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Winchester, TN Homes for Sale | Realty.com

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3 beds New construction

Homes for Sale in Winchester, TN

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24 of 176 Listings

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24 of 176 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

30Active
$389,000
2 bd · 1 ba · 3,560 sqft
3754 Aedc Rd, Winchester, TN
Adam Brock · Canopy Real Estate
11Active
$129,900
3 bd · 1 ba · 1,312 sqft
115 11th Ave, NW, Winchester, TN
Javier Reyes · Better Homes & Gardens Real Estate Heritage Group
31Active
$597,500
4 bd · 3 ba · 3,103 sqft
133 Westmeade Dr, Winchester, TN
Robert Baggett · Zach Taylor Real Estate

Open house Sun, Oct 11 · 12:00 PM16Active
$794,500
4 bd · 4 ba · 3,165 sqft
0 Ridgecrest Dr, Winchester, TN
Angela Privett · Benchmark Realty, LLC
30Active
$399,900
2 bd · 2 ba · 1,664 sqft
56 Deer Valley Cir, Winchester, TN
Ashley Lynch · Lynch Rigsby Realty & Auction, LLC
11Active
$200,000
2 bd · 1 ba · 1,348 sqft
107 Highland Dr, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
31Active
$217,900
3 bd · 2 ba · 1,064 sqft
417 Laura Ave, Winchester, TN
Candice Bedwell · Epique Realty
14Active
$189,900
2 bd · 1 ba · 784 sqft
407 Laura Ave, Winchester, TN
Angie Miller · John Smith Jr Realty and Auction LLC
60Active
$345,000
3 bd · 2 ba · 1,430 sqft
79 Charlotte Dr, Winchester, TN
Amberly Tomme · Legion Realty
23Active
$219,900
3 bd · 2 ba · 2,040 sqft
1110 Hunt St, Winchester, TN
Shawna Kay Denby · 1st Choice REALTOR
38Active
$350,000
3 bd · 3 ba · 1,833 sqft
6063 Mansford Rd, Winchester, TN
Eberley (Ebbie) Holloway · Southern Middle Realty
74Active
$639,900
3 bd · 2 ba · 1,889 sqft
93 Windjammer Ct, Winchester, TN
Cara Chadwick · The Hardy Group
46Active
$309,900
3 bd · 2 ba · 1,834 sqft
371 Myers Rd, Winchester, TN
Dawn Rigsby · eXp Realty
16Active
$264,900
3 bd · 2 ba · 1,592 sqft
114 Hillcrest Dr, Winchester, TN
Chris Hawkersmith · Lynch Rigsby Realty & Auction, LLC
99Active
$929,900
4 bd · 5 ba · 3,622 sqft
11 Hammock Dr, Winchester, TN
Megan Jones · Onward Real Estate
44Active
$525,000
3 bd · 3 ba · 2,357 sqft
314 Lookout Drive, Winchester, TN
Kierstin Murphy · The Agency Chattanooga
43Active
$989,000
4 bd · 4 ba · 2,471 sqft
47 Abby Cir, Winchester, TN
Sam Hatfield · Sam Hatfield Realty, Inc.
24Active
$249,000
3 bd · 2 ba · 1,344 sqft
222 Orchard Ln, Winchester, TN
Melissa K. Stewart · Swaffords Property Shop
31Active
$335,000
3 bd · 2 ba · 1,587 sqft
416 Colonial Dr, Winchester, TN
Susan Gatlin · Leading Edge Real Estate Group
66Active
$649,000
3 bd · 2 ba · 2,100 sqft
432 Meadowood Lane, Winchester, TN
B. J. Rigsby · Lynch Rigsby Realty & Auction, LLC
16Active
Price unavailable
2 bd · 1 ba · 1,075 sqft
308 Peaceful Ln, Winchester, TN
Thomas Ore · Winton Auction & Realty Co.
82Active
$579,000
3 bd · 4 ba · 2,579 sqft
319 Campfire Ct, Winchester, TN
Meredith Smith · Benchmark Realty, LLC
Price Reduced49Active
$369,125
3 bd · 2 ba · 1,428 sqft
36 Meadowwood Ln, Winchester, TN
Melissa Sterling · Better Homes & Gardens Real Estate Heritage Group
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

1 2…8

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: 2026-09-24 20:23:35 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-10-05 14:40:00 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

August 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 12, 2026

Median sale price: $236,600$135,000–$288,000 typical range
Price per sq. ft.: $149
Sales: 13
Paid in cash: 46.2%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $480,000
Homes for sale: 155
Median days on market: 87 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -12.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 12, 2026

Median home size: 1,752 sq. ft.

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

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Nearby areas

ZIP codes

37388 (185)
37398 (175)
37160 (165)
37355 (118)
37387 (60)
37380 (55)
37330 (50)
37356 (39)

Cities

Tullahoma (185)
Shelbyville (165)
Manchester (118)
Tracy City (60)
South Pittsburg (55)
Estill Springs (50)
Monteagle (39)
Lynchburg (30)

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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: 2026-09-24 20:23:35 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-10-05 14:40:00 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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Nearby areas

ZIP codes

37388 (185)
37398 (175)
37160 (165)
37355 (118)
37387 (60)
37380 (55)
37330 (50)
37356 (39)

Cities

Tullahoma (185)
Shelbyville (165)
Manchester (118)
Tracy City (60)
South Pittsburg (55)
Estill Springs (50)
Monteagle (39)
Lynchburg (30)

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

August 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 12, 2026

Median sale price: $236,600$135,000–$288,000 typical range
Price per sq. ft.: $149
Sales: 13
Paid in cash: 46.2%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $480,000
Homes for sale: 155
Median days on market: 87 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -12.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 12, 2026

Median home size: 1,752 sq. ft.