$58,500
Views: 16
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,152sqft
Single family home for sale
Homefirst Real Estate
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16 Denny Ave, Winchester, KY 40391 
Price Drop: $10K
528 Estes Dr, Winchester, KY 40391
No HOA
187 Hawthorne Dr, Winchester, KY 40391
107 Hibiscus Ln, Winchester, KY 40391
108 Franklin Ave, Winchester, KY 40391
3D Tour
314 Botts Ct, Winchester, KY 40391
Hot
135 E Broadway St, Winchester, KY 40391Price Drop: $10K3D Tour
209 Boone Ave, Winchester, KY 40391 Price Drop: $5K
444 Wellington Way, Winchester, KY 40391 Price Drop: $9K
101 Alabama St, Winchester, KY 40391 
1704 Pilot View Rd, Winchester, KY 40391
13 Euclid Ave, Winchester, KY 40391
326 W Lexington Ave, Winchester, KY 40391
230 Evergreen Dr, Winchester, KY 40391
225 Evergreen Dr, Winchester, KY 40391
220 Evergreen Dr, Winchester, KY 40391
200 Evergreen Dr, Winchester, KY 40391Hot
26 Holiday Rd, Winchester, KY 40391 3D Tour
25 W Hickman St, Winchester, KY 40391 Price Drop: $11K
5 S Burns Ave, Winchester, KY 40391 HotPrice Drop: $15K
443 S Maple St, Winchester, KY 40391 
106 Quail Ridge Rd, Winchester, KY 40391Price Drop: $20.89K
132 Lana Ln, Winchester, KY 40391 Hot
121 Bay Hl Dr, Winchester, KY 40391 
563 Constitution Dr, Winchester, KY 40391
322 Calmes Blvd, Winchester, KY 40391Price Drop: $10K
225 Buffalo Tr, Winchester, KY 40391 
410 W Lexington Ave, Winchester, KY 40391Price Drop: $6.5K
42 Mockingbird Valley Rd, Winchester, KY 40391 
122 Sunset Hts, Winchester, KY 40391Price Drop: $10K
32 Jackson St, Winchester, KY 40391 Price Drop: $5.9K
148 Hidden Grove Ln, Winchester, KY 40391 Hot
2550 Kiddville Rd, Winchester, KY 40391 3D Tour
5039 Combs Fry Rd, Winchester, KY 40391 
47 Cherokee Ct, Winchester, KY 40391
102 Quail Ridge Rd, Winchester, KY 40391
3 Nunnelly Ct, Winchester, KY 40391Price Drop: $10K
33 Bon Hvn Ave, Winchester, KY 40391 Hot
9930 Mount Sterling Rd, Winchester, KY 40391 HotPrice Drop: $1K
59 Hillcrest Dr, Winchester, KY 40391 Price Drop: $10K
491 Hidden Hills Way, Winchester, KY 40391 
6 French Ave, Winchester, KY 40391
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Winchester, KY Homes for Sale & Real Estate
368 Homes for Sale
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Price Drop: $10K$219,900
Views: 8
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,904sqft
Single family home for sale
Freedom Realty & Property Management
No HOA$415,000
Views: 7
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,027sqft
Single family home for sale
Keller Williams Commonwealth
$369,900
Views: 10
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,978sqft
Single family home for sale
Keller Williams Commonwealth
$140,000
Views: 9
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 630sqft
Single family home for sale
Lifstyl Real Estate
3D Tour$299,900
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,648sqft
Single family home for sale
Lifstyl Real Estate
Hot$350,000
Views: 11
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,592sqft
Multi family home for sale
Dream Maker Realty, Llc
Price Drop: $10K3D Tour$255,000
Views: 9
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,260sqft
Single family home for sale
Lois Ann Disponett Real Est
Price Drop: $5K$309,900
Views: 7
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,963sqft
Single family home for sale
The Agency
Price Drop: $9K$155,900
Views: 9
Bedrooms: 1Bd
Bathrooms: 2Ba
Area: 1,056sqft
Single family home for sale
Woods Realty Group
$69,000
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,164sqft
Sale Pending
Tom Goebel & Company
$250,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,893sqft
Single family home for sale
Keller Williams Legacy Group
$225,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 2,244sqft
Sale Pending
Noel Auctioneers And Real Estate Advisors
$462,738
Views: 1
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,806sqft
Single family home for sale
United Real Estate Bluegrass
$469,925
Views: 1
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,855sqft
Single family home for sale
United Real Estate Bluegrass
$513,600
Views: 3
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,268sqft
Single family home for sale
United Real Estate Bluegrass
$457,900
Views: 2
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,986sqft
Single family home for sale
United Real Estate Bluegrass
Hot$255,000
Views: 13
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,135sqft
Single family home for sale
Freedom Realty & Property Management
3D Tour$325,000
Views: 9
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 3,378sqft
Single family home for sale
Keller Williams Legacy Group
Price Drop: $11K$139,000
Views: 9
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,842sqft
Sale Pending
The Howard Realty Co
HotPrice Drop: $15K$325,000
Views: 16
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 3,261sqft
Single family home for sale
Keller Williams Commonwealth
$221,000
Views: 5
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,665sqft
Townhouse for sale
Ensor Real Estate, Llc
Price Drop: $20.89K$699,000
Views: 12
Bedrooms: 4Bds
Bathrooms: 5Ba
Area: 4,255sqft
Sale Pending
Napier Realtors
Hot$279,900
Views: 17
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,779sqft
Townhouse for sale
Exp Realty, Llc
$99,500
Views: 12
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 924sqft
Single family home for sale
Kentucky Residential Real Estate, Llc
$379,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,204sqft
Single family home for sale
Dream Maker Realty, Llc
Price Drop: $10K$189,900
Views: 13
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 915sqft
Sale Pending
The Brokerage
$299,900
Views: 4
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 4,456sqft
Single family home for sale
Bluegrass Home Group
Price Drop: $6.5K$439,000
Views: 11
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 2,961sqft
Single family home for sale
Mccallie Real Estate
$265,000
Views: 11
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,715sqft
Single family home for sale
Re/Max Creative, Winchester
Price Drop: $10K$189,000
Views: 12
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,152sqft
Sale Pending
Dream Maker Realty, Llc
Price Drop: $5.9K$169,000
Views: 11
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,100sqft
Sale Pending
Coldwell Banker Mcmahan
Hot$335,000
Views: 12
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,836sqft
Sale Pending
The Real Estate Co - W Liberty
3D Tour$2,299,000
Views: 9
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 8,389sqft
Mansion for sale
Bluegrass Sotheby'S International Realty
$289,900
Views: 8
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,254sqft
Single family home for sale
The Agency
$239,000
Views: 17
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,856sqft
Single family home for sale
Tom Goebel & Company
$205,000
Views: 14
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,319sqft
Single family home for sale
Black Mountain Realty
Price Drop: $10K$249,000
Views: 21
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,386sqft
Sale Pending
Plum Tree Realty
Hot$639,000
Views: 13
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,962sqft
Single family home for sale
Dream Maker Realty, Llc
HotPrice Drop: $1K$249,000
Views: 17
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,996sqft
Single family home for sale
The Agency
Price Drop: $10K$209,500
Views: 9
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,200sqft
Sale Pending
Homefirst Real Estate
$296,000
Views: 19
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,953sqft
Single family home for sale
Woods Realty Group
Showing 43 - 84 of 368 homes for sale in Winchester, KY
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Winchester, KY Housing Market Overview
Winchester is a balanced market, giving buyers and sellers room to negotiate. With 4.6 months of supply and homes averaging 49 days on the market, you can make decisions without the pressure of a highly competitive market.
Status
Balanced Market
Days on Market
49
Inventory
368
Sep 2021Mar 2024Mar 2026
Median Home Price
$220,000Up 0.01%
In Mar 2026 · YoY
Sep 2021Mar 2024Mar 2026
Mortgage Rates 30-Yr Fixed
6.23%Down 0.58%
Current rate · YoY
Loan Type
30-Year Fixed
Housing Supply
- Homes For Sale
- 368 Down 0.05%
- Newly Listed Homes
- 26 Down 0.24%
- Months of Supply
- 4.6 Down 0.70%
Housing Demand
- Homes Sold
- 13 Down 0.00%
- Sale-to-List Ratio
- 97.6% Up 2.34%
- Homes Sold Above List
- 7.7% Down 0.64%
30-yr fixed rate 6.23% · Data as of Mar 2026 · Source: Houzeo Research.
View Full Winchester Market ReportNo. of Homes
Prices
No. of Homes
No. of Homes
Based on information from the IMAGINE MLS® through Oct 30, 2026, 1:45 AM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.
Click to see all homes
368
Homes Available
$ 220,000
Median List Price
49 Days
Avg on Market