$445,500
5
3Bds
3Ba
2,961sqft
Single family home for sale
Mccallie Real Estate
$430,000
3
3Bds
2Ba
1,855sqft
Single family home for sale
United Real Estate Bluegrass
$430,000
3
3Bds
2Ba
1,855sqft
Single family home for sale
United Real Estate Bluegrass
$430,000
4
3Bds
2Ba
1,855sqft
Sale Pending
United Real Estate Bluegrass
$425,000
6
--Bds
--Ba
25.87acres lot
Land for sale
Keller Williams Commonwealth
$420,000
2
3Bds
2Ba
2,027sqft
Single family home for sale
Keller Williams Commonwealth
$419,900
12
4Bds
3Ba
1,500sqft
Single family home for sale
Dream Maker Realty, Llc
$419,000
4
3Bds
2Ba
2,942sqft
Single family home for sale
Ro&Co Real Estate
$410,000
3
4Bds
2Ba
2,435sqft
Sale Pending
Re/Max Creative, Winchester
$399,999
3
4Bds
5Ba
2,800sqft
Single family home for sale
The Brokerage
$399,900
3
3Bds
3Ba
2,289sqft
Single family home for sale
Marshall Lane Real Estate - Lexington
$399,000
1
--Bds
--Ba
11.3acres lot
Land for sale
Steven D Adams Real Estate Services, Llc
$395,000
8
3Bds
2Ba
1,855sqft
Sale Pending
United Real Estate Bluegrass
$394,999
4
3Bds
2Ba
1,604sqft
Single family home for sale
The Brokerage
$390,000
13
4Bds
1Ba
2,063sqft
Single family home for sale
Rector Hayden Realtors
Keller Williams Bluegrass Realty
$389,900
17
4Bds
3Ba
2,676sqft
Sale Pending
Christies International Real Estate Bluegrass
$389,900
5
3Bds
3Ba
2,516sqft
Single family home for sale
Dixon Properties
$389,000
5
3Bds
3Ba
2,204sqft
Single family home for sale
Dream Maker Realty, Llc
$388,000
6
5Bds
3Ba
2,762sqft
Multi family home for sale
$385,000
6
3Bds
2Ba
1,344sqft
Single family home for sale
Keller Williams Commonwealth
$380,000
5
3Bds
2Ba
1,677sqft
Single family home for sale
United Real Estate Bluegrass
$380,000
2
3Bds
2Ba
1,677sqft
Sale Pending
United Real Estate Bluegrass
$380,000
3
3Bds
2Ba
1,677sqft
Single family home for sale
United Real Estate Bluegrass
$379,000
4
4Bds
3Ba
1,978sqft
Single family home for sale
Keller Williams Commonwealth
$379,000
9
4Bds
2Ba
3,306sqft
Single family home for sale
Re/Max Creative, Winchester
$375,000
6
4Bds
2Ba
1,828sqft
Single family home for sale
Freedom Realty & Property Management
$369,900
4
4Bds
2Ba
1,636sqft
Sale Pending
Freedom Realty & Property Management
$365,900
4
3Bds
2Ba
1,635sqft
Single family home for sale
Ensor Real Estate, Llc
$365,900
1
3Bds
2Ba
1,558sqft
Single family home for sale
Ensor Real Estate, Llc
$359,900
3
3Bds
2Ba
2,269sqft
Single family home for sale
Freedom Realty & Property Management
Napier Realtors
$357,000
6
3Bds
3Ba
1,945sqft
Single family home for sale
Re/Max Creative, Winchester
$355,000
4
3Bds
2Ba
1,990sqft
Single family home for sale
Milton And Associates Real Estate
$355,000
4
3Bds
3Ba
2,166sqft
Single family home for sale
Weichert Realtors - Abg Properties
$355,000
10
1Bd
2Ba
2,179sqft
Single family home for sale
Re/Max Creative Realty
Dream Maker Realty, Llc
$350,000
2
--Bds
--Ba
7.31acres lot
Land for sale
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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 Report285
Homes Available
$ 220,000
Median List Price
49 Days
Avg on Market
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