$165,000
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 1,537sqft
Single family home for sale
Marshall Lane Real Estate - Lexington
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1494 Amster Grv Rd, Winchester, KY 40391 
Price Drop: $10K
527 Hidden Hills Way, Winchester, KY 40391
New Construction
1515 Sewell Shop Rd, Winchester, KY 40391
309 Gallahadion Ct, Winchester, KY 40391
11 Stoney Brk Dr #1, Winchester, KY 40391Price Drop: $10K
14 Cook Ave, Winchester, KY 40391 Price Drop: $2.5K
214 Center Dr, Winchester, KY 40391 
Hot
323 Skylark Dr, Winchester, KY 40391
119 Tower Ln, Winchester, KY 40391Hot
600 College St, Winchester, KY 40391 
109 5th Street, Winchester, KY 40391
208 Buffalo Tr, Winchester, KY 40391
654 Pine Ridge, Winchester, KY 40391Price Drop: $5.5K
198 Hilltop Dr, Winchester, KY 40391 
705 W Lexington Ave, Winchester, KY 40391New Construction
38 N Burns Ave, Winchester, KY 40391 Price Drop: $4K
13 Maryland Ave, Winchester, KY 40391 
103 Southern Ct, Winchester, KY 40391
119 Winterberry Cir, Winchester, KY 40391Price Drop: $5K
229 S Highland St, Winchester, KY 40391 
455 Davis Ln, Winchester, KY 40391
117 Colonial Park Dr, Winchester, KY 40391Hot
520 College St, Winchester, KY 40391 
131 Teal Ln, Winchester, KY 40391
8 Monroe Ave, Winchester, KY 40391New Construction
410 Fairholme Way, Winchester, KY 40391 
307 Mcdowell Dr, Winchester, KY 40391Hot
405 Nick Ln, Winchester, KY 40391 
48 Bon Hvn Ave, Winchester, KY 40391
546 Constitution Dr, Winchester, KY 40391
317 Vanover Way, Winchester, KY 40391
121 Ralston Ln, Winchester, KY 40391Price Drop: $10K
428 Waycross Dr, Winchester, KY 40391 
127 Lindberg Ave, Winchester, KY 40391
1780 Stoner Ephesus Rd, Winchester, KY 40391
285 Rose Dr, Winchester, KY 40391HotPrice Drop: $7.8K
107 S Burns Ave, Winchester, KY 40391 Price Drop: $10K
128 Cherokee Dr, Winchester, KY 40391 HotPrice Drop: $11K
11304 Irvine Rd, Winchester, KY 40391 
625 Pine Ridge Rd, Winchester, KY 40391
7440 Bybee Rd, Winchester, KY 40391
65 Fitch 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$219,500
Views: 14
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,130sqft
Sale Pending
The Agency
New Construction$565,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,878sqft
Single family home for sale
Kentucky Residential Real Estate, Llc
$349,000
Views: 7
Bedrooms: 3Bds
Bathrooms: 3Ba
Area: 1,945sqft
Single family home for sale
Re/Max Creative, Winchester
$349,000
Views: 6
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,990sqft
Single family home for sale
Milton And Associates Real Estate
Price Drop: $10K$209,000
Views: 10
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,261sqft
Sale Pending
United Real Estate Bluegrass
Price Drop: $2.5K$197,000
Views: 9
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,193sqft
Sale Pending
The Brokerage
Hot$424,500
Views: 15
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 3,674sqft
Sale Pending
Tom Goebel & Company
$220,000
Views: 7
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,272sqft
Single family home for sale
Wever Realty Llc
Hot$215,000
Views: 16
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,737sqft
Single family home for sale
The Brokerage
$265,000
Views: 5
Bedrooms: 5Bds
Bathrooms: 4Ba
Area: 1,714sqft
Single family home for sale
Guide Realty, Inc.
$149,000
Bedrooms: 2Bds
Bathrooms: 3Ba
Area: 2,080sqft
Single family home for sale
Hunter Real Estate
$275,000
Views: 7
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,680sqft
Single family home for sale
Exp Realty, Llc
Price Drop: $5.5K$269,500
Views: 12
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 1,752sqft
Sale Pending
Kentucky Residential Real Estate, Llc
$525,000
Views: 2
Bedrooms: 6Bds
Bathrooms: 5Ba
Area: 5,552sqft
Single family home for sale
Rogers Realty, Llc
New Construction$299,000
Views: 12
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,310sqft
Single family home for sale
Re/Max Creative Realty
Price Drop: $4K$155,000
Views: 6
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,472sqft
Sale Pending
Era Select Real Estate
$260,000
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,500sqft
Single family home for sale
Re/Max Creative, Winchester
$439,900
Views: 3
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,276sqft
Sale Pending
The Agency
Price Drop: $5K$160,000
Views: 5
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 3,462sqft
Sale Pending
Re/Max Creative, Winchester
$699,000
Views: 4
Bedrooms: 2Bds
Bathrooms: 3Ba
Area: 2,361sqft
Single family home for sale
Dream Maker Realty, Llc
$209,000
Views: 1
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,075sqft
Single family home for sale
Four Seasons Realty
Hot$199,900
Views: 15
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,272sqft
Single family home for sale
Mccallie Real Estate
$617,000
Views: 1
Bedrooms: 3Bds
Bathrooms: 4Ba
Area: 4,848sqft
Single family home for sale
Power House Realty
$299,900
Views: 9
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,444sqft
Single family home for sale
Woods Realty Group
New Construction$484,900
Views: 6
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,381sqft
Sale Pending
The Brokerage
$285,000
Views: 1
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,737sqft
Single family home for sale
The Brokerage
Hot$280,000
Views: 15
Bedrooms: 2Bds
Bathrooms: 1Ba
Area: 1,344sqft
Single family home for sale
Mccallie Real Estate
$249,000
Views: 4
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,512sqft
Single family home for sale
Re/Max Elite Lexington
$65,000
Views: 7
Bedrooms: 2Bds
Bathrooms: 2Ba
Area: 924sqft
Single family home for sale
Dream Maker Realty, Llc
$249,900
Views: 14
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,492sqft
Sale Pending
Rector Hayden Realtors
$56,700
Views: 4
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 1,052sqft
Single family home for sale
Coldwell Banker Mcmahan
Price Drop: $10K$279,900
Views: 11
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,970sqft
Sale Pending
Re/Max Creative Realty
$280,000
Views: 7
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 1,967sqft
Sale Pending
Re/Max Creative Realty
$488,000
Views: 8
Bedrooms: 4Bds
Bathrooms: 3Ba
Area: 2,496sqft
Single family home for sale
Dream Maker Realty, Llc
$434,000
Views: 1
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,928sqft
Sale Pending
Tom Goebel & Company
HotPrice Drop: $7.8K$359,900
Views: 12
Bedrooms: 4Bds
Bathrooms: 2Ba
Area: 2,352sqft
Single family home for sale
Christies International Real Estate Bluegrass
Price Drop: $10K$299,900
Views: 4
Bedrooms: 5Bds
Bathrooms: 2Ba
Area: 2,082sqft
Single family home for sale
Oak & Acre
HotPrice Drop: $11K$248,900
Views: 14
Bedrooms: 3Bds
Bathrooms: 1Ba
Area: 2,249sqft
Sale Pending
Dream Maker Realty, Llc
$475,000
Views: 16
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 2,174sqft
Sale Pending
Ky Local
$519,900
Views: 11
Bedrooms: 5Bds
Bathrooms: 3Ba
Area: 2,200sqft
Single family home for sale
Weichert Realtors - Ford Brothers
$139,900
Views: 11
Bedrooms: 3Bds
Bathrooms: 2Ba
Area: 1,680sqft
Single family home for sale
Ensor Real Estate, Llc
Showing 1 - 42 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 29, 2026, 11:45 PM. 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