$143,900
5
3Bds
2Ba
1,680sqft
Single family home for sale
Ensor Real Estate, Llc
$143,900
5
3Bds
2Ba
1,680sqft
Single family home for sale
Ensor Real Estate, Llc
$229,900
3
3Bds
2Ba
1,904sqft
Sale Pending
Freedom Realty & Property Management
$629,000
3
5Bds
4Ba
5,011sqft
Single family home for sale
Re/Max Elite Realty
$367,700
3
4Bds
2Ba
2,352sqft
Single family home for sale
Christies International Real Estate Bluegrass
$335,000
5
3Bds
2Ba
1,836sqft
Single family home for sale
The Real Estate Co - W Liberty
$1,125,000
3Bds
4Ba
3,672sqft
Single family home for sale
United Real Estate Bluegrass
$498,000
7
4Bds
3Ba
2,496sqft
Single family home for sale
Dream Maker Realty, Llc
$375,000
8
4Bds
2Ba
1,828sqft
Single family home for sale
Freedom Realty & Property Management
$5,495,000
7
3Bds
4Ba
5,800sqft
Single family home for sale
Bluegrass Sotheby'S International Realty
$699,000
5
4Bds
5Ba
4,255sqft
Single family home for sale
Napier Realtors
$379,000
10
4Bds
2Ba
3,306sqft
Single family home for sale
Re/Max Creative, Winchester
$309,900
22
3Bds
2Ba
2,138sqft
Sale Pending
Freedom Realty & Property Management
$184,900
6
3Bds
1Ba
1,046sqft
Single family home for sale
Bluegrass Properties Group
$389,900
21
4Bds
3Ba
2,676sqft
Sale Pending
Christies International Real Estate Bluegrass
$420,000
4
3Bds
2Ba
2,027sqft
Single family home for sale
Keller Williams Commonwealth
$265,000
6
3Bds
3Ba
2,260sqft
Single family home for sale
Lois Ann Disponett Real Est
$1,595,000
9
3Bds
3Ba
4,518sqft
Single family home for sale
Coldwell Banker Mcmahan
$390,000
14
4Bds
1Ba
2,063sqft
Single family home for sale
Rector Hayden Realtors
$399,900
4
3Bds
3Ba
2,289sqft
Single family home for sale
Marshall Lane Real Estate - Lexington
$379,000
5
4Bds
3Ba
1,978sqft
Single family home for sale
Keller Williams Commonwealth
$785,000
2
5Bds
3Ba
4,676sqft
Single family home for sale
Re/Max Creative, Winchester
$359,900
3
3Bds
2Ba
2,269sqft
Single family home for sale
Freedom Realty & Property Management
$270,000
14
4Bds
2Ba
2,170sqft
Single family home for sale
Exp Realty Llc
Marshall Lane Real Estate - Lexington
$5,500,000
20
7Bds
6Ba
9,769sqft
Mansion for sale
Keller Williams Commonwealth
$148,900
3
3Bds
1Ba
1,362sqft
Single family home for sale
Coldwell Banker Mcmahan
$198,900
6
5Bds
2Ba
2,444sqft
Single family home for sale
Coldwell Banker Mcmahan
$345,000
5
3Bds
3Ba
2,628sqft
Single family home for sale
Ky Property Hunters
$2,750,000
6
8Bds
8Ba
13,433sqft
Mansion for sale
Block + Lot Real Estate
$394,999
4
3Bds
2Ba
1,604sqft
Single family home for sale
The Brokerage
$355,000
4
3Bds
3Ba
2,166sqft
Single family home for sale
Weichert Realtors - Abg Properties
$275,000
14
4Bds
2Ba
1,924sqft
Single family home for sale
Keller Williams Commonwealth
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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.
Balanced Market
49
60
In Mar 2026 · YoY
Current rate · YoY
30-Year Fixed
30-yr fixed rate 6.23% · Data as of Mar 2026 · Source: Houzeo Research.
View Full Winchester Market Report38
Homes Available
$ 220,000
Median List Price
49 Days
Avg on Market
Do Real Estate on the Go!