Winchester, KY Homes

/2
$10,000 Pending
- Land
- 2,613 Sq Ft
- $166,667 per Acre
75 4th St, Winchester, KY 40391

Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

Bob Sophiea eXp Realty, LLC

75 4th St, Winchester, KY 40391
/5
$41,500 Sold Sep 15, 2025

434 Fairholme Way, Winchester, KY 40391
- Land
- 15,681 Sq Ft
- $115,278 per Acre
Last Sold Summary
- 8% Below List Price
- 6 Days On Market
Current Estimated Value $52,175

Last Listing Agent Justin Lee JL Realty Group, LLC

434 Fairholme Way, Winchester, KY 40391

/32
Est $211,526 Not Listed For Sale

303 Geronimo Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,088 Sq Ft
- Built 1998
303 Geronimo Ct, Winchester, KY 40391

Last Sold Summary
- 7% Above List Price
- $182/SF
- 6 Days On Market
- Last Sold Price $198,000
- Dec 11, 2024
Last Listing Agent Marie Waddell-Pearson RE/MAX

/2
$110,000
- Land
- 20,473 Sq Ft
- $234,043 per Acre
139 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

139 Jacob Ct, Winchester, KY 40391
/48
$330,000 Sold May 23, 2025

113 Holiday Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,090 Sq Ft
- Built 1970
Last Sold Summary
- 3% Below List Price
- $158/SF
- 35 Days On Market
Current Estimated Value $317,465

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

113 Holiday Rd, Winchester, KY 40391

/19
Est $192,858 Not Listed For Sale

125 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 932 Sq Ft
- Built 1997
125 Buffalo Trace, Winchester, KY 40391

Last Sold Summary
- 16% Above List Price
- $178/SF
- 43 Days On Market
- Last Sold Price $166,000
- Jan 24, 2025
Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

/32
$249,900
- 3 Beds
- 2 Baths
- 1,904 Sq Ft
528 Estes Dr, Winchester, KY 40391

Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

Josh Wood Freedom Realty & Property Management

528 Estes Dr, Winchester, KY 40391
/58
$830,000 Sold Feb 27, 2026

2395 Becknerville Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,234 Sq Ft
- Built 2012
Last Sold Summary
- 2% Below List Price
- $257/SF
- 8 Days On Market
Current Estimated Value $834,586

Last Listing Agent Crystal Towe The Real Estate Group

2395 Becknerville Rd, Winchester, KY 40391

/22
Est $184,624 Not Listed For Sale

113 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 960 Sq Ft
- Built 1998
113 Buffalo Trace, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $177/SF
- 2 Days On Market
- Last Sold Price $170,000
- Mar 28, 2024
Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

/33
$219,900 Pending
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
21 Kentucky St, Winchester, KY 40391

Updated, move-in ready, and right in the heart of Winchester. This is the kind of home that checks boxes and feels good the second you walk in. Start your mornings or wind down in the evenings on the inviting covered front porch—it's the kind of space that makes you want to slow down for a minute. Inside, everything has been updated so you can skip the projects and just enjoy your home from day

Jenny Mateyoke Keller Williams Legacy Group

21 Kentucky St, Winchester, KY 40391
/33
$364,900 Sold Feb 06, 2026

446 Tremont Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,811 Sq Ft
- Built 2005
Last Sold Summary
- 1% Below List Price
- $130/SF
- 15 Days On Market
Current Estimated Value $365,014

Last Listing Agent Dylan Langdon The Agency

446 Tremont Ln, Winchester, KY 40391

/47
Est $597,827 Not Listed For Sale

1305 Irvine Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 3,020 Sq Ft
- Built 1918
1305 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $179/SF
- 406 Days On Market
- Last Sold Price $542,000
- Aug 03, 2023
Last Listing Agent Bonnie Mays United Real Estate Bluegrass

/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 Keller Williams Legacy Group

Lot 1 - 7 Plantations Dr, Winchester, KY 40391
/38
$173,000 Sold Sep 22, 2025

44 5th St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,270 Sq Ft
- Built 1952
Last Sold Summary
- 2% Above List Price
- $136/SF
- 2 Days On Market
Current Estimated Value $173,736

Last Listing Agent Tirza Cooper The Howard Realty Co

44 5th St, Winchester, KY 40391

/99
Est $261,843 Not Listed For Sale

514 E Broadway St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,394 Sq Ft
- Built 1960
514 E Broadway St, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $172/SF
- 1 Day On Market
- Last Sold Price $239,900
- Oct 02, 2023
Last Listing Agent Josh Wood Freedom Realty & Property Management

/2
$150,000
- Land
- 2.11 Acres
- $71,090 per Acre
125 Knox 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 Knox Ct, Winchester, KY 40391
/18
$200,000 Sold Jan 14, 2026

245 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,074 Sq Ft
- Built 1940
Last Sold Summary
- 9% Below List Price
- $186/SF
- 2 Days On Market
Current Estimated Value $198,756

Last Listing Agent Anthony Gigilo ListWithFreedom.com

245 Ecton Rd, Winchester, KY 40391

/30
Est $196,919 Not Listed For Sale

1 Apache Trail, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,584 Sq Ft
- Built 1969
1 Apache Trail, Winchester, KY 40391

Last Sold Summary
- 27% Above List Price
- $98/SF
- 10 Days On Market
- Last Sold Price $155,000
- Jan 18, 2024
Last Listing Agent Peter doCouto Plum Tree Realty

/19
$300,000
- Land
- 15.27 Acres
- $19,652 per Acre
4025 Jackson Ferry Rd, Winchester, KY 40391

Opportunities like this are incredibly rare—15.266 combined acres backing to the Kentucky River, offering the ultimate private retreat. Located at the end of a scenic drive, these two tracts are being offered together, creating an expansive recreational property with unmatched access to the water. Ideal for camping, family getaways, or creating a multi-use outdoor haven, this land provides

Christa Joynt Keller Williams Commonwealth

4025 Jackson Ferry Rd, Winchester, KY 40391
/52
$500,000 Sold Aug 25, 2025

1778 Elkin Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,020 Sq Ft
- Built 2015
Last Sold Summary
- 7% Below List Price
- $248/SF
- 103 Days On Market
Last Listing Agent Vicki VanWinkle ERA Select Real Estate

1778 Elkin Rd, Winchester, KY 40391

/27
Est $206,756 Not Listed For Sale

7 Pocahontas Trail, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,550 Sq Ft
- Built 1969
7 Pocahontas Trail, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $123/SF
- 7 Days On Market
- Last Sold Price $190,000
- Apr 18, 2025
Last Listing Agent Mila Ensor Ensor Real Estate, LLC

/57
$275,000
- 3 Beds
- 2 Baths
- 1,779 Sq Ft
720 Terry Dr, Winchester, KY 40391

Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $275,000, this home offers exceptional value in a highly walkable and convenient neighborhood. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The thoughtful layout

Christa Joynt Keller Williams Commonwealth

720 Terry Dr, Winchester, KY 40391
/80
$524,000 Sold Dec 16, 2025

160 Agawam Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 4,933 Sq Ft
- Built 1978
Last Sold Summary
- 9% Below List Price
- $106/SF
- 51 Days On Market
Current Estimated Value $522,998

Last Listing Agent Megan McCoy Keller Williams Legacy Group

160 Agawam Rd, Winchester, KY 40391

/57
Est $192,292 Not Listed For Sale

17 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,000 Sq Ft
- Built 1968
17 Hiawatha Trail, Winchester, KY 40391

Last Sold Summary
- 13% Above List Price
- $170/SF
- 32 Days On Market
- Last Sold Price $170,000
- Dec 30, 2024
Last Listing Agent Josh Wood Freedom Realty & Property Management

/26
$269,000 Pending
- 4 Beds
- 2 Baths
- 2,295 Sq Ft
86 Bon-Haven Ave, Winchester, KY 40391

Welcome to this spacious 4-bedroom, 2 bath home offering plenty of room to grow and make your own. With generous living areas and a functional layout, this property is perfect for those seeking space, comfort and opportunity. The home features a 2-car attached garage along with an additional 676 SF detached 2-car garage, providing ample room for vehicles, storage or a workshop. Outside you will

Tracey Goebel Tom Goebel & Company

86 Bon-Haven Ave, Winchester, KY 40391
/28
$203,900 Sold Dec 10, 2025

25 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 925 Sq Ft
- Built 1968
Last Sold Summary
- 3% Below List Price
- $220/SF
- 35 Days On Market
Current Estimated Value $199,235

Last Listing Agent Sarah Hess Keller Williams Commonwealth

25 Hiawatha Trail, Winchester, KY 40391

/15
Est $193,947 Not Listed For Sale

13 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,006 Sq Ft
- Built 1968
13 Hiawatha Trail, Winchester, KY 40391

Last Sold Summary
- 5% Above List Price
- $184/SF
- 50 Days On Market
- Last Sold Price $185,000
- Aug 25, 2023
Last Listing Agent Patrick Arvin Keller Williams Commonwealth

/17
$124,500
- 2 Beds
- 1 Bath
- 876 Sq Ft
122 Calloway St, Winchester, KY 40391

Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

Darrell Tackett Dream Maker Realty, LLC

122 Calloway St, Winchester, KY 40391
/3
$220,000 Sold Jul 30, 2025

412 Paisley Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,300 Sq Ft
- Built 2005
Last Sold Summary
- 4% Below List Price
- $169/SF
- 38 Days On Market
Current Estimated Value $223,400

Last Listing Agent John Wilson Bluegrass Properties Group

412 Paisley Ct, Winchester, KY 40391

/29
Est $240,045 Not Listed For Sale

46 Hiawatha Trail, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- Built 1970
46 Hiawatha Trail, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $145/SF
- 2 Days On Market
- Last Sold Price $218,000
- Aug 18, 2023
Last Listing Agent Christina Baker United Real Estate Louisville

/75
$600,000 Pending
- 3 Beds
- 3.5 Baths
- 3,391 Sq Ft
905 Pretty Run Rd, Winchester, KY 40391

Welcome to this elevated farmhouse classic-refined yet unpretentious, elegant yet entirely inviting. The kind of home that feels just as suited for quiet family life as it does for hosting gatherings that spill effortlessly from indoors to out with the wrap around porch, deck, outdoor kitchen & grill, POOL and hot tub spa, firepit & so much more...Welcome to 905 Pretty Run Road! Greeted by a

Niki Wiley Bluegrass Sotheby's International Realty

905 Pretty Run Rd, Winchester, KY 40391
/41
$300,300 Sold Nov 07, 2025

37 Lynnway Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 3,220 Sq Ft
- Built 1976
Last Sold Summary
- $93/SF
- 58 Days On Market
Current Estimated Value $322,188

Last Listing Agent Donna Thwaites Thwaites Realtors LLC

37 Lynnway Dr, Winchester, KY 40391

/24
Est $258,126 Not Listed For Sale

108 Dixon Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,377 Sq Ft
- Built 2006
108 Dixon Way, Winchester, KY 40391

Last Sold Summary
- $187/SF
- 124 Days On Market
- Last Sold Price $257,500
- Aug 29, 2024
Last Listing Agent Angie Conley Dixon Dixon Properties

/25
$295,000 Pending
- Land
- 10 Acres
- $29,500 per Acre
398 Pine Ridge Rd, Winchester, KY 40391

**** CONTRACT ACCEPTED WITH 48 KICK OUT***Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment

Amie Hieneman ERA Select Real Estate

398 Pine Ridge Rd, Winchester, KY 40391
/41
$247,000 Sold Sep 19, 2025

3588 Stamper Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,530 Sq Ft
- Built 1987
Last Sold Summary
- 1% Below List Price
- $161/SF
- 4 Days On Market
Current Estimated Value $246,450

Last Listing Agent Zach Johnson The Brokerage

3588 Stamper Dr, Winchester, KY 40391

/19
Est $215,962 Not Listed For Sale

170 Center Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,517 Sq Ft
- Built 1961
170 Center Dr, Winchester, KY 40391

Last Sold Summary
- 49% Above List Price
- $96/SF
- 52 Days On Market
- Last Sold Price $145,000
- Jan 04, 2024
Last Listing Agent Larry Moore CENTURY 21 Simpson & Associates

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

A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..64 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

Melia Hord Keller Williams Legacy Group

102 Royal Oak Dr, Winchester, KY 40391
/20
$205,000 Sold Aug 19, 2025

202 Custer Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,113 Sq Ft
- Built 1999
Last Sold Summary
- 8% Above List Price
- $184/SF
- 2 Days On Market
Current Estimated Value $198,068

Last Listing Agent Brittany Beer EXP Realty, LLC

202 Custer Ct, Winchester, KY 40391

/58
Est $197,873 Not Listed For Sale

219 Locust Grove Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,191 Sq Ft
- Built 1955
219 Locust Grove Rd, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $151/SF
- 27 Days On Market
- Last Sold Price $180,000
- Sep 24, 2024
Last Listing Agent Josh Wood Freedom Realty & Property Management

/8
$1,500,000
1015 Old Stone Church Rd, Winchester, KY 40391

Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

Walker Mack Bluegrass Property Exchange

1015 Old Stone Church Rd, Winchester, KY 40391

Showing Results 201 - 240, Page 6 of 18

Kentucky Clark County Winchester

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