Homes Under $500K in Winchester, TN

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3 beds New construction With a pool

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21 of 92 Listings

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Homes Under $500K in Winchester, TN

21 of 92 Listings

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Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

New49Active
$443,900
3 bd · 2 ba · 2,290 sqft
108 Lookout Drive, Winchester, TN
MITCHELL BOWMAN · simpliHOM - The Results Team
New53Active
$424,900
4 bd · 2 ba · 1,890 sqft
124 Lookout Drive, Winchester, TN
MITCHELL BOWMAN · simpliHOM - The Results Team
Price Reduced41Active
$269,900
2 bd · 1 ba · 1,373 sqft
102 Oak Park, Winchester, TN
Shelia Lunsford · Benchmark Realty, LLC

Listing data & MLS disclosures

Greater Chattanooga REALTORS: IDX information is provided exclusively for consumers’ personal, noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data is deemed reliable but is not guaranteed accurate by the MLS.
Listing information ©2026 Greater Chattanooga Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-03 15:13:53 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-09-03 23:33:32 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Winchester housing market

June 2026

Selling at 97.5% of asking price

Buyers here are paying below asking. MLS · 36 sales · as of Jun 30, 2026

Homes that sold · County records, as of Jun 29, 2026

Median sale price: $319,000$183,000–$486,500 typical range
Price per sq. ft.: $200
Sales: 55
Paid in cash: 50.9%

Homes on the market · MLS, as of Jun 30, 2026

Median days on market: 31 days

Price trend · Assessor repeat sales, as of Jun 30, 2026

Year-over-year: 25.9%

Winchester, TN community profile

Population: 9,947
Median income: $58,811
Housing units: 4,383
People per sq. mi.: 83.2
Area: 119.5 sq. mi.

Source: HJN community data

Explore Winchester homes

Listing data & MLS disclosures

Greater Chattanooga REALTORS: IDX information is provided exclusively for consumers’ personal, noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data is deemed reliable but is not guaranteed accurate by the MLS.
Listing information ©2026 Greater Chattanooga Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-03 15:13:53 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-09-03 23:33:32 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Winchester, TN community profile

Population: 9,947
Median income: $58,811
Housing units: 4,383
People per sq. mi.: 83.2
Area: 119.5 sq. mi.

Source: HJN community data

Winchester housing market

June 2026

Selling at 97.5% of asking price

Buyers here are paying below asking. MLS · 36 sales · as of Jun 30, 2026

Homes that sold · County records, as of Jun 29, 2026

Median sale price: $319,000$183,000–$486,500 typical range
Price per sq. ft.: $200
Sales: 55
Paid in cash: 50.9%

Homes on the market · MLS, as of Jun 30, 2026

Median days on market: 31 days

Price trend · Assessor repeat sales, as of Jun 30, 2026

Year-over-year: 25.9%

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Listing data & MLS disclosures

Winchester housing market

Homes that sold · County records, as of Jun 29, 2026

Homes on the market · MLS, as of Jun 30, 2026

Price trend · Assessor repeat sales, as of Jun 30, 2026

Winchester, TN community profile

Explore Winchester homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Winchester, TN community profile

Winchester housing market

Homes that sold · County records, as of Jun 29, 2026

Homes on the market · MLS, as of Jun 30, 2026

Price trend · Assessor repeat sales, as of Jun 30, 2026