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3 beds New construction

174 listings

Homes for Sale in Winchester, TN

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23 of 174 Listings

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23 of 174 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Price Reduced56

Active

$479,900

4 bd · 3 ba · 2,578 sqft

70 Island Way, Winchester, TN

Dena Abbott · SimpliHOM

Price Reduced44Active

$435,000

5 bd · 3 ba · 2,420 sqft

71 David Crockett Hwy, Winchester, TN

Eberley (Ebbie) Holloway · Southern Middle Realty

Price Reduced41Active

$799,000

3 bd · 3 ba · 2,395 sqft

106 Clearview Cir, Winchester, TN

Sam Hatfield · Sam Hatfield Realty, Inc.

Price Reduced56Active

$574,900

3 bd · 2 ba · 1,909 sqft

794 River Watch Way, Winchester, TN

Shelia Lunsford · Benchmark Realty, LLC

Price Reduced54Active

$429,000

4 bd · 3 ba · 2,660 sqft

58 Island Way, Winchester, TN

Angie Miller · John Smith Jr Realty and Auction LLC

46Active

$695,900

4 bd · 4 ba · 2,560 sqft

59 Turtle Ct, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

Price Reduced86Active

$1,475,000

3 bd · 5 ba · 6,300 sqft

1485 Water Tank Rd, Winchester, TN

Sharon Swafford · Swaffords Property Shop

Price Reduced30Active

$959,000

4 bd · 4 ba · 3,034 sqft

117 Hammock Dr, Winchester, TN

Dawn Parrish · Leading Edge Real Estate Group

Price Reduced44Active

$375,000

3 bd · 2 ba · 1,632 sqft

802 Evans Rd, Winchester, TN

Hannah Monilaw · Better Homes & Gardens Real Estate Heritage Group

39Active

$325,000

3 bd · 1 ba · 1,490 sqft

1400 Holders Cove Rd, Winchester, TN

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

Price Reduced52Active

$549,000

3 bd · 3 ba · 1,952 sqft

16 Bingham Ct, Winchester, TN

Thomas Ore · Winton Auction & Realty Co.

Price Reduced48Active

$575,000

3 bd · 2 ba · 1,493 sqft

50 Maple Dr, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

73Active

$749,900

4 bd · 4 ba · 4,100 sqft

105 W Paradise Drive, Winchester, TN

Angel Griser · Tennessee Mountain Properties

36Active

$649,900

3 bd · 4 ba · 3,706 sqft

766 Awalt Dr, Winchester, TN

GREG SITZ · Parks Auction & Realty

Price Reduced41Active

$349,900

4 bd · 3 ba · 2,640 sqft

205 Houghton Dr, Winchester, TN

Danielle Wolff Holland · Coldwell Banker Southern Realty

39Active

$799,500

4 bd · 4 ba · 3,034 sqft

55 Windjammer Ct, Winchester, TN

Crystal Thomas · Luxury Homes of Tennessee

Price Reduced72Active

$612,086

4 bd · 3 ba · 2,893 sqft

49 Driftwood Ct, Winchester, TN

Tara Hays · Benchmark Realty, LLC

Price Reduced89Active

$1,050,000

4 bd · 4 ba · 2,906 sqft

208 Loop Dr, Winchester, TN

Jessica London · Southern Middle Realty

67Active

$2,095,000

3 bd · 5 ba · 5,404 sqft

1376 Old Mansford Rd, Winchester, TN

Sam Hatfield · Sam Hatfield Realty, Inc.

Price Reduced31Active

$499,000

3 bd · 3 ba · 2,276 sqft

23 Skidmore Ln, Winchester, TN

Ashley W. Nelson · Franklin County Realty

Price Reduced40Active

$320,000

2 bd · 2 ba · 1,200 sqft

667 Maple Bend Rd, Winchester, TN

Pam Ford · Benchmark Realty, LLC

Price Reduced99Active

$1,049,000

4 bd · 3 ba · 2,714 sqft

914 N Jefferson St, Winchester, TN

Danny Babel · Benchmark Realty, LLC

Price Reduced56Active

$899,000

4 bd · 5 ba · 2,376 sqft

369 Fanning Bend Dr, Winchester, TN

Ashley Lynch · Lynch Rigsby Realty & Auction, LLC

1…6 7 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: 2026-09-10 16:22:23 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-10-01 13:25:00 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

July 2026 · This period is still settling

Selling at 97.0% of asking price

Buyers here are paying below asking. MLS · 26 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 10, 2026

Median sale price: $407,500$268,000–$606,250 typical range
Sales: 12
Paid in cash: 50.0%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $480,000
Homes for sale: 159

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

By price

Homes Under $300K
Homes Under $400K
Homes Under $500K
Homes Under $600K
Homes Under $700K
Homes Under $800K
Homes Under $900K

By bedrooms

3 Bedroom Homes
4 Bedroom Homes

By feature

New Construction Homes

Nearby areas

ZIP codes

37398 (175)
37388 (172)
37160 (170)
37355 (118)
37330 (49)
37387 (48)
37356 (38)
37352 (30)

Cities

Tullahoma (172)
Shelbyville (170)
Manchester (118)
Estill Springs (49)
Tracy City (48)
Monteagle (38)
Lynchburg (30)
Fayetteville (23)

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #338714

Call Thomas

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: 2026-09-10 16:22:23 UTC
Realtracs: Based on information submitted to the MLS GRID as of 2026-10-01 13:25:00 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

July 2026 · This period is still settling

Selling at 97.0% of asking price

Buyers here are paying below asking. MLS · 26 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 10, 2026

Median sale price: $407,500$268,000–$606,250 typical range
Sales: 12
Paid in cash: 50.0%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $480,000
Homes for sale: 159

Median days on market

47 days

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

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,752 sq. ft.

Winchester, TN Homes for Sale — Page 7 | Realty.com

Nearby areas

ZIP codes

37398 (175)
37388 (172)
37160 (170)
37355 (118)
37330 (49)
37387 (48)
37356 (38)
37352 (30)

Cities

Tullahoma (172)
Shelbyville (170)
Manchester (118)
Estill Springs (49)
Tracy City (48)
Monteagle (38)
Lynchburg (30)
Fayetteville (23)