Homes Under $300K in Winchester, TN

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3 beds New construction With a pool

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24 of 32 Listings

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Homes Under $300K in Winchester, TN

24 of 32 Listings

16Active

32 listings

Homes Under $300K in Winchester, TN

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24 of 32 Listings

Map

Homes Under $300K in Winchester, TN

24 of 32 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

16Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

$264,900

3 bd · 2 ba · 1,592 sqft

114 Hillcrest Dr, Winchester, TN

Chris Hawkersmith · Lynch Rigsby Realty & Auction, LLC

24Active

$249,000

3 bd · 2 ba · 1,344 sqft

222 Orchard Ln, Winchester, TN

Melissa K. Stewart · Swaffords Property Shop

13Active

$285,000

3 bd · 1 ba · 1,154 sqft

814 S High St, Winchester, TN

April Smith Couch · John Smith Jr Realty and Auction LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

4Active

$299,900

3 bd · 2 ba · 1,288 sqft

260 Union Rd, Winchester, TN

Rachel Lynn Perryman · Homestead-Kent Davis Realty & Aucti

3Active

$299,900

3 bd · 2 ba · 1,288 sqft

220 Union Rd, Winchester, TN

Rachel Lynn Perryman · Homestead-Kent Davis Realty & Aucti

1Active

$215,900

3 bd · 2 ba · 1,014 sqft

0 Little St, Winchester, TN

Jennifer Savage · Freedom Realty Group

1Active

$229,900

3 bd · 2 ba · 1,014 sqft

0 S High St, Winchester, TN

Jennifer Savage · Freedom Realty Group

20Active

$259,900

3 bd · 2 ba · 1,875 sqft

114 Bel Aire Dr, Winchester, TN

Wayne Neese · Coldwell Banker Southern Realty

40Active

$99,900

3 bd · 2 ba · 1,500 sqft

1717 Georgia Crossing Rd, Winchester, TN

John Michael Peck · Century 21 Volunteer Realty

Active

$215,900

3 bd · 2 ba · 1,014 sqft

0 Little St, Winchester, TN

Daryl Welch · Freedom Realty Group

Active

$215,900

3 bd · 2 ba · 1,014 sqft

0 Little St, Winchester, TN

Daryl Welch · Freedom Realty Group

Price Reduced18Active

$110,000

4 bd · 3 ba · 2,052 sqft

605 Gin St, Winchester, TN

Carolyn Hall · Onward Real Estate

40Active

$299,900

4 bd · 2 ba · 1,999 sqft

206 Homeward Ave, Winchester, TN

Tekesha Fuqua-Taylor · Keller Williams Realty - Murfreesboro

2Active

$215,900

3 bd · 2 ba · 1,014 sqft

0 Little St, Winchester, TN

Stephanie Jo Dowdy · Freedom Realty Group

1Active

$239,000

3 bd · 2 ba · 1,100 sqft

0 Style St, Winchester, TN

Stephanie Jo Dowdy · Freedom Realty Group

32Active

$299,000

3 bd · 2 ba · 1,675 sqft

1790 Old Estill Springs Rd, Winchester, TN

Steven Paul · Keller Williams West Knoxville

Price Reduced41Active

$269,900

2 bd · 1 ba · 1,373 sqft

102 Oak Park, Winchester, TN

Shelia Lunsford · Benchmark Realty, LLC

54Active

$299,000

5 bd · 2 ba · 1,588 sqft

Address withheld · Winchester, TN

Lori Rowton · Keller Williams Nashville-Franklin

19Active

$199,900

3 bd · 1 ba · 1,271 sqft

203 W Petty Ln, Winchester, TN

John Michael Peck · Century 21 Volunteer Realty

16Active

$298,000

3 bd · 2 ba · 1,400 sqft

23 Woods Edge Rd, Winchester, TN

Sharon Swafford · Swaffords Property Shop

13Active

$125,000

3 bd · 1 ba · 1,150 sqft

406 2nd Ave, NW, Winchester, TN

Dustyn Reed · United Real Estate Middle Tennessee

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

Price Reduced8Active

$179,900

3 bd · 2 ba · 1,755 sqft

207 Melody Ln, Winchester, TN

Amanda Lynch · WEICHERT, REALTORS Joe Orr & Associates

32Active

$230,000

2 bd · 2 ba · 1,600 sqft

525 Sharp Springs Rd, Winchester, TN

Maddie Duncan · Steve Jernigan Realty

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: 2026-09-25 19:58:29 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-09-27 21:42:00 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

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: 2026-09-25 19:58:29 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-09-27 21:42:00 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%

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