2 Bedroom Homes in Winchester, TN

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3 beds New construction With a pool

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14 Listings

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2 Bedroom Homes in Winchester, TN

14 Listings

Price Reduced41

14 listings

2 Bedroom Homes in Winchester, TN

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14 Listings

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2 Bedroom Homes in Winchester, TN

14 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Price Reduced41

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Active

$269,900

2 bd · 1 ba · 1,373 sqft

102 Oak Park, Winchester, TN

Shelia Lunsford · Benchmark Realty, LLC

42Active

$369,900

2 bd · 2 ba · 1,818 sqft

76 Chase Cir, Winchester, TN

Sean Crabtree · Blue Door Realty Group

39Active

$238,000

2 bd · 2 ba · 1,370 sqft

404 S Jefferson St, Winchester, TN

Eric Fruehauf · BHGRE Baker & Cole

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

30Active

$419,000

2 bd · 2 ba · 1,664 sqft

56 Deer Valley Cir, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

Price Reduced27Active

$174,900

2 bd · 1 ba · 824 sqft

424 Laura Ave, Winchester, TN

Matt Sargent · Matt Sargent Homes

50Active

$999,000

2 bd · 2 ba · 1,428 sqft

52 Narrows Dr, Winchester, TN

Kaila Hampton Gentry · BMA Properties

Price Reduced5Active

$65,000

2 bd · 1 ba · 672 sqft

409 4th Ave SW, Winchester, TN

Kaydence Transue · Better Homes & Gardens Real Estate Heritage Group

32Active

$230,000

2 bd · 2 ba · 1,600 sqft

525 Sharp Springs Rd, Winchester, TN

Maddie Duncan · Steve Jernigan Realty

Price Reduced51Active

$1,150,000

2 bd · 3 ba · 2,460 sqft

645 Wildwood Trce, Winchester, TN

George W Weeks · Team George Weeks Real Estate, LLC

83Active

$399,900

2 bd · 2 ba · 1,450 sqft

924 Cline Ridge Rd, Winchester, TN

Dayla Bray- The Preferred Group · Keller Williams Russell Realty & Auction

39Active

$359,900

2 bd · 2 ba · 1,801 sqft

342 Chase Cir, Winchester, TN

John Michael Peck · Century 21 Volunteer Realty

Price Reduced24Active

$319,900

2 bd · 2 ba · 1,080 sqft

1687 Georgia Crossing Rd, Winchester, TN

John Michael Peck · Century 21 Volunteer Realty

Price Reduced40Active

$320,000

2 bd · 2 ba · 1,200 sqft

667 Maple Bend Rd, Winchester, TN

Pam Ford · Benchmark Realty, LLC

Price Reduced30Active

$399,000

2 bd · 1 ba · 3,560 sqft

3754 Aedc Rd, Winchester, TN

Adam Brock · Canopy Real Estate

Listing data & MLS disclosures

Realtracs: Based on information submitted to the MLS GRID as of 2026-09-04 15:03:54 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 2026-09-04 15:03:54 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