY 40391
/19
$199,900 Sold Feb 12, 2026

117 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,072 Sq Ft
- Built 1998
Last Sold Summary
- $186/SF
- 49 Days On Market
Current Estimated Value $198,528

Last Listing Agent Nena Honaker Tom Goebel & Company

117 Buffalo Trace, Winchester, KY 40391

/32
Est $243,336 Not Listed For Sale

200 Bracken Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,252 Sq Ft
- Built 2002
200 Bracken Ct, Winchester, KY 40391

Last Sold Summary
- 6% Above List Price
- $184/SF
- 3 Days On Market
- Last Sold Price $230,000
- Mar 21, 2025
Last Listing Agent Amy Diamond ERA Select Real Estate

/2
$195,000
6699 Boonesboro Rd, Winchester, KY 40391

READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

Jennifer Ray RE/MAX Elite Lexington

6699 Boonesboro Rd, Winchester, KY 40391
/44
$310,000 Sold Jun 27, 2025

2482 Mina Station Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,756 Sq Ft
- Built 1962
Last Sold Summary
- $177/SF
- 24 Days On Market
Current Estimated Value $315,426

Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

2482 Mina Station Rd, Winchester, KY 40391

/37
Est $296,051 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
- 1% Below List Price
- $128/SF
- 8 Days On Market
- Last Sold Price $298,000
- Nov 01, 2024
Last Listing Agent Robyn Bradley Woods Realty Group

/3
$670,000 New Construction
- 3 Beds
- 2 Baths
- 2,261 Sq Ft
113 Bella Shae Way, Winchester, KY 40391

Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

Shane Underwood Keller Williams Commonwealth

113 Bella Shae Way, Winchester, KY 40391
/12
$75,000 Sold Jun 17, 2025

120 Jacob Ct, Winchester, KY 40391
- Land
- 23,958 Sq Ft
- $136,364 per Acre
Last Sold Summary
- 32% Below List Price
- 210 Days On Market
Current Estimated Value $165,627

Last Listing Agent Keith Wilson Coldwell Banker McMahan

120 Jacob Ct, Winchester, KY 40391

/49
Est $295,879 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
- 7% Above List Price
- $173/SF
- 0 Days On Market
- Last Sold Price $275,500
- Apr 12, 2024
Last Listing Agent Sherry Stephens Murphy Realty Group

/100
$429,900
- 4 Beds
- 2.5 Baths
- 1,500 Sq Ft
240 Athens Boonesboro Rd, Winchester, KY 40391

Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

Darrell Tackett Dream Maker Realty, LLC

240 Athens Boonesboro Rd, Winchester, KY 40391
/51
$428,000 Sold Sep 04, 2025

17 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,181 Sq Ft
- Built 1960
Last Sold Summary
- 4% Below List Price
- $135/SF
- 34 Days On Market
Current Estimated Value $435,619

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

17 Hampton Ave, Winchester, KY 40391

/75
Est $280,339 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
- 2% Above List Price
- $150/SF
- 23 Days On Market
- Last Sold Price $276,000
- Sep 23, 2024
Last Listing Agent Sherry Stephens Murphy Realty Group

/31
$210,000 Pending
- 4 Beds
- 1.5 Baths
- 2,450 Sq Ft
34 Hays St, Winchester, KY 40391

This spacious 4-bedroom bungalow is tucked away in downtown Winchester in a great walkable location. Located less than a 5-minute walk to the College Park recreation center. This charming home blends timeless character with modern comfort. The kitchen and baths have been updated. The main living space has the original hardwood flooring and new flooring throughout the remaining house. The living

Vickie Skeens RE/MAX Elite Lexington

34 Hays St, Winchester, KY 40391
/26
$239,500 Sold Jul 15, 2025

129 Bay Hill Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,017 Sq Ft
- Built 1998
Last Sold Summary
- 2% Below List Price
- $119/SF
- 26 Days On Market
Current Estimated Value $242,501

Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

129 Bay Hill Dr, Winchester, KY 40391

/35
Est $277,368 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
- 29% Above List Price
- $111/SF
- 10 Days On Market
- Last Sold Price $215,000
- Feb 03, 2025
Last Listing Agent Keith Wilson Coldwell Banker McMahan

/33
$275,000 Pending
- 3 Beds
- 1.5 Baths
- 1,634 Sq Ft
402 Harney Dr, Winchester, KY 40391

This well-kept split-level home in the Westmeade neighborhood offers a practical layout in a location that's close to the bypass, restaurants, and shopping. Upstairs, you'll find a roomy living area with a freestanding electric fireplace, along with an open kitchen and dining space. There are also three bedrooms and a full shared bathroom on this level. Downstairs, you'll find a finished basement

Michelle Blackburn RE/MAX Creative, Winchester

402 Harney Dr, Winchester, KY 40391

Showing Results 321 - 360, Page 9 of 18

Kentucky Clark County Winchester

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