4 Bedroom Homes in Winchester, TN

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3 beds New construction With a pool

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24 of 49 Listings

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4 Bedroom Homes in Winchester, TN

24 of 49 Listings

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49 listings

4 Bedroom Homes in Winchester, TN

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24 of 49 Listings

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4 Bedroom Homes in Winchester, TN

24 of 49 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

New53

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Active

$424,900

4 bd · 2 ba · 1,890 sqft

124 Lookout Drive, Winchester, TN

MITCHELL BOWMAN · simpliHOM - The Results Team

62Active

$1,199,900

4 bd · 4 ba · 3,720 sqft

160 Wakeboard Way, Winchester, TN

Angela Privett · Benchmark Realty, LLC

53Active

$880,000

4 bd · 3 ba · 2,128 sqft

1478 Marble Hill Rd, Winchester, TN

Abigail Sysenkham · Southern Middle Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

37Active

$1,799,000

4 bd · 5 ba · 5,019 sqft

322 N Porter St, Winchester, TN

Tara Hays · Benchmark Realty, LLC

Price Reduced71Active

$451,500

4 bd · 3 ba · 2,228 sqft

270 Wood Bluff Rd, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

90Active

$1,499,000

4 bd · 4 ba · 4,035 sqft

136 Bay Cove Trl, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

Price Reduced81Active

$669,000

4 bd · 3 ba · 3,324 sqft

1136 Bible Crossing Rd, Winchester, TN

Dawn Rigsby · eXp Realty

54Active

$489,900

4 bd · 3 ba · 3,084 sqft

378 Crimson Dr, Winchester, TN

Pamela (Pam) Carver, ABR®, SRES®, AHWD, RESA® CSA · Southern Middle Realty

73Active

$685,700

4 bd · 4 ba · 3,705 sqft

356 Ridgecrest Dr, Winchester, TN

Sean Crabtree · Blue Door Realty Group

60Active

$510,000

4 bd · 3 ba · 2,116 sqft

218 Charlotte Dr, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

Price Reduced62Active

$459,000

4 bd · 4 ba · 2,209 sqft

220 Bryan Dr, Winchester, TN

Sharon Swafford · Swaffords Property Shop

74Active

$799,900

4 bd · 4 ba · 2,886 sqft

309 Campfire Ct, Winchester, TN

Shelia Lunsford · Benchmark Realty, LLC

Price Reduced57Active

$650,000

4 bd · 4 ba · 2,723 sqft

798 Haddon Ln, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

18Active

$115,000

4 bd · 3 ba · 2,052 sqft

605 Gin St, Winchester, TN

Carolyn Hall · Onward Real Estate

Price Reduced99Active

$729,900

4 bd · 5 ba · 3,960 sqft

323 Ridgecrest Dr, Winchester, TN

Daryl Welch · Freedom Realty Group

49Active

$464,900

4 bd · 3 ba · 2,645 sqft

2607 Old Tullahoma Rd, Winchester, TN

Elisa Chessor · Century 21 Coffee County Realty & Auction

53Active

$299,900

4 bd · 2 ba · 1,923 sqft

128 Bel Aire Dr, Winchester, TN

Jessica London · Southern Middle Realty

54Active

$849,900

4 bd · 4 ba · 2,986 sqft

92 Hammock Dr, Winchester, TN

Nicole Miller · Benchmark Realty, LLC

16Active

$794,500

4 bd · 4 ba · 3,165 sqft

0 Ridgecrest Dr, Winchester, TN

Angela Privett · Benchmark Realty, LLC

63Active

$2,119,040

4 bd · 6 ba · 6,160 sqft

318 N Porter St, Winchester, TN

Tara Hays · Benchmark Realty, LLC

53Active

$1,199,000

4 bd · 6 ba · 3,812 sqft

221 Hammock Dr, Winchester, TN

Howard Hicks · Benchmark Realty, LLC

100Active

$3,499,000

4 bd · 7 ba · 8,447 sqft

368 Chandler Dr, Winchester, TN

Maggie Hargrove · Benchmark Realty, LLC

57Active

$775,000

4 bd · 3 ba · 3,104 sqft

22 Hammock Dr, Winchester, TN

Lauren Bailey · Swaffords Property Shop

72Active

$774,900

4 bd · 5 ba · 3,090 sqft

210 Cascade Dr, Winchester, TN

MITCHELL BOWMAN · simpliHOM - The Results Team

Listing data & MLS disclosures

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Listing data & MLS disclosures

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, 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