Luxury Homes in Winchester, TN

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3 beds New construction With a pool

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19 Listings

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Luxury Homes in Winchester, TN

19 Listings

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Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

85Active
$2,815,000
5 bd · 6 ba · 5,581 sqft
131 Bluff Dr, Winchester, TN
Jenny Massey · Capstone Realty
22Active
$1,500,000
3 bd · 2 ba · 2,962 sqft
107 Brandi Way, Winchester, TN
Jackson Carroll · Compass
62Active
$1,199,900
4 bd · 4 ba · 3,720 sqft
160 Wakeboard Way, Winchester, TN
Angela Privett · Benchmark Realty, LLC

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-09-23 12:33:30 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: $323,000$198,000–$486,500 typical range
Price per sq. ft.: $200
Sales: 55
Paid in cash: 49.1%

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

Realtracs: Based on information submitted to the MLS GRID as of 2026-09-23 12:33:30 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, 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: $323,000$198,000–$486,500 typical range
Price per sq. ft.: $200
Sales: 55
Paid in cash: 49.1%

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%

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Co-ops

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

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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

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

Your local brokerage

Your local brokerage