$300,000
6
--Bds
--Ba
15.27acres lot
Land for sale
Keller Williams Commonwealth
$300,000
1
--Bds
--Ba
5.01acres lot
Land for sale
National Real Estate
$299,900
2
5Bds
2Ba
2,082sqft
Single family home for sale
Oak & Acre
$299,900
5
3Bds
2Ba
1,444sqft
Single family home for sale
Woods Realty Group
$299,000
5
--Bds
--Ba
8.26acres lot
Land for sale
Coldwell Banker Mcmahan
$296,000
14
4Bds
2Ba
1,953sqft
Single family home for sale
Woods Realty Group
$289,000
4
2Bds
2Ba
1,674sqft
Sale Pending
Dream Maker Realty, Llc
$285,000
3
3Bds
2Ba
1,780sqft
Sale Pending
Re/Max Creative Realty - Mountain Legacy Group
$280,000
7
4Bds
4Ba
3,276sqft
Townhouse for sale
Keller Williams Legacy Group
$280,000
4Bds
3Ba
1,850sqft
Single family home for sale
Lifstyl Real Estate
$280,000
8
2Bds
1Ba
1,344sqft
Single family home for sale
Mccallie Real Estate
$279,900
7
4Bds
3Ba
1,970sqft
Single family home for sale
Re/Max Creative Realty
$275,000
5
3Bds
2Ba
1,512sqft
Single family home for sale
Weichert Realtors - Abg Properties
$275,000
14
4Bds
2Ba
1,924sqft
Single family home for sale
Keller Williams Commonwealth
$275,000
8
3Bds
2Ba
1,500sqft
Single family home for sale
Ensor Real Estate, Llc
$270,000
4
4Bds
2Ba
1,539sqft
Single family home for sale
Keller Williams Commonwealth
$270,000
6
--Bds
--Ba
0.84acre lot
Land for sale
Ensor Real Estate, Llc
$270,000
3
4Bds
2Ba
1,984sqft
Single family home for sale
Woods Realty Group
$270,000
15
4Bds
2Ba
2,170sqft
Single family home for sale
Exp Realty Llc
$269,900
10
3Bds
1Ba
1,644sqft
Sale Pending
Keller Williams Commonwealth
$269,500
5
4Bds
2Ba
1,752sqft
Single family home for sale
Kentucky Residential Real Estate, Llc
$265,000
6
3Bds
3Ba
2,260sqft
Single family home for sale
Lois Ann Disponett Real Est
$265,000
6
3Bds
2Ba
1,650sqft
Single family home for sale
Keller Williams Legacy Group
$265,000
1
5Bds
4Ba
1,714sqft
Single family home for sale
Guide Realty, Inc.
$265,000
11
3Bds
2Ba
1,776sqft
Single family home for sale
Lifstyl Real Estate
$264,900
10
5Bds
2Ba
2,214sqft
Single family home for sale
Re/Max Elite Lexington
$264,900
16
3Bds
2Ba
1,323sqft
Sale Pending
Freedom Realty & Property Management
$258,900
6
2Bds
1Ba
849sqft
Single family home for sale
Wtc Realty Llc
$255,000
4
3Bds
2Ba
1,809sqft
Single family home for sale
Re/Max Creative, Winchester
$250,000
16
3Bds
2Ba
1,295sqft
Single family home for sale
Kentucky Residential Real Estate, Llc
$249,900
4
3Bds
2Ba
1,492sqft
Single family home for sale
Rector Hayden Realtors
$249,900
1
3Bds
1Ba
1,250sqft
Sale Pending
Freedom Realty & Property Management
$249,500
2
--Bds
--Ba
14.51acres lot
Land for sale
Keller Williams Commonwealth
$249,000
3
3Bds
3Ba
1,664sqft
Single family home for sale
Freedom Realty & Property Management
$249,000
7
4Bds
2Ba
1,996sqft
Single family home for sale
The Agency
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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 Report222
Homes Available
$ 220,000
Median List Price
49 Days
Avg on Market
Do Real Estate on the Go!