Winchester, KY Homes

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$429,900 Pending
- 3 Beds
- 2.5 Baths
- 2,258 Sq Ft
233 Cunningham Ln, Winchester, KY 40391

Welcome to 233 Cunningham Lane in Winchester, KY — a versatile mini farm offering 6.7 acres, multiple outbuildings, and a functional one-level ranch floor plan designed for comfort and flexibility. Conveniently located less than two miles from the Mountain Parkway, this property combines rural space with easy accessibility for commuting and everyday travel. The ranch-style home features 3

Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

233 Cunningham Ln, Winchester, KY 40391
/15
$241,500 Sold May 01, 2026

318 Buffalo Trace, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2026
Last Sold Summary
- 3% Above List Price
- $201/SF
- 1 Day On Market
Current Estimated Value $180,330

Last Listing Agent Nena Honaker Tom Goebel & Company

318 Buffalo Trace, Winchester, KY 40391

/52
Est $272,956 Not Listed For Sale

14 Lisle Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,673 Sq Ft
- Built 1955
14 Lisle Ln, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $149/SF
- 1 Day On Market
- Last Sold Price $250,000
- Nov 25, 2024
Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

/21
$200,000
- 3 Beds
- 2 Baths
- 1,140 Sq Ft
265 Cunningham Ln, Winchester, KY 40391

There's nothing sweeter than countryside views! 30 Minutes to Hamburg in Lexington & USDA eligible at 0% down! Located off the Mountain Parkway & Ironworks Rd, this property features over an acre of land, a fenced-in backyard, and a new septic tank system. Well maintained and only 2 years old, this home is the perfect opportunity to start your mini farm. (3rd bedroom not photographed, being used

Kierstin Shaffer Berkshire Hathaway HomeServices Foster Realtors

265 Cunningham Ln, Winchester, KY 40391
/27
$245,000 Sold Jun 13, 2025

8 Seneca Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,728 Sq Ft
- Built 1968
Last Sold Summary
- 2% Above List Price
- $142/SF
- 8 Days On Market
Current Estimated Value $251,514

Last Listing Agent Michael Hilario The Agency

8 Seneca Dr, Winchester, KY 40391

/20
Est $221,533 Not Listed For Sale

18 Lisle Ln, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,082 Sq Ft
- Built 1950
18 Lisle Ln, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $185/SF
- 0 Days On Market
- Last Sold Price $200,000
- Sep 22, 2023
Last Listing Agent Lukas Owens The Brokerage

/28
$84,900 Pending
- 3 Beds
- 2 Baths
- 1,946 Sq Ft
300 Aspen Ln, Winchester, KY 40391

Welcome home to this well-maintained 3 bedroom, 2 bathroom double wide manufactured home in Treehaven, offering close to 2,000 square feet of comfortable living space...a rare find for buyers looking for room, functionality, and flexibility. Inside, you'll love the open-concept layout that connects the large living room, kitchen, and dining area, making it ideal for both everyday living and

Christa Joynt Keller Williams Commonwealth

300 Aspen Ln, Winchester, KY 40391
/26
$239,900 Sold Jun 23, 2025

134 Boone Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,878 Sq Ft
- Built 1920
Last Sold Summary
- 3% Below List Price
- $128/SF
- 74 Days On Market
Current Estimated Value $256,164

Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

134 Boone Ave, Winchester, KY 40391

/54
Est $334,434 Not Listed For Sale

35 Lisle Ln, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,816 Sq Ft
- Built 1953
35 Lisle Ln, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $157/SF
- 27 Days On Market
- Last Sold Price $285,000
- Oct 02, 2023
Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

/6
$204,900 Pending
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
500 Hidden Hills Way, Winchester, KY 40391

Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

Sondra Clark Taylor Real Estate, LLC

500 Hidden Hills Way, Winchester, KY 40391
/32
$310,000 Sold May 01, 2026

113 Strawberry Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,780 Sq Ft
- Built 2023
Last Sold Summary
- 2% Below List Price
- $174/SF
- 1 Day On Market
Current Estimated Value $314,130

Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

113 Strawberry Ln, Winchester, KY 40391

/32
Est $258,522 Not Listed For Sale

540 S Maple St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,740 Sq Ft
- Built 1940
540 S Maple St, Winchester, KY 40391

Last Sold Summary
- 130% Above List Price
- $65/SF
- 86 Days On Market
- Last Sold Price $112,360
- Aug 24, 2023
Last Listing Agent Keith Wilson Coldwell Banker McMahan

/3
$146,000
- 3 Beds
- 1 Bath
- 1,020 Sq Ft
228 Jackson St, Winchester, KY 40391

Here's your chance to own a nice investment property. This single family home has a 3 bed 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

David Espinosa Bluegrass Realty Pros, Inc

228 Jackson St, Winchester, KY 40391
/31
$240,200 Sold Oct 28, 2025

203 Inverness Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,935 Sq Ft
- Built 2004
Last Sold Summary
- 2% Below List Price
- $124/SF
- 16 Days On Market
Current Estimated Value $245,499

Last Listing Agent Kymberly McCreary EXP Realty, LLC

203 Inverness Ln, Winchester, KY 40391

/37
Est $256,628 Not Listed For Sale

17 Short St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,783 Sq Ft
- Built 1942
17 Short St, Winchester, KY 40391

Last Sold Summary
- 20% Above List Price
- $120/SF
- 27 Days On Market
- Last Sold Price $214,000
- Jul 28, 2023
Last Listing Agent Dustin Sparrow ERA Select Real Estate

/33
$285,000 Pending
- 3 Beds
- 2 Baths
- 1,790 Sq Ft
211 Lindsey Ct, Winchester, KY 40391

Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been

Lesley Ward Biederman Real Estate

211 Lindsey Ct, Winchester, KY 40391
/44
$847,000 Sold Apr 22, 2026

7075 Ecton Rd, Winchester, KY 40391
- Land
- 83.71 Acres
- $10,118 per Acre
Last Sold Summary
- 39 Days On Market
Current Estimated Value $833,000

Last Listing Agent Jonathan Noel Noel Auctioneers and Real Estate Advisors

7075 Ecton Rd, Winchester, KY 40391

/34
Est $320,356 Not Listed For Sale

214 Boone Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,928 Sq Ft
- Built 1930
214 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 30% Above List Price
- $84/SF
- 107 Days On Market
- Last Sold Price $247,000
- Oct 23, 2023
Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

/16
$97,500
- Land
- 7.99 Acres
- $12,201 per Acre
3991 Jackson Ferry Rd, Winchester, KY 40391

Offering the same peaceful setting and rare river access, this tract provides a fantastic opportunity for recreational land ownership at an affordable price. Backing directly to the Kentucky River, it's an ideal spot for camping, weekend retreats, arrowhead hunting or enjoying the outdoors with kayaking, fishing, and more right at your fingertips. This property's fertile soil opens the door for

Christa Joynt Keller Williams Commonwealth

3991 Jackson Ferry Rd, Winchester, KY 40391
/13
$38,700 Sold May 20, 2025

11 Spring St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- Built 1945
Last Sold Summary
- 3% Below List Price
- $35/SF
- 33 Days On Market
Current Estimated Value $45,000

Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

11 Spring St, Winchester, KY 40391

/65
Est $352,099 Not Listed For Sale

408 S Maple St, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 3,372 Sq Ft
- Built 1910
408 S Maple St, Winchester, KY 40391

Last Sold Summary
- 14% Above List Price
- $92/SF
- 62 Days On Market
- Last Sold Price $310,000
- Jan 26, 2024
Last Listing Agent Craig Bridgewater Bridgewater Real Estate

/9
$1,350,000
- Land
- 3.02 Acres
- $447,020 per Acre
155 April Way, Winchester, KY 40391

Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

Greg Leveridge Block + Lot Real Estate

155 April Way, Winchester, KY 40391
/36
$345,000 Sold Jun 02, 2025

1173 Lafayette Blvd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,910 Sq Ft
- Built 1996
Last Sold Summary
- 3% Below List Price
- $181/SF
- 36 Days On Market
Current Estimated Value $356,501

Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

1173 Lafayette Blvd, Winchester, KY 40391

/57
Est $442,228 Not Listed For Sale

402 S Maple St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,864 Sq Ft
- Built 1896
402 S Maple St, Winchester, KY 40391

Last Sold Summary
- 7% Above List Price
- $107/SF
- 24 Days On Market
- Last Sold Price $415,000
- Aug 20, 2024
Last Listing Agent Kristy Hall The Agency

/2
$100,000
- Land
- 13,503 Sq Ft
- $322,581 per Acre
215 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

215 Duclair Dr, Winchester, KY 40391
/43
$339,000 Sold Feb 12, 2026

106 Gibson Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,064 Sq Ft
- Built 2021
Last Sold Summary
- $164/SF
- 1 Day On Market
Current Estimated Value $340,731

Last Listing Agent Brittany Nester RO&CO Real Estate

106 Gibson Way, Winchester, KY 40391

/60
Est $432,941 Not Listed For Sale

405 Boone Ave, Winchester, KY 40391
- 3 Beds
- 4 Baths
- 2,718 Sq Ft
- Built 1945
405 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $147/SF
- 16 Days On Market
- Last Sold Price $400,000
- Oct 30, 2023
Last Listing Agent Diane K Scott The Brokerage

/43
$559,000 Pending
- 4 Beds
- 4.5 Baths
- 4,185 Sq Ft
556 Earlymeade Dr, Winchester, KY 40391

As you walk in the front door of this house you will immediately be thrilled because the owners have loved this house and this is evident from the gleaming hardwood floors to the fresh coats of paint. This house is located in the most desirable neighborhood of Earlymeade. It is near lots of popular destinations, including Hamburg in Lexington and the I-64 and I-75 corridors so you can be in

Craig Bridgewater Bridgewater Real Estate

556 Earlymeade Dr, Winchester, KY 40391
/36
$472,500 Sold Sep 09, 2025

208 Royal Oak Dr, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,593 Sq Ft
- Built 2007
Last Sold Summary
- 1% Above List Price
- $182/SF
- 1 Day On Market
Current Estimated Value $469,830

Last Listing Agent Megan McCoy Keller Williams Legacy Group

208 Royal Oak Dr, Winchester, KY 40391

/57
Est $291,227 Not Listed For Sale

10 Northern Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,270 Sq Ft
- Built 1957
10 Northern Ave, Winchester, KY 40391

Last Sold Summary
- 16% Above List Price
- $110/SF
- 0 Days On Market
- Last Sold Price $250,000
- Mar 28, 2024
Last Listing Agent Jeanne Beaven Rector Hayden Realtors

/34
$275,700 Pending
- 3 Beds
- 2 Baths
- 1,682 Sq Ft
404 Wellington Way, Winchester, KY 40391

This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family and friends. The sellers added fiber optics

Craig Bridgewater Bridgewater Real Estate

404 Wellington Way, Winchester, KY 40391
/6
$51,000 Sold May 14, 2025

214 Ashton Oak Way, Winchester, KY 40391
- Land
- 10,890 Sq Ft
- $204,000 per Acre
Last Sold Summary
- 7% Below List Price
- 325 Days On Market
Current Estimated Value $54,792

Last Listing Agent Melia Hord Keller Williams Legacy Group

214 Ashton Oak Way, Winchester, KY 40391

/28
Est $373,590 Not Listed For Sale

29 Manor Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,148 Sq Ft
- Built 1962
29 Manor Dr, Winchester, KY 40391

Last Sold Summary
- 3% Above List Price
- $169/SF
- 247 Days On Market
- Last Sold Price $363,000
- Apr 07, 2025
Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

/2
$100,000
- Land
- 13,939 Sq Ft
- $312,500 per Acre
155 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

155 Duclair Dr, Winchester, KY 40391
/32
$259,000 Sold Apr 30, 2026

414 Wellington Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,251 Sq Ft
- Built 2007
Last Sold Summary
- $207/SF
- 53 Days On Market
Current Estimated Value $254,943

Last Listing Agent Amy Diamond ERA Select Real Estate

414 Wellington Way, Winchester, KY 40391

/35
Est $341,102 Not Listed For Sale

121 Hampton Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,248 Sq Ft
- Built 1958
121 Hampton Ave, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $137/SF
- 60 Days On Market
- Last Sold Price $307,500
- Mar 08, 2024
Last Listing Agent Patrick Arvin Keller Williams Commonwealth

/22
$150,000
- Land
- 9.39 Acres
- $15,971 per Acre
3821 Jackson Ferry Rd, Winchester, KY 40391

If you've been dreaming of building a home with river access, this is it. Located along a breathtaking stretch of Jackson Ferry Road, this 9.392-acre tract offers a rare combination of a viable build site and direct access to the scenic Kentucky River. Whether it's morning coffee overlooking the countryside or afternoons spent kayaking and fishing, this property delivers a lifestyle that's hard

Christa Joynt Keller Williams Commonwealth

3821 Jackson Ferry Rd, Winchester, KY 40391
/23
$135,000 Sold Jul 02, 2025

2100 Old Log Lick Rd, Winchester, KY 40391
- Land
- 5 Acres
- $27,000 per Acre
Last Sold Summary
- 10% Below List Price
- 69 Days On Market
Current Estimated Value $142,767

Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

2100 Old Log Lick Rd, Winchester, KY 40391

/50
Est $445,737 Not Listed For Sale

33 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,580 Sq Ft
- Built 1958
33 Hampton Ave, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $106/SF
- 16 Days On Market
- Last Sold Price $380,000
- Jan 21, 2025
Last Listing Agent Robert Coburn Kentucky Realty Group, LLC

/47
$499,000 Pending
- 5 Beds
- 3.5 Baths
- 3,823 Sq Ft
595 Earlymeade Dr, Winchester, KY 40391

Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

Craig Bridgewater Bridgewater Real Estate

595 Earlymeade Dr, Winchester, KY 40391

Showing Results 561 - 600, Page 15 of 18

Kentucky Clark County Winchester

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Winchester, KY Homes

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