$385,000
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
2725 Goshen Rd, Winchester, KY 40391
Christa Joynt
Keller Williams Commonwealth
16,242
Winchester, KY Homes
-
2725 Goshen Rd, Winchester, KY 40391
-
Call for Price
- 1 - 3 Beds
300 C G Stephenson Dr, Winchester, KY 40391
300 C G Stephenson Dr, Winchester, KY 40391This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy
Cambridge Square Apartments - Income Based
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$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 $108,274
Last Listing Agent Brian Lewis Guide Realty, Inc.
61 Melbourne St, Winchester, KY 40391 -
Est $904,192
Not Listed For Sale511 Boone Ave, Winchester, KY 40391
- 4 Beds
- 4.5 Baths
- 4,698 Sq Ft
- Built 1885
Last Sold Summary
- 318 Days On Market
Last Listing Agent Greg Leveridge Block + Lot Homes
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$515,000
$41K PRICE DROP- 5 Beds
- 3 Baths
- 3,102 Sq Ft
110 White Conkwright Rd, Winchester, KY 40391
110 White Conkwright Rd, Winchester, KY 40391
Philip 'PJ' Elder
Omega Real Estate Brokerage LLC
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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
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$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 $336,222
Not Listed For Sale275 Cross Brook Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,111 Sq Ft
- Built 1998
Last Sold Summary
- 2 Days On Market
Last Listing Agent Amanda Stewart Stewart & Co Realty LLC
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$399,000
$21K PRICE DROP- 4 Beds
- 2.5 Baths
- 1,978 Sq Ft
107 Hibiscus Ln, Winchester, KY 40391
107 Hibiscus Ln, Winchester, KY 40391
Christa Joynt
Keller Williams Commonwealth
-
Call for Price
- 1 - 3 Beds
900 Westwood Dr, Winchester, KY 40391
900 Westwood Dr, Winchester, KY 40391Pick up your application for our WAIT LIST at the office door! Westwood is a charming property in a great location in Winchester, Kentucky with rents based on income. Spacious one, two and three bedroom apartments for rent, each featuring a fully equipped kitchen, your choice of a patio or balcony, and they are wired for cable. Fun in the sun is just a outside your door at our playground, or
Westwood Apartments - Income Based
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$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 $731,156
Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
1783 Gay Evans Rd, Winchester, KY 40391 -
Est $258,021
Not Listed For Sale13385 Ironworks Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
- Built 1980
Last Sold Summary
- 4 Days On Market
Last Listing Agent Joshua Davis The Agency
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$675,000
$124K PRICE DROP- 4 Beds
- 2.5 Baths
- 4,928 Sq Ft
186 Chardonnay Ct, Winchester, KY 40391
186 Chardonnay Ct, Winchester, KY 40391
Brenda Sipes
WEICHERT REALTORS - ABG Properties
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Starting at $814 Per Month
- Studio
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
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$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 $307,636
Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty
202 Dubuy Dr, Winchester, KY 40391 -
Est $226,961
Not Listed For Sale13365 Ironworks Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,420 Sq Ft
- Built 1973
Last Sold Summary
- 10 Days On Market
Last Listing Agent Joshua Davis The Agency
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$239,900
$10K PRICE DROP Pending- 3 Beds
- 1 Bath
- 1,204 Sq Ft
10 Chickadee Ln, Winchester, KY 40391
10 Chickadee Ln, Winchester, KY 40391
Christa Joynt
Keller Williams Commonwealth
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Starting at $1,049 Per Month
- 2 - 3 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
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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 $115,881
Last Listing Agent Rony Jo Ballou Power House Realty
15 Sycamore St, Winchester, KY 40391 -
Est $315,852
Not Listed For Sale705 Oil Springs Rd, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,572 Sq Ft
- Built 1979
Last Sold Summary
- 35 Days On Market
Last Listing Agent Victoria Byrd HomeFirst Real Estate
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$229,000
$18K PRICE DROP- 3 Beds
- 1 Bath
- 1,050 Sq Ft
30 Virginia Ave, Winchester, KY 40391
30 Virginia Ave, Winchester, KY 40391
Brenda Sipes
WEICHERT REALTORS - ABG Properties
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$2,595 Per Month
- 4 Beds
- 3 Baths
- 2,160 Sq Ft
- House for Rent
721 Wayland Dr, Winchester, KY 40391
721 Wayland Dr, Winchester, KY 40391Welcome home to the perfect blend of peaceful country living and modern convenience. Located in Winchester, Kentucky, this beautifully remodeled 4-bedroom, 3 full-bath home offers an easy commute to Hamburg and all the shopping, dining, and entertainment Lexington has to offer. Step inside to discover a stunning kitchen designed to be the heart of the home—perfect for gathering with family and
S Ann Wesley Assurance Realty & Property Management
-
$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 $199,336
Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester
2721 Pretty Run Rd, Winchester, KY 40391 -
Est $462,121
Not Listed For Sale1927 Kiddville Rd, Winchester, KY 40391
- 5 Beds
- 4 Baths
- 2,056 Sq Ft
- Built 2001
Last Sold Summary
- 22 Days On Market
Last Listing Agent Megan McCoy Keller Williams Legacy Group
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$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
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$1,145 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 offering comfortable and affordable living in the heart of Winchester, KY. With a spacious living area, a functional kitchen, and a thoughtfully designed layout, this home is perfect for students, working professionals, or anyone looking to downsize.Property Features:1 Bedroom1 Full
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$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 $322,800
Last Listing Agent Bradley Warford Century 21 Pinnacle
329 Hanover Dr, Winchester, KY 40391 -
Est $446,317
Not Listed For Sale372 Arrowhead Ln, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,744 Sq Ft
- Built 2001
Last Sold Summary
- 2 Days On Market
Last Listing Agent Lori Tolson Lifstyl Real Estate
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$315,000
Pending- 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
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$1,700 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 40391Welcome to this beautifully renovated 3-bedroom, 2-bathroom home, offering the perfect combination of modern style and everyday comfort. The bright and spacious living area flows seamlessly into a stylish, updated kitchen, creating an inviting space for relaxing or entertaining. Thoughtfully designed with contemporary finishes and a functional layout, this move-in-ready home is ideal for
-
$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 $579,068
Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate
2615 Crowe Ridge Rd, Winchester, KY 40391 -
Est $786,112
Not Listed For Sale703 Kiddville Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,311 Sq Ft
- Built 1980
Last Sold Summary
- 276 Days On Market
Last Listing Agent Tyson Walters Kassie & Associates
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$420,000
- 3 Beds
- 2 Baths
- 2,027 Sq Ft
187 Hawthorne Dr, Winchester, KY 40391
187 Hawthorne Dr, Winchester, KY 40391
Christa Joynt
Keller Williams Commonwealth
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$1,300 Per Month
- 3 Beds
- 1 Bath
- House for Rent
101 E Lexington Ave, Winchester, KY 40391
101 E Lexington Ave, Winchester, KY 40391Make yourself at home in this charming 2-bedroom, 1-bathroom house, offering a spacious yet practical layout designed for comfortable everyday living. With bright living spaces, a functional kitchen, and two well-sized bedrooms, this home is ideal for small families, roommates, or anyone looking for extra space.This well-maintained home provides a welcoming atmosphere and the convenience
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$431,000
Sold May 12, 20262 Stoney Brook Dr, Winchester, KY 40391
- 3 Beds
- 3.5 Baths
- 3,633 Sq Ft
- Built 1983
Last Sold Summary
- 1% Below List Price
- $119/SF
- 1 Day On Market
Current Estimated Value $433,148
Last Listing Agent Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors
2 Stoney Brook Dr, Winchester, KY 40391 -
Est $410,459
Not Listed For Sale700 Vienna Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,826 Sq Ft
- Built 2004
Last Sold Summary
- 18 Days On Market
Last Listing Agent Sheridan Sims Keller Williams Commonwealth
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$247,500
$7K PRICE DROP- 3 Beds
- 1.5 Baths
- 1,533 Sq Ft
377 Crescent Ave, Winchester, KY 40391
377 Crescent Ave, Winchester, KY 40391
Bill VanWinkle
Joyce Marcum Realty
-
$1,550 Per Month
- 2 Beds
- 1 Bath
- Condo for Rent
202 S Maple St Unit C, Winchester, KY 40391
202 S Maple St Unit C, Winchester, KY 40391Bright and comfortable 2-bedroom, 1-bathroom upstairs unit with all bills paid! Conveniently located at the corner of Hickman and Maple, directly across from Walgreens and Speedway gas station.Move-In Special:Free application50% off on your first month’s rent if you apply within 24 hourSecurity Deposit: $1,550.00Contact us today to schedule a showing or
-
$175,000
Sold Nov 18, 2025612 Boone Ave, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 1,262 Sq Ft
- Built 1958
Last Sold Summary
- 12% Below List Price
- $139/SF
- 13 Days On Market
Current Estimated Value $182,810
Last Listing Agent Garnett Davis Tom Goebel & Company
612 Boone Ave, Winchester, KY 40391 -
Est $480,530
Not Listed For Sale2430 Log Lick Rd, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 2,700 Sq Ft
- Built 1938
Last Sold Summary
- 184 Days On Market
Last Listing Agent E Anthony Phillips RE/MAX Creative Realty
Showing Results 1 - 40, Page 1 of 18
Home Prices in Winchester, KY
The median home sale price in Winchester, KY is $265,000, up 10% year-over-year. Homes in Winchester sell in 33 days on average, compared to the national average of 56 days.
Home Price Trends
|
Median Sale Price
$265,000
|
Median Single Family Sale Price
$270,000
|
|
Median Townhouse Sale Price
$192,000
|
Median 2 Bedroom Sale Price
$167,500
|
|
Median 1 Bedroom Sale Price
$107,450
|
Average Price Per Sq Ft
$161
|
|
Number of Homes for Sale
79
|
Last 12 months Home Sales
309
|
|
Months of Supply
3.10
|
Median List Price
$275,000
|
|
Median Change From 1st List Price
2%
|
Median Home Sale Price YoY Change
10%
|
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