$550,000
$6K PRICE DROP
- 5 Beds
- 3 Baths
- 3,102 Sq Ft
110 White Conkwright Rd, Winchester, KY 40391
Philip 'PJ' Elder
Omega Real Estate Brokerage LLC
(859) 695-3879
16,370
Winchester, KY Homes
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110 White Conkwright Rd, Winchester, KY 40391
-
Starting at $800 Per Month
- 1 - 3 Beds
260 Oxford Dr, Winchester, KY 40391
260 Oxford Dr, Winchester, KY 40391The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer
Summit Apartments
(859) 577-9164
-
$15,000
Sold Dec 30, 202561 Melbourne St, Winchester, KY 40391
- Land
- 4,356 Sq Ft
- $150,000 per Acre
Last Sold Summary
- 40% Below List Price
- 57 Days On Market
Current Estimated Value $80,682
Last Listing Agent Brian Lewis Guide Realty, Inc.
61 Melbourne St, Winchester, KY 40391 -
Est $240,305
Not Listed For Sale13 Fairview Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2025
Last Sold Summary
- 2 Days On Market
-
$84,900
$5K PRICE DROP- 3 Beds
- 2 Baths
- 1,946 Sq Ft
300 Aspen Ln, Winchester, KY 40391
300 Aspen Ln, Winchester, KY 40391
Christa Joynt
Keller Williams Commonwealth
(859) 903-5711
-
Starting at $814 Per Month
- Studio - 1 Bed
27 E Washington St, Winchester, KY 40391
27 E Washington St, Winchester, KY 40391*One Month Free Rent!* All Utilities Included! Nice Studio Apt Near Downtown Winchester!Marketing DescriptionStudio Apartment Available at Studio 29 Apartments, Winchester, KY! One Bath; Only 5 Minutes from Downtown! Off-Street Parking, Small Pets Ok; All Utilities Included! Kitchen includes a Stove, Refrigerator, and Microwave; Non-smoking.Conveniently located near Shopping, Grocery
Studio 28
(859) 249-8752
-
$189,500
Sold Dec 18, 202513015 Irvine Rd, Winchester, KY 40391
Last Sold Summary
- 17% Below List Price
- 134 Days On Market
Last Listing Agent Mendel Tipton Natural Bridge Realty
13015 Irvine Rd, Winchester, KY 40391 -
Est $277,585
Not Listed For Sale14 Calloway St, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Built 1940
Last Sold Summary
- 75 Days On Market
-
$724,999
$74K PRICE DROP- 4 Beds
- 2.5 Baths
- 7,058 Sq Ft
186 Chardonnay Ct, Winchester, KY 40391
186 Chardonnay Ct, Winchester, KY 40391
Brenda Sipes
WEICHERT REALTORS - ABG Properties
(859) 470-2071
-
Starting at $1,049 Per Month
- 2 Beds
510 College St, Winchester, KY 40391
510 College St, Winchester, KY 40391Lovely 2 Bedroom and One Bath Apartment at the Lofts of Winchester, located at 508 College Street, Winchester, KY! Near Downtown, Shopping, Restaurants, Hwy 64 and Hwy 60. Off-street Parking; Small Pets Ok! Beautiful Updated Flooring and Stainless Steel Appliances. Kitchen includes Stove and Refrigerator. Central Heat & AC.Local Schools are: Willis H. Justice Elementary; Robert D.
The Lofts at Winchester
(859) 249-8853
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$272,000
Sold Jun 26, 2025205 Beaumont Place, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 1995
Last Sold Summary
- 5% Above List Price
- $194/SF
- 4 Days On Market
Current Estimated Value $288,526
Last Listing Agent Terry Billiter Premier Property Consultants
205 Beaumont Place, Winchester, KY 40391 -
Est $108,202
Not Listed For Sale27 Oliver St, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 1,242 Sq Ft
- Built 1940
Last Sold Summary
- 8 Days On Market
-
$280,000
- 4 Beds
- 3.5 Baths
- 3,276 Sq Ft
133 Bay Hill Dr, Winchester, KY 40391
133 Bay Hill Dr, Winchester, KY 40391
Dustin Pennington
Keller Williams Legacy Group
(859) 636-6943
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$996 Per Month
- 1 Bed
- 1 Bath
- 872 Sq Ft
- Condo for Rent
362 S Main St Unit A, Winchester, KY 40391
362 S Main St Unit A, Winchester, KY 40391Property Id: 2574447Large 1 bedroom, i bath newly painted apartment. Close to shopping, gym and local grocery. Resevved off street parking, in house laundry.
(859) 577-7730
-
$750,000
Sold May 21, 20261783 Gay Evans Rd, Winchester, KY 40391
- 5 Beds
- 3.5 Baths
- 2,904 Sq Ft
- Built 1998
Last Sold Summary
- 6% Below List Price
- $258/SF
- 135 Days On Market
Current Estimated Value $758,759
Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
1783 Gay Evans Rd, Winchester, KY 40391 -
Est $386,474
Not Listed For Sale512 Boone Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,149 Sq Ft
- Built 1950
Last Sold Summary
- 58 Days On Market
-
$270,000
$5K PRICE DROP- 3 Beds
- 2 Baths
- 1,779 Sq Ft
720 Terry Dr, Winchester, KY 40391
720 Terry Dr, Winchester, KY 40391
Christa Joynt
Keller Williams Commonwealth
(859) 903-5709
-
$1,750 Per Month
- 3 Beds
- 1 Bath
- 1,974 Sq Ft
- House for Rent
136 Alabama St, Winchester, KY 40391
136 Alabama St, Winchester, KY 40391Welcome home to this spacious 3-bedroom, 1-bath residence offering the perfect combination of comfort and convenience. With generous living space, well-sized bedrooms, and a functional layout, this home is ideal for families, roommates, or anyone looking for extra room to spread out.Enjoy comfortable living in a home designed to meet your everyday needs. Contact us today for more
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$315,000
Sold Jun 27, 2025408 Calmes Blvd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,848 Sq Ft
- Built 1991
Last Sold Summary
- 6% Below List Price
- $170/SF
- 46 Days On Market
Current Estimated Value $338,031
Last Listing Agent Josh Wood Freedom Realty & Property Management
408 Calmes Blvd, Winchester, KY 40391 -
Est $221,674
Not Listed For Sale138 Linden Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
- Built 2024
Last Sold Summary
- 17 Days On Market
-
$325,000
$100K PRICE DROP- 3 Beds
- 2 Baths
- 1,512 Sq Ft
4305 Old Boonesboro Rd, Winchester, KY 40391
4305 Old Boonesboro Rd, Winchester, KY 40391
Brenda Sipes
WEICHERT REALTORS - ABG Properties
(859) 549-3072
-
$1,190 Per Month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
1028 W Lexington Ave Unit 4, Winchester, KY 40391
1028 W Lexington Ave Unit 4, Winchester, KY 40391Welcome to 1028 W Lexington Ave — a cozy and well-maintained 1-bedroom, 1-bathroom apartment located in the heart of Winchester, KY.This home features a spacious living area, a functional kitchen, and all the essentials needed for comfortable everyday living. Ideal for students, professionals, or anyone looking to downsize, this apartment offers the perfect balance of comfort and
-
$302,500
Sold Jan 05, 2026202 Dubuy Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
- Built 2022
Last Sold Summary
- 1% Below List Price
- $168/SF
- 5 Days On Market
Current Estimated Value $306,425
Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty
202 Dubuy Dr, Winchester, KY 40391 -
Est $270,360
Not Listed For Sale244 Bay Hill Ct, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,536 Sq Ft
- Built 2006
Last Sold Summary
- 10 Days On Market
-
$14,100,000
- Land
- 274.52 Acres
- $51,362 per Acre
2395 Paris Rd, Winchester, KY 40391
2395 Paris Rd, Winchester, KY 40391 -
$1,800 Per Month
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- Condo for Rent
135 Winn Ave Unit A, Winchester, KY 40391
135 Winn Ave Unit A, Winchester, KY 40391Step into this beautifully renovated 3-bedroom, 2-bathroom home featuring a bright and open living area and a modern kitchen on the ground floor. Designed for comfort and style, this residence offers contemporary finishes, spacious layouts, and all the amenities you need for modern living. Perfect for families or anyone seeking a move-in ready home with a fresh, modern feel.
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$88,500
Sold Aug 08, 202515 Sycamore St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
- Built 1945
Last Sold Summary
- 12% Below List Price
- $77/SF
- 28 Days On Market
Current Estimated Value $98,044
Last Listing Agent Rony Jo Ballou Power House Realty
15 Sycamore St, Winchester, KY 40391 -
Est $464,278
Not Listed For Sale210 Candlewood Dr, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,046 Sq Ft
- Built 2006
Last Sold Summary
- 49 Days On Market
-
$97,500
- Land
- 7.99 Acres
- $12,201 per Acre
3991 Jackson Ferry Rd, Winchester, KY 40391
3991 Jackson Ferry Rd, Winchester, KY 40391 -
$1,190 Per Month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
1028 W Lexington Ave Unit 3, Winchester, KY 40391
1028 W Lexington Ave Unit 3, Winchester, KY 40391This cozy 1-bedroom, 1-bathroom apartment features a comfortable living area and a functional kitchen. Pets are welcome with an additional pet fee. Tenants are responsible for all utility payments, giving you full control over your monthly expenses. Ideal for anyone seeking a convenient and pet-friendly home.
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$190,000
Sold Mar 06, 20262721 Pretty Run Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
- Built 2000
Last Sold Summary
- 37% Below List Price
- $130/SF
- 12 Days On Market
Current Estimated Value $199,524
Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester
2721 Pretty Run Rd, Winchester, KY 40391 -
Est $199,553
Not Listed For Sale120 Heather Ln, Winchester, KY 40391
- 2 Beds
- 1.5 Baths
- 1,140 Sq Ft
- Built 1990
Last Sold Summary
- 3 Days On Market
-
$150,000
- Land
- 9.39 Acres
- $15,971 per Acre
3821 Jackson Ferry Rd, Winchester, KY 40391
3821 Jackson Ferry Rd, Winchester, KY 40391 -
$829 Per Month
- 1 Bed
- 1 Bath
- 850 Sq Ft
- Condo for Rent
18 Calloway St Unit 4, Winchester, KY 40391
18 Calloway St Unit 4, Winchester, KY 40391Available May 26,2026! – Recently Renovated Winchester Apartment!Welcome to your next home in the heart of Winchester! This beautifully updated 1-bedroom, 1-bath apartment is nestled just off Lexington Avenue and Bypass Road close to shopping, dining, and just minutes from downtown Winchester.At Bluegrass Rental Management, we strive to provide an experience that is cost-effective
-
$308,000
Sold Oct 03, 2025329 Hanover Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,903 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $162/SF
- 5 Days On Market
Current Estimated Value $319,964
Last Listing Agent Bradley Warford Century 21 Pinnacle
329 Hanover Dr, Winchester, KY 40391 -
Est $303,346
Not Listed For Sale8 Chickadee Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
- Built 1970
Last Sold Summary
- 130 Days On Market
-
$775,000
- 5 Beds
- 3 Baths
- 4,437 Sq Ft
465 Morris Rd, Winchester, KY 40391
465 Morris Rd, Winchester, KY 40391
Brenda Leigh Walters
United Real Estate Bluegrass
(859) 459-0504
-
$825 Per Month
- Studio
- 1 Bath
- 300 Sq Ft
- Studio Apt All Utilities Included!
401 N Maple St Unit 6, Winchester, KY 40391
401 N Maple St Unit 6, Winchester, KY 40391Welcome to this charming renovated studio apartment located at 401 North Maple Street. This cozy unit is perfect for those seeking a comfortable and affordable living space.Step inside and be greeted by the stylish LVP flooring that adds a touch of elegance to the interior. The open layout creates a seamless flow between the living area, kitchenette, and sleeping quarters.One of
-
$599,500
Sold Aug 18, 20252615 Crowe Ridge Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,222 Sq Ft
- Built 2018
Last Sold Summary
- $270/SF
- 1 Day On Market
Current Estimated Value $580,680
Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate
2615 Crowe Ridge Rd, Winchester, KY 40391 -
Est $266,347
Not Listed For Sale234 Prescott Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,463 Sq Ft
- Built 2005
Last Sold Summary
- 17 Days On Market
Showing Results 1 - 40, Page 1 of 18
Home Prices in Winchester, KY
The median home sale price in Winchester, KY is $259,950, up 9% year-over-year. Homes in Winchester sell in 32 days on average, compared to the national average of 58 days.
Home Price Trends
|
Median Sale Price
$259,950
|
Median Single Family Sale Price
$265,000
|
|
Median Townhouse Sale Price
$187,000
|
Median 2 Bedroom Sale Price
$172,450
|
|
Median 1 Bedroom Sale Price
$164,900
|
Average Price Per Sq Ft
$164
|
|
Number of Homes for Sale
83
|
Last 12 months Home Sales
312
|
|
Months of Supply
3.20
|
Median List Price
$270,000
|
|
Median Change From 1st List Price
2%
|
Median Home Sale Price YoY Change
9%
|
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