5 Bedroom Homes in Winchester, TN

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3 beds New construction With a pool

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11 Listings

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5 Bedroom Homes in Winchester, TN

11 Listings

54Active

11 listings

5 Bedroom Homes in Winchester, TN

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11 Listings

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5 Bedroom Homes in Winchester, TN

11 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

54Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

$299,000

5 bd · 2 ba · 1,588 sqft

Address withheld · Winchester, TN

Lori Rowton · Keller Williams Nashville-Franklin

Price Reduced63Active

$975,000

5 bd · 5 ba · 3,191 sqft

171 Cypress Point Dr, Winchester, TN

B. J. Rigsby · Lynch Rigsby Realty & Auction, LLC

Price Reduced57Active

$587,900

5 bd · 4 ba · 2,753 sqft

8 Latitude Dr, Winchester, TN

Tara Hays · Benchmark Realty, LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

52Active

$299,000

5 bd · 2 ba · 1,600 sqft

1200 Little St, Winchester, TN

Lori Rowton-Walker · Keller Williams Realty Nashville/Franklin

Price Reduced75Active

$389,900

5 bd · 3 ba · 2,632 sqft

6933 Winchester Hwy, Winchester, TN

Charlie Gonzales, ABR, SRS, e-PRO | 931-808-5521 · Southern Middle Realty

Price Reduced64Active

$470,000

5 bd · 2 ba · 3,922 sqft

309 2nd Ave NW, Winchester, TN

Robert Duncan · eXp Realty

Price Reduced44Active

$445,000

5 bd · 3 ba · 2,420 sqft

71 David Crockett Hwy, Winchester, TN

Eberley (Ebbie) Holloway · Southern Middle Realty

Price Reduced64Active

$449,900

5 bd · 3 ba · 2,160 sqft

103 Anderton Dr, Winchester, TN

Tara Hays · Benchmark Realty, LLC

Price Reduced41Active

$1,049,000

5 bd · 5 ba · 3,670 sqft

232 Loop Dr, Winchester, TN

Gabriel Besleaga · Bill Jakes Realty

75Active

$879,900

5 bd · 5 ba · 3,095 sqft

53 River Watch Way, Winchester, TN

John Michael Peck · Century 21 Volunteer Realty

Price Reduced41Active

$875,500

5 bd · 3 ba · 3,640 sqft

182 Loop Dr, Winchester, TN

Kay Caldwell · Swaffords Property Shop

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 2026-09-01 23:22:29 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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

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 2026-09-01 23:22:29 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: $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

Your local brokerage

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

Your local brokerage

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